Chapter 22
Substituted Hydrocarbons
and Their Reactions
BIG Idea The substitution of
different functional groups for
hydrogen atoms in hydrocarbons
results in a diverse group of
organic compounds.
22.1 Alkyl Halides and
Aryl Halides
MAIN Idea A halogen atom can
replace a hydrogen atom in some
hydrocarbons.
22.2 Alcohols, Ethers,
and Amines
MAIN Idea Oxygen and nitrogen
are two of the most-common atoms
found in organic functional groups.
22.3 Carbonyl Compounds
MAIN Idea Carbonyl compounds
contain a double-bonded oxygen in
the functional group.
22.4 Other Reactions
of Organic Compounds
MAIN Idea Classifying the
chemical reactions of organic
compounds makes predicting
products of reactions much easier.
22.5 Polymers
MAIN Idea Synthetic polymers
are large organic molecules made
up of repeating units linked together
by addition or condensation
reactions.
ChemFacts
• The larva of the Cerura vinula moth
squirts formic acid when threatened.
• The feathery antennae of the adult
moth contains chemoreceptors for
detecting organic compounds.
784
(inset)©SCIENCE PICTURES LTD/SCIENCE PHOTO LIBRARY/Photo Researchers Inc, (bkgd)©Waina Cheng/PHOTOLIBRARY
Formic acid
Start-Up Activities
LAUNCH Lab
Functional Groups Make the
following Foldable to organize
information about the functional
groups of organic compounds.
How do you make slime?
In addition to carbon and hydrogen, most organic
substances contain other elements that give the
substances unique properties. How do the properties of
substances change when groups form bonds called crosslinks between the chains?
Procedure
1. Read and complete the lab safety form.
2. Use a graduated cylinder to measure 20 mL of
4% polyvinyl alcohol solution. Pour the solution
into a small disposable plastic cup. Note the viscosity
of the solution as you stir it with a stirring rod.
3. While stirring, add 6 mL of 4% sodium tetraborate
solution to the polyvinyl alcohol solution. Continue
to stir until there is no further change in the consistency
of the product.
4. Use a gloved hand to scoop the material out of the cup.
Knead and stretch the polymer..
Analysis
1. Compare and contrast the physical properties of
the product and the reactants.
2. Explain how the crosslinking of the molecular chains
affected the viscosity of the solution.
Inquiry What is the ratio of sodium tetraborate solution
to polyvinyl alcohol solution? What would you create if the
ratio was changed?
STEP 1 Layer
seven sheets of paper
as shown.
STEP 2 Make
a 3-cm horizontal cut
through all seven
sheets on about the
sixth line from the top.
STEP 3 Make
a vertical cut from the
bottom to meet the
horizontal cut.
STEP 4 Place a full
sheet at the bottom of
the cut sheets. Align the
tops and sides of all
sheets. Staple the
Foldable or place in a
notebook. Label the tabs
as shown.
Alcohol
Ether
Amine
Aldehyde
Ketone
Carbolic acid
Ester
Amide
&/,$!",%3 Use this Foldable with Sections 22.1, 22.2,
22.3, and 22.4. As you read these sections, summarize
what you learn about the classes of organic compounds.
Include their structures, and give examples.
Visit glencoe.com to:
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Organic Compounds
Chapter 22 • Substituted Hydrocarbons and Their Reactions 785
Matt Meadows
Section 22.1
Objectives
◗ Define functional group, and give
examples.
◗ Compare and contrast alkyl and
aryl halide structures.
◗ Evaluate the boiling points of
organic halides.
Review Vocabulary
aliphatic compound: a nonaromatic
hydrocarbon, such as an alkane,
an alkene, or an alkyne
New Vocabulary
functional group
halocarbon
alkyl halide
aryl halide
plastic
substitution reaction
halogenation
Alkyl Halides
and Aryl Halides
-!). )DEA A halogen atom can replace a hydrogen atom in some
hydrocarbons.
Real-World Reading Link If you have ever played on a sports team, were
individual players substituted during the game? For example, a player who is
rested might substitute for a player who is tired. After the substitution, the
characteristics of the team change.
Functional Groups
You read in Chapter 21 that in hydrocarbons, carbon atoms are linked
only to other carbon atoms or hydrogen atoms. But carbon atoms
can also form strong covalent bonds with other elements, the most
common of which are oxygen, nitrogen, fluorine, chlorine, bromine,
iodine, sulfur, and phosphorus.
Atoms of these elements occur in organic substances as parts of functional groups. In an organic molecule, a functional group is an atom or
group of atoms that always reacts in a certain way. The addition of a
functional group to a hydrocarbon structure always produces a substance with physical and chemical properties that differ from those of
the parent hydrocarbon. All the items—natural and synthetic—in
Figure 22.1 contain functional groups that give them their individual
characteristics, such as smell. Organic compounds containing several
important functional groups are shown in Table 22.1. The symbols R
and R´ represent carbon chains or rings bonded to the functional group.
An * represents a hydrogen atom, carbon chain, or carbon ring.
Keep in mind that double and triple bonds between two carbon atoms
are considered functional groups even though only carbon and hydrogen
atoms are involved. By learning the properties associated with a given
functional group, you can predict the properties of organic compounds
for which you know the structure, even if you have never studied them.
Figure 22.1 All of these items
contain at least one of the functional
groups that you will study in this chapter.
For example, the fruit and flowers have
sweet-smelling aromas that are due to
ester molecules.
■
786
Chapter 22 • Substituted Hydrocarbons and Their Reactions
Matt Meadows
Table 22.1
Interactive Table Explore
functional groups at glencoe.com.
Organic Compounds and
Their Functional Groups
Compound Type
General Formula
Functional Group
R—X (X = F, Cl, Br, I)
Halogen
R—OH
Hydroxyl
Ether
R—OH—R'
Ether
Amine
R—NH 2
Amino
Alcohol
O
Carbonyl
—
—
Aldehyde
*—C—H
O
Carbonyl
—
—
Ketone
R — C — R
O
Carboxyl
—
—
Carboxylic acid
* — C — OH
0
Ester
—
—
Ester
—$—0—R
O
—
—
Amide
H
Amide
—
Halocarbon
*—C—N—R
Organic Compounds Containing Halogens
The most simple functional groups can be thought of as substituent
groups attached to a hydrocarbon. Recall that a substituent group is a side
branch attached to a parent chain. The elements in group 17 of the periodic table —fluorine, chlorine, bromine, and iodine—are the halogens.
Any organic compound that contains a halogen substituent is called a
halocarbon. If you replace any of the hydrogen atoms in an alkane with
a halogen atom, you form an alkyl halide. An alkyl halide is an organic
compound containing a halogen atom covalently bonded to an aliphatic
carbon atom. The first four halogens—fluorine, chlorine, bromine, and
iodine—are found in many organic compounds. For example, chloromethane is the alkyl halide formed when a chlorine atom replaces one
of methane’s four carbon atoms, as shown in Figure 22.2.
Figure 22.2 Chloromethane is an
alkyl halide that is used in the manufacturing process for silicone products, such as
window and door sealants.
■
—
H
—
Cl — C — H
H
Chloromethane
Section 22.1 • Alkyl Halides and Aryl Halides 787
©David Hoffman Photo Library/Alamy
An aryl halide is an organic compound containing a halogen
atom bonded to a benzene ring or other aromatic group. The
structural formula for an aryl halide is created by first drawing
the aromatic structure and then replacing its hydrogen atoms
with the halogen atoms specified, as shown in Figure 22.3a.
a
Cl
Chlorobenzene
—
—
—
H
H—C—C—C—F
H
H
H
H
Fluoroethane and 1, 2-Difluoropropane
—
—
—
—
H
—
Cl
—
F
—
Br
—
c
H
H
H
1-Bromo-3-chloro-2-fluorobutane
I
d
F
I
to
Naming halocarbons Organic molecules containing functional groups are given IUPAC names based on their main-chain
alkane structures. For the alkyl halides, a prefix indicates which
halogen is present. The prefixes are formed by changing the
-ine at the end of each halogen name to -o. Thus, the prefix for
fluorine is fluoro-, chlorine is chloro-, bromine is bromo-, and
iodine is iodo-, as shown in Figure 22.3b.
If more than one kind of halogen atom is present in the
same molecule, the atoms are listed alphabetically in the name.
The chain also must be numbered in a way that gives the lowest
position number to the substituent that comes first in the
alphabet. Note how the alkyl halide in Figure 22.3c is named.
Similarly, the benzene ring in an aryl halide is numbered
to give each substituent the lowest position number possible,
as shown in Figure 22.3d.
H — C1 — C2 — C3 — C4 — H
H
Earth Science
Alkyl halides are widely used
as refrigerants. Until the late 1980s, alkyl halides called chlorofluorocarbons (CFCs) were widely used in refrigerators and
air-conditioning systems. Recall from Chapter 1 how CFCs
affect the ozone layer. CFCs have been replaced by HFCs
(hydrofluorocarbons), which contain only hydrogen and fluorine atoms bonded to carbon. One of the more common HFCs
is 1,1,2-trifluoroethane, also called R134a.
H
—
H—C—C—F
F
—
H
—
—
—
H
—
H
—
b
Connection
Br
Fluorobenzene and 1-Bromo-3,5-diiodobenzene
Figure 22.3 Organic molecules containing
functional groups are named based on their mainchain alkane structure using IUPAC conventions.
■
Reading Check Infer why the lowest possible position number is used to name an aryl halide instead of using a randomly
chosen position number.
PRACTICE Problems
Extra Practice Page 991 and glencoe.com
Name the alkyl or aryl halide whose structure is shown.
—
—
—
—
H
—
F
—
F
—
H
—
1.
Cl
H
H
H
H—C—C—C—C—H
H
—
—
—
—
—
—
—
Br
—
H
—
2.
H
—
H
H—C—C—C—C—C—H
H
3.
H
Br
Cl
Br
788
Chapter 22 • Substituted Hydrocarbons and Their Reactions
H
H
H
CH 4
CH 3Cl
Name
Boiling Point
(°C)
Density (g/mL)
in Liquid State
methane
-162
0.423 at -162°C
(boiling point)
chloromethane
-24
0.911 at 25°C
(under pressure)
36
0.626
CH 3CH 2CH 2CH 2CH 3
pentane
CH 3CH 2CH 2CH 2CH 2F
1-fluoropentane
62.8
0.791
CH 3CH 2CH 2CH 2CH 2Cl
1-chloropentane
108 Increases
0.882 Increases
CH 3CH 2CH 2CH 2CH 2Br
1-bromopentane
130
1.218
CH 3CH 2CH 2CH 2CH 2I
1-iodopentane
155
1.516
Properties and uses of halocarbons It is easiest to talk about
properties of organic compounds containing functional groups by comparing those compounds with alkanes, whose properties were discussed
in Chapter 21. Table 22.2 lists some of the physical properties of certain
alkanes and alkyl halides.
Note that each alkyl chloride has a higher boiling point and a higher
density than the alkane with the same number of carbon atoms. Note
also that the boiling points and densities increase as the halogen changes
from fluorine to chlorine, bromine, and iodine. This trend occurs primarily because the halogens from fluorine to iodine have increasing
numbers of electrons that lie farther from the halogen nucleus. These
electrons shift position easily and, as a result, the halogen-substituted
hydrocarbons have an increasing tendency to form temporary dipoles.
Because the dipoles attract each other, the energy needed to separate the
molecules also increases. Thus, the boiling points of halogen-substituted
alkanes increase as the size of the halogen atom increases.
Reading Check Explain the relationship between the number of
electrons in the halogen and the boiling point.
Figure 22.4 Polytetrafluoroethene
(PTFE) is made up of hundreds of units.
PTFE provides a nonstick surface for many
kitchen items, including bakeware.
■
F
—
Structure
A Comparison of Alkyl Halides
and Their Parent Alkanes
—C—
—
Table 22.2
F
PTFE
Organic halides are seldom found in nature, although human thyroid
hormones are organic iodides. Halogen atoms bonded to carbon atoms
are more reactive than the hydrogen atoms they replace. For this reason,
alkyl halides are often used as starting materials in the chemical industry. Alkyl halides are also used as solvents and cleaning agents because
they readily dissolve nonpolar molecules, such as greases. Figure 22.4
shows an application of polytetrafluoroethene (PTFE), a plastic made
from gaseous tetrafluoroethylene. A plastic is a polymer that can be
heated and molded while relatively soft. Another plastic commonly
called vinyl is polyvinyl chloride (PVC). It can be manufactured soft or
hard, as thin sheets, or molded into objects.
Reading Check Explain why alkyl halides are often used in the
chemical industry as starting materials instead of alkanes.
PTFE Application
Section 22.1 • Alkyl Halides and Aryl Halides 789
©DK Limited/Corbis
Table 22.3
Substitution Reactions
Generic Substitution Reaction
R-CH 3 + X 2 → R-CH 2X + HX
where X is fluorine, chlorine, or bromine
Example of General Substitution Reaction
(Halogenation)
C 2H 6 + Cl 2 → C 2H 5Cl + HCl
Ethane
Chloroethane
General Alkyl Halide-Alcohol Reaction
R-X + OH - → R-OH + X Alkyl halide
Alcohol
Example of an Alkyl Halide-Alcohol Reaction
CH 3CH 2Cl + OH - → CH 3CH 2OH + Cl Chloroethane
Ethanol
General Alkyl Halide-Ammonia Reaction
R-X + NH 3 → R-NH 2 + HX
Alkyl halide
Amine
Example of an Alkyl Halide-Ammonia Reaction
CH 3(CH 2) 6CH 2Br + NH 3 → CH 3(CH 2) 6CH 2NH 2 + HBr
1-Bromooctane
Octaneamine
Substitution Reactions
From where does the immense variety of organic compounds come?
Amazingly enough, the ultimate source of nearly all synthetic organic
compounds is petroleum. The oil-field workers shown in Figure 22.5 are
drilling for petroleum, which is a fossil fuel that consists almost entirely
of hydrocarbons, especially alkanes. How can alkanes be converted into
compounds as different as alkyl halides, alcohols, and amines?
One way is to introduce a functional group through substitution, as
shown in Table 22.3. A substitution reaction is one in which one atom
or a group of atoms in a molecule is replaced by another atom or group
of atoms. With alkanes, hydrogen atoms can be replaced by atoms of
halogens, typically chlorine or bromine, in a process called halogenation.
One example of a halogenation reaction, shown in Table 22.3, is the
substitution of a chlorine atom for one of ethane’s hydrogen atoms.
Figure 22.6 shows another halogenated hydrocarbon commonly called
halothane (2-bromo-2-chloro-1,1,1-trifluoroethane), which was first
used as a general anesthetic in the 1950s.
Equations for organic reactions are sometimes shown in generic form.
Table 22.3 shows the generic form of a substitution reaction. In this
reaction, X can be fluorine, chlorine, or bromine, but not iodine. Iodine
does not react well with alkanes.
Reading Check Draw the molecular structure of halothane.
Figure 22.5 These oil-field workers
are drilling for petroleum. A single oil well
can extract more than 100 barrels per day.
Explain the relationship between
petroleum and synthetic organic
compounds.
■
790 Chapter 22 • Substituted Hydrocarbons and Their Reactions
©Keith Wood/Getty Images
Figure 22.6 Halothane was introduced into medicine in the 1950s as a general
anesthetic for patients undergoing surgery.
■
Further substitution Once an alkane has been halogenated, the
resulting alkyl halide can undergo other types of substitution reactions
in which the halogen atom is replaced by another atom or group of
atoms. For example, reacting an alkyl halide with a basic solution results
in the replacement of the halogen atom by an –OH group, forming
an alcohol. An example of an alkyl halide-alcohol reaction is shown in
Table 22.3. The generic form of the alkyl halide-alcohol reaction is also
shown in Table 22.3.
Reacting an alkyl halide with ammonia (NH 3) replaces the halogen
atom with an amino group (–NH 2), forming an alkyl amine, also shown
in Table 22.3. The alkyl amine is one of the products produced in this
reaction. Some of the newly formed amines continue to react, resulting
in a mixture of amines.
Section 22.1
&/,$!",%3
Incorporate information
from this section into
your Foldable.
Assessment
Section Summary
4.
◗ The substitution of functional groups
for hydrogen in hydrocarbons creates
a wide variety of organic compounds.
5. Draw structures for the following molecules.
a. 2-chlorobutane
c. 1,1,1-trichloroethane
b. 1,3-difluorohexane
d. 4-bromo-1-chlorobenzene
◗ An alkyl halide is an organic compound that has one or more halogen
atoms bonded to a carbon atom in an
aliphatic compound.
6. Define functional group and name the group present in each of the following
structures. Name the type of organic compound each substance represents.
O
a. CH 3CH 2CH 2OH
d.
b. CH 3CH 2F
CH3C — OH
c. CH 3CH 2NH 2
Compare and contrast alkyl halides and aryl halides.
—
—
MAIN Idea
7. Evaluate How would you expect the boiling points of propane and
1-chloropropane to compare? Explain your answer.
8. Interpret Scientific Illustrations
Examine the pair of substituted
hydrocarbons illustrated at right, and
decide whether it represents a pair of
optical isomers. Explain your answer.
Self-Check Quiz glencoe.com
Section 22.1 • Alkyl Halides and Aryl Halides 791
©Paul Almasy/CORBIS
Section 22.2
Objectives
Alcohols, Ethers, and Amines
◗ Identify the functional groups that
characterize alcohols, ethers, and
amines.
◗ Draw the structures of alcohols,
ethers, and amines.
◗ Discuss the properties and uses of
alcohols, ethers, and amines.
Real-World Reading Link The last time you had a vaccination, the nurse
probably disinfected your skin with an alcohol wipe before giving you the
injection. Did you know that the nurse was using a substituted hydrocarbon?
Review Vocabulary
Alcohols
miscible: describes two liquids that
are soluble in each other
Many organic compounds contain oxygen atoms bonded to carbon
atoms. Because an oxygen atom has six valence electrons, it commonly
forms two covalent bonds to gain a stable octet. An oxygen atom can
form a double bond with a carbon atom, replacing two hydrogen atoms,
or it can form one single bond with a carbon atom and another single
bond with another atom, such as hydrogen. An oxygen-hydrogen
group covalently bonded to a carbon atom is called a hydroxyl group
(–OH). An organic compound in which a hydroxyl group replaces
a hydrogen atom of a hydrocarbon is called an alcohol. As shown in
Table 22.4, the general formula for an alcohol is ROH. Table 22.4 also
illustrates the relationship of the simplest alkane, methane, to the simplest
alcohol, methanol.
Ethanol and carbon dioxide are produced by yeasts when they
ferment sugars, such as those in grapes and bread dough. Ethanol is
found in alcoholic beverages and medicinal products. Because it is an
effective antiseptic, ethanol can be used to swab skin before an injection
is given. It is also a gasoline additive and an important starting material
for the synthesis of more complex organic compounds.
Figure 22.7 shows a model of an ethanol molecule and a model of a
water molecule. As you compare the models, notice that the covalent
bonds from the oxygen in ethanol are at roughly the same angle as the
bonds around the oxygen in the water molecule. Therefore, the hydroxyl groups of alcohol molecules are moderately polar, as with water, and
are able to form hydrogen bonds with the hydroxyl groups of other alcohol molecules. Due to this hydrogen bonding, alcohols have much higher boiling points than hydrocarbons of similar shape and size.
ROH
R represents carbon
chains or rings bonded to
the functional group
792
Chapter 22 • Substituted Hydrocarbons and Their Reactions
Simple Alcohol and Simple Hydrocarbon
H
— OH
H—C—H
H
H
—
General Formula
Alcohols
H — C — OH
—
Table 22.4
—
hydroxyl group
alcohol
denatured alcohol
ether
amine
—
New Vocabulary
-!). )DEA Oxygen and nitrogen are two of the most-common
atoms found in organic functional groups.
H
Methane (CH4)
Methanol (CH3OH)
Alkane
Alcohol
Figure 22.7 The covalent bonds
from oxygen have approximately the same
bonding angle in ethanol and water.
■
Water
Reading Check Explain why numbers are not used to name the
compound shown in Figure 22.8c.
—
—
—
—
—
H
—
H
—
H
H
H
H — C1 — C2 — C3 — C4 — H
OH H
H
H
a. 1-Butanol
—
—
—
—
—
H
—
H
H — C1 — C2 — C3 — C4 — H
H
OH H
H
b. 2-Butanol
OH
c. Cyclohexanol
‡
‡
‡
H
‡
H
‡
H
‡
Now look at Figure 22.8c. The compound’s ring structure contains six
carbons with only single bonds, so you know that the parent hydrocarbon
is cyclohexane. Because an –OH group is bonded to a carbon, it is an
alcohol and the name will end in -ol. No number is necessary because
all carbons in the ring are equivalent. This compound is called cyclohexanol. It is a poisonous compound used as a solvent for certain plastics
and in the manufacture of insecticides.
A carbon chain can also have more than one hydroxyl group. To
name these compounds, prefixes such as di-, tri-, and tetra- are used
before the -ol to indicate the number of hydroxyl groups present. The
full alkane name, including -ane, is used before the prefix.
Figure 22.8d shows the molecule 1,2,3-propanetriol, commonly
called glycerol. It is another alcohol containing more than one hydroxyl
group. Glycerol is often used as an antifreeze and as an airplane
deicing fluid.
H
—
Reading Check Explain why the names 3-butanol and 4-butanol
cannot represent real substances.
Figure 22.8 The names of alcohols
are based on alkane names.
■
—
Also, because of polarity and hydrogen bonding, ethanol is completely miscible with water. In fact, once they are mixed, it is difficult to
separate water and ethanol completely. Distillation is used to remove ethanol from water, but even after that process is complete, about 5% water
remains in the ethanol-water mixture.
On the shelves of drugstores, you can find bottles of ethanol labeled
denatured alcohol. Denatured alcohol is ethanol to which small
amounts of noxious materials, such as aviation gasoline or other organic
solvents, have been added. Ethanol is denatured in order to make it unfit
to drink. Because of their polar hydroxyl groups, alcohols make good
solvents for other polar organic substances. For example, methanol, the
smallest alcohol, is a common industrial solvent found in some paint
strippers, and 2-butanol is found in some stains and varnishes.
Note that the names of alcohols are based on alkane names, like the
names of alkyl halides. For example, CH 4 is methane and CH 3OH is
methanol; CH 3CH 3 is ethane and CH 3CH 2OH is ethanol. When
naming a simple alcohol based on an alkane carbon chain, the IUPAC
rules call for naming the parent carbon chain or ring first and then
changing the -e at the end of the name to -ol to indicate the presence
of a hydroxyl group. In alcohols of three or more carbon atoms, the
hydroxyl group can be at two or more positions. To indicate the position,
a number is added, as shown in Figure 22.8a and 22.8b.
—
Ethanol
H—C—C—C—H
OH OH OH
d. 1,2,3-Propanetriol (glycerol)
Section 22.2 • Alcohols, Ethers, and Amines 793
Table 22.5
Ethers
General Formula
Methanol and Methyl ether
ROR'
where R and R' represent
carbon chains or rings bonded
to functional groups
Methanol
bp = 65°C
Methyl ether
bp = -25°C
Examples of Ethers
O
CH3CH2CH2 — O — CH2CH2CH3
Cyclohexyl ether
Propyl ether
CH3CH2 — O — CH2CH2CH2CH3
CH3CH2 — O — CH3
Butylethyl ether
Ethylmethyl ether
Ethers
VOCABULARY
ACADEMIC VOCABULARY
Bond
to connect, bind, or join
An oxygen atom bonds to two carbon
atoms in an ether.
&/,$!",%3
Incorporate information
from this section into
your Foldable.
Ethers are another group of organic compounds in which oxygen is
bonded to carbon. An ether is an organic compound containing an
oxygen atom bonded to two carbon atoms. Ethers have the general formula ROR', as shown in Table 22.5. The simplest ether is one in which
oxygen is bonded to two methyl groups. Note the similarity between
methanol and methyl ether shown in Table 22.5.
The term ether was first used in chemistry as a name for ethyl ether,
the volatile, highly flammable substance that was commonly used as
an anesthetic in surgery from 1842 until the twentieth century. As time
passed, the term ether was applied to other organic substances having
two hydrocarbon chains attached to the same oxygen atom.
Because ethers have no hydrogen atoms bonded to the oxygen atom,
their molecules cannot form hydrogen bonds with each other. Therefore,
ethers are generally more volatile and have much lower boiling points
than alcohols of similar size and mass. Ethers are much less soluble
in water than alcohols because they have no hydrogen to donate to a
hydrogen bond. However, the oxygen atom can act as a receptor for
the hydrogen atoms of water molecules.
Reading Check Infer why ethyl ether is undesirable as an anesthetic.
When naming ethers that have two identical alkyl chains bonded
to oxygen, first name the alkyl group and then add the word ether.
Table 22.5 shows the structures and names of two of these symmetrical
ethers, propyl ether and cyclohexyl ether. If the two alkyl groups are
different, the groups are listed in alphabetical order and then followed
by the word ether. Table 22.5 contains two examples of these asymmetrical ethers, butylethyl ether and ethylmethyl ether.
794
Chapter 22 • Substituted Hydrocarbons and Their Reactions
Amines
Table 22.6
Amines contain nitrogen atoms bonded to carbon atoms
in aliphatic chains or aromatic rings and have the general
formula RNH 2, as shown in Table 22.6.
Chemists consider amines derivatives of ammonia
(NH 3). Amines are considered primary, secondary, or
tertiary amines depending on whether one, two, or three
of the hydrogens in ammonia have been replaced by
organic groups.
When naming amines, the –NH 2 (amino) group
is indicated by the suffix -amine. When necessary, the
position of the amino group is designated by a number,
as shown in the examples in Table 22.6. If more than
one amino group is present, the prefixes di-, tri-, tetra-,
and so on are used to indicate the number of groups.
The amine aniline is used in the production of dyes
with deep shades of color. The common name aniline is
derived from the plant in which it was historically
obtained. Cyclohexylamine and ethylamine are important in the manufacture of pesticides, plastics, pharmaceuticals, and rubber that is used to make tires.
All volatile amines have odors that humans find
offensive, and amines are responsible for many of the
odors characteristic of dead, decaying organisms. Two
amines found in decaying human remains are putrescine and cadaverine. Specially trained dogs are used to
locate human remains using these distinctive odors.
Sniffer dogs are often used after catastrophic events,
such as tsunamis, hurricanes, and earthquakes. They are
also used in forensic investigations.
General Formula
RNH 2
where R represents a carbon chain or
ring bonded to the functional group
Examples of Amines
—
CH3CH2
NH2
NH2
Ethylamine
Aniline
NH2
Cyclohexylamine
—
—
CHCH2CH2CH
—
NH2
CH2CH2CH2
NH2
NH2
1,1,4,4-Butanetetraamine
—
—
NH2
—
NH2
NH2
1,3-Propanediamine
Assessment
Section Summary
◗ Alcohols, ethers, and amines are
formed when specific functional
groups substitute for hydrogen in
hydrocarbons.
◗ Because they readily form hydrogen
bonds, alcohols have higher boiling
points and higher water solubilities
than other organic compounds.
9.
MAIN Idea
Identify two elements that are commonly found in functional groups.
10. Identify the functional group present in each of the following structures. Name
the substance represented by each structure.
a.
b.
NH2
OH
—
Section 22.2
Amines
CH3CHCH3
c. CH3 — O — CH2CH2CH3
11. Draw the structure for each molecule.
a. 1-propanol
b. 1,3-cyclopentanediol
c. propyl ether
d. 1,2-propanediamine
12. Discuss the properties of alcohols, ethers, and amines, and give one use of each.
13. Analyze Based on the molecular structures below, which compound would you
expect to be more soluble in water? Explain your reasoning.
OH
—
CH3 — O — CH3
CH3CH2
Self-Check Quiz glencoe.com
Section 22.2 • Alcohols, Ethers, and Amines 795
Section 22.3
New Vocabulary
carbonyl group
aldehyde
ketone
carboxylic acid
carboxyl group
ester
amide
condensation reaction
Table 22.7
Real-World Reading Link Have you ever eaten a piece of fruit-flavored candy
that tasted like real fruit? Many natural fruits, such as strawberries, contain
dozens of organic molecules that combine to give the distinctive aroma and
flavor of fruits. The carbonyl group is found in many common types of artificial
flavorings.
Organic Compounds
Containing the Carbonyl Group
The arrangement in which an oxygen atom is double-bonded to a carbon
atom is called a carbonyl group. This group is the functional group in
organic compounds known as aldehydes and ketones.
Aldehydes An aldehyde is an organic compound in which a carbonyl
group located at the end of a carbon chain is bonded to a carbon atom on
one side and a hydrogen atom on the other. Aldehydes have the general
formula *CHO, where * represents an alkyl group or a hydrogen atom,
as shown in Table 22.7.
Aldehydes are formally named by changing the final -e of the name
of the alkane with the same number of carbon atoms to the suffix -al.
Thus, the formal name of the compound methanal, shown in Table 22.7,
is based on the one-carbon alkane methane. Because the carbonyl group
in an aldehyde always occurs at the end of a carbon chain, no numbers
are used in the name unless branches or additional functional groups
are present. Methanal is also commonly called formaldehyde. Ethanal
has the common name acetaldehyde. Scientists often use the common
names of organic compounds because they are familiar to chemists.
Aldehydes
General Formula
—
O
—C—
—
C—
H
O
H—C—C—H
H—C—H
Methanal (formaldehyde)
Carbonyl group
H
Ethanal (acetaldehyde)
C—
O
H
O
—
CH — CH — C—
OH
Benzaldehyde
796
H
O
—
*CHO
*represents an alkyl group
or a hydrogen atom
Examples of Aldehydes
—
electronegative: indicates the
relative ability of an element’s atoms
to attract electrons in a chemical bond
-!). )DEA Carbonyl compounds contain a double-bonded oxygen
in the functional group.
—
Review Vocabulary
Carbonyl Compounds
—
◗ Identify the structures
of carbonyl compounds, including
aldehydes, ketones, carboxylic acids,
esters, and amides.
◗ Discuss the properties of
compounds containing the carbonyl
group.
—
Objectives
Chapter 22 • Substituted Hydrocarbons and Their Reactions
Salicylaldehyde
Cinnamaldehyde
O
H
An aldehyde molecule contains a polar, reactive structure. However,
like ethers, aldehyde molecules cannot form hydrogen bonds among
themselves because the molecules have no hydrogen atoms bonded to
an oxygen atom. Therefore, aldehydes have lower boiling points than
alcohols with the same number of carbon atoms. Water molecules
can form hydrogen bonds with the oxygen atom of aldehydes, so aldehydes are more soluble in water than alkanes but not as soluble as
alcohols or amines.
Formaldehyde has been used for preservation for many years, as
shown in Figure 22.9. Industrially, large quantities of formaldehyde are
reacted with urea to manufacture a type of grease-resistant, hard plastic
used to make buttons, appliance and automotive parts, and electrical
outlets, as well as the glue that holds the layers of plywood together.
Benzaldehyde and salicylaldehyde, shown in Table 22.7, are two components that give almonds their natural flavor. The aroma and flavor of
cinnamon, a spice that comes from the bark of a tropical tree, are produced largely by cinnamaldehyde, also shown in Table 22.7.
Reading Check Identify two uses for aldehydes.
Ketones A carbonyl group can also be located within a carbon chain
rather than at the end. A ketone is an organic compound in which the
carbon of the carbonyl group is bonded to two other carbon atoms.
Ketones have the general formula shown in Table 22.8. The carbon
atoms on either side of the carbonyl group are bonded to other atoms.
The simplest ketone, commonly known as acetone, has only hydrogen
atoms bonded to the side carbons, as shown in Table 22.8.
Ketones are formally named by changing the -e at the end of the
alkane name to -one, and including a number before the name to indicate
the position of the ketone group. In the previous example, the alkane
name propane is changed to propanone. The carbonyl group can be
located only in the center, but the prefix 2- is usually added to the name
for clarity, as shown in Table 22.8.
Ketones and aldehydes share many chemical and physical properties
because their structures are similar. Ketones are polar molecules and are
less reactive than aldehydes. For this reason, ketones are popular solvents for other moderately polar substances, including waxes, plastics,
paints, lacquers, varnishes, and glues. Like aldehydes, ketone molecules
cannot form hydrogen bonds with each other but can form hydrogen
bonds with water molecules. Therefore, ketones are somewhat soluble
in water. Acetone is completely miscible with water.
Ketones
where R and R’ represent
carbon chains or rings bonded to
functional groups
2-Propanone
(acetone)
—
H
—
H
—
H
O
—
H
—
H—C—C—C—H
H
—
H
—
O
—
—
R — C — R
H
—
—
O
Examples of Ketones
—
General Formula
H—C—C—C—C—H
—
Table 22.8
Figure 22.9 A water solution of
formaldehyde was used in the past to
preserve biological specimens. However,
formaldehyde’s use has been restricted in
recent years because studies indicate it
might cause cancer.
■
H
H
H
2-Butanone
(methyethyl ketone)
Section 22.3 • Carbonyl Compounds 797
©Bill Aron/PhotoEdit
Table 22.9
Carboxylic Acids
General Formula
where R represents carbon
chains or rings bonded to
functional groups
H
O
—
— OH
—
*—C
H — C — C — OH
—
—
O
Examples of Carboxylic Acids
H
Ethanoic acid (acetic acid)
O
——
H—C
O—H
Methanoic acid (formic acid)
Carboxylic Acids
A carboxylic acid is an organic compound that has a carboxyl group.
A carboxyl group consists of a carbonyl group bonded to a hydroxyl
group. Thus, carboxylic acids have the general formula shown in
Table 22.9. One diagram shown in Table 22.9 is the structure of a
familiar carboxylic acid—acetic acid, the acid found in vinegar.
Although many carboxylic acids have common names, the formal name
is formed by changing the -ane of the parent alkane to -anoic acid. Thus,
the formal name of acetic acid is ethanoic acid.
A carboxyl group is usually represented in condensed form by writing
–COOH. For example, ethanoic acid can be written as CH 3COOH. The
simplest carboxylic acid consists of a carboxyl group bonded to a single
hydrogen atom, HCOOH, shown in Table 22.9. Its formal name is methanoic acid, but it is more commonly known as formic acid. Some insects
produce formic acid as a defense mechanism, as shown in Figure 22.10.
Reading Check Explain how the name ethanoic acid is derived.
■ Figure 22.10 Stinging ants defend
themselves with a venom that contains
formic acid.
Identify another name for formic acid.
Carboxylic acids are polar and reactive. Those that dissolve in water
ionize weakly to produce hydronium ions, the anion of the acid in equilibrium with water, and the unionized acid. The ionization of ethanoic
acid is an example.
CH 3COOH(aq) + H 2O(l) ⥩ CH 3COO -(aq) + H 3O +(aq)
Ethanoic acid (acetic acid)
Ethanoate ion (acetate ion)
Carboxylic acids can ionize in water solution because the two oxygen
atoms are highly electronegative and attract electrons away from the
hydrogen atom in the –OH group. As a result, the hydrogen proton
can transfer to another atom that has a pair of electrons not involved
in bonding, such as the oxygen atom of a water molecule. Because they
ionize in water, soluble carboxylic acids turn blue litmus paper red and
have a sour taste.
Some important carboxylic acids, such as oxalic acid and adipic acid,
have two or more carboxyl groups. An acid with two carboxyl groups is
called a dicarboxylic acid. Others have additional functional groups
such as hydroxyl groups, as in the lactic acid found in yogurt. Typically,
these acids are more soluble in water and often more acidic than acids
with only a carboxyl group.
Reading Check Evaluate Using the information above, explain why
carboxylic acids are classified as acids.
798
Chapter 22 • Substituted Hydrocarbons and Their Reactions
©Norm Thomas/Photo Researchers, Inc.
Table 22.10
Esters
General Formula
Example of an Ester
Ethanoate group
O
—
—
O
—C—O—R
Propyl group
CH3 — C — O — CH2CH2CH3
Ester group
Ester group
Propyl ethanoate
(propyl acetate)
Organic Compounds Derived
from Carboxylic Acids
Several classes of organic compounds have structures in which the
hydrogen or the hydroxyl group of a carboxylic acid is replaced by
a different atom or group of atoms. The two most common classes are
esters and amides.
Esters An ester is any organic compound with a carboxyl group in
which the hydrogen of the hydroxyl group has been replaced by an alkyl
group, producing the arrangement shown in Table 22.10. The name of
an ester is formed by writing the name of the alkyl group followed by
the name of the acid with the -ic acid ending replaced by -ate, as illustrated by the example shown in Table 22.10. Note how the name propyl
results from the structural formula. The name shown in parentheses is
based on the name acetic acid, the common name for ethanoic acid.
Esters are polar molecules and many are volatile and sweet-smelling.
Many kinds of esters are found in the natural fragrances and flavors of
flowers and fruits, as shown in Figure 22.11. Natural flavors, such as
apple or banana, result from mixtures of many different organic molecules, including esters, but some of these flavors can be imitated by a
single ester structure. Consequently, esters are manufactured for use
as flavors in many foods and beverages and as fragrances in candles,
perfumes, and other scented items.
VOCABULARY
SCIENCE USAGE V. COMMON USAGE
Class
Science usage: a group, set, or kind
that share common traits
Esters are a class of organic molecules.
Common usage: a group of students
that meet at regular intervals to study
the same subject
Students meet for chemistry class
during fourth period.
Figure 22.11 Esters are responsible
for the flavors and aromas of many fruits.
The aroma of strawberries is due in part to
methyl hexanoate. Ethyl butanoate contributes to the aroma of pineapple. Most natural
aromas and flavors are mixtures of esters,
aldehydes, and alcohols.
■
CH3(CH2)4C — O — CH3
Methyl hexanoate
O
—
—
O
CH3CH2CH2C — O — CH2CH3
Ethyl butanoate
Section 22.3 • Carbonyl Compounds 799
(l)©Royalty Free/Masterfile, (r)©J.Garcia/photocuisine/Corbis
Make an Ester
How can you recognize an ester?
Procedure
1. Read and complete the lab safety form.
2. Prepare a hot-water bath by pouring 150 mL
of tap water into a 250-mL beaker. Place the
beaker on a hot plate set to medium.
3. Use a balance and weighing paper to measure 1.5 g of salicylic acid. Place the salicylic
acid in a small test tube and add 3 mL of
distilled water. Use a 10-mL graduated cylinder to measure the water. Then add 3 mL of
methanol. Use a Beral pipette to add 3 drops
of concentrated sulfuric acid to the test tube.
WARNING: Concentrated sulfuric acid can cause
burns. Methanol fumes are explosive—keep away
from open flame. Handle chemicals with care.
4. When the water is hot but not boiling, place
the test tube in the bath for 5 min. Use a
test-tube clamp to remove the test tube
from the bath and place in a test-tube holder
until needed.
5. Place a cotton ball in a petri dish half. Pour
the contents of the test tube onto the cotton
ball. Record your observation of the odor of
the product.
Analysis
1. Name The common name of the ester that
you produced is oil of wintergreen. Name
some products that you think could contain
the ester.
2. Evaluate the advantages and disadvantages
of using synthetic esters in consumer
products as compared to using natural esters.
Amides An amide is an organic compound in
which the –OH group of a carboxylic acid is replaced
by a nitrogen atom bonded to other atoms. The
general structure of an amide is shown in Table 22.11.
Amides are named by writing the name of the
alkane with the same number of carbon atoms, and
then replacing the final -e with -amide. Thus, the
amide shown in Table 22.11 is called ethanamide,
but it can also be named acetamide from its common name, acetic acid.
Reading Check Name three foods that contain
acetic acid.
The amide functional group is found repeated
many times in natural proteins and some synthetic
materials. For example, you might have used a nonaspirin pain reliever containing acetaminophen. In
the acetaminophen structure shown in Table 22.11,
notice that the amide (–NH–) group connects a
carbonyl group and an aromatic group.
One important amide is caramide (NH 2CONH 2),
or urea, as it is commonly known. Urea is an end
product in the metabolic breakdown of proteins in
mammals. It is found in the blood, bile, milk, and
perspiration of mammals. When proteins are broken down, amino groups (NH 2) are removed from
the amino acids. The amino groups are then converted to ammonia (NH 3) that are toxic to the body.
The toxic ammonia is converted to nontoxic urea in
the liver. The urea is filtered out of the blood in the
kidneys and passed from the body in urine.
Because of the high nitrogen content of urea
and because it is easily converted to ammonia in the
soil, urea is a common commercial fertilizer. Urea
is also used as a protein supplement for ruminant
animals, such as cattle and sheep. These animals
use urea to produce proteins in their bodies.
Reading Check Identify an amide that is found
in the human body.
Amides
Amide group
800
H—C—C—N
H
H
Ethanamide (acetamide)
Chapter 22 • Substituted Hydrocarbons and Their Reactions
O
—
H
CH3 — C
N
—
*
O
—
—N
H
—
*—C
H
—
—
O
Examples of Amides
—
General Formula
H
Acetaminophen
—
Table 22.11
OH
O
—
H
HO — CCH3 →
H
O
Salicylic acid
Acetic acid
O
C — OH
+ H2O
O — CCH3
—
—
OH
H
—
—
C — OH
H
Figure 22.12 To synthesize aspirin,
two organic molecules are combined
in a condensation reaction to form a
larger molecule.
■
—
H
—
H
—
H
H
O
Acetylsalicylic acid
(aspirin)
Water
Condensation Reactions
Many laboratory syntheses and industrial processes involve the reaction
of two organic reactants to form a larger organic product, such as
the aspirin shown in Figure 22.12. This type of reaction is known as
a condensation reaction.
In a condensation reaction, two smaller organic molecules combine
to form a more complex molecule, accompanied by the loss of a small
molecule such as water. Typically, the molecule lost is formed from one
particle from each of the reactant molecules. In essence, a condensation
reaction is an elimination reaction in which a bond is formed between
two atoms not previously bonded to each other.
The most common condensation reactions involve the combining
of carboxylic acids with other organic molecules. A common way to
synthesize an ester is by a condensation reaction between a carboxylic
acid and an alcohol. Such a reaction can be represented by the following
general equation.
&/,$!",%3
Incorporate information
from this section into
your Foldable.
RCOOH + R'OH → RCOOR' + H 2O
Assessment
14.
MAIN Idea Classify each of the carbonyl compounds as one of the types of
organic substances you have studied in this section.
◗ Carbonyl compounds are organic
compounds that contain the C=O
group.
a.
◗ Five important classes of organic
compounds containing carbonyl
compounds are aldehydes, ketones,
carboxylic acids, esters, and amides.
b.
O
—
c.
O
CH3CH2— O — C — CH3
O
CH3CH2CH2C — NH2
d.
O
—
Section Summary
—
Section 22.3
CH3CH2CH2CH
15. Describe the products of a condensation reaction between a carboxylic acid
and an alcohol.
16. Determine The general formula for alkanes is C nH 2n+2. Derive a general formula to represent an aldehyde, a ketone, and a carboxylic acid.
17. Infer why water-soluble organic compounds with carboxyl groups exhibit acidic
properties in solutions, whereas similar compounds with aldehyde structures do
not exhibit these properties.
Self-Check Quiz glencoe.com
Section 22.3 • Carbonyl Compounds 801
Section 22.4
Objectives
◗ Classify an organic reaction into
one of five categories: substitution,
addition, elimination, oxidationreduction, or condensation.
◗ Use structural formulas to write
equations for reactions of organic
compounds.
◗ Predict the products of common
types of organic reactions.
Review Vocabulary
catalyst: a substance that increases
the rate of a chemical reaction by
lowering activation energies but is not
consumed in the reaction
New Vocabulary
elimination reaction
dehydrogenation reaction
dehydration reaction
addition reaction
hydration reaction
hydrogenation reaction
Other Reactions
of Organic Compounds
MAIN Idea Classifying the chemical reactions of organic
compounds makes predicting products of reactions much easier.
Real-World Reading Link As you eat lunch, the oxidation of organic
compounds is probably not on your mind. However, that is exactly what is about
to occur as your cells break down the food that you eat to obtain energy for
your body.
Classifying Reactions
of Organic Substances
Organic chemists have discovered thousands of reactions by which
organic compounds can be changed into different organic compounds.
By using combinations of these reactions, chemical industries convert
simple molecules from petroleum and natural gas into the large, complex
organic molecules found in many useful products—including lifesaving
drugs and many other consumer products as shown in Figure 22.13.
You have already read about substitution and condensation reactions
in Sections 22.1 and 22.3. Two other important types of organic reactions
are elimination and addition.
Elimination reactions One way to change an alkane into a chemically reactive substance is to form a second covalent bond between two
carbon atoms, producing an alkene. The formation of alkenes from
alkanes is an elimination reaction, a reaction in which a combination
of atoms is removed from two adjacent carbon atoms, forming an additional bond between the carbon atoms. The atoms that are eliminated
usually form stable molecules, such as H 2O, HCl, or H 2.
Reading Check Define elimination reaction in your own words.
Figure 22.13 Many consumer
products, such as plastic containers,
fibers in ropes and clothing, and oils
and waxes in cosmetics, are made from
petroleum and natural gas.
■
802 Chapter 22 • Substituted Hydrocarbons and Their Reactions
©Cordelia Molloy/Photo Researchers, Inc.
Figure 22.14 Low density polyethylene (LDPE)
is made from gaseous ethene under high pressure in the
presence of a catalyst. LDPE is used for playground equipment because it is easy to mold into various shapes, it is
easy to dye into many colors, and it is durable.
■
Ethene, the starting material for the playground equipment shown in
Figure 22.14, is produced by the elimination of two hydrogen atoms
from ethane. A reaction that eliminates two hydrogen atoms is called a
dehydrogenation reaction. Note that the two hydrogen atoms form a
molecule of hydrogen gas.
— —
— —
H
H—C—C—H →
H
H
H—
H
C — C — + H2
H
H
—
H
Ethene
Ethane
Alkyl halides can undergo elimination reactions to produce an alkene
and a hydrogen halide, as shown here.
R—CH 2—CH 2—X
Alkyl halide
→
R—CH=CH 2 +
HX
Alkene
Hydrogen halide
Likewise, alcohols can also undergo elimination reactions by losing
a hydrogen atom and a hydroxyl group to form water, as shown below.
An elimination reaction in which the atoms removed form water is called
a dehydration reaction. In the dehydration reaction, the alcohol is
broken down into an alkene and water.
Personal Tutor For help identifying
organic reactions, visit glencoe.com.
H
O
H
H
—
—
R — C — C — OH
H H
Alcohol
H
R
—
—
H
C— C
→
H
+
H
Alkene
H2O
Water
The generic form of this dehydration reaction can be written as follows.
R—CH 2—CH 2—OH → R—CH=CH 2 + H 2O
Section 22.4 • Other Reactions of Organic Compounds 803
©Chuck Franklin/Alamy
Summary of Addition Reactions
Addition Reactant
Alcohol
—
H
H
R—C—C—H
H—O
H
—
—
X
H
H
H—X
—
Alkyl halide
—
Hydrogen halide
H
—
H
H
R—C—C—H
—
H
C —C
—
Alkane
H—H
R
H
—
Hydrogen (hydrogenation)
OH
—
H
H
—
Water (hydration)
Product
—
Reactant Alkene
—
Table 22.12
X
X
R—C—C—H
H
—
—
X—X
—
Alkyl dihalide
—
Halogen
H
R—C—C—H
H
H
Addition reactions Another type of organic reaction appears to
be an elimination reaction in reverse. An addition reaction results
when other atoms bond to each of two atoms bonded by double or triple
covalent bonds. Addition reactions typically involve double-bonded
carbon atoms in alkenes or triple-bonded carbon atoms in alkynes.
Addition reactions occur because double and triple bonds have a rich
concentration of electrons. Therefore, molecules and ions that attract
electrons tend to form bonds that use some of the electrons from the
multiple bonds. The most common addition reactions are those in which
H 2O, H 2, HX, or X 2 add to an alkene, as shown in Table 22.12.
A hydration reaction, also shown in Table 22.12, is an addition
reaction in which a hydrogen atom and a hydroxyl group from a water
molecule add to a double or triple bond. The generic equation shown
in Table 22.12 shows that a hydration reaction is the opposite of a dehydration reaction.
A reaction that involves the addition of hydrogen to atoms in a double
or triple bond is called a hydrogenation reaction. One molecule of H 2
reacts to fully hydrogenate each double bond in a molecule. When H 2
adds to the double bond of an alkene, the alkene is converted to an alkane.
Reading Check Identify the reaction that is the reverse of a
hydrogenation reaction.
804
Chapter 22 • Substituted Hydrocarbons and Their Reactions
Catalysts are usually needed in the hydrogenation of alkenes
because the reaction’s activation energy is too large without them.
Catalysts such as powdered platinum or palladium provide a surface that
absorbs the reactants and makes their electrons more available to bond
to other atoms.
Hydrogenation reactions are commonly used to convert the liquid
unsaturated fats found in oils from plants such as soybean, corn, and
peanuts into saturated fats that are solid at room temperature. These
hydrogenated fats are then used to make margarine and solid shortening.
Alkynes can also be hydrogenated to produce alkenes or alkanes. One
molecule of H 2 must be added to each triple bond in order to convert an
alkyne to an alkene, as shown here.
R—C≡C—H + H 2 → R—CH=CH 2
After the first molecule of H 2 is added, the alkyne is converted to an
alkene. A second molecule of H 2 follows the hydrogenation reaction.
R—CH=CH 2 + H 2 → R—CH 2—CH 3
In a similar mechanism, the addition of hydrogen halides to alkenes
is an addition reaction useful to industry for the production of alkyl
halides. The generic equation for this reaction is shown below.
R—CH=CH—R´ + HX → R—CHX—CH 2—R´
Data Analysis lab
Based on Real Data*
Interpret Data
What are the optimal conditions to hydrogenate canola oil? Edible vegetable oil is hydro-
genated to preserve its flavor and to alter its
melting properties. Because evidence suggests
that trans-fatty acids are associated with
increased risk of heart disease and cancer, the
minimum amount of trans-fatty acids and the
maximum amount of cis-oleic acid are desired.
Computer models were used to simulate processing conditions and to alter eight variables to
optimize the output of the desirable oil.
Multiple optimal operating conditions were
determined. A small-scale industrial plant was
used to confirm the results of the computer
simulation.
Data and Observations
The table at right shows some of the data from
this investigation.
Think Critically
1. Calculate the percent yield for each of the
trials shown in the table.
Data for Canadian Canola Oil
Computer Simulation
Experimental
Trial
Run
trans-Fatty
Acids
(wt. %)
cis-Oleic
Acid
(wt. %)
trans-Fatty cis-Oleic
Acids
Acid
(wt. %)
(wt. %)
1
4.90
69.10
5.80
70.00
2
4.79
63.75
4.61
64.00
3
4.04
68.96
4.61
67.00
4
5.99
62.80
7.10
65.00
5
4.60
68.10
5.38
66.50
Data obtained from Izadifar, M. 2005. Application of genetic algorithm for optimization
of vegetable oil hydrogenation process. Journal of Food Engineering. 78 (2007) 1-8.
2. Evaluate Which trial(s) produced the highest
yield of cis-oleic acid and the lowest yield of
trans-fatty acids?
3. Explain why the techniques used in this
investigation are useful in manufacturing
processes.
Section 22.4 • Other Reactions of Organic Compounds 805
Table 22.13
Oxidation-Reduction Reactions
The conversion of methane to methanol
H
—
—
H — C — H + [O]
→
H—C—O—H
—
—
H
H
H
Methane
Methanol
Producing an aldehyde
—
H
→
O
H—C—H
→
O
Methanal
(formaldehyde)
Oxidation
H — C — OH
(gain of
oxygen)
(loss of
hydrogen)
Methanol
(methyl alcohol)
Oxidation
—
H — C — OH
Oxidation
—
—
H
→
O—
—C—
—O
(loss of
hydrogen)
Methanoic acid
(formic acid)
Carbon dioxide
Further oxidation of the reaction
1-Propanol
(loss of
water)
CH3 — C — CH3 + [O]
H
Propanal
2-Propanol
O
—
H — C — CH2 — CH3
—
H
→
Oxidation
—
(loss of
water)
H — C — CH2 — CH3 + [O]
OH
O
—
—
Oxidation
—
OH
→ CH3 — C — CH3
2-Propanone
Oxidation-reduction reactions Many organic compounds can
be converted to other compounds by oxidation and reduction reactions.
For example, suppose you want to convert methane, the main constituent of natural gas, to methanol, a common industrial solvent and raw
material for making formaldehyde and methyl esters. The conversion of
methane to methanol can be represented by the equation shown in
Table 22.13, in which [O] represents oxygen from an agent such as
copper(II) oxide, potassium dichromate, or sulfuric acid.
What happens to methane in this reaction? Before answering, it might
be helpful to review the definitions of oxidation and reduction. Oxidation
is the loss of electrons, and a substance is oxidized when it gains oxygen
or loses hydrogen. Reduction is the gain of electrons, and a substance is
reduced when it loses oxygen or gains hydrogen. Thus, methane is
oxidized as it gains oxygen and is converted to methanol. Of course,
every redox reaction involves both an oxidation and a reduction;
however, organic redox reactions are described based on the change in
the organic compound.
Oxidizing the methanol shown in Table 22.13 is the first step in the
sequence of reactions that can be used to produce an aldehyde, which
are also shown in Table 22.13. For clarity, oxidizing agents are omitted.
Preparing an aldehyde by this method is not always a simple task because
the oxidation might continue, forming the carboxylic acid.
Reading Check Identify Use Table 22.13 to identify two possible
products that are produced when the aldehyde is further oxidized.
806 Chapter 22 • Substituted Hydrocarbons and Their Reactions
However, not all alcohols can be oxidized to aldehydes and, subsequently, carboxylic acids. To understand why, compare the oxidations
of 1-propanol and 2-propanol, shown in Table 22.13. Note that oxidizing 2-propanol yields a ketone, not an aldehyde. Unlike aldehydes,
ketones resist further oxidation to carboxylic acids. Thus, while the propanal formed by oxidizing 1-propanol easily oxidizes to form propanoic
acid, the 2-propanone formed by oxidizing 2-propanol does not react to
form a carboxylic acid.
Real-World Chemistry
Polycyclic Aromatic
Hydrocarbons (PAHs)
Reading Check Write the equation using molecular structures like
those in Table 22.13 for the formation of propanoic acid.
How important are organic oxidations and reductions? You have
seen that oxidation and reduction reactions can change one functional
group into another. That ability enables chemists to use organic redox
reactions, in conjunction with the substitution and addition reactions
you read about earlier in the chapter, to synthesize a tremendous variety
of useful products. On a personal note, all living systems—including
you—depend on the energy released by oxidation reactions. Of course,
some of the most dramatic oxidation-reduction reactions are combustion reactions. All organic compounds that contain carbon and hydrogen burn in excess oxygen to produce carbon dioxide and water. For
example, the highly exothermic combustion of ethane is described by
the following thermochemical equation.
2C 2H 6(g) + 7O 2(g) → 4CO 2(g) + 6H 2O(l)
Biological molecules
Hydrocarbons composed of multiple
aromatic rings are called PAHs. They
have been found in meteorites and
identified in the material
surrounding dying stars. Scientists
simulated conditions in space and
found that about 10% of the PAHs
were converted to alcohols, ketones,
and esters. These molecules can be
used to form compounds that are
important in biological systems.
∆H = -3120 kJ
As you read in Chapter 9, much of the world relies on the combustion of
hydrocarbons as a primary source of energy. Our reliance on the energy
from organic oxidation reactions is illustrated in Figures 22.15.
Predicting Products of Organic Reactions
The generic equations representing the different types of organic
reactions you have learned—substitution, elimination, addition,
oxidation-reduction, and condensation—can be used to predict the
products of other organic reactions of the same types. For example,
suppose you were asked to predict the product of an elimination reaction
in which 1-butanol is a reactant. You know that a common elimination
reaction involving an alcohol is a dehydration reaction.
Figure 22.15 People around the
world depend on the oxidation of hydrocarbons to get to work and to transport
products.
■
Section 22.4 • Other Reactions of Organic Compounds 807
(t)©NASA/ESA/STScI/SCIENCE PHOTO LIBRARY/Photo Researchers Inc, (b)©Royalty-Free/Corbis
The generic equation for the dehydration of an alcohol is as follows.
R—CH 2—CH 2—OH → R—CH=CH 2 + H 2O
&/,$!",%3
Incorporate information
from this section into
your Foldable.
To determine the actual product, first draw the structure of 1-butanol.
Then use the generic equation as a model to see how 1-butanol
would react. The generic reaction shows that the —OH and a H—
are removed from the carbon chain. Finally, draw the structure of the
likely products, as shown in the following equation.
CH 3—CH 2—CH 2—CH 2—OH → CH 3—CH 2—CH=CH 2 + H 2O
1-Butanol
1-Butene
As another example, suppose that you wish to predict the product of
the reaction between cyclopentene and hydrogen bromide. Recall that
the generic equation for an addition reaction between an alkene and
an alkyl halide is as follows.
R—CH=CH—R´ + HX → R—CHX—CH 2—R´
First, draw the structure for cyclopentene, the organic reactant, and
add the formula for hydrogen bromide, the other reactant. From the
generic equation, you can see that a hydrogen atom and a halide atom
add across the double bond to form an alkyl halide. Finally, draw the
formula for the likely product. If you are correct, you have written
the following equation.
+
Cyclopentene
Hydrogen bromide
Br
Bromocyclopentane
Assessment
Section Summary
◗ Most reactions of organic compounds
can be classified into one of five
categories: substitution, elimination,
addition, oxidation-reduction,
and condensation.
◗ Knowing the types of organic
compounds reacting can enable you
to predict the reaction products.
→
18.
MAIN Idea Classify each reaction as substitution, elimination, addition,
or condensation.
a. CH3CH — CHCH2CH3 + H2 → CH3CH2—CH2CH2CH3
b. CH3CH2CH2CHCH3 → CH3CH2CH — CHCH3 + H2O
—
Section 22.4
HBr
OH
19. Identify the type of organic reaction that would best accomplish each conversion.
a. alkyl halide → alkene
c. alcohol + carboxylic acid → ester
b. alkene → alcohol
d. alkene → alkyl dihalide
—
20. Complete each equation by writing the condensed structural formula for the
product that is most likely to form.
a. CH3CH — CHCH2CH3 + H2 →
b. CH3CH2CHCH2CH3 + OH- →
Cl
21. Predicting Products Explain why the hydration reaction involving 1-butene
might yield two distinct products, whereas the hydration of 2-butene yields only
one product.
808 Chapter 22 • Substituted Hydrocarbons and Their Reactions
Self-Check Quiz glencoe.com
Section 22.5
Polymers
Objectives
◗ Diagram the relationship between
a polymer and the monomers from
which it forms.
◗ Classify polymerization reactions
as addition or condensation.
◗ Predict polymer properties based
on their molecular structures and
the presence of functional groups.
MAIN Idea Synthetic polymers are large organic molecules made
up of repeating units that are linked together by addition or
condensation reactions.
Real-World Reading Link Think how different your life would be without
plastic sandwich bags, plastic foam cups, nylon and polyester fabrics, vinyl siding
on buildings, foam cushions, and a variety of other synthetic materials. These
products all have at least one thing in common—they are made of polymers.
Review Vocabulary
The Age of Polymers
molecular mass: the mass of one
molecule of a substance
The compact discs shown in Figure 22.16 contain polycarbonate, which
is made of extremely long molecules with groups of atoms that repeat in
a regular pattern. This molecule is an example of a synthetic polymer.
Polymers are large molecules consisting of many repeating structural
units. In Figure 22.16, the letter n beside the structural unit of polycarbonate represents the number of structural units in the polymer chain.
Because polymer n values vary widely, molecular masses of polymers
range from less than 10,000 amu to more than 1,000,000 amu. A typical
chain in nonstick coating on skillets has about 400 units, giving it a
molecular mass of around 40,000 amu.
Before the development of synthetic polymers, people were limited
to using natural substances such as stone, wood, metals, wool, and cotton.
By the turn of the twentieth century, a few chemically treated natural
polymers such as rubber and the first plastic, celluloid, had become
available. Celluloid is made by treating cellulose from cotton or wood
fiber with nitric acid.
The first synthetic polymer, synthesized in 1909, was a hard, brittle
plastic called Bakelite. Because of its resistance to heat, it is still used
today in stove-top appliances. Since 1909, hundreds of other synthetic
polymers have been developed. Because of the widespread use of polymers, people might refer to this time as the Age of Polymers.
New Vocabulary
polymer
monomer
polymerization reaction
addition polymerization
condensation polymerization
thermoplastic
thermosetting
Figure 22.16 Compact discs are
made of polycarbonate and contain long
chains of the structural unit shown.
■
O
C
CH3
O
—
CH3
O–C
n
Section 22.5 • Polymers 809
©ALAN L. DETRICK/SCIENCE PHOTO LIBRARY/Photo Researchers Inc
Reactions Used to Make
Polymers
Figure 22.17 Polyethylene is a nontoxic, unbreakable
polymer that is used to make toys for children.
■
Polymers are relatively easy to manufacture. Polymers
can usually be synthesized in one step in which the major
reactant is a substance consisting of small, simple organic
molecules called monomers. A monomer is a molecule
from which a polymer is made.
When a polymer is made, monomers bond together
one after another in a rapid series of steps. A catalyst is
usually required for the reaction to take place at a reasonable pace. With some polymers, such as polyester
fabric and nylon, two or more kinds of monomers bond
to each other in an alternating sequence. A reaction in
which monomer units are bonded together to form a
polymer is called a polymerization reaction. The
repeating group of atoms formed by the bonding of the
monomers is called the structural unit of the polymer.
The structural unit of a polymer made from two different monomers has the components of both monomers.
Figure 22.17 shows unbreakable children’s toys that
are made of low-density polyethylene (LDPE), which is
synthesized by polymerizing ethene under pressure.
Ethene is also the starting product for polyethylene
terephthalate (PETE), a plastic that is used to make bottles. When made into fiber, it is called polyester fiber.
Figure 22.18 shows milestones leading to the Age
of Polymers and highlights of polymer development.
Although the first synthetic polymer was developed in
1909, the industry did not flourish until after World
War II.
Reading Check Compare and contrast a monomer
and a structural unit of a polymer.
■
Figure 22.18
The Age of Polymers
▼
810
1865 The structure of
benzene is determined.
It becomes the basis
for the production of
aromatic compounds.
1840S Physicians begin
using ether as an anesthetic during surgery.
▼
Scientists working to understand the structure and properties of organic compounds
have developed products that affect people
everywhere. Their contributions helped usher
in the Age of Polymers.
1909 The first plastic
made from synthetic
polymers, Bakelite,
is developed.
1879 Saccharin is
1899 Aspirin is widely distrib-
accidentally discovered
by a chemist working
with coal-tar
derivatives.
uted by physicians as a pain
treatment. It quickly becomes
the number-one selling drug
worldwide.
Chapter 22 • Substituted Hydrocarbons and Their Reactions
(t)©Myrleen Ferguson Cate/PhotoEdit, (bl)©SSPL/The Image Works, (br)©VICTOR DE SCHWANBERG/SCIENCE PHOTO LIBRARY/Photo Researchers Inc
—
O
—
O
nHOOC — (CH2)4 — COOH + nH2N — (CH2)6 — NH2 → — C — (CH2)4 — C — NH — (CH2)6 — NH — + nH2O
Adipic acid
■
1,6–Diamino hexane
Nylon 6,6
n
Figure 22.19 Nylon is a polymer consisting of thin strands that resemble silk.
Addition polymerization In addition polymerization, all of the
atoms present in the monomers are retained in the polymer product.
When the monomer is ethene, an addition polymerization results in
the polymer polyethylene. Unsaturated bonds are broken in addition
polymerization, just as they are in addition reactions. The difference
is that the molecule added is a second molecule of the same substance,
ethene. Note that the addition polymers in Table 22.14 on the next page
are similar in structure to polyethylene. That is, the molecular structure
of each is equivalent to polyethylene in which other atoms or groups of
atoms are attached to the chain in place of hydrogen atoms. All of these
polymers are made by addition polymerization.
Condensation polymerization Condensation polymerization
takes place when monomers containing at least two functional groups
combine with the loss of a small by-product, usually water. Nylon and
a type of bulletproof fabric are made this way. Nylon was first synthesized in 1931 and soon became popular because it is strong and can be
drawn into thin strands resembling silk. Nylon 6,6 is the name of one
type of nylon that is synthesized. One monomer is a chain, with the end
carbon atoms being part of carboxyl groups, as shown in Figure 22.19.
The other monomer is a chain having amino groups at both ends. These
monomers undergo a condensation polymerization that forms amide
groups linking the subunits of the polymer, as shown by the tinted box
in Figure 22.19. Note that one water molecule is released for every new
amide bond formed.
▼
1939–1945 During
1959 Spandex, an
World War II, nylon is allocated solely for military
items such as parachutes,
as shown in the photo,
tents, and ponchos.
elastic fiber, is commercially produced.
nonstick coating
(PTFE), including bearings, bushings, gears,
and cookware, become
commercially available.
▼
1946 Products with
2006 Researchers develop a paper-thin,
radiation-resistant, liquid-crystal polymer in
which electronic circuits can be imbedded,
making it useful in space applications.
1988 The world’s
first polymer banknote
is issued by the Reserve
Bank of Australia. By
1996, all Australians
use plastic money.
Interactive Time Line To learn more
about these discoveries and others,
visit glencoe.com.
Section 22.5 • Polymers 811
(l)©Bettmann/CORBIS, (r)©Danita Delimont/Alamy
Structural Unit
H
H
H
H
H
— —
H
— —
Plastic pipes, meat wrap,
upholstery, rainwear, house
siding, garden hose
— —
Applications
— —
Polyvinyl chloride
(PVC)
Common Polymers
— —
Polymer
Interactive Table Explore
polymers at glencoe.com.
— —
Table
22.14
... — C — C — C — C — C — C — ...
Cl
H
Cl
H
n
Cl
H
Polyvinyl chloride
Fabrics for clothing and
upholstery, carpet
— CH2 — CH
—
Polyacrylonitrile
C—Nn
Polyvinylidene
chloride
Food wrap, fabrics
CI
— CH2 — C —
CI
“Nonbreakable” (acrylic
glass) windows, inexpensive
lenses, art objects
O
—
Polymethyl
methacrylate
n
C — O–CH3
— CH2 — C
CH3
Polypropylene (PP)
Beverage containers, rope,
netting, kitchen appliances
n
— CH2 — CH —
CH3
Polystyrene (PS) and
styrene plastic
Foam packing and insulation,
plant pots, disposable food
containers, model kits
H
H
C
C
H
812
Foam furniture cushions,
waterproof coatings, parts
of shoes
—
O
O
—
O
C
C
O
n
O
H
H
C
C
H
H
n
O
—
Polyurethane
Soft-drink bottles, tire cord,
clothing, recording tape,
replacements for blood
vessels
—
Polyethylene
terephthalate (PETE)
n
— C — NH — CH2 — CH2 — NH — C — O — CH2 — CH2 — O —
Chapter 22 • Substituted Hydrocarbons and Their Reactions
(t)©Siede Preis/Photodisc Green/Getty Images, (tc)©David Young-Wolff/PhotoEdit, (b)©Royalty-Free/Corbis, (bc)©Dorling Kindersley/Getty Images
n
Figure 22.20 Plastic lumber is made
from recycled plastic, such as used soft-drink
bottles, milk jugs, and other polyethylene
waste.
■
Properties and Recycling of Polymers
Why do we use so many different polymers today? One reason is that
they are easy to synthesize. Another reason is that the starting materials
used to make them are inexpensive. Still another, more important, reason
is that polymers have a wide range of properties. Some polymers can be
drawn into fine fibers that are softer than silk, while others are as strong
as steel. Polymers do not rust like steel does, and many polymers are
more durable than natural materials such as wood. Fencing and decking
materials made of plastic, like those shown in Figure 22.20, do not
decay and do not need to be repainted.
Properties of polymers Another reason why polymers are in
such great demand is that it is easy to mold them into different shapes
or to draw them into thin fibers. It is not easy to do this with metals
and other natural materials because they must be heated either to high
temperatures, do not melt at all, or are too weak to be used to form
small, thin items.
As with all substances, polymers have properties that result directly
from their molecular structure. For example, polyethylene is a longchain alkane. Thus, it has a waxy feel, does not dissolve in water, is nonreactive, and is a poor electrical conductor. These properties make it
ideal for use in food and beverage containers and as an insulator in
electrical wire and TV cable.
Polymers fall into two different categories, based on their melting
characteristics. A thermoplastic polymer is one that can be melted
and molded repeatedly into shapes that are retained when cooled.
Polyethylene and nylon are examples of thermoplastic polymers.
A thermosetting polymer is one that can be molded when it is first
prepared, but after it cools, it cannot be remelted. This property is
explained by the fact that thermosetting polymers begin to form networks of bonds in many directions when they are synthesized. By the
time they have cooled, thermosetting polymers have become, in
essence, a single large molecule. Bakelite is an example of a thermosetting polymer. Instead of melting, Bakelite decomposes when overheated.
Careers In chemistry
Polymer Chemist Does the
thought of developing new and better polymers sound inspiring and
challenging to you? Polymer chemists develop new polymers and create uses or manufacturing processes
for older ones. For more information
on chemistry careers, visit
glencoe.com.
VOCABULARY
WORD ORIGIN
Thermoplastic
thermo- comes from the Greek word
thermē which means heat; plastic
comes from the Greek word plastikos
which means to mold or form
Reading Check Compare and contrast thermoplastic and
thermosetting polymers.
Section 22.5 • Polymers 813
©DAVID R. FRAZIER Photolibrary, Inc.
1
2
3
PETE
Polyethylene
terephthalate
HDPE
High–density
polyethylene
V
Vinyl
Figure 22.21 Codes on plastic products
aid in recycling because they identify the
composition of the plastic.
4
LDPE
Low–density
polyethylene
5
6
7
PP
Polypropylene
PS
Polystyrene
OTHER
All other
plastics
■
Assessment
◗ The functional groups present in polymers can be used to predict polymer
properties.
a. Addition
b. Condensation
CH—CH
—
Cl
O
NH2 — CH2CH2 — C — OH
Cl
23. Label the following polymerization reaction as addition or condensation. Explain
your answer.
CH2 — CH
→ — CH2 — CH
—
◗ Polymers are synthesized through
addition or condensation reactions.
MAIN Idea Draw the structure for the polymer that could be produced from
each of the following monomers by the method stated.
—
◗ Polymers are large molecules formed
by combining smaller molecules
called monomers.
22.
—
Section Summary
—
Section 22.5
Recycling polymers The starting materials for the synthesis of
most polymers are derived from fossil fuels. As the supply of fossil
fuels becomes depleted, recycling plastics becomes more important.
Recycling and buying goods made from recycled plastics decreases the
amount of fossil fuels used, which conserves fossil fuels.
Currently, about 5% of the plastics used in the United States are
recycled. Plastics recycling is somewhat difficult due to the large variety
of different polymers found in products. Usually, the plastics must be
sorted according to polymer composition before they can be reused.
Thermosetting polymers are more difficult to recycle than thermoplastic polymers because only thermoplastic materials can be melted and
remolded repeatedly. The task of separating plastics can be timeconsuming and expensive. The is why the plastics industry and the
government have tried to improve the process by providing standardized
codes that indicate the composition of each plastic product. The standardized codes for plastics are shown in Figure 22.21. These codes
provide a quick way for recyclers to sort plastics.
C—N
C—Nn
24. Identify Synthetic polymers often replace stone, wood, metals, wool, and cotton in many applications. Identify some advantages and disadvantages of using
synthetic materials instead of natural materials.
—
25. Predict the physical properties of the polymer that is made from the following
monomer. Mention solubility in water, electrical conductivity, texture, and chemical reactivity. Do you think it will be thermoplastic or thermosetting? Give reasons for your predictions.
CH2— CH
CH3
814
Chapter 22 • Substituted Hydrocarbons and Their Reactions
Self-Check Quiz glencoe.com
Garlic: Pleasure and Pain
Did you know that the flavors of fresh and roasted
garlic are very different? Fresh garlic, shown in
Figure 1, contains substances that cause a burning
sensation in your mouth. However, roasted garlic
does not produce this sensation. These sensations,
pleasure or pain, are because of chemical reactions.
When raw garlic is bruised, cut, or crushed, it
produces a chemical called allicin, as shown in
Figure 2. The production of allicin is a chemical
defense mechanism for the garlic plant against
other organisms. Allicin is an unstable compound
and is converted to other compounds over time or
when garlic is heated or roasted, which explains why
roasted garlic does not cause the burning sensation
in your mouth.
Figure 1 Fresh garlic contains a pain-producing chemical as a
defense against predators.
Allicin also activates neurons. Allicin apparently
acts on a pair of ion channel proteins called TRPA1
and TRPV1. When the chemical allicin is present,
these channels allow ions to enter the nerve cell.
The additional electric charge in the nerve cell
signals the brain, where the signal is interpreted
by the brain as a burning sensation.
Sensing temperature and pain Temperature
and pain are sensed by neurons embedded in the
skin, including the skin inside your mouth. These
neurons have temperature-detecting molecules
on their surfaces that are called transient receptor
potential (TRP) ion channels. Different TRP channels
are activated by different temperature ranges. For
example, when a person touches something hot,
some of the TRP ion channels open and allow
charged calcium ions to enter the nerve cell. This
increases the charge within the nerve cell. When
the charge increases enough, an electrical signal
is sent to the brain, where it is interpreted as
a hot sensation.
Probing pain receptors While it is interesting to
know why tasting raw garlic is painful, the understanding of how allicin causes that pain sensation
is even more interesting and useful. Researchers
hope that a further understanding of how these
receptors work will lead to new methods for controlling chronic pain in patients.
—
2H2C — CH — CH2 — S — CH2 — CH — COONH2
O
—
Alliin
Alliinase
+ H2O
O
—
—
O
H2C — CH — CH2 — S — S — CH2 — CH — CH2 + 2 CH3 — C — COO- + 2NH4+
Allicin
Figure 2 When garlic is bruised or damaged, alliin and the enzyme
alliinase produce allicin. When you taste fresh garlic, neurons
embedded in your mouth cause an electrical signal to be sent to your
brain. The brain interprets the electrical signal as a burning sensation.
Pyruvate
Chemistry
Research and prepare a poster that shows other
chemical reactions in plants. For more information,
visit www.glencoe.com.
Everyday Chemistry 815
©Neil Emmerson/Robert Harding World Imagery/Getty Images
IDENTIFY AN
INTERNET:
OBSERVE
UNKNOWN
PROPERTIES
GAS
OF ALCOHOLS
Background: Alcohols are organic compounds that
contain the –OH functional group. How fast various
alcohols evaporate indicates the strength of intermolecular forces in alcohols. The evaporation of a liquid
is an endothermic process, absorbing energy from the
surroundings. This means that the temperature will
decrease as evaporation occurs.
Question: How do intermolecular forces differ in
three alcohols?
Materials
nonmercury thermometer
stopwatch
facial tissue
cloth towel
Beral pipettes (5)
methanol
ethanol (95%)
2-propanol (99%)
wire twist tie or small
rubber band
piece of cardboard for
use as a fan
Safety Precautions
WARNING: Alcohols are flammable. Keep liquids and
vapors away from open flames and sparks.
Procedure
1.
2.
3.
4.
5.
6.
7.
8.
816
Read and complete the lab safety form.
Prepare data tables for recording data.
Cut five 2-cm by 6-cm strips of tissue.
Place a thermometer on a folded towel lying on
a flat table so that the bulb of the thermometer
extends over the edge of the table. Make sure the
thermometer cannot roll off the table.
Wrap a strip of tissue around the bulb of the thermometer. Secure the tissue with a wire twist tie
placed above the bulb of the thermometer.
Choose one person to control the stopwatch and
read the temperature on the thermometer. A second
person will put a small amount of the liquid to be
tested into a Beral pipette.
When both people are ready, squeeze enough liquid
onto the tissue to completely saturate it. At the same
time, the other person starts the stopwatch, reads the
temperature, and records it in the data table.
Fan the tissue-covered thermometer bulb with
a piece of cardboard or other stiff paper. After 1 min,
read and record the final temperature in the data
table. Remove the tissue and wipe the bulb dry.
Chapter 22 • Substituted Hydrocarbons and Their Reactions
Matt Meadows
9. Repeat Steps 5 through 8 for each of the three
alcohols: methanol, ethanol, and 2-propanol.
10. Obtain the classroom temperature and humidity
data from your teacher.
11. Cleanup and Disposal Place the used tissues in the
trash. Pipettes can be reused.
Analyze and Conclude
1. Observe and Infer What can you conclude about
the relationship between heat transfer and the differences in the temperature changes you observed?
2. Evaluate Molar enthalpies of vaporization (kJ/mol)
for the three alcohols at 25°C are: methanol, 37.4;
ethanol, 42.3; and 2-propanol, 45.4. What can you
conclude about the relative strength of intermolecular
forces existing in the three alcohols?
3. Compare Make a general statement comparing the
molecular size of an alcohol in terms of the number
of carbons in the carbon chain to the rate of evaporation of that alcohol.
4. Observe and Infer Post your data on the Internet
at glencoe.com. Infer why there are differences
between your data and those of other students.
5. Error Analysis Determine where errors might have
been introduced in your procedure.
INQUIRY EXTENSION
Design an Experiment Suggest a way to make this
experiment more quantitative and controlled.
Design an experiment using your new method.
Download quizzes, key
terms, and flash cards
from glencoe.com.
BIG Idea The substitution of different functional groups for hydrogen atoms in hydrocarbons
results in a diverse group of organic compounds.
Section 22.1 Alkyl Halides and Aryl Halides
MAIN Idea A halogen atom can replace a hydrogen atom in
some hydrocarbons.
Vocabulary
• alkyl halide (p. 787)
• aryl halide (p. 788)
• functional group (p. 786)
• halocarbon (p. 787)
• halogenation (p. 790)
• plastic (p. 789
• substitution reaction (p. 790)
Key Concepts
• The substitution of functional groups for hydrogen in
hydrocarbons creates a wide variety of organic
compounds.
• An alkyl halide is an organic compound that has one or
more halogen atoms bonded to a carbon atom in an
aliphatic compound.
Section 22.2 Alcohols, Ethers, and Amines
MAIN Idea Oxygen and nitrogen are two of the mostcommon atoms found in organic functional groups.
Vocabulary
• alcohol (p. 792)
• amine (p. 795)
• denatured alcohol (p. 793)
• ether (p. 794)
• hydroxyl group (p. 792)
Key Concepts
• Alcohols, ethers, and amines are formed when specific
functional groups substitute for hydrogen in
hydrocarbons.
• Because they readily form hydrogen bonds, alcohols have
higher boiling points and higher water solubilities than
other organic compounds.
Section 22.3 Carbonyl Compounds
Key Concepts
• Carbonyl compounds are organic compounds that
contain the C=O group.
•
Five
important classes of organic compounds containing
• carboxylic acid (p. 798)
carbonyl
compounds are aldehydes, ketones, carboxylic
• condensation reaction (p. 801)
acids,
esters,
and amides.
• ester (p. 799)
MAIN Idea Carbonyl compounds contain a double-bonded
oxygen in the functional group.
Vocabulary
• aldehyde (p. 796)
• amide (p. 800)
• carbonyl group (p. 796)
• carboxyl group (p. 798)
• ketone (p. 797)
Section 22.4 Other Reactions of Organic Compounds
MAIN Idea Classifying the chemical reactions of organic
compounds makes predicting products of reactions much easier.
Vocabulary
• addition reaction (p. 804)
• dehydration
reaction (p. 803)
• dehydrogenation
reaction (p. 803)
• elimination reaction (p. 802)
• hydrogenation
reaction (p. 804)
• hydration reaction (p. 804)
Key Concepts
• Most reactions of organic compounds can be classified
into one of five categories: substitution, elimination,
addition, oxidation-reduction, and condensation.
• Knowing the types of organic compounds reacting can
enable you to predict the reaction products.
Section 22.5 Polymers
MAIN Idea Synthetic polymers are large organic molecules
made up of repeating units linked together by addition or
condensation reactions.
Vocabulary
• addition
polymerization (p. 811)
• condensation
polymerization (p. 810)
• monomer (p. 810)
• polymer (p. 809)
• polymerization
reaction (p. 810)
• thermoplastic (p. 813)
• thermosetting (p. 813)
Key Concepts
• Polymers are large molecules formed by combining
smaller molecules called monomers.
• Polymers are synthesized through addition or
condensation reactions.
• The functional groups present in polymers can be used to
predict polymer properties.
Vocabulary PuzzleMaker glencoe.com
Chapter 22 • Study Guide 817
Section 22.1
Section 22.2
Mastering Concepts
Mastering Concepts
bromomethane?
■
—
O
C
H
OH
O
OH
O
OCH3
b Vanillin
Figure 22.22
31. Circle and name each of the functional groups circled in
the structures shown in Figure 22.22.
32. Draw structures for these alkyl and aryl halides.
a.
b.
c.
d.
e.
chlorobenzene
1-bromo-4-chlorohexane
1,2-difluoro-3-iodocyclohexane
1,3-dibromobenzene
1,1,2,2-tetrafluoroethane
33. For 1-bromo-2-chloropropane:
a. Draw the structure.
b. Does the compound have optical isomers?
c. If the compound has optical isomers, identify the
chiral carbon atom.
34. Draw and name all of the structural isomers possible
for an alkyl halide with no branches and the molecular
formula C 5H 10Br 2.
35. Name one structural isomer created by changing the
position of one or more halogen atoms in each alkyl
halide.
a. 2-chloropentane
c. 1,3-dibromocyclopentane
b. 1,1-difluropropane
d. 1-bromo-2-chloroethane
818
36. How is the compound shown in Figure 22.23
ether that is used for each of the following purposes.
a. antiseptic
c. antifreeze
b. solvent in paint
d. anesthetic
strippers
e. dye production
38. Explain why an alcohol molecule will always have a
higher solubility in water than an ether molecule having
an identical molecular mass.
Mastering Problems
■
Figure 22.23
37. Practical Applications Name one alcohol, amine, or
in order going down the column of halides in the
periodic table, from fluorine through iodine.
a Acetylsalicylic acid
H
denatured? What is the name of the compound?
30. Explain why the boiling points of alkyl halides increase
O
—
H
28. What reactant would you use to convert methane to
condensed formulas.
a. CH 3(CH 2) 3CH 2NH 2
b. CH 3(CH 2) 5CH 2NH 2
c. CH 3(CH 2) 2CH(NH 2)CH 3
d. CH 3(CH 2) 8CH 2NH 2
—
H—C—C—O—H
aryl halides.
29. Name the amines represented by each of the
—
27. Describe and compare the structures of alkyl halides and
H
—
H
26. What is a functional group?
Chapter 22 • Substituted Hydrocarbons and Their Reactions
39. Explain why ethanol has a much higher boiling point
than aminoethane, even though their molecular masses
are nearly equal.
Mastering Problems
40. Name one ether that is a structural isomer of each alcohol.
a. 1-butanol
b. 2-hexanol
41. Draw structures for the following alcohol, amine, and
ether molecules.
a. 1,2-butanediol
b. 5-aminohexane
c. isopropyl ether
d. 2-methyl-1-butanol
e. butyl pentyl ether
f. cyclobutyl methyl ether
g. 1,3-diaminobutane
h. cyclopentanol
Section 22.3
Mastering Concepts
42. Draw the general structure for each of the following
classes of organic compounds.
a. aldehyde
d. ester
b. ketone
e. amide
c. carboxylic acid
43. Common Uses Name an aldehyde, ketone, carboxylic
acid, ester, or amide used for each of the following
purposes.
a. preserving biological specimens
b. solvent in fingernail polish
c. acid in vinegar
d. flavoring in foods and beverages
44. What type of reaction is used to produce aspirin from
salicylic acid and acetic acid?
Chapter Test glencoe.com
51. Use structural formulas to write equations for the fol-
Mastering Problems
45. Draw structures for each of the following carbonyl
compounds.
a. 2,2-dichloro-3-pentanone
b. 4-methylpentanal
c. isopropyl hexanoate
d. octanoamide
e. 3-fluoro-2-methylbutanoic acid
f. cyclopentanal
g. hexyl methanoate
46. Name each of the following carbonyl compounds.
O
52. What type of reaction converts an alcohol into each of
the following types of compounds?
a. ester
c. alkene
b. alkyl halide
d. aldehyde
53. Use structural formulas to write the equation for the con-
densation reaction between ethanol and propanoic acid.
——
a.
lowing reactions.
a. the substitution reaction between 2-chloropropane
and water yielding 2-propanol and hydrogen chloride
b. the addition reaction between 3-hexene and chlorine
yielding 3,4-dichlorohexane
Section 22.5
O
—
b.
CH3 — CH2 — CH2 — C — H
O
—
c.
CH3 —
( CH2 —
)4 C — NH2
O
—
d.
CH3 —
( CH2 —
)4 C — OH
Section 22.4
Mastering Concepts
47. Synthetic Organic Compounds What is the starting
material for making most synthetic organic compounds?
48. Explain the importance of classifying reactions.
49. List the type of organic reaction needed to perform
each of the following transformations.
a. alkene → alkane
b. alkyl halide → alcohol
c. alkyl halide → alkene
d. amine + carboxylic acid → amide
e. alcohol → alkyl halide
f. alkene → alcohol
Mastering Problems
50. Classify each of the following organic reactions as sub-
stitution, addition, oxidation-reduction elimination, or
condensation.
a. 2-butene + hydrogen → butane
b. propane + fluorine → 2-fluoropropane + hydrogen
fluoride
c. 2-propanol → propene + water
d. cyclobutene + water → cyclobutanol
Chapter Test glencoe.com
Mastering Concepts
54. Explain the difference between addition polymerization
and condensation polymerization.
55. Which type of polymer is easier to recycle, thermoset-
ting or thermoplastic? Explain your answer.
Mastering Problems
56. Manufacturing Polymers What monomers react to
make each polymer?
a. polyethylene
b. polyethylene terephthalate
c. polytetrafluoroethylene
57. Name the polymers made from the following
monomers.
a. CF 2=CF 2
b. CH 2=CCl 2
58. Choose the polymer of each pair that you expect to have
the higher water solubility.
OH
a.
C— O
CH3
— CH — CH2 — — CH2 — C — CH2 —
n
I
n
II
b. — CH — CH — — CH — CH —
2
2
2
n
n
OH
59. Examine the structures of the following polymers in
Table 22.14. Decide whether each is made by addition
or condensation polymerization.
a. nylon
c. polyurethane
b. polyacrylonitrile
d. polypropylene
60. Human Hormones Which halogen is found in
hormones made by a normal human thyroid gland?
Chapter 22 • Assessment 819
Mixed Review
HO
OH
61. Describe the properties of carboxylic acids.
a. butanone
b. propanal
c. hexanoic acid
d. heptanoamide
64. List two uses for each of the following polymers.
c. polytetrafluoroethylene
d. polyvinvyl chloride
65. Draw structures of and supply names for the organic
compounds produced by reacting ethene with each of
the following substances.
a. water
c. hydrogen chloride
b. hydrogen
d. fluorine
66. Environmentally-Safe Propellants Hydrofluoroalkanes
(HFAs) are replacing chlorofluorocarbons in hand-held
asthma inhalers, because of CFC damage to the ozone
layer. Draw the structures of the HFAs listed below.
a. 1,1,1,2,3,3,3-heptafluoropropane
b. 1,1,1,2,-tetrafluoroethane
Think Critically
67. Interpret Scientific Illustrations List all the functional
—
——
—
groups present in each of the following complex organic
molecules.
NH2
O
a.
b.
O
—
CH3 C CH3
OH
CH2
OH
OH
CH2—
OH
OH
the following reactions.
a. elimination from an alcohol
b. addition of hydrogen chloride to an alkene
c. addition of water to an alkene
d. substitution of a hydroxyl group for a halogen atom
CH — C
CH —
Vitamin C
63. Name the type of organic compound formed by each of
a. polypropylene
b. polyurethane
O
—
O
62. Draw structures of the following compounds.
CH3
O
Progesterone
■
Figure 22.24
70. Interpret Scientific Illustrations Human cells
require vitamin C to properly synthesize materials
that make up connective tissue such as that found in
ligaments. List the functional groups present in the
Vitamin C molecule shown in Figure 22.24.
71. Identify Draw the structure of an example of an organ-
ic molecule that has four carbons and falls into each of
the compound types listed.
a. ester
c. ether
b. aldehyde
d. alcohol
72. Predict A monohalogenation reaction describes a sub-
stitution reaction in which a single hydrogen atom is
replaced by a halogen. A dihalogenation reaction is a
reaction in which two hydrogen atoms are replaced by
two halogen atoms.
a. Draw the structures of all the possible monohalogenation products that can form when pentane reacts
with Cl 2.
b. Draw the structures of all the possible dihalogenation
products that can form when pentane reacts with Cl 2.
Table 22.15 Alcohol Solubility in Water (mol/100 g H 2O)
Name
Alcohol
Solubility
Methanol
CH 3OH
infinite
Ethanol
C 2H 5OH
infinite
Propanol
C 3H 7OH
infinite
Butanol
C 4H 9OH
0.11
Pentanol
C 5H 11OH
0.030
Hexanol
C 6H 13OH
0.0058
Heptanol
C 7H 15OH
0.0008
Levadopa
68. Evaluate Ethanoic acid (acetic acid) is very
soluble in water. However, naturally occurring longchain carboxylic acids, such as palmitic acid
(CH 3(CH 2) 14COOH), are insoluble in water. Explain.
69. Communicate Write structural formulas for all
structural isomers of molecules having the following
formulas. Name each isomer.
a. C 3H 8O
b. C 2H 4Cl 2
820
Chapter 22 • Substituted Hydrocarbons and Their Reactions
73. Evaluate Examine Table 22.15 comparing some
alcohols and their solubility in water. Use the table to
answer the following questions.
a. What type of bond forms between the –OH group of
alcohols and water?
b. State a relationship between water solubility and
alcohol size from the data in the table.
c. Provide an explanation for the relationship you stated
in Part b.
Chapter Test glencoe.com
74. Recognize Most useful organic molecules are made
from raw materials using several steps. This is called a
multistep synthesis pathway. Label the types of reaction
or process taking place in each step of the multistep synthesis pathway below.
petroleum → ethane → chloroethane → ethene →
ethanol → ethanoic (acetic) acid
Additional Assessment
Chemistry
82. Historical Perspective Write a short story describing
how your life would differ if you lived in the 1800s,
before the development of synthetic polymers.
Challenge Problem
Document-Based Questions
O
■
Figure 22.25
75. Animal Pheromones Catnip contains an organic
chemical known as nepetalactone, shown in Figure 22.25,
that is thought to mimic feline sex pheromones. Cats
will rub in it, roll over it, paw at it, chew it, lick it, leap
about, then purr loudly, growl, and meow for several
minutes before losing interest. It takes up to two hours
for the cat to “reset” and then have the same response to
the catnip.
a. What type of organic compound is nepetalactone?
b. Draw the structural formula for nepetalactone on
a sheet of paper and then draw in all the missing
hydrogen atoms. Remember that carbon atoms must
have four bonds to be stable.
c. Write the molecular formula for nepetalactone.
Cumulative Review
76. Explain why the concentration of ozone over Antarctica
decreases at about the same time every year. (Chapter 1)
Figure 22.26 shows the concentration after one dose of the
drug beclomethasone in the blood of volunteers using a CFC
or an HFA propellant in the inhaler.
Data obtained from: Anderson, P.J. 2006. Chest: The Cardiopulmonary and Critical
Care Journal. 120:89–93
Drug Concentration After First Dose
Blood concentration (ng mL-1)
O
Pharmaceutical Propellants Many inhaled medications
used to treat asthma contained chlorofluorocarbon (CFC).
However, the Montreal Protocol called for a ban of CFCs as a
propellant in pharmaceutical products by 2008. Two hydrofluoroalkanes (HFAs) appear to be effective in delivering
asthma medications to the lungs. However, the medication
dosage had to be cut in half with the new HFA propellents.
77. Why do the following characteristics apply to transition
metals? (Chapter 6)
a. Ions vary in charge.
b. Many of their solids are colored.
c. Many are hard solids.
78. Determine the number of atoms in each of the following.
(Chapter 10)
a. 56.1 g Al
b. 2 moles C
HFA Propellant
CFC Propellant
0.4
0.2
0
2
4
6
8
10
12
Time (h)
■
Figure 22.26
83. After one dose of the drug beclomethasone was given,
which propellant resulted in the highest concentration of medication in the blood, HFA or CFC?
79. What is a rate-determining step? (Chapter 16)
84. When does the drug reach its peak concentration?
80. According to Le Châtelier’s principle, how would
85. Only one-half the amount of medication is needed
increasing the volume of the reaction vessel affect the
equilibrium 2SO 2(g) + O 2(g) → 2SO 3(g)? (Chapter 17)
81. Compare and contrast saturated and unsaturated hydro-
carbons. (Chapter 21)
Chapter Test glencoe.com
with the HFA propellant when compared to the CFC
propellant to achieve a similar blood-concentration
level. Infer the advantages of using a lower dose of
medication to get similar results.
Chapter 22 • Assessment 821
Cumulative
Standardized Test Practice
Multiple Choice
1. What are the products of this reaction?
CH 3CH 2CH 2Br + NH 3 → ?
A. CH 3CH 2CH 2NH 2Br and H 2
B. CH 3CH 2CH 2NH 3 and Br 2
C. CH 3CH 2CH 2NH 2 and HBr
D. CH 3CH 2CH 3 and NH 2Br
6. Diprotic succinic acid (H 2C 4H 4O 4) is an important
part of the process that converts glucose to energy in
the human body. What is the K a expression for the
second ionization of succinic acid?
A. K a = [H 3O +][HC 4H 4O 4 −] / [H 2C 4H 4O 4]
B. K a = [H 3O +][HC 4H 4O 4 2−] / [HC 4H 4O 4 −]
C. K a = [H 2C 4H 4O 4] / [H 3O +][HC 4H 4O 4 −]
D. K a = [H 2C 4H 4O 4] / [H 3O +][C 4H 4O 4 2−]
2. What kind of reaction is this?
H O
C
NH2
—
—
—
—
C OH + H3C
C
CH2CH3
—
—
C C
NH2
CH3 — C — CH2CH2CH3
N
H
C
H
C
—
CH3
—
—
H
—
NH2
H O
A.
B.
C.
D.
Use the figure below to answer Question 7.
OH →
OH + H2O
O
H C
H O
substitution
condensation
addition
elimination
3. What are the oxidation numbers of the elements in
CuSO 4?
A. Cu = +2, S = +6, O = -2
B. Cu = +3, S = +5, O = -2
C. Cu = +2, S = +2, O = -1
D. Cu = +2, S = 0, O = -2
4. The corrosion, or rusting, of iron is an example of a
naturally occurring voltaic cell. To prevent corrosion,
sacrificial anodes are sometimes attached to rustsusceptible iron. Sacrificial anodes must
A. be more likely to be reduced than iron.
B. have a higher reduction potential than iron.
C. be more porous and abraded than iron.
D. lose electrons more easily than iron.
—
—
—
H2N — C — C — C — C — H
H H H
A. amine
B. amide
822
Chapter 22 • Assessment
7. Which is the correct name for this compound?
A. 3-methyl hexane
B. 2-ethyl pentane
C. 2-propyl butane
D. 1-ethyl 1-methyl butane
8. A strip of metal X is immersed in a 1M solution of
X + ions. When this half-cell is connected to a standard hydrogen electrode, a voltmeter reads a positive
reduction potential. Which is true of the X electrode?
A. It accepts electrons more readily than H + ions.
B. It is undergoing oxidation.
C. It is adding positive X + ions to its solution.
D. It acts as the anode in the cell.
9. What is the mass of one molecule of barium
hexafluorosilicate (BaSiF 6)?
C. 2.16 × 10 21 g
A. 4.64 × 10 −22 g
D. 6.02 × 10 -23 g
B. 1.68 × 10 26 g
10. Which type of compound accepts H + ions?
A. an Arrhenius acid
B. an Arrhenius base
C. a Brønsted-Lowry acid
D. a Brønsted-Lowry base
—
—
—
—
—
5. What type of compound does this molecule
represent?
O H H H
H
C. ester
D. ether
11. Which substituted hydrocarbon has the general
formula R–OH?
A. alcohol
C. ketone
B. amine
D. carboxylic acid
Standardized Test Practice glencoe.com
Short Answer
SAT Subject Test: Chemistry
Use the figure below to answer Questions 12 and 13.
OH
12. What is the functional group present in this
compound?
17. Which type of reaction is shown below?
13. Give the name for this compound.
—
H
H
H
H—C—C—C—H
—
Extended Response
Use the graph below to answer Question 14.
H
H
Br2
H
H
→
H—C—C—C—H
Energy Diagram for the Reaction
of Compounds A and B
H
Potential energy (kJ)
+
— —
H
— —
H
— —
H
—
—
—
H—C—C—C—C
O
——
—
—
—
H
—
H
—
H
16. To electroplate an iron fork with silver,
A. the silver electrode must have more mass than
the fork.
B. the iron fork must act as the anode in the cell.
C. electric current must be applied to the iron fork.
D. iron ions must be present in the cell solution.
E. the electric current must be pulsed.
A.
B.
C.
D.
E.
C
A+B
Br
Br
condensation
dehydration
polymerization
halogenation
hydration
Use the table below to answer Question 18.
Experimental Data for A + B → C
Reaction coordinate
14. Discuss the reaction that results in the shape of the
energy graph shown.
Time
[A]M
[B]M
[C]M
0.00 sec
0.35
0.50
0.00
5.00 sec
0.15
0.30
0.40
Use the figure below to answer Question 15.
—
CH2 — CH3
CH3 CH3
—
—
CH3
CH3
—
—
CH2 — CH — CH3
CH2 — CH — CH2
15. The two structures above both have the molecular
formula C 6H 14. Are they isomers of one another?
Explain how you can tell.
18. Which is the rate of this reaction in terms of moles
of product per second?
A. 0.40 mol/s
B. 0.85 mol/s
C. 0.08 mol/s
D. 0.17 mol/s
E. 0.93 mol/s
NEED EXTRA HELP?
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Question . . .
1
Review Section . . . 22.4
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
22.4
19.1
20.1
22.2
18.2
21.2
20.1
10.3
18.1
22.2
22.1
22.3
16.1
21.4
20.1
22.4
16.3
Standardized Test Practice glencoe.com
Chapter 22 • Assessment 823
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