1028 CHAPTER 22 Organic Chemistry

CH3 CH CH3
CH3 CH CH3
38. Determine whether each compound exhibits optical isomerism. 42. Name
CH3eachCH
alkane.
CH 3 CH3
a. CH3CH2CHClCH3 b. CH3CCl2CH3 a. CH3 CH3 CH
CH 3
NH3 CH3 CH3
CH CH3
3
NH3 CH3 CH3
CH CH3
3
CH2 O CH3 CH
CH CH2 CH
CH CH2
3 3
CH2 O CH3 CH
CH CH2 CH
CH CH2
c. d. CH3 C C OH 3 3
b. CH3 CH CH2 CH CH32
CH3 C C OH CH32
Br CH3 CH CH2 CH
CH
Br CH3 CH3 CH3
CH
CH2 CH3 CH3 CH3
39. Determine whether the molecules CHthe
in each pair are 2 same or CH3 C
CH3 CCH3 CH3
H H
enantiomers. MISSED THIS? Read Section 22.3 c. CH3 C
CH3 CCH3 CH3
CH3CH2 H H CH CH CH
Cl Cl 2 3 CH3 C 3 CH
C 3 CH3
CH3CH2 H Cl Cl
H CH2CH3
CH3 C 3 CH
CH C 3 CH3
a. CH3CH2 CH3 Cl Cl CHCH 3 2CH3 CH3 CH3 CH3
CH3 CH3 CH3 CH3
CH3 CH3 CH3
H H CH3 CH
CH23
H H CH3 CH
CH23
H 3C d. CH3
H Cl HO H CH3 CH
CH CH2 CH CH
CH CH2 CH2 CH3
b. H3C 3 2
HO Cl HO Cl CH3 CH3 CH
CH3 CH 2 CH CH
CH2 CH 2 CH2 CH3
H 3C CH
HO Cl HO Cl CH3 CH3 CH CH2 CH3 CH CH2 CH2 CH3
HO Cl CHa3 structure
43. Draw CH CHeach
for CH
CH 3 CH
alkane. CH2 CH2 CH3
CH3 CH3 2
MISSED THIS? Read SectionCH322.4; Watch IWE 22.3
CH3 H H CH3 CH3
CHCH3 H H HC CH3 a. 3-ethylhexane
c. CH3 CH
C CH3 H 3C H HC CH3
C b. 3-ethyl-3-methylpentane
CH3 CH H C CH3 H C C C HC CH3
C 3 c. 2,3-dimethylbutane
CH3
H3C C C CH3 H 3 C C C CH3 CH3 d. 4,7-diethyl-2,2-dimethylnonane
H3C C
CH C
CH 2 CH3
2
44. Draw a structure for each alkane.
40. DetermineH3CH
Cwhether
3 CHthe CH3
2 molecules
CH CH
in each2pair are3 the same or
H3C CH3Cl CH2 CH3CH CH2 a. 2,2-dimethylpentane
enantiomers.
3 b. 3-isopropylheptane
H3CHOCH3Cl Cl CH
OH3CH
Cl 3 c. 4-ethyl-2,2-dimethylhexane
a. H3CHO OHCH3 d. 4,4-diethyloctane
Cl
Cl
HOH HOH 45. Complete and balance each hydrocarbon combustion reaction.
H3C H H MISSED THIS? Read Section 22.6
Br Br CH3
b. H3H CN H H a. CH3CH2CH3 + O2 ¡
2 Br NHCH2 3
Br b. CH3CH2CH ‚ CH2 + O2 ¡
H3H C2N NH
Br Br CH
2
3 c. CH ‚ CH + O2 ¡
HH2N H NH2 CH3 46. Complete and balance each hydrocarbon combustion reaction.
3
H H CH
H3 C HC 3 a. CH3CH2CH2CH3 + O2 ¡
CCl3 H
H3 CH C
H C HC CH CH 33 b. CH2 “ CHCH3 + O2 ¡
c. CH3 CCl 3 Cl 3 C H CH3 c. CH ‚ CCH2CH3 + O2 ¡
C C HC
CH Cl3C CH 47. List all the possible products for each alkane substitution
CH3 CH3 CCl3 C
3 CH
3
CH Cl C CH 3 reaction. (Assume monosubstitution.)
Alkanes CH3 CH 3 3
CH3 MISSED THIS? Read Section 22.6
CH3 a. CH3CH3 + Br2 ¡
41. Name each alkane.
MISSED THIS? Read Section 22.4; Watch IWE 22.3 b. CH3CH2CH3 + Cl2 ¡
a. CH
CH
CH2¬ CH
CH33 ¬ CH CH¬ CH
CH22 CH2
CH¬
CH
2
3 CH
3
c. CH2Cl2 + Br2 ¡
3 3
d. CH3 ¬ CH ¬ CH3 + Cl2 ¡
b. CH3 CH2 CH3 CH3 ƒ
CH3
CH3
CH3
CH3 48. List all the possible products for each alkane substitution
CH3 reaction. (Assume monosubstitution.)
CH3 CH3 CH3
CH3 CH CH3 a. CH4 + Cl2 ¡
CH3 b. CH3CH2Br + Br2 ¡
CH3 CH2 CH CH32 CH2 CH3
c. CH3 CH CH2 CH CH2 CH2 CH3 c. CH3CH2CH2CH3 + Cl2 ¡
CH CH CH2 CH CH2 CH CH3 d. CH3CHBr2 + Br2 ¡
d. CH33 CH CH2 CH CH2 CH23
CH3 CH CH2 CH CH2 CH3
CH3 CH3 CH2 CH2 CH
CH23 CH3 Alkenes and Alkynes
CH3 CH2 CH3 49. Write structural formulas for each of the possible isomers of
CH3 CH2 CH3 n-hexene that are formed by moving the position of the double
bond. MISSED THIS? Read Section 22.5

M22_TRO4371_05_SE_C22_988-1035v3.0.2.indd 1028 15/11/18 1:24 PM

 CH3
CH3
CH3
CH3 C C CH CH CH2 CH3
CH3 C C CH CH CH2 CH3
CH3
CH3 Exercises 1029
CH3
50. Write structural formulas for each of the possible isomers of CH3
CH C C CH2 CH3
n-pentyne
CH2 CH that are
CHformed
CHby moving the position of the triple
2 3
bond. c. CH C C CH2 CH3
CH 2 CH CH CH 2 3 CH2
51. Name
CH2eachCH
alkene. CH3THIS? Read Section 22.5
CHMISSED
23 CH2
3 CH3
a. CH2 CH3 CH23 CH3
CH3 CH CH C CH CH3 CH3
CH 3 3
CH3 CH C CH CH3 CH3
CH3 CH3
b. CH32 CH
HC C CH CHCH2 CHCH
3 2 CH3 CH3
d. CH3 C C CH C CH3
c. CH32 CH
HC C CH CHCH2 CHCH
3 2 CH3
CH CH CH CH3 C C CH C CH3
CH2 HC3 CH 2 CH2 CH3 CH2 CH3
CH 3
HC CH CH
CH2 CH CH2 CH2 CH3 CH2 CH3
CH3 CH3 CH3
CH
CH3 CH3 55. Draw the correct structure
CH3 for each compound.
CH3 CH3 MISSED THIS? Read Section 22.5
CH3 CH3 a. 4-octyne
d. CH
CH33 CHCH2 CH
CH CH CCH CHCH3 2 CH3
3
CH3 CH CH C CH3 b. 3-nonene
CH3 CH23 CH CH
CH CH CH
CH23 CH3 c. 3,3-dimethyl-1-pentyne
CH
CH33 CHCH CH CH C 2 CH
CH 33
52. Name each alkene. CH2 CHCH 3 d. 5-ethyl-3,6-dimethyl-2-heptene
CH
CH33 CHCH2 CH CH CCH CHCH3 2 CH3
a. CH
CH33 CH
CH32 CH CH
CH CH CH
CH2 CH
CH3 23 CH3 56. Draw the correct structure for each compound.
CH2 CH3 a. 2-hexene
b. CH3 CH3 CH CH CH3
CH3 CH CH CH CH3 b. 1-heptyne
CH3
CH3 c. 4,4-dimethyl-2-hexene
CH3 CH d. 3-ethyl-4-methyl-2-pentene
CH3 CH32 CH3 CH CH CH3 + Cl2
57. ListCH
the products of eachCH
alkene addition reaction.
CH3 CH
CH3 CH CH
C 23 CH CH3 3 CH CH 3 + Cl2
CH3 MISSED
CH THIS?
CH Read
CH Section
CH 22.6
+ Cl
CH33 CH CH CH3 CH32 + HBr
c. CH3 CH 3 CH CH2
C CH
CH3 CH3 a. CH
CH3 CH CH CH3 +CH Cl2 + HBr
3 CH CH CH 3
CH3 CH2 CH3 CH
CH3 CH CH C CH3 CH3 b. CH3 CH CH CH3 + HBr
CH3 CH
CH3 CH CH CH3 + HBr
CH3 CH
CH CH CHC CH CH3
3 3 CH
CH3 CH3 CH 3
2 CH CH CH3 + Br2
CH CH CH3
d. CH3 C 3 CH C 3 CHCH
2 3 CH3 c. CH3 CH 2 CH CH CH3 + Br2
CH3 C 3 CH
C CH CH3 CH2 CH CH CH CH3 + Br2
CH3 CH
C CH
C3 3 CH2 CH3 3
CH CH3 CH2 CH CH CH CH3 + Br2
CH3 C 33 C
CH CHCH
3 3 3
53. Name Read d. CH3 CH CH C CH 3 + HCl
CH3eachCH
Calkyne.
C MISSED
3 CH CH
CH
C3 CH THIS?
2 CH 3 Section 22.5 CH3
3 CH CH CH CH 2 + Br2
a. CH
CH 3
3
C
C CH
C CHC
CH33
CH 2 CH 3 CH33 CH CH CH3 CH3 + HCl
C
CH3 CH3 CH
CH C 2 CH+ 3Br+
CH3 C C C
CH3
CH
CH 2 HCl
CH3 CH2 CH3 58. What are the
CH33products
CH of
CH3 CH3 CH C each
CH + alkene
2 CH 3Br+
2 HCl
addition reaction?
CH3 C C C 3 CH2
CH CH3 CH3 CH
CH3 CH2 a. CH3 CH CH2 + Br2
b. CH3 C C C CH3 CH2 CH3 CH3 + Cl2
CH3 C C CH3 CH2
C CH3
CH2 CH3 CH + Cl
CH
CH CH 3 3 2
CH C CH 2 CH2 CH3
b. CH2 CH3 CH3 + Cl2
c. CH C CH CHCH3
2 CH2 CH3 CH CH3 + Cl2
CH CH CH2 CH
CH C CH CH32 CH2 CH3 CH3 C 3 CH CH2 + HCl
CH C CH
CH CH
CH32 CH2 CH3 CH3
CH3 CH3
CH c. CH3 C
CH CH CH2 + HCl
CH3
CH3 CH3
CH CH3 C 3 CH CH2 + HCl
CH3 CH3 CH3 CH
C CH2 + HCl
CH3 CH3
CH3 CH3 CH3
CH3
d. CH3 CH C C CH
CH 3
CH2 CH3
CH3 CH C C CH CH2 d. CH3 CH CH C CH3 + HBr
CH 3 CH3
CH3 CH2 C
CH C CH CH
CH22 CH3 CH CH C CH3 + HBr
CH3 CH CH3
CH3 CH2 C
CH C CH CH22
CH CH3 CH CH 3 C CH3 + HBr
CH
CH32 CH
CH32 59. Complete each
CH 3 hydrogenation
CH3 C CHreaction.
CH3 CH CH 3 + HBr
54. Name eachCH
alkyne.
CH 3 CH3
CH MISSED THIS?CH3 ReadCHSection
3 22.6
catalyst
CH C 2 CH CH3 2
CH2 CH CH + H catalyst
a. CH
CH
C 3 CH
CH3 CH CH3 CH CH3 + H2 catalyst
CH3 a. CH22 CH CH333 + H22
CH3 CH CH3
3 catalyst
CH3 CH CH CH CH2 + H2 catalyst
b. CH33 CH CH CH2 + H2 catalyst
CH3 CH CH CH2 + H2
CH3 CH3
CH3 CH3
CH3
b. CH3 C C CH CH CH2 CH3 catalyst
CH3 C C CH CH CH2 CH3 c. CH3 CH C CH2 + H2 catalyst
CH3 CH C CH2 + H2 catalyst
CH3 CH3 CH C CH2 + H2
CH3 CH3 CH3
CH3 CH3
CH3 CH3
CH3
CH3
CH C C CH2 CH3
CH C C CH2 CH3
CH2
CH2
CH3
CH3
CH3
CH3
M22_TRO4371_05_SE_C22_988-1035v3.0.2.indd
CH C C1029 CH C CH3 15/11/18 1:24 PM
3
 2 2 2

1030 CHAPTER 22 Organic Chemistry

catalyst
CH3 CH2 +reaction.
CH2 hydrogenation
CH H catalyst
60. Complete
CH3 each
CH2 CH CH2 + H22 65. Name each disubstituted benzene.
catalyst
a. CH3 CH2 CH CH2 + H2 MISSED THIS? Read Section 22.7
CH3 CH3 Br a. Br Br b.CH2 CH2CH
CH32CH3CH3 c. F F F
CH3 CH3
CH catalyst Cl Cl Cl
CH CH2 C 3 CH
C 3 CH3 + H2 catalyst
b. CH33 CH2 C C CH3 + H2 catalyst
CH3 CH2 C C CH3 + H catalyst
2
c. CH3 CH2 C CH2 + H2 catalyst CH32CH3CH3
CH2 CH2CH
CH3 CH2 C CH2 + H2
catalyst
Br Br Br
CH3 CH2 CH3 CH2 + H2
C
CH3 66. Name each disubstituted benzene.
CH3
Aromatic Hydrocarbons a.Br Br
Br b. ClCl Cl c. II I

61. Name each monosubstituted benzene. ClCl Cl

MISSED THIS? Read Section 22.7
a. CHCH
CH333 b. BrBr
Br c. ClCl
Cl II I
CH
CH2 2 CH2 3 3 CH3
CH
CH
67. Draw the structure for each compound.
MISSED THIS? Read Section 22.7
62. Name each monosubstituted benzene. a. isopropylbenzene
H2C CH3 F
Ha.
2C H2CCH3 CH3 b. F F c. CH3 b. meta-dibromobenzene
CH3 CH3
c. 1-chloro-4-methylbenzene
H3C C CH3
H3C H3CC CCH3 CH3 68. Draw the structure for each compound.
a. ethylbenzene
b. 1-iodo-2-methylbenzene
c. para-diethylbenzene
63. Name each compound in which the benzene ring is best treated 69. What are the products of each aromatic substitution reaction?
as a substituent. MISSEDCH
THIS?
3 Read Section 22.7 MISSED THIS?
H Read Section 22.7
H FeBr3
CH3 CH CH2 CH
CH3 CH2 CH CH2 CH3 H H + Br2 FeBr3
H H + Br2
CH3 CH CH CH
CH3 CH2 CH CH2 CH3
CH 2 CH23 a.
a. CH3 CH CH CH CH2 CH CH2 CH3 H H
CH 2 CH23 H H
H
CH2 CH3 H
CH3
CH3 AlCl3
b. + CH3 CH
Cl AlCl3
CH3 CH CH CH CH2 CH2 CH2 CH3 + CH3 Cl CH
H
b. CH3 CH CH CH CH2 CH2 CH2 CH3 70. What are the products of each aromatic
FeCl 3
substitution reaction?
H H H + Cl2
CH3 CH CH CH CH2 CH2 CH2 CH3 FeCl3
H H + Cl2
a. H H
H H H
c. CH3 C C CH CH CH CH2 CH3
H
CH3 C CH
CH C CH CH CH2 CH3
3 CH3 CH3
64. Name
CH3eachCcompound
C CHin which
CH the
CHbenzene
CH2 ring
CHis3best treated CH AlCl3
CH 3 CH3 b. + CH3 C 3 Cl
as a substituent. AlCl3
CH3 CH3 + CH3 C Cl
CH3
H3C CH2 CH CH CH2 CH3 Alcohols CH3
H3C CH2 CH CH CH2 CH3 CH3eachCH CHMISSED
OH THIS? Read Section 22.9
H C 71. Name alcohol.
2 2
a. H3C CH2 CH 3 CH CH2 CH3
H 3C a. CH3 CH2 CH2 OH
H 3C CH2 CH3
CH2 CH
b. CH3 CH CH23 CH CH3
CH3 CH3
CH CH2 CH CH3 CH3
OH
CH2 CH2 CH2 CH2 C C CH3 CH3 CH
CH3 CH2 CH CH2 CH
CH3 CH3
OH
b. CH2 CH2 CH2 CH2 C C CH3
c. CH3 CH CH2 CH
OH CH2 CH CH3
CH2 CH2 CH2 CH2 C C CH3
OH
CH3 HO
CH3
c. CH3 CH CH C CH CH CH2 CH3 d. H3C CH2 HO
C CH2 CH3
CH3
CH3 CH CH C CH CH CH2 CH3 H3C CH2 H C CH2 CH3
CH3
CH3
CH
CH3
CH C CH CH CH2 CH3 3C
CH3 CH3 H3C
CH3 CH3

M22_TRO4371_05_SE_C22_988-1035v3.0.2.indd 1030 15/11/18 1:24 PM

 Exercises 1031

72. Draw the structure for each alcohol. Carboxylic Acids and Esters
a. 2-butanol 79. Name each carboxylic acid
Oor ester.
b. 2-methyl-1-propanol O 22.11
MISSED THIS? Read Section
c. 3-ethyl-1-hexanol CH3 CH2 CH2 O
C O CH3
O
d. 2-methyl-3-pentanol CH3 CH2 CH2 C O CH3
CH3 CH2 CH2 OH + HBr CH CH2 CH2 C O CH3
73. List the products of each alcohol reaction. a. CH33 CH2 CH2 C O CH3
O
CH3 CH2 CH2 OH + HBr O
MISSED THIS? Read Section 22.9 H2SO4
CH3 CH2 CH CH22 OHOH + HBr CH3 CH2 O
C OH
a. CH3 CH2 CH OH +H2HBr SO4 O
CH3 CH CH22 OH CH3 CH2 C OH
CH3 H 2 SO4 b. CH3 CH2 C OH
b. CH3 CH CH2 OH H2SO4 CH3 CH2 C OH
O
CH3 CH 3 CH2 OH O
CH3 CH23 OH + Na
CH CH3 CH CH2 CH2 CH2 O
C OH
CH O
c. CH3 CH23 OH + Na c. CH3 CH CH2 CH2 CH2 C OH
CH3 CH CH2 CH2 CH2 C OH
CH3 CH23 OH + Na
CH CH3 CH3 CH2 CH2 CH2 C OH
CH3 CH2 OH + Na CH3
CH3 Na2Cr2O7 CH3
d. CH3 C CH2 CH2 OH CH3
NaH22Cr
SO2O O
CH3 4 7
O
CH3 CCH33 CH2
CH CH2 OH
CH3 H
Na 22SO
Cr 2O
4 7 d. CH3 CH2 CH2 CH2 OC O CH2 CH3
CH3 CCH3 CH2 HCH OH Na2Cr2O7 O
2SO24 H2SO4 CH3 CH2 CH2 CH2 C O CH2 CH3
74. ListCH
CHthe
3 C
CCH3 CH
products of
OH2 each
CHalcohol
2 OH reaction.
3 H2SO4 H2SO4 CH3the structure
80. Draw CH2 CHof2eachCH C acid
carboxylic
2 O or
CHester.
2 CH3
CH3 CH
CCH33 OH H2SO4 CH3 CH2 CH 2 CH 2 C O CH 2 CH3
CH3 CCH
CH33 OH H2SO4 a. pentanoic acid
a. CH3 CCH3 OH b. methyl hexanoate
CH3
c. 3-ethylheptanoic acid
CH33
CH
CH3 d. butyl ethanoate
Na2Cr2O7
CH3 CH
CH3 CH2 CH2 OH NaH22Cr
SO2O 81. Determine the products of each carboxylic acid reaction.
CH 4 7
CH CH3 CH2 CH2 OH Na2Cr2O
b. CH33 CH CH2 CH2 OH H2SO4
7 MISSED THIS? Read Section 22.11
NaH22Cr
SO2O4 7
CH
CH33 CH
CH2 CH2OH + HCl
CH2 OH O
H2SO4 O
c. CH3 CH2 OH + HCl
CH3 CH2 OH + HCl
a. CH
CH33 CH
CH22 CH
CH22 CH
CH22 C
C OH +
OH +
CH3 CH23
CH OH + HCl
CH3 H
H22SO
SO44
d. CH3 CH
CH3 CH2 OH + Na CH
CH33 CH
CH22 OH
OH
CH3 OCH
CH3 CH2 OH + Na O
CH3 CH CH2 OH + Na O
Aldehydes and
O Ketones
CH33
CH CCH CH CH
2 2 CH3
OH + Na C
75. Name eachOaldehyde or ketone. MISSED THIS? Read Section 22.10 C OH
CH3 C CH2 CH3 OH
O b. CH
CH22
CH3 C CH2 CH3 O heat
heat
a. CH3 C CH2 CH3 O CH
CH22 C OH
CH3 CH2 CH2 CH2 CH C OH
O CH
CH22
CH3 CH2 CH2 CH2 CH O
O O
b. CH3 CH32 CH2 CHCH
3 2 CH O
82. Determine the products of each carboxylic acid reaction.
CH3 CH32 CH2 CHCH
3 2 CH O
CH3 C CH2 CH CH2 C H O
CH3 CH3 O
c. CH3 C CH2 CH CH2 C H
CH3 CH3 O a. CH3 CH2 C OH + NaOH
CH3 C CH2 CH CH2 C H
CH
CH3 C 3 CH2 CH CH2 C H O
CH3 O
CH3 O b. CH3 CH2 CH2 C OH +
d. CH3 CH CH2
C CH3
O H2SO4
CH3 CH CH2 C CH3 CH3 CH2 CH2 OH
CH2 CH3 O
CH3 CH CH2 C CH3
76. Draw the structure
CH2 CHof each aldehyde or ketone. Ethers
CH3 CH CH23 C CH3
a. hexanalCH2 CH3
83. Name each ether. MISSED THIS? Read Section 22.12
b. 2-pentanone
CH2 CH3
c. 2-methylbutanal a. CH3 ¬ CH2 ¬ CH2 ¬ O ¬ CH2 ¬ CH3
d. 4-heptanone b. CH3 ¬ CH2 ¬ CH2 ¬ CH2 ¬ CH2 ¬ O ¬ CH2 ¬ CH3
c. CH3 ¬ CH2 ¬ CH2 ¬ O ¬ CH2 ¬ CH2 ¬ CH3
77. Determine the product of the addition reaction.
d. CH3 ¬ CH2 ¬ O ¬ CH2 ¬ CH2 ¬ CH2 ¬ CH3
MISSED THIS? Read Section 22.10
84. Draw the structure for each ether.
O
a. ethyl propyl ether
NaCN
CH3 CH2 CH2 CH + H C N b. dibutyl ether
c. methyl hexyl ether
78. Determine the product of the addition reaction. d. dipentyl ether
O
NaCN
CH3 C CH2 CH3 + HCN

M22_TRO4371_05_SE_C22_988-1035v3.0.2.indd 1031 15/11/18 1:24 PM

 1032 CHAPTER 22 Organic Chemistry

Amines 87. Classify each amine reaction as acid–base or condensation and

list its products. MISSED THIS? Read Section 22.13
85. Name each amine. MISSED THIS? Read Section 22.13
a. CH3NHCH3 + HCl ¡
a. CH3 CH2 N CH2 CH3 b. CH3CH2NH2 + CH3CH2COOH ¡
CH3 CH2 N CH2 CH3
CH3 CH2 N CH2 CH3 c. CH3NH2 + H2SO4 ¡
H N(CH2CH3)3 + HNO3
H 88. ListN(CH
the products of HNO
each amine reaction.
CH CH2 H
CH2 N CH3 CH ) +
2 3 3 3
b. CH33 CH2 CH2 N CH3 a. N(CH2CH
CH3 CH2 CH2 N CH3 H 3)3 + HNO3
H H
H
H
CH3 CH3 N
H CH CH3 + HCN
CH3 b. CH3 N CH CH3 + HCN
CH3
CH3 CH2 CH2 N CH2 CH2 CH2 CH3 CH3 N CH3 CH + HCN
CH
CH CH2 CH2 N CH2 CH2 CH2 CH3 3
c. CH33 CH2 CH2 N CH2 CH2 CH2 CH3 CH3
H CH3
86. Draw the structure for each amine.
H
a. isopropylamine c. CH3 N CH CH3 +
H
b. triethylamine CH3 N CH CH3 +
c. butylethylamine CH3 N CH3
CH CH3 + CH3 O
CH3 CH3 O
CH3 CH3 CH
CH CH2 C
O OH
3
CH3 CH CH2 C OH
CH3 CH CH2 C OH

CUMULATIVE PROBLEMS CH3 O

O CH3 O
89. Identify each organic compound as an alkane, alkene, alkyne, CH3 CH2 CH
CH3 CH2 C
O OH
O
H3C hydrocarbon,
aromatic HC CH2 C O
alcohol, CH3 aldehyde, ketone, car-
ether, CH3 CH2 CH CH2 C OH
O
H3C acid,
HC ester,
CH2or amine,
C CHprovide c. CH3 CH2 CH CH2 C OH
boxylic O O and 3 a name for the H
H C HCCH3 CH C O CH
compound.
3 2 O 3 H
H3C CH3 CH
HC C O CH3 CH3 CH N
H CH2 CH2 CH2 CH3
2 O
H3C HCCH3 CHCH2 3 C O CH3 d. CH3 CH N CH2 CH2 CH2 CH3
a. H3C HCCH3 CH CH3 CH3 CH3
CH N CH2 CH2 CH2 CH3
CH23 C O
CH3 CHCH CH3
2 3 CH
CH3 CH2 O CH2 CH3
CH3 CHCH CH3
2 3 CHCH3 CH2 O CH2 CH3 CH2 OH
CH3 CH2 CH
CH3 CH 2 O CH 2 CH 3 CH2 OH
H2C CH3
CHC3 CH2 CH2 O CH2 CH3 e. CH3 CH CH2 CH
CH2 CH
OH3
H 2 CH 3
CH 3
b. CH3 CH2 CH CH2 O CH2 CH3 CH3 CH CH2 CH CH3
H2C CH3 CH3 CH2
CH CH23
CH CH CH3
CH3 CH2 CH CH2 O CH2 CH3
c. H2C CH3 CH2 CH3
H2C CHCH
3 3 CH2 CH3 O
H2C CHCH
3 3
f. CH3 CH2 CH2 C CH CH3
CH3 CH2 CH3
CH3 CH2 CH3 CH3
CH3 C CHC3 CH CH
CH2 CH CH23 CH3
CH3 C CHC3 CH CH 91. Name each compound.
CH
CH33
CH2 CH CH2
3
CH3 CH3
d. CH3 C C CH
CH3 CH CH CH CH3
CH2 2
CH3 3 CH CH CH CH CH
CH 3 CH 2 CH CH22 CH CH CH22 CH
CH22 CH
CH22 CH
CH33
CH3 C C CH CH3 CH CH2 CH CH23 CH3 CH33 CH22 CH CH 2 CH CH 2 CH 2 CH 2 CH 3
CH3 CH a. CH3 CH2 CH CH2 CH CH2 CH2 CH2 CH3
CH3 C C CH O CH2 CH3 HC
HC CH CH33
CH3 OCH HC CH 3
CH3 C C CH CH2 CH3 HC CH3
H3C CH2 CHCH CH
2 3 CH
O CH
CH2
2
2
e. H3C CH2 CHCH2 3 CH
O CH2
CH
CH33
H3C CH2 OH CH2 CH
O CH 3
CH3
H3C CH2 OH CH2 O CH
O
O
f. H3C CH 2 CH CH
OH 22 CH O
H3C CH2 CH
CH CH CH O
OH22 CH
CH33 CH
CH CH
CH22 C
C CH
CH22 CH
CH33
H
H3C 3 CHC CH b. CH3 CH CH 2 C CH 2 CH3
OH 2
CH3 CH CH2 C CH2 CH3
90. Identify 3C
H3C Heach
CH organic
CH2 compound as an alkane, alkene, alkyne,
OH CH
CH33
H C CH 3
aromatic CH CH2
H3C 3hydrocarbon, alcohol, ether, aldehyde, ketone, car- CH3
boxylic C ester,
H3C Hacid,
3CH CH2 or amine, and provide a name for the OH
OH
H3C OH
compound. H3C OH
H3C c. CH
CH33 CH
CH CH
CH CH
CH33
H3C CH3 CH CH CH3
H3C HC C C CH3 CH3 CH CH CH3
CH
CH33
a. H3C HC C C CH3 CH 3
CH3 CH3 CH3
CH
CH33
CH3 CH3 CH 3
CH3
CH3 CH3 CH
CH 2 CH
CH33
CH3 CH3 CH22 CH 3
CH2 CH3
b. CH3 C CH2 CH CH2 CH3 d. CH
CH33 CH
CH CH
CH CH
CH C
C C
C H
H
CH3 C CH2 CH CH2 CH3 CH 3 CH CH CH C C H
CH3 CH CH CH C C H
CH3 CH
CH33
CH3 CH 3
CH3

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 CH3

CH3 CH CH2 O CH2 CH3

CH3
Exercises 1033
CH3 CH2 CH2 O CH2 CH2
CH3 CH3
92. Name each compound. CH
CH33
CH3
CH3 c. CH3 O
CH3 CH CH C 3
CH CH
CH3 CH2 CH3
CH3 CH CH C CH CH2 CH3 CH3 CH CH2 C CH2 CH3
CH3 CH CH C CH CH2 CH3
a. CH3 CH CH CH
C 2 CH CH2 CH3
CH2 O
CH2
CH
CH32
CH3 CH3 CH CH2 C CH2
CH3
Br CH3
CH3 CH3
b. Br
Br
95. What minimum amount of hydrogen gas, in grams, is required
Br
to completely hydrogenate 15.5 kg of 2-butene?
96. How many kilograms of CO2 does the complete combustion of
CH2 CH3
CH2
CH2
CH3
CH3 3.8 kg of n-octane produce?
CH2 CHCH3 97. Classify each organic reaction as combustion, alkane substitu-
3 O CH3
CH3 O CH3 tion, alkene addition or hydrogenation, aromatic substitution,
CH3 O CH3
CH3 CH2 CH3 CH2
CH C
O O CH
CH3 CH3 or alcohol substitution, elimination, or oxidation.
c. CH3 CH2 CH CH2 C O CH CH3 22 CH
CH3CH
CH CH2 ++ 99 O
CH O2 CO2 ++ 66 H
66 CO H2O
O
CH3 CH2 CH CH2 C O CH CH3 a. 2 CH33CH CH22 + 9 O22 6 CO22 + 6 H22O
CH3 CH2 CH CH
O 2 C O CH CH3
b. CH CH2CH
CH3CH CH3 ++ Cl
Cl2 CH3CH
CH CH2CH
CH2Cl
Cl ++ HCl
HCl
O CH33CH22CH33 + Cl22 CH33CH22CH22Cl + HCl
O
d. CH3 CH CH2 CH
O H2SO
H SO4
CH3 CH CH2 CH c. CH
CH3 CH2
CH CH
CH CH2
CH OH
OH
2
H2SO4
4
CH3 CH CH2 CH CH33 CH22 CH CH22 OH
CH3 CH
CH3 CH2 CH
CH3 CH3
CH CH3 CH2 C CH CH2
CH CH C
93. DetermineCHwhether
3 the two structures are isomers or the same CH33 CH33 CH22 C CH22
CH3
molecule drawn in two different ways. CH3
O
O II CH
CH33
O I
CH
CH33 CH
CH22 C
C O
O CH
CH33 FeI3
FeI
a. CH CH C O CH d. ++ II22 ++ HI
HI
3
3 2 3 FeI3
O
O + I2 + HI
O
CH
CH33 C
C O
O CH
CH22 CH
CH33 98. Determine the products of each reaction.
CH 3 C O CH 2 CH 3
a. CH3 CH2 C CH2 + H2
II II
I I
II CH3
I
b.
b. CH3 CH2 CH2 CH2 OH + HCl
II
I
c. CH HC CH CH CH3 O
CH33
CH HC
HC CH
CH CH33
CH
3 3
CH c. CH3 CH2 CH CH2 C OH +
CH33 CH
CH CH3
3 CH33
CH CH3CH2OH
CH33
CH 3
CH
CH33 HC
HC CH
CH CH
CH33 H
CH 3 HC CH CH 3
CH
CH33 d. CH3 CH2 N CH2 CH3 + HCl
CH 3
94. Determine whether the two structures are isomers or the same
99. Draw the structure that corresponds to each name and indicate
molecule drawn two different ways.
which structures can exist as stereoisomers.
a. CH3 CH2 CH CH2 CH3
a. 3-methyl-1-pentene b. 3,5-dimethyl-2-hexene
CH3 c. 3-propyl-2-hexene
100. Identify the two compounds that display stereoisomerism and
CH3 draw their structures.
CH2 a. 3-methyl-3-pentanol b. 2-methyl-2-pentanol
c. 3-methyl-2-pentanol d. 2-methyl-3-pentanol
CH3 CH2 CH CH3 e. 2,4-dimethyl-3-pentanol
b. CH3 101. There are 11 structures (ignoring stereoisomerism) with the
formula C4H8O that have no carbon branches. Draw the
CH3 CH CH2 O CH2 CH3 structures and identify the functional groups in each.
102. There are eight structures with the formula C3H7NO in which
CH3
the O is part of a carbonyl group. Draw the structures and
CH3 CH2 CH2 O CH2 CH2 identify the functional groups in each.
103. Explain why carboxylic acids are much stronger acids than
CH3 O
alcohols.
CH3 CH CH2 C CH2 CH3 104. The hydrogen at C-1 of 1-butyne is much more acidic than the
one at C-1 in 1-butene. Explain.
O

CH3 CH CH2 C CH2

CH3 CH3

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 1034 CHAPTER 22 Organic Chemistry

CHALLENGE PROBLEMS
105. Determine the one or two steps it takes to get from the starting 107. For the chlorination of propane, the two isomers shown here
material to the product using the reactions found in this are possible.
chapter. CH3CH2CH3 + Cl2
O O Cl
C H2C C
H2C OH CH3 CH2 CH2 Cl + CH3 CH CH3
a. O 1-Chloropropane 2-Chloropropane
H2C OH
C H2C C
Propane has six hydrogen atoms on terminal carbon atoms—
O called primary (1°) hydrogen atoms—and two hydrogen atoms on
O
the interior carbon atom—called secondary (2°) hydrogen atoms.
CH2 OH a. If the two different types of hydrogen atoms were equally
reactive, what ratio of 1-chloropropane to 2-chloropropane
b. CH3 CH CH2 CH CH3
would we expect as monochlorination products?
CH2 CH3 b. The result of a reaction yields 55% 2-chloropropane and
CH2 45% 1-chloropropane. What can we conclude about the
relative reactivity of the two different kinds of hydrogen
CH3 CH CH2 C CH3 atoms? Determine a ratio of the reactivity of one type of
CH2 CH3 hydrogen atom to the other.
108. There are two isomers of C4H10. Suppose that each isomer is
Br treated with Cl2 and the products that have the composition
C4H8Cl2 are isolated. Find the number of different products that
c. CH3 CH2 C CH2 CH3 CH2 C CH3 form from each of the original C4H10 compounds. Do not con-
sider optical isomerism.
CH3 CH3
109. Identify the compounds formed in the previous problem that
are chiral.
106. Given the following synthesis of ethyl 3-chloro-3-methylbu-
tanoate, fill in the missing intermediates or reactants. 110. Nitromethane has the formula CH3NO2, with the N bonded to
the C and without O ¬ O bonds. Draw its two most important
(a) contributing structures.
CH3 CH CH2 CH2 OH (b)
a. What is the hybridization of the C, and how many hybrid
CH3 orbitals are in the molecule?
b. What is the shortest bond?
c. Between which two atoms is the strongest bond found?
O d. Predict whether the HCH bond angles are greater or less
(c) than 109.5° and justify your prediction.
CH3 CH CH2 C O CH2 CH3
111. Free radical fluorination of methane is uncontrollably violent,
CH3 and free radical iodination of methane is a very poor reaction.
Explain these observations in light of bond energies.
Cl O 112. There are two compounds with the formula C3H6, one of which
(d) does not have a multiple bond. Draw its structure and explain
CH3 C CH2 C O CH2 CH3 why it is much less stable than the isomer with the double bond.
CH3 113. Consider molecules that have two carbons and two chlorines.
Draw the structures of three of these with no dipole moment
and two with a dipole moment.

Cl
CONCEPTUAL PROBLEMS
HC Cl CH
3
114. Pick the more oxidized structure in each pair. 115. DrawClthe structure and name a compound with the formula
HC CH3
C 8H18 that
HC CHforms only one product CH
with
3 the formula C8H17Br
O 3
when it is treated with Br2. CH3
CH3 whether each structure CH
116. Determine CH
is chiral.
3 CH CH3
a. CH3 CH or CH3 CH2 OH
a. Cl b. CH3 CH
Cl CH
CH3 CH3
CH3 CH CH CH3
b. CH3 CH2 OH or CH3 CH3 HC CH3 Cl CH3
Cl CH3 CH3 CH2 OH
O O CH3
CH3 CH2 OH
c. CH3 CH2 OH d. Cl
c. CH3 CH2 CH or CH3 CH2 C OH CH3 CH CH CH3
Cl
HC CH2
Cl Cl CH3
HC
CH3 CH
Br 2
HC CH2
CH3 CH2 OH CH3 Br
CH3 Br
Cl

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