APPENDIX A
ANSWERS TO THE SELF-TESTS
CHAPTER 1
A-1.
(a) P; 1s 22s 22p63s 23p3
(b)
A-2.
(a)
(c)
Formal
charge:
N
C
S
1
0
0
O
(b)
Formal
charge:
A-3.
N
1
(a)
Formal
charge:
(b)
1 1
C
0
0 1
O
N
O
0 1
0
O
HC
Net charge: 1
Formal
charge:
NH2
0 1
Net charge: 0
Net charge: 1
S
Net charge: 1
Net charge: 1
O
0
HC
(c)
1
O
N
Formal
charge:
S2; 1s 22s 22p63s 23p6
Formal
charge:
NH2
0
0
Net charge: 0
The more stable Lewis structures are
O
(a)
N
C
S
(b)
O
N
O
(c)
HC
H
A-4.
(a)
H
C
N
H
H
H
(b)
H
NH2
H
H
C
C
O
H
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APPENDIX A
O
A-5.
(a)
C12H20O
(c)
C14H24O
(d)
C9H6BrN
OH
(b) C10H22
N
A-6.
Br
has only sp3-hybridized carbon atoms
(a)
has only sp2-hybridized carbon atoms
(b)
Br
N
O
has only one sp2-hybridized carbon atom
(c)
O
A-7.
S2
O
O
O
C
N
Formal
charge: 1
0
0
A-8.
(a)
H
C
S2
S2
O
O
H
H
H
C
C
C
Trigonal
planar
H
O
H
Tetrahedral
O
O
O
Net charge: 1
H
A-9.
O
Bent
H
Tetrahedral
Cl Cl
(b)
Pyramidal;
N
yes, it is polar.
Cl
A-10. (a)
Linear
A-11. (a)
(b)
D
A, B
(b)
(c)
(d)
Linear
None
B
(c)
(e)
(f)
Bent
None
A, D
(g)
(h)
A
C
O
A-12. H
N
C
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APPENDIX A
A-13. (a)
11 ; 1 A-14. (a)
H3C
9 ; 2 (b)
CH
sp3
CH
12 ; 4 (c)
(d)
(c) All carbons are sp2.
CH3
sp3
sp2
sp2
sp
O
(b)
H
C
C
CH2
(b)
(a)
(b)
(d )
B-2.
B-6.
B-10.
B-14.
(d)
CH3
C
sp2
sp3
sp
B-1.
B-5.
B-9.
B-13.
13 ; 4 (b)
(b)
(d)
(b)
B-3.
B-7.
B-11.
B-15.
(c)
(a)
(b)
(d)
N
sp3
B-4. (d)
B-8. (d)
B-12. (e)
CHAPTER 2
A-1.
Common:
Systematic:
CH3CH2CH2CH2
CH3CH2CHCH3
n-Butyl
Butyl
sec-Butyl
1-Methylpropyl
CH3
CH3
CH3CHCH2
CH3C
CH3
Common:
Systematic:
Isobutyl
2-Methylpropyl
A-2.
(a)
28 (8 CGC; 20 CGH)
A-3.
(a)
Oxidized
(b)
tert-Butyl
1,1-Dimethylethyl
Neither
(b)
27(9 CGC; 18 CGH)
(c)
Neither
(b)
Six methyl groups, three isopropyl
groups
(b)
(1,2-Dimethylpropyl)cyclohexane
(d)
Reduced
CH3CHCH3
A-4.
(a)
CH3CHCHCHCH3
CH3
A-5.
(a)
A-6.
(a)
(b)
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CH3
3,4-Dimethylheptane
Primary
Secondary
Tertiary
4
3
3
5
2
3
1,3-Dimethylbutyl; secondary
1,1-Diethylpropyl; tertiary
2,2-Diethylbutyl; primary
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APPENDIX A
CH3
A-8.
CH3CHCHCH2CH3 C7H16
C7H16 11O2
7CO2 8H2O
CH3
A-9.
Cyclopentane
Methylcyclobutane
1,1-Dimethylcyclopropane
1,2-Dimethylcyclopropane
A-10. (a)
Ethylcyclopropane
(c)
4-Ethyl-3-methylheptane
3-Ethyl-2,3dimethylhexane
(b)
(2-Methylbutyl)cyclohexane
A-11. (a) CH3CH2CH2CH2CH2CH2CH2CH3
(c)
(CH3)2CHCHCH(CH3)2
CH3
(b) (CH3)3CC(CH3)3
(d)
(CH3)3CC(CH3)3
2,2-Dimethylpentane
2,4-Dimethylpentane
A-12.
2,3-Dimethylpentane
3-Ethylpentane
3,3-Dimethylpentane
A-13. Alcohol, alkene, ester, ketone
A-14. 10,049 kJ/mol
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B-1.
B-5.
B-9.
B-13.
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(b)
(a)
(d )
B-2.
B-6.
B-10.
B-14.
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(d)
(a)
(a)
(d )
B-3. (d)
B-7. (c)
B-11. (b)
B-4. (c)
B-8. (c)
B-12. (e)
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APPENDIX A
CHAPTER 3
Cl
A-1.
Cl
H
H
CH3
H
H
H
H
H
H
CH3
Gauche
Anti
H3C CH3
A-2.
(a)
Cl
Cl
Cl
Cl
H
H
Cl
Cl
(b)
H
H
H
H
Cl
H
H
Cl
(Eclipsed)
A-3.
(CH3)3CCH2C(CH3)3 2,2,4,4-tetramethylpentane
A-4.
(CH3)3C
H
H
CH3
CH3
Axial
H
A-5.
(CH3)3C
Equatorial
H
A-6.
CH3
H
H
HO
O
H
HO
A-7.
(a)
C
Equatorial
OH
OH
(b)
H
A and B
(c)
CH(CH3)2
A-8.
H
D
(d) A
CH3
H
CH(CH3)2
H3C
H
H
More stable
A-9.
cis-1-Ethyl-3-methylcyclohexane has the lower heat of combustion.
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A-10. Tricyclic; C10H16
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APPENDIX A
A-11. The form of the curve more closely resembles ethane than butane.
HH
CH3
H
Potential energy
H
CH3
H
H
CH3
H
H
H
H3C
H
H
H
CH3
CH3
Torsion angle
A-12.
S
B-1.
B-5.
B-9.
B-13.
(d)
(c)
(c)
(d )
A-1.
(a)
(b)
B-2.
B-6.
B-10.
B-14.
(b)
(a)
(e)
(b)
B-3. (c)
B-7. (d)
B-11. (b)
B-4. (a)
B-8. (e)
B-12. (a)
CHAPTER 4
trans-1-Bromo-3-methylcyclopentane
2-Ethyl-4-methyl-1-hexanol
OH
CH3
A-2.
(a)
ICH2CCH2CH2CH2CH2CH3
(b)
CH(CH3)2
Cl
A-3.
(a)
(b)
A-4.
Functional class: 1-ethyl-3-methylbutyl alcohol
Substitutive:
5-methyl-3-hexanol
Functional class: 1,1,2-trimethylbutyl chloride
Substitutive:
2-chloro-2,3-dimethylpentane
Conjugate acid CH3OH2 ; conjugate base CH3O OH
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APPENDIX A
A-6.
(a)
CH3CH2O NH3
Conjugate
base
CH3CH2OH NH2 (K 1)
Conjugate
acid
A-7.
(b)
CH3CH2O
(a)
Three
Stronger
acid
Stronger
base
H
NH2
CH3
CH3 CH3
CH3
CH3
CH3CHCHCHCH3
(b, c) CH3CCH2CHCH3
CH2CHCH2CHCH3
(Least stable)
(Most stable)
CH3
A-8.
CH3
CH3CCH3 Cl2
CH3CCH2Cl HCl
CH3
A-9.
CH3
CH3
Br HBr Br
Br2
Br
A-10. H ° 57 kJ (13.5 kcal)
A-11. (a)
(CH3)3C
OH H
(CH3)3C
OH2
Br
CH3
(b)
C
(CH3)3C
Br
H
O
H
H3C
(c)
OH2 Br
H2O (CH3)3C
(CH3)3C Br H3C
(CH3)3C
Water is displaced directly from the oxonium ion of 1-butanol by bromide ion. A primary carbocation is not involved.
Br CH3CH2CH2CH2
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A-12. (a)
(b)
B-1. (e)
B-5. (e)
B-9. (c)
B-13. (a)
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H2O CH3CH2CH2CH2Br
OH2
3-Methyl-3-pentanol
KOC(CH3)3
B-2. (c)
B-3.
B-6. (c)
B-7.
B-10. (d)
B-11.
B-14. (c)
B-15.
(c)
(d)
(b)
(d)
(c)
(c)
Fluorine (F2)
.
Ethyl radical, CH3CH2
B-4. (c)
B-8. (a)
B-12. (e)
B-16. (c)
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Cl2
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APPENDIX A
CHAPTER 5
A-1.
A-2.
(a)
2,4,4-Trimethyl-2-pentene
(b)
(E)-3,5-Dimethyl-4-octene
(c)
(E)-2,7-Dibromo-3-(2-methylpropyl)2-heptene
(d) 5-Methyl-4-hexen-3-ol
(a)
(c)
2,3-Dimethyl-2-pentene
1,6-Dimethylcyclohexene
Cl
OH
(b)
(d)
4-Methyl-4-penten-2-ol
5-Chloro-2-methyl-1-hexene
A-3.
(a)
1
(b)
2
Isomer 5
3
(c)
Isomers 1 and 4
3
2
4
2
A-4.
Two sp C atoms; four sp C atoms; three sp
A-5.
(a)
(d)
5
6
Isomers 2 and 3
sp bonds
3
(c)
OH
Cl
(b)
Cl
A-6.
(Z )-3-Methyl-3-hexene
A-7.
(a)
(E)-3-Methyl-3-hexene
CCH2CH2CH3 (CH3)2C
H2C
CHCH2CH3 (major)
CH3
CH3
CH2
(b)
(major)
X
(c)
(CH3)2CHCHCH(CH3)2
(X Cl, Br, I)
CH3
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APPENDIX A
CH3
A-8.
CH3CH2CCH2Br
CH3
A-9.
Step 1: Protonation
OH
H
OH2
OH2
Step 2: Dissociation
OH2
H2O
Step 3: Deprotonation
H3O
OH2
H
H
NaOCH2CH3
A-10.
CH3CH2OH
Br
(major)
CH3O CH3
H
CH3
Br
A-11.
Br
A-12. Cis isomer:
(CH3)2CH
(CH3)2CH
Cl
Cl
Trans isomer:
CH(CH3)2
(CH3)2CH
Cl
Cl
The trans isomer will react faster because its most stable conformation (with the isopropyl
group equatorial) has an axial Cl able to undergo E2 elimination.
A-13. Rearrangement (hydride migration) occurs to form a more stable carbocation.
H3PO4
OH
OH2
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H
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H
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APPENDIX A
A-14.
3-Ethyl-4,4-dimethyl-2-pentene
Br
A
B-1.
B-5.
B-9.
B-13.
(c)
(a)
(a)
(a)
A-1.
Five;
B
B-2.
B-6.
B-10.
B-14.
(c)
(b)
(d)
(c)
B-3.
B-7.
B-11.
B-15.
(d)
(a)
(b)
(a)
B-4. (c)
B-8. (a)
B-12. (c)
CHAPTER 6
3,4-Dimethyl1-pentene
2,3-Dimethyl2-pentene
(E)-3,4-Dimethyl2-pentene
2,3-Dimethyl1-pentene
(Z)-3,4-Dimethyl2-pentene
OH
A-2.
(a)
(CH3)2CCH2CH3
(c)
(b) HBr, peroxides
CH3
OH
(d)
Br
A-3.
(a)
CH3
OH
H2SO4 (conc)
heat
CH3
1. B2H6
CH3
2. H2O2, HO
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APPENDIX A
(b)
O
Cl
NaOCH3
CH3CH2CHCH(CH3)2
CH3CH2CH
CH3OH
O
CH3COOH
C(CH3)2
CH3CH2CH C(CH3)2
(c)
CH3ONa
(CH3)3CCHCH3
CH3OH
(CH3)3CCH
ROOR
or heat
CH2
HBr
Peroxides
(CH3)3CCH2CH2Br
Br
A-4.
Initiation:
light
2RO
RO HBr
Br
Propagation:
ROH Br
CH3CH2CH
CH2
CH3CH2CHCH2Br
CH3CH2CHCH2Br HBr
CH3CH2CH2CH2Br Br
A-5.
C
Cl2
C
H3C
H
H3C
H
C
C
C
H
CH3
Cl CH3CH2
CH2CH3
C
C
H
A-7.
Cl
Cl
CH3
H
(E)-2-Butene
A-6.
H3C H
Cl
C C
C
H
H
Cl
H3C
H3C
Cl
CH3
H
O
O
CH3COOH
CH3CH2
H
H
C
C
CH2CH3
H
Step 1: Protonation to form a carbocation
H
Cl
Cl Step 2: Nucleophilic addition of chloride ion
Cl Cl
CH3
A-8.
H2C
CCH2CH3
Cl
or
(CH3)2C
CHCH3
HCl
CH3CCH2CH3
CH3
2-Methyl-1-butene
2-Methyl-2-butene
2-Chloro-2methylbutane
A-9.
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OH
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APPENDIX A
HCl
A-10.
hydride
shift
Cl Cl Cl
Cl
CH3
A-11. (CH3)2CHC
CH3
HBr
CH2
(CH3)2CHCCH3
NaOCH2CH3
CH3CH2OH
(CH3)2C
C(CH3)2
Br
B
A
C
1. O3
(CH3)2C
2. H2O, Zn
C
O (2 mol)
B-1.
(c)
B-2.
(a)
B-3.
(c)
B-4.
(d)
B-5.
(d)
B-6.
(e)
B-7.
(b)
B-8.
(b)
B-9.
(b)
B-10. (b)
B-11. (a)
B-12. (e)
B-13. (e)
CHAPTER 7
A-1.
(a)
(b)
(c)
(d)
(e)
A-2.
3:
1 and 2, both achiral; identical
3 and 4, both chiral; enantiomers
5 chiral, 6 achiral (meso); diastereomers
7 and 8, both chiral; diastereomers
9 and 10, both chiral; diastereomers
(R)-2-Chlorobutane;
R
R
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OH
6:
7:
(2S,3R)-2,3-Dibromopentane;
8:
9:
(2E,5R)-5-Chloro-2-hexene;
10:
(a) Three; meso form is possible.
(b) Eight; no meso form possible.
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(S)-2-Chlorobutane
HO
OH
5:
A-3.
4:
HO
S
R
(2R,3R)-2,3-Dibromopentane
(2Z,5S)-5-Chloro-2-hexene
(c) Four; no meso form possible.
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APPENDIX A
H3C
A-4.
(a)
Cl
H
C
C
OH
H
CH3
(b)
CH3
H
H
Br
H
CH3
(c)
CH3
H
HO
H
A-5.
CH3
H
H
H
Cl
CH3
Br
CH3
Chiral stereoisomers:
CH3
H
Cl
Cl
CH3
Cl
H
and
H
H
Cl
CH3
CH3
(2S,3S)-2,3Dichlorobutane
Meso stereoisomer (achiral);
plane of symmetry indicated
with dashed line
(2R,3R)-2,3Dichlorobutane
H
CH3
Cl
H
Cl
CH3
meso-2,3-Dichlorobutane
A-6.
A-7.
(a)
[] 31.2°
(b)
CH3
CH3
(a)
HBr
CH3
Br
(b)
C
H
CH3
CH3 CH3
CH3
CH3
Br
CH3
H CH
Cl
H
H3C
30% S
Cl2
C
H3C
CH3
3
C
H
C
Cl
Meso form
(only stereoisomer)
O
(c)
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O
CH3COOH
H
H3C
HC
H
3
CH2CH3
H
O
CH2CH3
H
(2S,3S)-1,3-Dibromo-2-chlorobutane
(R)-1-Ethylcyclohex-2-en-1-ol
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APPENDIX A
A-9.
Two: (2R,3S)-2-bromo-3-chlorobutane and (2S,3S)-2-bromo-3-chlorobutane; they are diastereomers.
A-10.
OH
Racemic mixture
B-1.
B-5.
B-9.
B-13.
(c)
(b)
(b)
(e)
A-1.
(a)
B-2.
B-6.
B-10.
B-14.
(c)
(c)
(c)
(b)
B-3. (b)
B-7. (d)
B-11. (d )
B-4. (d)
B-8. (d)
B-12. (d)
CHAPTER 8
CH3CH2CH2CH2OCH2CH3
C(CH3)3
(e)
N3
X
(b)
( f)
CH3S
H
CH3
(X OTs, Br, I)
CH3
H
HS
CH3
(c)
CH3CHCH2CH2I
(g)
H
F
CH2CH3
(d)
A-2.
A-3.
(CH3)2CHONa CH3CH2CH2Br
(a)
CH3
H
OTs
CH2CH3
NaBr
DMSO
CH3
Br
H
CH2CH3
NaCN
CH3
H
CN
CH2CH3
(b)
CH3CH2CH2 H
C
H3 C
OH
CH3CH2CH2 H
C
SO2Cl
pyridine
H3C
A-4.
▲
▲
CH3
|
CH3S
H CH CH CH
2
2
3
C
CH3
Step 1: Ionization to form a secondary carbocation
CH3C
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H3C
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Cl
CHCH3
CH3
H2 O
CHCH3 Cl
CH3C
CH3
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APPENDIX A
Step 2: Rearrangement by methyl migration to form a more stable tertiary carbocation
CH3
CH3
CH3C
CHCH3
CH3C
CH3
CHCH3
CH3
Step 3: Capture of the carbocation by water, followed by deprotonation
CH3
CH3C
H2O
H2 O
CHCH3
CH3C
CH3
A-5.
(a)
CH3
OH
CHCH3
H
(CH3)2C
CH(CH3)2
CH3
(CH3)3CBr
CH3OH
(CH3)3COCH3
SN1, unimolecular substitution; rate k[(CH3)3CBr]
Cl
(b)
NaN3
N3
SN2, bimolecular substitution; rate k[C6H11Cl][NaN3]
A-6.
(a)
(b)
Sodium iodide is soluble in acetone, whereas the byproduct of the reaction, sodium
bromide, is not. According to Le Chatelier’s principle, the reaction will shift in the
direction that will replace the component removed from solution, in this case toward
product.
Protic solvents such as water form hydrogen bonds to anionic nucleophiles, thus stabilizing them and decreasing their nucleophilic strength. Aprotic solvents such as DMSO
do not solvate anions very strongly, leaving them more able to express their nucleophilic character.
O Na
OH
A-7.
A
CH3CH2OH
CH3CH2Br
C
D
B
CH3
H3C Br
slow
A-8.
CH3
H3C
H3C
H
OCH2CH3
fast
HOCH2CH3
H
OCH2CH3
H3C
OCH2CH3
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H
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APPENDIX A
A-9.
Dissociation to give a secondary carbocation
CH3CH2CH2CHCH(CH3)2
CH3CH2CH2CHCH(CH3)2
Br
Rearrangement by hydride migration to give a tertiary carbocation
CH3CH2CH2CHC(CH3)2
CH3CH2CH2CH2C(CH3)2
H
Capture of the carbocation by water to give product
OH
CH3CH2CH2CH2C(CH3)2 OH2
B-2.
B-6.
B-10.
B-14.
(c)
(a)
(a)
(c)
B-3. (d)
B-7. (c)
B-11. (a)
(H)
CH3CH2CH2CH2C(CH3)2
B-1.
B-5.
B-9.
B-13.
(b)
(d)
(c)
(c)
B-4. (c)
B-8. (d )
B-12. (c)
A-1.
(a)
(b)
4,5-Dimethyl-2-hexyne
4-Ethyl-3-propyl-1-heptyne
(c)
6,6-Dimethylcyclodecyne
A-2.
(a)
Cl
(e)
(CH3)2CHC
CHAPTER 9
CH3CH2CH2C
CH
CH2
Cl
(b)
( f ) Na, NH3(l)
CH3CH2CH2CCH3
Cl
Cl
H3C
(c)
(g)
H2O, H2SO4, HgSO4
C
Cl
(d)
C
H
A-3.
CH2CH3
CH3
CH3
H3C
C
(h)
C
CH3CH2CH2CHCO2H CH3CH2CO2H
H
Reaction (2) is effective; the desired product is formed by an SN2 reaction.
CH3
CH3CH2CHC
CH3
CNa CH3I
CH3CH2CHC
CCH3 NaI
Reaction (1) is not effective, owing to E2 elimination from the secondary bromide.
Br
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APPENDIX A
A-4.
(a)
CH3CH2Br
KOC(CH3)3
H2C
DMSO
1. NaNH2, NH3
BrCH2CH2Br
2. H2O
Br2
CH2
HC
BrCH2CH2Br
1. NaNH2
CH
HC
2. CH3CH2Br
CCH2CH3
(b)
HC
NaNH2
CCH2CH3
NaC
CCH2CH3
CH3CH2Br
CH3CH2C
CCH2CH3
(c)
Cl
H2C
CHCH2CH3
HC
CCH2CH3
(d)
HC
CH
Cl2
As in part (b)
NaNH2
1. 3NaNH2, NH3
ClCH2CHCH2CH3
CH3CH2C
HC
2. H2O
HC
CCH2CH3
CCH2CH3
(CH3)2CHCH2Br
CNa
HC
CCH2CH(CH3)2
O
HC
CCH2CH(CH3)2
CH3CCH2CH(CH3)2
HgSO4
H
H3C
C
A-5.
H2O, H2SO4
C
CH2CH2CH2CH3
H
(E)-2-Heptene
A-6.
(CH3)3CC
CH
(CH3)3CC
B
A
A-7.
CH3CH2CH2OH
CH3CH2CH2Br
C
D
E: HC
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CCH2CH3
C
A-8.
B-1.
B-5.
B-9.
C Na
(a)
(b)
(b)
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CH
B-2. (c)
B-6. (b)
B-10. (a)
F: CH3CH2C
H2
Lindlar Pd
B-3. (a)
B-7. (e)
B-11. (d)
CCH2CH3
CH
CH2
1. B2H6
2. H2O2, HO
CH2CH2OH
B-4. (d)
B-8. (c)
B-12. (b)
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APPENDIX A
CHAPTER 10
A-1.
H2C
CHCH2CH
CH2
H2C
CHCH
CHCH3
(Conjugated)
H2C
CHC
CH2
CH3
H2C
C
CHCH2CH3
H2C
C
C(CH3)2
CH3CH
C
Allenes
CHCH3
(Conjugated)
H2C
CH
C
A-2.
H2C
CH3
H
CH
C
C
H
H
CHC
CH2
CH3
CH3
H
(3Z)-1,3-Pentadiene
H2C
C
(3E)-1,3-Pentadiene
2-Methyl-1,3-butadiene
A-3.
OH
H2 O
H2 O
Br
CH3
CH3
Br
A-4.
(a)
CH3CH
OH
CH3
CH3
CH3
Br
CHCHCHCH3 CH3CHCH
CHCHCH3
Br
Br
(Direct addition)
(Conjugate addition)
Cl
(b)
H2C
CHCHCH3 ClCH2CH
CHCH3
O
O
(c)
O
(d)
O
(e)
N
Br (NBS), heat
O
CO2CH3
CO2CH3
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APPENDIX A
CH3
A-6.
C
Br
Br
CH3
C
CH3
CH3
CH3
CH3
Br
C
C
CH3
CH3
Br
Br
A-7.
I
A:
B:
Br
Br2
CH3CH2ONa
light, heat
CH3CH2OH
A-8.
B-1.
B-5.
B-9.
(b)
(a)
(a)
A-1.
(a)
(b)
B-2. (c)
B-6. (d)
B-10. (d)
B-3.
B-7.
(a)
(a)
B-4.
B-8.
Br
NBS
heat
(c)
(a)
CHAPTER 11
m-Bromotoluene
2-Chloro-3-phenylbutane
CO2H
(c) o-Chloroacetophenone
(d) 2,4-Dinitrophenol
OCH3
NH2
CH2Cl
CH3
A-2.
(a)
(b)
Cl
(c)
Cl
Br
NO2
A-3.
(a)
(d)
CH3
(b)
(10 electrons)
(14 electrons)
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(c)
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Eight electrons. No, the substance is not aromatic.
6 electrons. Yes, it is aromatic.
14 electrons. Yes, it is aromatic.
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APPENDIX A
A-5.
Br
A-6.
(a)
(d) Na2Cr2O7, H2SO4, H2O, heat
(b) C6H5CH2X (X Cl, Br, I, OTs)
(e)
O
OH
(c)
C6H5CHCHCH3
(f)
OH
Br
Br
A-7.
C6H5CH
(I)
HBr
CHCH3
C6H5CHCH2CH3
Br
Br2
(II) C6H5CH2CH2CH3
CH
light
(or NBS, heat)
CH3
CH
C6H5CHCH2CH3
CH3
CH3
CH
A-8.
CH3
CH
A-9.
A-10. (CH3)3C
B-1.
B-5.
B-9.
B-13.
(c)
(a)
(b)
(c)
CH2CH3
B-2.
B-6.
B-10.
B-14.
(c)
(d)
(d)
(d)
B-3.
B-7.
B-11.
B-15.
(a)
(b)
(a)
(c)
B-4. (b)
B-8. (d)
B-12. (b)
CHAPTER 12
A-1.
CH3
CH3
H
Br
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APPENDIX A
HO3S
NO2
A-2.
(a)
(c)
Cl
Cl
SO3H
NO2
Slower
Slower
CH2CH3
Br
CH2CH3
(b)
Br
Faster
A-3.
(a)
NO2
(b)
Br
Br
FeBr3
(c)
SO3
O
O
CCH(CH3)2
NO2
A-4.
(a)
(d)
C(CH3)3
(b)
(e)
S
H3C
CH3
O
(c)
Cl
O O
C6H5CCl, AlCl3
CH3COCCH3, AlCl3
or
NO2
O
O
Cl
A-5.
(a)
(c)
Cl
CH3
Cl
Cl
CN
Cl
CN
(b)
(d)
CH3CH2
OH
Cl
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APPENDIX A
A-6.
(a)
SO3
CH(CH3)2
HO3S
H2SO4
Na2Cr2O7, H2O
CH(CH3)2
HO3S
H2SO4, heat
CO2H
( ortho isomer)
O
O
C6H5CH2CCl
(b)
O
Cl2, FeCl3
CCH2C6H5
AlCl3
CCH2C6H5
Cl
Zn(Hg), HCl
or N2H4, KOH,
heat
CH2CH2C6H5
Cl
O
CH
N2H4, KOH, heat
(c)
O
CH3
CH3
(CH3C)2O
or Zn(Hg), HCl
AlCl3
CH3C
O
Br
(d)
H2SO4
Br2
heat
FeBr3
SO3H
SO3H
(e)
(CH3)2CHCl
CH3
A-7.
(a)
HNO3
(CH3)2CH
AlCl3
(CH3)2CH
H2SO4
CO2H
NO2
CO2H
Na2Cr2O7
HNO3 (excess)
H2O, H2SO4, heat
H2SO4
NO2
O2N
(b)
Br
(CH3)2CH
NO2
Br2
light
(CH3)2C
CH3
NO2
NaOCH2CH3
H2C
C
NO2
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[Prepared from benzene as in
Problem A-6(e)]
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APPENDIX A
(c)
CH3
CH3
O
CH3
(CH3)2CHCCl
Cl2
AlCl3
FeCl3
O
CH3
Cl
Cl
Zn(Hg), HCl
CCH(CH3)2
CCH(CH3)2
O
CH2CH(CH3)2
A-8.
HNO3
CH3O
CH3O
H2SO4
Br2
NO2
CH3O
FeBr3
Br
( ortho)
B-1.
B-5.
B-9.
B-13.
(c)
(a)
(c)
(c)
A-1.
1:
2:
A-2.
(a)
B-2.
B-6.
B-10.
B-14.
(b)
(b)
(a)
(c)
B-3.
B-7.
B-11.
B-15.
(c)
(c)
(e)
(c)
NO2
B-4. (b)
B-8. (b)
B-12. (c)
CHAPTER 13
6.10 ppm
1305 Hz
3:
4:
Two signals
BrCH2CH2CH2Br
a
a:
200 MHz
0.00 ppm
b
triplet
b:
a
pentet
Cl
(b)
CH3CH2CCH2CH3
Two signals
a
a:
(c)
b
triplet
a
Three signals, all singlets
O
A-3.
b
Cl
b: quartet
O
A: CH3COC(CH3)3
B: CH3OCC(CH3)3
O
A-4.
CH2CCH2CH3
(a)
HO
(b)
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HC(COCH2CH3)3
(c)
OH
OH
C(CH3)2
Seven signals:
a: 10–30 ppm
b: 20–40 ppm
c: 190–220 ppm
d–g: 110–175 ppm
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(CH3)2C
(d)
C
N
O
g
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f
e
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c b
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APPENDIX A
A-6.
Pentane: three signals; 2-methylbutane: four signals; 2,2-dimethylpropane: two signals
A-7.
2,3-Dimethylbutane: (CH3)2CHCH(CH3)2
B-1.
B-5.
B-9.
B-13.
(d)
(b)
(c)
(a)
B-2.
B-6.
B-10.
B-14.
A-1.
(a)
X
(a)
(a)
(a)
(a)
B-3.
B-7.
B-11.
B-15.
(b)
(b)
(c)
(d)
B-4. (b)
B-8. (a)
B-12. (c)
CHAPTER 14
Li
2Li
LiX
(X Cl, Br, I)
(b)
(CH3)3CBr Mg
(c)
2C6H5CH2Li CuX
(CH3)3CMgBr
(C6H5CH2)2CuLi LiX
(X Cl, Br, I)
HO
OH
A-2.
(a)
(C6H5)2CCH3 CH3CH2OH
CH2CH3
(d)
Br
(b)
(CH3)2CHCH2D
(e)
H3C
H
H3C
(c)
Br
H
CH3
CH2OH
O
A-3.
(a)
O
C6H5CH (CH3)3CMgX
and
(X Cl, Br, I)
C6H5MgX (CH3)3CCH
(X Cl, Br, I)
(b)
O
O
CH3CH2CH2CH CH3CH2CH2CH2MgX
and
CH3CH2CH2CH2CH CH3CH2CH2MgX
(X Cl, Br, I)
A-4.
(a)
(b)
(CH3CH2CH2)2CuLi
(CH3)2CHMgX
(X Cl, Br, I)
(c)
CH2I2, Zn(Cu)
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(X Cl, Br, I)
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APPENDIX A
A-5.
Solvents A, B, and E are suitable; they are all ethers. Solvents C and F have acidic hydrogens
and will react with a Grignard reagent. Solvent D is an ester which will react with a Grignard
reagent.
A-6.
CH3(CH2)3OH
PBr3
or HBr
2Li
CH3(CH2)3Br
2CH3(CH2)3Li CuBr
CH3(CH2)3Li LiBr
CH3(CH2)3Br
(C4H9)2CuLi
CH3(CH2)6CH3
O
A-7.
(I)
(CH3)2CHCCH3 CH3MgBr
OH
1. diethyl ether
O
(II)
(CH3)2CHC(CH3)2
2. H3O
CH3CCH3 (CH3)2CHMgBr
(III) (CH3)2CHCO2CH3 2CH3MgBr
CH3
Br
A-8.
NBS
peroxides, heat
C6H5CH2CH3
CH3
C6H5CHCH3
C6H5CHMgBr
2. H3O
C6H5CHMgBr
diethyl ether
CH3
O
1. CH3CH
Mg
C6H5CHCHCH3
OH
OH
A-9.
CCH2CH3
(a)
OH
(c)
C
CH3
CCH3
(b)
OH
B-1.
B-5.
B-9.
(c)
(e)
(e)
B-2. (a)
B-6. (c)
B-10. (b)
B-3. (d)
B-7. (b)
B-11. (b)
B-4. (a)
B-8. (a)
B-12. (b)
CHAPTER 15
O
A-1.
(a)
(d)
OsO4, (CH3)3COOH, (CH3)3COH, HO
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C6H5CO2CH2CH3
(c)
1. B2H6; 2. H2O2, HO
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APPENDIX A
O
A-2.
C6H5CH2CH
(a)
(c)
(C6H5CH2CH2)2O
O
(b)
(d) K2Cr2O7, H+, H2O, heat
CH3CCl, pyridine; or
O
(CH3C)2O; or CH3CO2H, H
A-3.
(a)
(CH3)2CHONa
(e)
(CH3)2CHOSO2
CH3
O
(b)
(CH3)2C
O
(f)
CH3CH2
COCH(CH3)2
O
(c)
(CH3)2C O
(g)
CH3COCH(CH3)2
O
CH3COCH(CH3)2
(d)
A-4.
(I)
O
(CH3)2CHBr Mg
(CH3)2CHMgBr
(CH3)2CHCH2Br Mg
(II)
(CH3)2CHCH2MgBr
1. H2C
O
2. H3O
(CH3)2CHCH2CH2OH
(CH3)2CHCH2CH2OH
H3C
H
(a)
CH2
2. H3O
(CH3)2CHCH2MgBr
O
A-5.
1. H2C
H
C
(c)
C
CH3
H
O
HO
(b)
OH
A-6.
(a)
(b)
(c)
(d)
PCC or PDC in CH2Cl2
Na2Cr2O7, H, H2O, heat
1. LiAlH4; 2. H2O
OsO4, (CH3)3COOH, (CH3)3COH, HO
OH
O
A-7.
▲
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A
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APPENDIX A
A-8.
(a)
OH
(CH3)2C
CHCH3
1. B2H6
2. H2O2, HO
(CH3)2CHCHCH3
(CH3)2CHCCH3
OH
O
1. CH3CH2MgBr
CH
(b)
O
PDC
CH2Cl2
O
CHCH2CH3
2. H3O
Na2Cr2O7
CCH2CH3
H , H2 O
(c)
O
C6H5CH3
NBS
peroxides, heat
Mg
C6H5CH2Br
C6H5CH2MgBr
1.H2C
CH2
2. H3O
C6H5CH2CH2CH2OH
K2Cr2O7
H, H2O
heat
C6H5CH2CH2CO2CH2CH3
B-1.
B-5.
B-9.
B-13.
(e)
(b)
(d)
(e)
B-2.
B-6.
B-10.
B-14.
(d)
(b)
(a)
(a)
A-1.
CH3OCH2CH2CH3
B-3.
B-7.
B-11.
B-15.
(c)
(a)
(b)
(c)
CH3CH2OH
H
C6H5CH2CH2CO2H
B-4. (c)
B-8. (a)
B-12. (d)
CHAPTER 16
Methyl propyl ether
CH3OCH(CH3)2
Isopropyl methyl ether
CH3CH2OCH2CH3
Diethyl ether
CH3
H
A-2.
(a)
OH
C
CH3CH2
CH3
OCH3
(d)
SCH2CH3
CH3
HO
(b)
H3C
H
H3C H
C C
(e)
OH
O
I
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APPENDIX A
OH
A-3.
O Na
Na
(a)
O
A-4.
H2SO4
CH3CH2OH
H2C
heat
O
CH3COOH
CH2
OCH2CH3
CH3CH2I
H2C
CH2
O
Na
CH3CH2OH
CH2
CH3CH2OCH2CH2OH
CH3CH2OH
O
NaSCH3
O
CH3
H2SO4
COH
(b)
C
heat
CH3
A-6.
A:
CH2
B:
1. CH3MgBr
2. H3O
CH3
A-8.
B-1.
B-6.
(a)
(e)
A-1.
(a)
(b)
(c)
(d)
CH3
H2SO4
heat
H3C
O
B-2.
B-7.
CH2
CH3
H3C OH
O
(a)
(a)
OH
H3 O
CH3COOH
H
H2N
H3C
HO
C
CH2OCH2CH3
H3C OH
A-7.
O
CH3COOH
CH3
CH2OH
O
SCH3
HO
NaOH
(a)
H 2C
CH3CH2O Na
Br
HO
A-5.
B-3.
B-8.
(c)
(c)
B-4.
B-9.
(d)
(d)
B-5. (d )
B-10. (d)
CHAPTER 17
3,4-Dimethylhexanal
2,2,5-Trimethylhexan-3-one
trans-4-Bromo-2-methylcyclohexanone
5-Methyl-4-hexen-3-one
O
O
H
CH3C
C
A-2.
C
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APPENDIX A
A-3.
OH
(a)
NNHC6H5
(e)
CN
CH3
(b)
(f)
NH2OH
CH3CH2CH2CH(OCH2CH3)2
O
(c)
O
(CH3)2CHCH HOCH2CH2CH2OH
C6H5CCH2CH3 (CH3)2NH
(g)
O
A-4.
(d)
(C6H5)3P
(a)
(C6H5)3P
CHCH2CH3
CH2CH(CH3)2 Br
(C6H5)3P
A
C6H5CH
CH3CH2CH2COH
(h)
CHCH(CH3)2
B
CHCH(CH3)2
C
O
(b)
A-5.
O
C6H5CH2CCH3
C6H5CH2OCCH3
D
E
(a)
(1) CH3MgI; (2) H3O; (3) H2SO4, heat
(b)
(C6H5)3P
(c)
HOCH2CH2OH, H(cat), heat
C4H9Li
CH2 [from (C6H5)3P CH3I
]
O
(d)
CH3COOH
(a)
H3C
O
A-6.
HO
OH
CH3
OH
O
HO
O
H3C
(b)
H3C
A-7.
CH3CCH2CH2CH2CCH2OH
CH3
OH
(a)
CH3CH2I (C6H5)3P
(C6H5)3P
CH2CH3 I
C4H9Li
O
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CH3COOH
CHCH3
(C6H5)3P
O
(CH3)2C
CHCH3
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APPENDIX A
(b)
O
CH3
O
O
HOCH2CH2OH
O
CH3
CH3
PCC
CH2Cl2
H
OH
O
O
2. H3O
OH
HO CH3
O
O
O
O
O
HOCH2CH2OH
(c)
2. H2O
CO2H
CO2H
O
O
CH2OH
O
O
H3 O
PBr3
CH2OH
A-8.
CH2Br
O
H
CH3CH
O
1. LiAlH4
H(cat)
O
CH3
1. CH3MgI
OH
CH2Br
OH
CH3OH
CH3CH
OH
H
CH3CH
CH3CH
OCH3
HOCH
3
OH
H
CH3CH
HOCH3
OH2
CH3CH
OCH3
CH3OH
CH3CHOCH3
OCH3
OCH3
H
CH3CH
OCH3
CH3CH
OCH3
O
CH2CCH3
A-9.
B-1.
B-5.
B-9.
B-13.
(c)
(b)
(e)
(d)
B-2.
B-6.
B-10.
B-14.
(d)
(b)
(c)
(e)
B-3.
B-7.
B-11.
B-15.
(a)
(a)
(c)
(a)
B-4.
B-8.
B-12.
B-16.
(c)
(b)
(c)
(c)
CHAPTER 18
OH
A-1.
(a)
H2C
CCH2CH3
O
(b)
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CH3C
CHCH3
(c)
Na
O
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OH
O
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APPENDIX A
O
O
A-2.
C6H5CH2CH
CCH
(CH3CH2)2CHCH2CCH2CH3
C6H5
A
B
OH
OH
O
CH3CH2CHCHCH
A-3.
CH3CHCHC(CH3)2
CH3
CH3 HC
O
OH
OH
CH3CH2CHC(CH3)2
CH3CHCHCHCH
HC
O
CH3
O
CH3
O
A-4.
PCC
CH2Cl2
CH3CH2OH
CH3CH
O
2CH3CH
OH
NaOH
O
OH
CH3CHCH2CH
NaBH4, CH3OH
CH3CHCH2CH2OH
or 1. LiAlH4
2. H2O
A-5.
O
O
O
CH2CH3
K2CO3
CH3CH2I
H2 C
CHCCH3
O
CH2CH3
CH2CH2CCH3
KOH
O
O
O
O
O
A-6.
(a)
CH3CH2CH2CHCH
Br
OH
(b)
O
CH3CH2CH2CH2CHCHCH
CH2CH2CH3
O
(c)
CH
CH3
CH3
O
(d)
CHCH2C
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APPENDIX A
A-7.
O
O
O
CH3CHCH CH3CHCH
OH
H2 C
CH3CHCH
O
H
CH2
O
O
HO
O
H
CH3CHCH
CH2OH
O
CH CH3CH2CCH2CH3
A-8.
B-1.
B-5.
B-9.
(a)
(a)
(c)
B-2. (c)
B-6. (c)
B-10. (b)
B-3. (b)
B-7. (c)
B-11. (a)
B-4. (b)
B-8. (e)
B-12. (a)
A-1.
(a)
(b)
(c)
A-2.
4-Phenylbutanoic acid is C6H5CH2CH2CH2CO2H.
CHAPTER 19
4-Methyl-5-phenylhexanoic acid
Cyclohexanecarboxylic acid
3-Bromo-2-ethylbutanoic acid
heat
C6H5CH2CH2CH(CO2H)2
C6H5CH2CH2CH2Br
C6H5CH2CH2CH2Br
1. CN
2. H, H2O, heat
1. Mg
2. CO2
3. H3O
O
A-3.
C6H5CH2CO2H CH3CH2OH
H(cat)
Br
A-4.
C6H5CH2COCH2CH3 H2O
I
(CH3)2CHCH2CHCO2H
(CH3)2CHCH2CHCO2H
O
C6H5CC(CH3)2
CO2H
A
A-5.
(a)
(b)
B
Mg
C
MgBr
1. LiAlH4
CH3CH2CH2CH2OH
2. H2O
Br O
(c)
Br2, P
CH3CH2CHCOH
CN
(d)
CH3CH2CH
H , H 2 O
heat
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APPENDIX A
A-6.
CH3CH2CHCO2H
Br
A-7.
OH
HCOH
OCH2CH2CH2CH3
O
A-8.
OH
H
CH3COH
OH
CH3COH HOCH3
OH
H
CH3COH
CH3COH
HOCH
3
OH
CH3COH
(b)
(c)
(e)
A-1.
(a)
(b)
OH
CH3C
OCH3
B-1.
B-5.
B-9.
OH
H
OCH3
O
H
CH3COCH3 H2O
OH2
CH3COCH3
OCH3
B-2. (a)
B-6. (d)
B-10. (c)
B-3. (c)
B-7. (c)
B-11. (e)
B-4.
B-8.
(d)
(d)
CHAPTER 20
Propyl butanoate
N-Methylbenzamide
(c)
O O
A-2.
(a)
4-Methylpentanoyl chloride
O
O
C6H5COCC6H5
(b)
CH3CNHCHCH2CH3
(c)
C6H5COC6H5
CH3
O
A-3.
(a)
SOCl2
(b)
Br2, NaOH, H2O
C6H5COCH3
(c)
O
A-4.
(a)
CH3CO2H O
(b)
OH
(d)
CH3CH2CN(CH3)2 CH3CH2OH
(e)
H3C
CO2H CH3NH3 HSO4
C6H5CO
O
COCH2CH3
(c)
COH
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APPENDIX A
OH
A-5.
C6H5
H3C
C
O
O
from
C6H5C
O
CH2
CH2
N
CH2
CH2
HN
CH3
O
CO2H
CCl
SOCl2
A-6.
O
CH3
CNH2
NH3
CH3
CH3
A
C
P4O10
B
B
N
heat
CH3
Br2, NaOH
H2 O
D
NH2
CH3
C
OH
A-7.
(a)
O OH
CH3COCH3
(b)
CH3COCCH3
OH
NH2
A-8.
H3C
Mg
Br
H3C
MgBr
1. CO2
2. H3O
H3C
CO2H
SOCl2
O
O
H3C
Br2, NaOH
NH2
H2 O
A-9.
Na2Cr2O7
CH3
H2SO4, H2O, heat
Toluene
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CNH2
H3C
CCl
CO2H
Benzoic acid
CO2H
Benzoic acid
H3C
NH3
1. LiAlH4
2. H2O
CH2OH
Benzyl alcohol
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APPENDIX A
O
CO2H H
CH2OH
Benzoic acid
COCH2
Benzyl alcohol
Benzyl benzoate
A-10. The compound is 2-chloropropanamide.
O
CH3CHC
NH2
Cl
2-Chloropropanamide
The compound may be prepared from propanoic acid as shown.
Cl2
CH3CH2CO2H
CH3CHCO2H
P
O
SOCl2
CH3CHC
Cl
Propanoic acid
(a)
(d)
(b)
(b)
B-2. (b)
B-6. (c)
B-10. (a)
CH3CHC
Cl
2-Chloropropanoyl
chloride
B-3. (b)
B-7. (d)
B-11. (d)
O
Cl
Cl
2-Chloropropanoic
acid
B-1.
B-5.
B-9.
B-13.
NH3
NH2
2-Chloropropanamide
B-4. (c)
B-8. (d)
B-12. (b)
CHAPTER 21
O
A-1.
(a)
O
O
CH3CH2CH2CCHCOCH2CH3
(e)
CH2CH3
(f)
C6H5CH2COCH2CH3
CO2H
Cl
1. HO, H2O
2. H3O
3. heat
O
CO2H
(c)
CH3CCHCOCH2CH3
CH2C6H5
O
(b)
O
(g)
CH3CCH2CH2CO2H
Cl
O
(d)
(CH3CH2O2C)2CHCH2CH2COCH2CH3
O
O
A-2.
O
O
CH3CH2OC(CH2)4COCH2CH3
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CH2CH3
B
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APPENDIX A
O
O
O
CH2CH3
CH3CH2CH2CCHCOCH2CH3
CH2CH3
C
D
O
CH3CH2CH2CCH2CH2CH3
E
A-3.
O
(a)
O
O
CH3CCH2COCH2CH3
1. NaOCH2CH3
O
O
CH3CCHCOCH2CH3
2. BrCH2COCH2CH3
CH2COCH2CH3
O
1. HO, H2O
2. H3O
3. heat
O
CH3CCH2CH2COH
O
(b)
O
O
O
C6H5CCH3 CH3CH2OCOCH2CH3
NaOCH2CH3
O
O
C6H5CCH2COCH2CH3
1. NaOCH2CH3
O
2. H2C
O
C6H5CCHCOCH2CH3
CHCCH3
CH2CH2CCH3
O
1. HO, H2O
2. H3O
3. heat
O
O
C6H5CCH2CH2CH2CCH3
A-4.
O
2CH3CH2COCH2CH3
O
NaOCH2CH3
O
CH3CHCOCH2CH3
CH3CHCOCH2CH3
CH3CH2COCH2CH3
CH3CH2C
OCH2CH3
O
O
CH3CH2O
O
O
CH3CCOCH2CH3
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CH3CHCOCH2CH3
CH3CH2C
O
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APPENDIX A
A-5.
CH3
Enolization of the Claisen condensation product is necessary for completion of the reaction.
The condensation product of ethyl 3-methylbutanoate can enolize; the product from condensation of ethyl 2-methylpropanoate cannot.
O
CH3
NaOCH2CH3
2CH3CHCH2COCH2CH3
CH3 O
CH3CHCHCOCH2CH3
CH3CHCH2C
Ethyl 3-methylbutanoate
O
H
CH3CHCCOCH2CH3
CH3CHCH2C
O
CH3
O
CH3
O
H3C O
NaOCH2CH3
2CH3CH2CHCOCH2CH3
CH3CH2CCOCH2CH3
CH3CH2CHC
CH3
O
CH3
Ethyl 2-methylbutanoate
B-1.
B-5.
(b)
(c)
A-1.
(a)
(b)
(c)
B-2.
B-6.
(d)
(c)
Claisen product cannot enolize
B-3.
B-7.
(c)
(b)
B-4.
B-8.
(b)
(d)
CHAPTER 22
1,1-Dimethylpropylamine or 2-methyl-2-butanamine; primary
N-Methylcyclopentylamine or N-methylcyclopentanamine; secondary
m-Bromo-N-propylaniline; secondary
O
A-2.
(a)
NaN3
(b)
KCN
N K
(c)
O
A-3.
(a)
O
NHCCH3
NHCCH3
O2N
N2 Cl
H3C
O
(e)
CH2CH3
CH2CH3
NO2
O
(b)
H3C
Br
(c)
H3PO2
(f)
(g)
N
N(CH3)2
NCH2CH3
N
O
O
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O
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CH3CCl
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APPENDIX A
A-4.
(a)
I
N
N
N
CH2CH3
H3C
CH2CH3
A
C
N
A-5.
CH2CH3
H3C
B
(b)
OH
O
NHCH2CH3
NCH2CH3
D
E
(a)
C(CH3)3
C6H6
C(CH3)3
(CH3)3CCl
HNO3
AlCl3
H2SO4
C(CH3)3
1. Sn, HCl
2. NaOH
NH2
NO2
NaNO2, HCl
H2O
C(CH3)3
C(CH3)3
KI
N2 Cl
I
NO2
NO2
(b)
C6H6
HNO3
NH2
Cl2, FeCl3
1. Sn, HCl
2. NaOH
H2SO4
Cl
Cl
(c)
C6H5NH2
A-6.
NaNO2, HCl
H2O
C6H5N2 Cl
C6H5N(CH3)2
O
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N
N(CH3)2
In the para isomer, resonance delocalization of the electron pair of the amine nitrogen involves
the nitro group.
NH2
A-7.
C6H5N
N
O
O
NH2
N
O
Strongest base: C, an alkylamine
Weakest base: D, a lactam (cyclic amide)
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APPENDIX A
O
NHCCH3
NH2
NH2
Cl
Br
Cl
Cl
Cl
A-8.
C(CH3)3
C(CH3)3
A
B
B-1.
B-5.
B-9.
B-13.
(b)
(c)
(d)
(c)
B-2.
B-6.
B-10.
B-14.
A-1.
(a)
CF3
(d)
(e)
(e)
(c)
C(CH3)3
C(CH3)3
C
D
B-3. (c)
B-7. (d )
B-11. (c)
B-4. (d)
B-8. (c)
B-12. (b)
CHAPTER 23
CF3
(c)
C(CH3)3
C(CH3)3
NH2
NH2
NH2
NH2
CH3O
(b)
NO2
Cl
CF3
A-2.
C(CH3)3
(a)
(c)
CH3O
Cl
(b)
Cl
O
N
O
Cl
A-3.
Cl
NO2
NO2
Cl
NH2
NaNH2, NH3
(CH3)2CHCl
AlCl3
CH(CH3)2
CH(CH3)2
▲
▲
( ortho isomer)
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NaOCH3
heat
Cl
(b)
NO2
HNO3, H2SO4
(a)
OCH3
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APPENDIX A
O
NO2
Y
NO2
N
Y
A-4.
O
X
X
O
N
O
X
Y
NO2
X
Y
Y
X
The mechanism for para substitution is similar.
A-5.
Product:
Intermediate:
B-1.
B-5.
(a)
(b)
A-1.
p-Hydroxybenzaldehyde is the stronger acid. The phenoxide anion is stabilized by conjugation with the aldehyde carbonyl.
B-2.
B-6.
(a)
(a)
B-3.
B-7.
(c)
(a)
B-4.
B-8.
(d)
(a)
CHAPTER 24
O
OH
O
H C
O
C
O
H
OH
H
HNO3
A-2.
C
H
CH3
CH3
O2N
O
OH
OH
CH3
NO2
o-Cresol
OH
OH
OH
O2N
HNO3
CH3
CH3
CH3
NO2
m-Cresol
OH
OH
NO2
HNO3
CH3
CH3
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APPENDIX A
OH O
CCH2CH3
OH
O
AlCl3
CH3CH2CCl
A-3.
CH3
CH3
(Friedel–Crafts acylation)
O
OH
OCCH2CH3
O
(absence of AlCl3)
CH3CH2CCl
CH3
CH3
(Esterification)
A-4.
OH BrCH(CH3)2
(a)
(c)
CO2, 125C, 100 atm
O Na
Br
BrCH2CH(CH3)2
(b)
(d )
CH3
OCH2CH
OH
CHCH2CH3
OH CH2CH3
CHCH CH2
A-5.
A
B
A-6.
C(CH3)3
C(CH3)3
C(CH3)3
C(CH3)3
HNO3
1. Sn, HCl
1. NaNO2, H2SO2, H2O
H2SO4
2. NaOH
2. H2O, heat
NO2
B-1.
B-5.
(d)
(c)
B-2.
B-6.
(d)
(b)
A-1.
(a)
CHO
HO
H
NH2
B-3.
B-7.
(b)
(b)
B-4.
B-8.
OH
(a)
(c)
CHAPTER 25
(b)
CHO
H
OH
CHO
HO
H
or
HO
H
CH2OH
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HO
H
CH2OH
L-Threose
H
OH
CH2OH
D-Threose
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APPENDIX A
O
(c)
H
H
H OH
OH
OH
R
(e)
H
-D-Erythrofuranose
O
(d)
CHO
H
OH
OH
CH2OH
R
OH
H
H H
OH
OH
-D-Erythrofuranose
A-2.
(a)
HO
H
(a)
OH
H
OH
H
OH
CH2OH
H
OH
CH2OH
O
H
HO
A-5.
The products are diastereomers.
HO
H
HOCH2
H
OH
H
OH
CH2OH
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B-1.
B-6.
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HO
HO
HCl
CH3OH
D-Mannose
H
OH
OH
O
B-2.
B-7.
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OH
HOCH2
H
HO
HO
OCH3
Methanol
(b)
(c)
H
H
-D-Idopyranose ( -pyranose form of D-idose)
CHO
H
OH
OH
A-4.
HO
H
H
HO H
OH
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(c)
OH
H
HOCH2 O
H H
O
HO
H
HO
5HCO2H H2C?O
(c)
H
H
OH
(b)
CO2
HO
H
HO
H
A-3.
(b)
CH2OH
HO
H
Methyl
-D-mannopyranoside
(d)
(a)
B-3.
B-8.
(b)
(c)
B-4.
B-9.
(a)
(c)
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O
OCH3
H
Methyl
-D-mannopyranoside
B-5. (c)
B-10. (c)
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APPENDIX A
CHAPTER 26
O
CH2OH
O CH2OCC17H35
A-1.
C17H35COCH
CHOH 3C17H35CO2 Na
3NaOH
O
CH2OCC17H35
CH2OH
Tristearin
A-2.
Fats are triesters of glycerol. A typical example is tristearin, shown in the preceding problem.
A wax is usually a mixture of esters in which the alkyl and acyl group each contain 12 or
more carbons. An example is hexadecyl hexadecanoate (cetyl palmitate).
O
C15H31COC16H33
A-3.
(a)
Monoterpene;
(b)
Sesquiterpene;
(c)
Diterpene;
CO2H
A-4.
O
(CH2)7CO2H
CH3(CH2)7
C
C
H
HC
O
C(CH2)6CH2 H
H
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APPENDIX A
O
HC
O
C(CH2)6CH2 H
O
NaNH2
Na C
O
C(CH2)6CH2 H
O
CH3(CH2)6CH2Br
CH3(CH2)7C
O
C(CH2)6CH2 H
H 3O O
(CH2)7CO2H
CH3(CH2)7
C
H2
C
H
CH3(CH2)7C
Lindlar Pd
C(CH2)7CO2H
Na2Cr2O7
H2SO4, H2O
CH3(CH2)7C
C(CH2)7CH
H
OPP
A-5.
H
OPP
Limonene
Geranyl pyrophosphate
B-1.
B-5.
(b)
(a)
B-2.
B-6.
(a)
(a)
B-3.
(c)
B-4.
(c)
CHAPTER 27
O
A-1.
O
C6H5CH2CH
(a)
(b)
C6H5CH2OCNHCHCO2H
(c)
DCCI
CH(CH3)2
A-2.
O2N
NHCHCO2H
NO2
A-3.
CH2C6H5
(a)
O
O
CH3CNHCH(CO2CH2CH3)2
NaOCH2CH3
ethanol
O
CH3CNHC(CO2CH2CH3)2
(CH3)2CHCH2Br
CH3CNHC(CO2CH2CH3)2
CH2CH(CH3)2
1. H3O
2. heat
H3NCHCO2
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CH2CH(CH3)2
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APPENDIX A
CH(CH3)2
O
Leu-Val H3NCHC
(b)
NHCHCO2
CH2CH(CH3)2
O
O
1. NaOH, H2O
N-Protect leucine: C6H5CH2OCCl H3NCHCO2
C6H5CH2OCNHCHCO2H
2. H
CH2CH(CH3)2
CH2CH(CH3)2
(Z-Leu)
O
H
C-Protect valine: C6H5CH2OH H3NCHCO2
H3NCHCOCH2C6H5
CH(CH3)2
CH(CH3)2
O
O
Couple: Z-Leu H2NCHCOCH2C6H5
DCCI
Deprotect:
O
O
CH2CH(CH3)2
O
CH(CH3)2
C6H5CH2OCNHCHCNHCHCOCH2C6H5
Leu-Val-Gly-Ala-Phe
A-5.
(a)
(b)
A-6.
(a)
Pentapeptide
Four
O2N
(c)
(d)
NO2
O
CH(CH3)2
H2, Pd
H3NCHCNHCHCO2
CH2CH(CH3)2
O
CH2CH(CH3)2
A-4.
CH(CH3)2
C6H5CH2OCNHCHCNHCHCOCH2C6H5
CH(CH3)2
O
O
Serine
Glycine
(e)
Ser-Ala-Leu-Phe-Gly
H3NCH2CO2 H3NCHCO2 H3NCHCO2
NHCHCOH
CH2C6H5
CH2CH(CH3)2
CH3
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Leu
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APPENDIX A
O
(b)
O
H3NCHCNHCH2CNHCHCO2 H3NCHCO2
CH3
CH2C6H5
CH2CH(CH3)2
Leu
Ala-Gly-Phe
(c)
Same as part b; Ala-Gly-Phe Leu
O
(d)
O
O
O
CH2CH(CH3)2
C6H5CH2OCNHCHCNHCH2CNHCHCNHCHCO2H
CH2C6H5
CH3
Z-Ala-Gly-Phe-Leu
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B-1.
B-5.
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(c)
(b)
B-3.
B-7.
(a)
(c)
B-4.
B-8.
(d)
(a)
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APPENDIX B
TABLES
Table B-1 Bond Dissociation Energies of Some Representative Compounds*
Bond dissociation
energy, kJ/mol
(kcal/mol)
Bond
Bond
Bond dissociation
energy, kJ/mol
(kcal/mol)
Diatomic molecules
H@H
F@F
Cl@Cl
Br@Br
I@I
435 (104)
159 (38)
242 (58)
192 (46)
150 (36)
H@F
H@Cl
H@Br
H@I
568 (136)
431 (103)
366 (87.5)
297 (71)
CH3 @CH3
CH3CH2 @CH3
(CH3)2CH@CH3
(CH3)3C@CH3
368
355
351
334
Alkanes
CH3 @H
CH3CH2 @H
CH3CH2CH2 @H
(CH3)2CH@H
(CH3)3C@H
435 (104)
410 (98)
410 (98)
397 (95)
380 (91)
(88)
(85)
(84)
(80)
Alkyl halides
CH3 @F
CH3 @Cl
CH3 @Br
CH3@I
CH3CH 2@Cl
CH3CH2CH2 @Cl
451 (108)
349 (83.5)
293 (70)
234 (56)
338 (81)
343 (82)
(CH3)2CH@F
(CH3)2CH@Cl
(CH3)2CH@Br
(CH3)3C@Cl
(CH3)3C@Br
439 (105)
339 (81)
284 (68)
330 (79)
263 (63)
Water and alcohols
HO@H
CH3O@H
CH3 @OH
497 (119)
426 (102)
380 (91)
CH3CH2 @OH
(CH3)2CH@OH
(CH3)3C@OH
380 (91)
385 (92)
380 (91)
*Note: Bond dissociation energies refer to bonds indicated in structural formula for each substance.
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822
APPENDIX B
Table B-2 Acid Dissociation Constants*
Acid
Formula
Hydrogen fluoride
Acetic acid
Hydrogen cyanide
Phenol
Water
Ethanol
Alkyne (terminal; R alkyl)
Ammonia
Alkene C@H
Alkane C@H
H@F
CH3CO2 @H
H@CN
C6H5O@H
HO@H
CH3CH2O@H
RC>C@H
NH2 @H
RCH?CH@H
RCH2CH2 @H
Conjugate
base
Dissociation
constant
pKa
F
CH3CO2
CN
C6H5O
HO
CH3CH2O
RC>C
NH2
RCH?CH
RCH2CH2
3.5 104
1.8 105
7.2 1010
1.3 1010
1.8 1016
1016
1026
1036
1045
1062
3.5
4.7
9.1
9.8
15.7
16
26
36
45
62
*Note: Acid strength decreases from top to bottom of the table; conjugate base strength increases from top to bottom.
Table B-3 Chemical Shifts of Representative Types of Protons
Type of proton
H
C
R
H
C
C
C
Chemical shift
(), ppm*
Type of proton
Chemical shift
(), ppm*
0.9–1.8
H
C
NR
2.2–2.9
1.6–2.6
H
C
Cl
3.1–4.1
O
H
C
C
2.1–2.5
H
C
Br
2.7–4.1
H
C
C
2.5
H
C
O
3.3–3.7
H
C
Ar
2.3–2.8
H—NR
H
C
C
4.5–6.5
H
OR
0.5–5†
H
Ar
6.5–8.5
H
OAr
6–8†
O
O
H
C
1–3†
9–10
H
OC
10–13†
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*These are approximate values relative to tetramethylsilane; other groups within the molecule can cause a proton signal to
appear outside of the range cited.
† The chemical shifts of protons bonded to nitrogen and oxygen are temperature- and concentration-dependent.
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APPENDIX B
Table B-4 Chemical Shifts of Representative Carbons
Chemical shift
(), ppm*
Type of carbon
RCH3
0–35
R2CH2
15–40
R3CH
25–50
RCH2NH2
35–50
RCH2OH
50–65
@C>C@
65–90
Type of carbon
C
C
Chemical shift
(), ppm*
100–150
110–175
C
190–220
O
* Approximate values relative to tetramethylsilane.
Table B-5 Infrared Absorption Frequencies of Some Common Structural Units
Frequency, cm1
Structural unit
Frequency, cm1
Structural unit
Stretching vibrations
Single bonds
Double bonds
@O@H (alcohols)
3200–3600
C
C
@O@H (carboxylic acids)
2500–3600
C
O
1620–1680
3350–3500
Aldehydes and ketones
sp C@H
sp2 C@H
sp3 C@H
3310–3320
3000–3100
2850–2950
sp2 C@O
sp3 C@O
1200
1025–1200
Carboxylic acids
Acid anhydrides
Acyl halides
Esters
Amides
N
H
1710–1750
1700–1725
1800–1850 and 1740–1790
1770–1815
1730–1750
1680–1700
Triple bonds
@C>C@
@C>N
2100–2200
2240–2280
Bending vibrations of diagnostic value
Alkenes
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Cis-disubstituted
Trans-disubstituted
Trisubstituted
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960–980
790–840
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Substituted derivatives of benzene
Monosubstituted
730–770 and 690–710
Ortho-disubstituted
735–770
Meta-disubstituted
750–810 and 680–730
Para-disubstituted
790–840
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