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634
20
Organic Chemistry
""'""-
C_ti_Q~ter
Key Terms
organic chemistry (p. 595)
biomolecules (p. 596)
hydrocarbon (20.2)
alkane (20.2)
normal (straight-chain or unbranched) hydrocarbons (20.2)
structural isomerism (20.3)
combustion reaction (20.6)
substitution reaction (20.6)
dehydrogenation reaction (20.6)
alkene (20.7)
alkyne (20.7)
addition reaction (20.7)
hydrogenation reaction (20.7)
halogenation (20.7)
polymerization (20.7)
aromatic hydrocarbon (20.8)
phenyl group (20.9)
hydrocarbon derivative (20.10)
functional group (20.10)
alcohol (20.11)
phenol (20.12)
ketone (20.13)
aldehyde (20.13)
carboxylic acid (20.15)
ester (20.15)
polymer (20.16)
addition polymerization (20.16)
condensation polymerization (20.16)
summary
1. The study of carbon-containing compounds and their
properties is called organic chemistry. Most organic compounds contain chains or rings of carbon atoms. The organic molecules responsible for maintaining and reproducing life are called biomolecules.
2. Hydrocarbons are organic compounds composed of carbon and hydrogen. Those that contain only C-C single
bonds are saturated and are called alkanes, and those with
carbon-carbon multiple bonds are unsaturated. Unsaturated hydrocarbons can become saturated by the addition
of hydrogen, halogens, and/or other substituents.
3. All alkanes can be represented by the general formula
C Il H 2n + 2. Methane, CH 4, is the simplest alkane, and the
next three in the series are ethane, C2 H 6 ; propane, C3H g ;
Review
and butane, C4HIO. In a saturated hydrocarbon, each carbon atom is bonded to four other atoms. Alkanes containing long chains of carbon atoms are called normal,
or straight-chain, hydrocarbons.
4. Stmctural isomerism in alkanes involves the formation
of branched structures. Specific mles for systematically
naming alkanes indicate the point of attachment of any
substituent group, the length of the root chain, and so on.
5. Alkanes can undergo combustion reactions to form carbon dioxide and water or substitution reactions in which
hydrogen atoms are replaced by other atoms. Alkanes can
also undergo dehydrogenation to form unsaturated hydrocarbons.
6. Hydrocarbons with carbon-carbon double bonds are
called alkenes. The simplest alkene is ethylene, C2H4.
Alkynes are unsaturated hydrocarbons with a carboncarbon triple bond. The simplest in the series is acetylene, C2H2 .
7. Unsaturated hydrocarbons undergo addition reactions
such as hydrogenation (addition of hydrogen atoms) and
halogenation (addition of halogen atoms). Ethylene and
substituted ethylene molecules can undergo polymerization, a process by which many molecules (monomers)
are joined together to form a large chain-like molecule.
8. Organic molecules that contain elements in addition to
carbon and hydrogen can be viewed as hydrocarbon
derivatives: hydrocarbons with functional groups. Each
functional group exhibits characteristic chemical properties.
9. Alcohols contain the -OH functional group. Aldehydes
and ketones contain the carbonyl functional group,
"c=o
/
In aldehydes this group is bonded to at least one hydrogen atom. Carboxylic acids are characterized by the carboxyl functional group,
-1'0
-C
"OH
They can react with alcohols to form esters.
10. Polymers can be formed by addition polymerization, in
which monomers add together, or by condensation polymerization, which involves the splitting out of small molecules (such as water) as the monomers react.
Questions and Problems
Questions and Problems
All even-numbered exercises have answers in the back of this
book and solutions in the Solutions Guide.
20.1 • Carbon Bonding
QUESTIONS
1. What makes carbon able to form so many different compounds?
2. What is the maximum number of other atoms to which
a given carbon atom can be attached? Why?
--3. What does a double bond represent? Give two examples
of molecules in which double bonds occur, and draw the
Lewis structures of those molecules.
4. What does a triple bond represent? How many pairs of
electrons are shared between the atoms in a triple bond?
Draw the Lewis structure of a molecule with a triple
bond.
5. When a carbon atom is bonded to four other atoms, what
geometric arrangement occurs around the carbon atom?
Why?
6. The structures of the organic molecules propane and butane are given in Figure 20.3. How many other atoms
is each carbon bonded to in these molecules? What is
the geometry around each carbon atom in these molecules?
635
PROBLEMS
11. Write structural formulas for the normal (straight-chain)
alkanes with:
a. eleven carbon atoms
c. twenty carbon atoms
b. fifteen carbon atoms
12. Write structural formulas for the normal (straight-chain)
alkanes with:
a. eight carbon atoms
c. twelve carbon atoms
b. ten carbon atoms
13. For each of the following straight-chain alkanes, draw the
structural formula.
c. propane
a. heptane
d. decane
b. nonane
14. Draw the structural formula for each of the following
straight-chain alkanes.
c. pentane
a. butane
b. octane
d. hexane
20.3 • Structural Formulas and Isomerism
QUESTIONS
15. What are structural isomers? Which is the smallest alkane
that has a structural isomer? Draw structures to illustrate
the isomers.
16. What is a small chain of carbon atoms called when it is
attached to a longer chain of carbon atoms?
----
PROBLEMS
20.2 • Alkanes
QUESTIONS
7. What does it mean to say that a hydrocarbon is saturated? To how many other atoms is each carbon atom in
a saturated hydrocarbon bonded? What name is given to
the family of saturated hydrocarbons?
17. Draw structural formulas for at least five isomeric alkanes having the formula C7H 16.
18. Draw the structural formulas for at least five isomeric
alkanes having the formula CSH IS '
----
20.4 • Naming Alkanes
8. What is an unsaturated hydrocarbon? In what respect is
such a hydrocarbon "unsaturated"? What structural feature characterizes unsaturated hydrocarbons?
QUESTIONS
19. Give the root names for the alkanes with five through ten
carbon atoms.
9. Although alkanes in which the carbon atoms form long,
unbranched chains are often called "straight-chain" alkanes, why is such a chain not really straight? What is
the bond angle between carbon atoms in a straight-chain
alkane?
20. To what does the root name for a branched hydrocarbon
correspond?
10. Write the names and structural formulas of the first ten
straight-chain alkanes without looking at your textbook.
By what group of atoms does each successive member
of this family differ from the previous member?
---
----
21. What is an alkyl group? How is a given alkyl group related to its parent alkane?
22. How is the position of substituents along the longest chain
of a hydrocarbon indicated?
---23. How is the number of multiple substituents of the same
type indicated in the systematic name of a hydrocarbon?
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20
Organic Chemistry
24. In giving the name of a hydrocarbon with several substituents, in what order do we list the substituents?
PROBLEMS
25. Give the systematic name for each of the following alkanes.
CH3
a.
CH3
c.
.
CH 3
CH 3
CH 3
CH 3
CH 3
20.5 • Petroleum
29. What are the major constituents of crude petroleum?
What is the major constituent of natural gas? How were
these mixtures formed?
b. ?Hz-CHz-CHz-?H-CHz-CHz-?Hz
CH 3
3-methylpentane
4-tert-butylheptane
5-propylnonane
2,4,6,9-tetramethyldecane
QUESTIONS
I
CH 3-C-CHz-CH-CHz-CH3
I
I
CH 3
a.
b.
c.
d.
.
CH 3
I
I
CH 3 -C-CHz-C-CH3
I
I
30. List several petroleum fractions and tell how each fraction is primarily used.
--31. What is pyrolytic cracking, and why is the process applied to the kerosene fraction of petroleum?
32. Why was tetraethyl lead, (CZHS)4Pb, added to gasoline
in the past? Why is the use of this substance being phased
out?
20.6 • Reactions of Alkanes
QUESTIONS
26. Give the systematic name for each of the following alkanes.
33. Explain why alkanes are relatively unreactive.
34. What is a combustion reaction? How have we made use
of the combustion reactions of alkanes?
35. What is a substitution reaction? Give an example of a reactive molecule that is able to replace the hydrogen atoms
of an alkane.
36. What is a dehydrogenation reaction? What results when
an alkane is dehydrogenated?
PROBLEMS
37. Complete and balance each of the following chemical
equations that represent combustion reactions.
a. C3H 8(g) + Oz(g) -t
b. CSH1Z(I) + Oz(g) -t
c. C7H 16(l) + Oz(g) -t
27. Draw a structural formula for each of the following
compounds.
a. 2-methylheptane
b. 3-methylheptane
c. 4-methylheptane
d. 2,2-dimethylheptane
e. 2,4-dimethylheptane
28. Draw the structural formula for each of the following
compounds.
38. Complete and balance each of the following chemical
equations.
a. CZH 6(g) + 02(g) -t ? + ?
b. CHzClz(l) + Clz(g) -t HCI(g) + ?
c. CHz=CH-CHz-CH3(l) + Brz(l) -t ?
20.7 • Alkenes and Alkynes
QUESTIONS
39. What is an alkene? What structural feature characterizes
alkenes? Give the general formula for alkenes.
Questions and Problems
40. What is an alkyne? What structural feature characterizes
alkynes? Give the general formula for alkynes.
---
41. How is the root name of an alkane modified to indicate
that a given hydrocarbon contains a double or triple bond
in its longest continuous chain?
42. How is the location of a double or triple bond in the
longest continuous chain of an unsaturated hydrocarbon
indicated?
43. Describe some addition reactions that unsaturated hydrocarbons undergo. Give the specific name of the type
of addition process, and indicate what atoms are added
to the double or triple bond.
44. How is a liquid fat, such as com oil, converted into a
solid form for use as a table spread or shortening?
PROBLEMS
45. Give the systematic name for each of the following unsaturated hydrocarbons and substituted unsaturated compounds.
a. CH3-CH=CH-CH3
b. CH3-
H-CH=CH 2
T
CH
3
c. CH-C-CH2-CH3
d. CH2=CH-CH-CH3
I
CI
46. Give the systematic name for each of the following unsaturated hydrocarbons.
a. CH=C-CH3
b. CH3-CH2-C
C-CH2-CH3
c. CH3-CH2-CH=CH-CH2-CH3
---
47. Draw structural formulas for at least four isomeric hydrocarbons containing eight carbon atoms and one double bond.
48. Draw structural formulas showing all possible molecules containing six carbon atoms and having one triple
bond.
20.9 • Naming Aromatic Compounds
QUESTIONS
51. How is a monosubstituted benzene named? Give the
structures and names of two examples. Also give two examples of monosubstituted benzenes that have special
names.
52. How is the benzene ring named if it is considered a substituent in another molecule? Give the structures and
names of two examples.
--53. If a benzene ring contains several substituents, how are
the relative locations of the substituents numbered in the
systematic name given to the molecule?
54. What do the prefixes ortho-, meta-, and para- refer to in
terms of the relative location of substituents in a disubstituted benzene?
PROBLEMS
55. Draw a structural formula for each of the following aromatic or substituted aromatic compounds.
a. 3-bromochlorobenzene
b. I A-dichlorobenzene
c. 4-bromo-I-methylbenzene (4-bromotoluene)
d. naphthalene
e. I A-dimethylbenzene
56. Name each of the following aromatic or substituted aromatic compounds.
a.
O=CH
3
CH 3
b.
CI
CI*CI
CI
CI
CI
'000
20.8 • Aromatic Hydrocarbons
QUESTIONS
49. What structure do all aromatic hydrocarbons have in
common?
50. Benzene exhibits resonance. Explain this statement in
terms of the different Lewis structures that can be drawn
for benzene.
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"CIOO
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20
Organic Chemistry
20.10 • Functional Groups
PROBLEMS
57. On the basis of the functional groups listed in Table 20.5,
identify the family of organic compounds to which each
of the following belongs.
a. CH3-CH2-CH-CH2-CH3
I
OH
b. CH 3-CH2-
20.12 • Properties and Uses of Alcohols
=O
r
H
QUESTIONS
c. CH3-CH2-CH2-CH2-r=O
CH2-CH2-CH3
d. CH3-CH-NH2
I
CH 3
58. On the basis of the functional groups listed in Table 20.5,
identify the family of organic compounds to which each
of the following belongs.
a. CH3CH2-0-CH2CH2CH3
b. CH3CH 2CH2CH 2-OH
c. CH3CH 2CHCH3
I
OH
d. CH3CH2CH 2CH2COOH
63. Why is methanol sometimes called wood alcohol? Describe the modern synthesis of methanol. What are some
uses of methanol?
64. Write the equation for the fermentation of glucose to
form ethanol. Why can't ethanol solutions of greater than
about 13% concentration be made directly by fermentation? How can the ethanol content be increased beyond
this level in beverages?
--65. Write the equation for the synthesis of ethanol from ethylene. What are some commercial uses of ethanol made
by this process?
66. Give the names and structural formulas of two other commercially important alcohols. Cite the major use of each.
---
20.13 • Aldehydes and Ketones
QUESTIONS
20.11 • Alcohols
67. What functional group is common to both aldehydes and
ketones?
QUESTIONS
59. What functional group characterizes an alcohol? What
ending is added to the name of the parent hydrocarbon
to show that a molecule is an alcohol?
60. Distinguish among primary, secondary, and tertiary alcohols. Give a structural formula for an example of each
type.
PROBLEMS
61. Give the systematic name for each of the following alcohols. Indicate whether the alcohol is primary, secondary, or tertiary.
a. CH3CH2CH2CH2CH2-0H
b.
CH 3
I
CH3CCH2CH3
I
OH
c. CH3CH2CHCH?CH3
I
62. Draw structural formulas for each of the following alcohols. Indicate whether the alcohol is primary, secondary,
or tertiary.
a. I-propanol
b. 2-pentanol
c. 2-methyl-l-propanol
d. 3-methyl-3-pentanol
----
-
OH
d. CH3CH2CH2-OH
68. What structural feature distinguishes aldehydes from ketones?
69. Mention some commercial uses of specific aldehydes and
ketones.
70. How are aldehydes and ketones most often produced
commercially? Write an equation as an example of each
process.
20.14. Naming Aldehydes and Ketones
QUESTIONS
71. What ending is added to the root name of the parent hydrocarbon to indicate that the molecule contains the aldehyde functional group? What systematic ending is used
to show that a molecule is a ketone?
72. Describe the alternative system for naming ketones. Give
two examples of ketones, along with their names in both
systems.
Questions and Problems
73. Give the systematic name for each of the following:
c.
CH3
I
a. CH 3-CHz-CHz-C=O
CH 3-C-CH3
I
I
CHz-CH3
Cl
c.
I
Cl
79. Draw the general structural formula for an ester. From
what two families of organic compounds are esters synthesized?
I
H
80. Draw the structure of acetylsalicylic acid, and circle the
portion of the molecule that shows that it is an ester. From
what acid and alcohol is acetylsalicylic acid synthesized?
----
CH3
I
CH3-CH-CH-CHz -C=O
I
I
CH 3
oxidation
----'>
OH
b. CH3-CH-CH-C=O
I
639
H
PROBLEMS
d.
CH3
81. Give the systematic name for each of the following:
I
CH3-CH-C=O
a. CH 3-
I
H
e.
H-CH z-COOH
CH 3
CH3-CH26°
b.
Ol-COOH
c. CH 374. Draw a structural formula for each of the following:
a. ethyl phenyl ketone
b. diethylketone
c. 3-pentanone
d. 2-chloropropanal
e. 2,3-dimethylpentanal
20.15 •
r
Carboxylic Acids and Esters
QUESTIONS
75. Draw the structure of the group that characterizes organic
(carboxylic) acids. Give the general condensed formula
for an organic acid.
76. Are carboxylic acids typically strong acids or weak acids?
Write an equation showing the acid CH3CH zCOOH ionizing in water.
--77. What systematic ending is used to show that a molecule
is a carboxylic acid? Give an example.
78. Draw the structure of the principal organic product of
each of the following reactions.
r
H-COOH
OH
d.
CH 3
I
CH 3-CHz-CH-CH-CHz-COOH
I
CH 3
82. Draw a structural formula for each of the following:
a. ethyl butanoate
b. 4-chloro-2-hydroxybenzoic acid
c. methyl pentanoate
d. propyl benzoate
e. 2,3-dimethylbutanoic acid
----
20.16 • Polymers
QUESTIONS
83. What, in general terms, is a polymer? What is a monomer?
84. What is addition polymerization? Give an example of a
common addition polymer.
---
85. What is condensation polymerization, and how does it
differ from addition polymerization? Give an example of
a common condensation polymer.
OXIdatIOn
86. What is a polyester? What structural feature characterizes polyesters? Give an example of a common polyester.
b. CH 3-CHz-?H-CH3
OH
oxidation
->
PROBLEMS
87. Draw the structures of acrylonitrile and butadiene. Also
draw the structures of the basic repeating units when each
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20
Organic Chemistry
of these substances polymerizes. Give several uses of
each polymeric substance.
other atoms attach themselves to the carbon atoms of the
double or triple bond.
88. For the polymeric substances nylon and Dacron, sketch
representations of the repeating unit in each.
102. Unsaturated fats may be converted to saturated fats by
the process of
_
----
103. Benzene is the parent member of the group of hydrocar-
bons called
104. An atom or group of atoms that imparts new and char-
Additional problems
acteristic properties to an organic molecule is called a
_ _ _ group.
89. The first "organic" compound to be synthesized in the
laboratory, rather than being isolated from nature, was
____, which was prepared from
_
90. An organic compound whose carbon-carbon bonds are
all single bonds is said to be
_
91. The general orientation of the four pairs of electrons
around the carbon atoms in alkanes is
_
92. Alkanes in which the carbon atoms form a single unbranched chain are said to be
alkanes.
93. Structural isomerism occurs when two molecules have
the same number of each type of atom but exhibit different arrangements of the
between those
atoms.
94. The systematic names of all saturated hydrocarbons have
the ending
added to a root name that indicates
the number of carbon atoms in the molecule.
95. For a branched hydrocarbon, the root name for the hy-
drocarbon comes from the number of carbon atoms in
the
continuous chain in the molecule.
96. The positions of substituents along the hydrocarbon
_
frame work of a molecule are indicated by the
of the carbon atom to which the substituents are attached.
97. Kerosene may be converted to gasoline by
_
which means that the larger, heavier kerosene components are broken down by heat into smaller, lighter gasoline fragments.
98. Tetraethyllead, (C2Hs)4Pb, was added to gasoline in the
agent.
past as an
99. The major use of alkanes has been in
as a source of heat and light.
reactions,
100. With very reactive agents, such as the halogen elements,
alkanes undergo
reactions, whereby a new
atom replaces one or more hydrogen atoms of the alkane.
101. Alkenes and alkynes are characterized by their ability to
undergo rapid, complete
hydrocarbons.
reactions, by which
105. A
alcohol is one in which there is only one hydrocarbon group attached to the carbon atom holding the
hydroxyl group.
106. The simplest alcohol, methanol, is prepared industrially
by the hydrogenation of
_
107. Ethanol is commonly prepared by the
of cer-
tain sugars by yeast.
108. Both aldehydes and ketones contain the
group,
but they differ in where this group occurs along the hydrocarbon chain.
109. Aldehydes and ketones can be prepared by
of
the corresponding alcohol.
1l0. Organic acids, which contain the
typically weak acids.
group, are
111. The typically sweet-smelling compounds called
_
result from the condensation reaction of an organic acid
with an
_
112. In
polymerization, the monomer units simply
combine over and over again to form the polymer's long
chain.
113. Write the general formula for a normal alkane. How does
a given alkane differ from the previous or the following
member of the series?
114. Draw structural formulas for all isomeric alkanes having
the general formula CSH 12 .
115. As the size of an organic molecule increases, the num-
ber of structural isomers that are possible increases dramatically. For the general alkane formula C2oH42 , draw
structures showing the carbon framework of at least ten
isomers. (You do not have to show all the hydrogen
atoms.)
116. Give the systematic name of each of the following sub-
stituted alkanes.
Additional Problems
123. Draw a structure corresponding to each of the following
names.
a. 2-methylpentanal
b. 3-hydroxybutanoic acid
c. 2-aminopropanal
d. 2,4-hexanedione
e. 3-methylbenzaldehyde
d. CH3-CH-CH-CH-CH3
I
CI
I
CI
I
CI
117. Give some examples of molecules containing "fused"
benzene rings.
118. Draw a structural formula for each of the following compounds.
a.
b.
c.
d.
e.
3-chloro-3-hexene
1,2-dibromoethane
1,1 ,2,2-tetrachloroethane
3-bromo-l-hexyne
1,2-dichloro-2,3,3,4-tetramethyloctane
119. Draw the structural formula(s) for, and give the name(s)
of, the organic product(s) of each of the following reactions. If a mixture of several, similar products is expected,
indicate the type of product expected.
a. CH3-CH3
+ Clz ~
c. CH 3 -CH z"
/C=CH-CH 3 + Brz
641
~
CH 3 -CH z
120. For the general formula C6 H 140, draw the structures of
three isomeric alcohols that illustrate primary, secondary,.
and tertiary alcohol structures.
121. The alcohol glycerol (glycerine), which is produced in
the human body by the digestion of fats, has the following structure. Give the systematic name of glycerol.
124. Draw a structure corresponding to each of the following
names.
a. diphenylketone
b. 2-methyl-2-propanol
c. methylisopropylketone
d. 1,2-ethanediol
e. methyl propanoate
125. Salicylic acid is an interesting molecule; it is both an acid
and an alcohol, having a hydroxyl group attached to the
aromatic ring (phenol). For this reason, salicylic acid clm
undergo two different esterification reactions, depending
on which functional group of salicylic acid reacts. For
example, as discussed in this chapter, when treated with
acetic acid-a stronger acid-salicylic acid behaves as
an alcohol, and the ester produced is acetylsalicylic acid
(aspirin). On the other hand, when reacted with methyl
alcohol, salicylic acid behaves as an acid, and the ester
methyl salicylate (oil of wintergreen) is produced. Methyl
salicylate is also an analgesic and is part of the formulation of many liniments for sore muscles. Write an equation for the production of each of these esters of salicylic
acid.
126. Alpha amino acids are organic acid molecules that also
happen to contain an amino group (-NH z) on the second carbon atom of the acid's chain. Proteins are condensation polymers of such alpha amino acids. The reaction by which the long chain of the protein forms is
very similar to the reaction by which nylon forms, resulting in the formation of the linkage
-N-C=O
I
H
I
which is called an "amide" (or "peptide") linkage. Show
how the following two arilino acids could react with each
other to produce an amide linkage, resulting in the formation of a dimer (a "dipeptide").
HO-C=O
122. The sugar glucose could conceivably be given the name
2,3,4,5,6-pentahydroxyhexanal (though this name is never
used, because the actual sugar glucose is only one possible isomer having this name). Draw the structure implied by this name.
I
CH3-CH-N-H
I
H
How could this dipeptide then go on to react with additional amino acids to form a polypeptide?
."
642
20
Organic Chemistry
127. Write structural formulas for the normal (straight-chain)
alkanes with:
a. seven carbon atoms
b. eleven carbon atoms
c. sixteen carbon atoms
128. For each of the following numbers of carbon atoms, give
the structure of the straight-chain alkane with that number of carbon atoms, and give its name.
a. eight carbon atoms
b. six carbon atoms
c. four carbon atoms
d. five carbon atoms
129. Draw structural formulas for all isomeric alkanes having
the general formula C 7H 16 .
b. CH3CH=CHCH2CH2CH2CH3
c. CH3CH 2C=CCH3
134. Draw suuctural fOlmulas showing all the isomers of the
sU'aight-chain alkyne with eight carbon atoms. "Name
each isomer.
135. Name each of the following aromatic or substituted aromatic compounds.
a
b
130. Give the systematic name for each of the following
alkanes.
a.
0=::
"'IQ('
Br
CH 3
I
CH 3-CH-CH-CH 3
I
CH3
136. On the basis of the functional groups listed in Table 20.5,
identify the family of organic compounds to which each
of the following belongs.
131. Draw a structural formula for each of the following compounds.
a. 2,2-dimethylhexane
b. 2,3-dimethylhexane
c. 3,3-dimethylhexane
d. 3,4-dimethylhexane
e. 2,4-dimethylhexane
132. Write the formula for the missing reactant or product in
each of the following chemical equations.
a. CH4(g) + CI2(g)
b.
c.
+ HCl(g)
CH3CH2CH3(g) ~ CH3CH=CH2(g) +
CHCI3(l) + CI2(g) ~ CCI 4 (l) +
_
d.
~
_
133. Give the systematic name for each of the following unsaturated hydrocarbons.
a. CH3CH=CHCH2CH2CH2CH2CH2CH2CH3
137. Draw a structural formula for each of the following alcohols. Indicate whether the alcohol is primary, secondary, or tertiary.
a. 2-propanol
I
I
Additional Problems
b. 2-methyl-2-propanol
c. 4-isopropyl-2-heptanol
d. 2,3-dichloro-I-pentanol
138. Draw a structural formula for each of the following:
a. 3-methylpentanal
b. 3-methyl-2-pentanone
c. methyl phenyl ketone
d. 2-hydroxybutanal
e. propanal
I
I
139. How are carboxylic acids synthesized? Give an example
of an organic acid and the molecule from which it is synthesized. What type of reaction is this?
I
I
643
140. Draw a structural formula for each ofthe following:
a. 3-methylbutanoic acid
b. 2-chlorobenzoic acid
c. hexanoic acid
d. acetic acid
141. Draw the structure of the monomer and the basic repeating unit for each of the following polymeric substances.
a. polyethylene
b. polyvinyl chloride
c. Teflon
d. polypropylene
e. polystyrene