CH 13
CH 13
CH 13
CH3
CH3CHCHCHCHCH3
OH
A)
B)
C)
D)
E)
CH3
4-isopropyl-3,4-dimethyl-2-butanol
2,3,4-trimethyl-4-pentanol
1,1,2,3-tetramethyl-4-pentanol
3,4,5-trimethyl-2-hexanol
3,4,5,5-tetramethyl-2-pentanol
Ans: D
CH3CH2CCH2CH3
OH
A)
B)
C)
D)
E)
1,1,1-triethylmethanol
1,1-diethyl-1-propanol
2-ethyl-3-pentanol
3-ethyl-3-pentanol
t-heptanol
Ans: D
A)
B)
C)
D)
E)
1-isopropyl-4-cyclopentanol
3-isopropyl-1-cyclopentanol
1-isopropyl-3-cyclopentanol
1-isopropyl-4-hydroxycyclopentane
None of these
Ans: B
CH2CH3
CH3CH2CCH2CH2Cl
OH
A)
B)
C)
D)
E)
CH3CHCHCH2CH2Cl
OH
II
CH3CH2CHCH2CHCl CH3CH2CHCHCH2Cl
III
I
II
III
IV
None of these
Ans: D
HO
A)
B)
C)
D)
E)
2-methyl-5-bromocyclohexanol
3-bromo-2-methylcyclohexanol
1-bromo-4-methylcyclohexanol
4-bromo-6-methylcyclohexanol
4-bromo-2-methylcyclohexanol
Ans: E
CH2CH3
CH2CH3
OH
IV
OH
CH3CH2C=CCH2CH3
CH3
A)
B)
C)
D)
E)
3-methyl-4-ethyl-3-hexen-6-ol
4-ethyl-3-methyl-3,6-hexenol
3-ethyl-4-methyl-3-hexen-1-ol
3-methyl-4-(2-hydroxyethyl)-3-hexene
3-(2-hydroxyethyl)- 3-methyl-3-hexene
Ans: C
A)
B)
C)
D)
E)
4-penten-2-methyl-2-ol
4-methyl-1-penten-2-ol
2-methyl-4-penten-2-ol
4-methyl-1-penten-4-ol
4-hydroxy-4-methyl-1-pentene
Ans: C
C
C
CC
H
2 CH
3
A)
B)
C)
D)
E)
(R)-3-hexyn-2-ol
(S)-3-hexyn-2-ol
(R)-2-hexyn-4-ol
(S)-2-hexyn-4-ol
(S)-2-hydroxy-3-hexyne
Ans: B
Br
Br
Br
CH3CCH2CH2CH2CHOH
CH3CH2CH2CH2CCH(CH3)OH
I
Br
Br
II
OH
III
OH
Br
Br
Br
Br
IV
A)
B)
C)
D)
E)
CH3
I
II
III
IV
V
Ans: D
III
II
OH
HO
OH
A)
B)
C)
D)
E)
I
II
III
IV
V
Ans: E
IV
OH
Ans: 7-ethyl-8-methyl-4-nonanol
Topic: Nomenclature of alcohols
Section: 13.1
Difficulty Level: Hard
14. What is the IUPAC name for the following compound?
HO
Ans: (R)-3-ethyl-2-methyl-3-heptanol
Topic: Nomenclature of alcohols
Section: 13.1
Difficulty Level: Hard
15. What is the IUPAC name for the following compound?
Br
OH
Ans: (1R,2S)-2-bromo-1-methylcyclopentanol
Topic: Nomenclature of alcohols
Section: 13.1
Difficulty Level: Hard
Ans: 7-cyclohexyl-2,8-dimethyl-3-decanol
Topic: Nomenclature of alcohols
Section: 13.1
Difficulty Level: Hard
17. Provide the structure for (E)-4,5,5-trimethyl-3-hepten-1-ol?
Ans:
OH
OH
OH
Ans: 4-isobutyl-2-methyl-3-octanol
Topic: Nomenclature of alcohols
Section: 13.1
Difficulty Level: Hard
21. What is the IUPAC name for the following compound?
HO
H
C
CH3(CH2)4
C
C
H
Ans: (S)-1-octyn-3-ol
Topic: Nomenclature of alcohols
Section: 13.1
Difficulty Level: Medium
22. What is the IUPAC name for the following compound?
HO
Ans: 4,5,6-tripropyl-4-decanol
Topic: Nomenclature of alcohols
Section: 13.1
Difficulty Level: Medium
23. What is the IUPAC name for the following compound?
HO
Ans: 3-ethyl-3-cyclohexen-1-ol
A)
B)
C)
D)
E)
OH
OH
II
OH
OH
III
IV
I
II
III
IV
V
Ans: A
Br
OH
OH
OH
Br
IV
Br
Br
Br
A)
B)
C)
D)
E)
I
II
III
IV
V
Ans: B
II
III
OH
Br
A)
B)
C)
D)
E)
3,4-dibromophenol
2,4-dibromophenol
2,5-dibromophenol
3,6-dibromophenol
2,6-dibromophenol
Ans: C
Ans: 2-sec-butyl-5-ethylphenol
Topic: Nomenclature of alcohols
Section: 13.5
Difficulty Level: Medium
284. What is the IUPAC name for the following compound?
HOCH2CH2CH2OH
A) 1,2-butanediol
B) isopropanol
C) 1-propanol
D) 1,3-propanediol
E) 1,2-ethanediol
Ans: D
Topic: Nomenclature of alcohols
Section: 13.5
Difficulty Level: Hard
OH
A)
B)
C)
D)
E)
cis-1,2-cyclopentanediol
meso-1,2-cyclopentanediol
(1R,2R)-1,2-cyclopentanediol
(1R,2S)-1,2-cyclopentanediol
(1S,2S)-1,2-cyclopentanediol
Ans: E
OH
OH
Ans: 3,5-dimethyl-2,4-heptanediol
Topic: Nomenclature of alcohols
Section: 13.5
Difficulty Level: Hard
3127. Provide the structure for (2R, 3S)- 2-bromo-1,3-pentanediol.
Ans:
OH
OH
Br
3228. Explain why cyclohexanol has a pKa of 18 and phenol has a pKa of 10. Use structural
drawings to explain your reasoning.
Ans: The conjugate base of phenol is resonance stabilized. The negative charge on
oxygen is delocalized over the aromatic ring. This makes the conjugate base more
stable and thus a weaker base, making phenol a stronger acid.
O
Br
Ans: II>I>III
Topic: Acidity of alcohols and phenols
Section: 13.2
Difficulty Level: Medium
OH
OH
OH
II
III
OH
OH
OH
III
II
Ans: I
Topic: Acidity of alcohols and phenols
Section: 13.2
Difficulty Level: Medium
351. Rank the following alcohols in decreasing order of acidity. Explain your answer.
F
OH
OH
OH
F
III
II
Ans: I>III>II
The negative charge on the conjugate base of compound I is stabilized by three
electron withdrawing fluorine atoms via inductive effect, making it the weakest
base and the alcohol strongest acid.
The negative charge on the conjugate base of compound II is not stabilized, as it
does not have any electronegative atoms on the carbon chain, making it a stronger
base and the alcohol weakest acid.
The negative charge on the conjugate base of compound III is less stabilized than
I, because it has only one fluorine atom connected. Thus making it a stronger acid
than II, but a weaker acid than I.
OH
Ans: I>III>II
Topic: Acidity of alcohols and phenols
OH
II
NC
OH
III
Section: 13.2
Difficulty Level: Medium
373. Predict the product(s) for the following reaction.
OH
Na
ONa
Ans:
1
H2
2
Li
Ans:
O Li
1
H2
2
1. NaH
2. CH3CH2Br
Ans:
3540. Provide the reagents necessary to carry out the following conversion.
CH3CH2CH2CHCH3
CH3CH2CH2CH2CH2OH
Br
Ans:
1.
2.
3.
4.
(CH3)3COK
BH3
THF
H2O2/NaOH/H2O
CH2OH
OH
OH
+ enantiomer
I
A)
B)
C)
D)
E)
I
II
III
IV
None of these
Ans: B
OH
+ enantiomer
II
III
IV
1. Hg(OAc)2, H2O
2. NaBH4
CH2OH
OH
OH
II
A)
B)
C)
D)
E)
OH
III
IV
I
II
III
IV
None of these
Ans: C
3-methyl-3-hexanol
Ans: H3O+
OR
1. Hg(OAc)2, H2O
2. NaBH4
Topic: Preparation of Alcohols
Section: 13.3
Difficulty Level: Medium
3944. Predict the major product for the following reaction.
H3O+
Ans:
OH
1. Hg(OAc)2, H2O
2. NaBD4
OH
OH
A)
B)
C)
D)
E)
OH
OH
III
II
OH
IV
I
II
III
IV
V
Ans: C
Ans: NaOH
Topic: Preparation of Alcohols
Section: 13.3
Difficulty Level: Hard
OH
472. Provide the reagents necessary to carry out the following conversion.
OH
Cl
A)
B)
C)
D)
E)
NaOH/H2O
1. NaOCH3, 2. H3O+
1. (CH3)3COK, 2. BH3, THF, 3. H2O2/NaOH/H2O
1. (CH3)3COK, 2. H3O+
B&D
Ans: D
II
A)
B)
C)
D)
E)
I. +1, II. +2
I. +2, II. +2
I. +1, II. +3
I. +3, II. +2
I. +2, II. +1
Ans: E
494. What is the oxidation state of the carbon atoms I and II in the following reaction?
O
CH3CH
I
A)
B)
C)
D)
E)
CH3COH
II
I. +1, II. +2
I. +2, II. +2
I. +1, II. +3
I. +3, II. +2
I. +2, II. +1
Ans: C
Ans: Oxidized.
The carbon atom bonded to OH in the starting compound has a zero oxidation
state and the carbonyl carbon atom in the product has an oxidation state of +2.
Topic: Oxidation states
Section: 13.4
Difficulty Level: Medium
5146. For the following conversion, identify if the starting material has been oxidized, reduced
or neither.
Cl
Cl
Ans: Oxidized.
Topic: Oxidation states
Section: 13.4
Ans: Neither.
The oxidation state of the carbon atoms is not changed.
Topic: Oxidation states
Section: 13.4
Difficulty Level: Hard
4853. For the following conversion, identify if the starting material has been oxidized, reduced
or neither.
O
H
A)
B)
C)
D)
reduced
oxidized
neither
A& B
Ans: B
A)
B)
C)
D)
reduced
oxidized
neither
A& B
Ans: C
CH3CCH2CH2CH3
NaBH4/CH3OH
OH
Ans:
CH3CHCH2CH2CH3
Topic: Preparation of Alcohols via Reduction
Section: 13.4
Difficulty Level: Medium
560. Predict the product for the following reaction.
O
NaBH4/CH3OH
OH
A)
B)
C)
D)
I
II
III
IV
Ans: A
OH
OH
OH
II
III
OH
IV
571. Which one of the following compounds gives 5-methyl-3-heptanol with LiAlH4
followed by water?
O
O
O
H
II
III
A)
B)
C)
D)
E)
I
II
III
IV
V
Ans: A
IV
CCH2CH2CH3
CH3CHCH2CH2CH3
H2.Pd
OH
A)
B)
C)
D)
I
II
III
IV
Ans: C
OH
II
NaBH4 / H2O
Ans:
OH
OH
COCH3
H
HO
III
OH
IV
1. LiAlH4 excess
2. H2O
O
CH2OH
Ans:
H
HO
Ans:
OH
NaBH4/CH3OH
O
O
H
II
O
III
IV
A)
B)
C)
D)
E)
I
II
III
IV
V
Ans: A
cyclohexene
KMnO4, NaOHcold
KMnO4, H3O+, 75oC
H2SO4, heat
1. mCPBA 2. H3O+
none of these
Ans: A
cis-1,2-cyclohexanediol
HO
A)
B)
C)
D)
E)
HO
OH
HO
HO
II
OH
III
I
II
III
Both I & II
None of these
Ans: BA
cyclohexene
KMnO4, NaOH
KMnO4, H3O+, 75oC
H2SO4, heat
1. mCPBA 2. H3O+
none of these
Ans: D
trans-1,2-cyclohexanediol
Br2
h
mCPBA
Ans:
NaOH/H2O
D
CH3
CH3
Br
OH
OH
+ enantiomer
+ enantiomer
D
excess
H
OH
NaBH4/CH3OH
OH
OH
OH
II
I
OH
III
OH
OH
OH
OH
IV
A)
B)
C)
D)
E)
I
II
III
IV
V
Ans: C
H3O+
OH
OH
H
O
OH
A)
B)
C)
D)
E)
OH
OH
II
IV
III
I
II
III
IV
none of these
Ans: C
OH
Ans: 1. mCPBA
2. H3O+ OR NaOH/H2O
Topic: Preparation of Diols
Section: 13.5
Difficulty Level: Hard
6571. Provide the reagent(s) necessary to carry out the following conversion.
OH
OH
Ans:
1.
2.
3.
4.
O3
(CH3)2S
excess NaBH4/CH3OH
1. excess LiAlH4
2. H2O
Ans:
OH
OH
OH
1. CH3CH2MgBr
2. H2O
Ans:
HO
1.
Mg/ether
Br
2. H2O
Ans:
OH
OH
1. CH3CH2CH2MgBr/ether
2. H2O
OH
OH
HO
OH
A)
B)
C)
D)
E)
III
II
I
II
III
IV
None of these
Ans: A
Br
1.
Mg/ether
2. H2O
Ans:
OH
IV
78. Using Grignard reaction, show how you could prepare the following alcohol.
OH
Ans:
MgBr
1.
O
C
H
2. H2O
OH
Ans:
1. MgBr
2. H2O
OR
1.
MgBr
2. H2O
80. Using Grignard reaction, show how you could prepare the following alcohol.
HO
Ans:
MgBr
1.
O
2. H2O
OR
1.
MgBr
2. H2O
OR
1.
O
MgBr
2. H2O
Ans: 1. HBr
2. Mg/ether
O
3. H
4. H2O
Ans:
MgBr
1.
2. H2O
OCH3
excess
1. CH3CH2CH2MgBr
2. H2O
Ans:
OH
excess
1. CH3CH2MgBr
2. H2O
Ans:
OH
OH
2. H2O
Ans:
OH
2. H2O
Ans:
OH
Mechanism
O
CH3CH2MgBr
O
CH3CH2MgBr
+ CH3OMgBr
O
CH3CH2MgBr
O
+ CH3OMgBr
O
O
H
HO
+ OH
7587. Provide the reagent(s) necessary to carry out the following conversion.
OH
HO
Br
HO
3.
4. H2O
5. TBAF
Topic: Protection of alcohols
Section: 13.7
Difficulty Level: Hard
88. Provide the reagent(s) necessary to carry out the following conversion.
OH
HO
HO
3. H2O
4. TBAF
Topic: Protection of alcohols
Section: 13.7
Difficulty Level: Medium
7689. Predict the structure of each product(A-D)s) for the following reaction sequence.
OH
O
1.
Br
(CH3)3SiCl
Mg/ ether
(CH3CH2)3N
2. H2O
Ans:
OSi(CH3)3
OSi(CH3)3
MgBr
Br
OH
OSi(CH3)3
HO
HO
OH
(CH3)3SiCl
Br
A)
B)
C)
D)
E)
2,4-heptanediol
1,4-heptanediol
2,5-octanediol
1,5-octanediol
none of these
Ans: B
(CH3CH2)3N
Mg/ ether
O
H
2. H2O
TBAF
TBAF
7891. Provide the reagents necessary to carry out the following conversion.
HO
HO
Ans:
1.
2.
3.
4.
(CH3)3SiCl / (CH3CH2)3N
NaNH2
CH3CH2CH2Br
TBAF
CH3CH2CH2CH=CH2 +
CH3CH2CH2CH2CH2OH
CH3CH2CH2CH2CH2OH
CH3CH2CH2CH2CH2OH
CH3CH2CH2CH=CH2 +
Ans: B
HBr
+ PBr3
+ NaBr
+ Br2
Br2
PBr3
Br
Ans:
HBr
Ans:
Br
Mechanism
OH
Br
OH2
+ Br
H
Br
Br
+ H2O
OH
HCl
Ans:
Cl
Ans:
Cl
CH3
H
1. TsCl /pyridine
2. NaI
H
I
CH3
A)
B)
C)
D)
E)
II
OTs
Ts
CH3
CH3
CH3
III
IV
I
II
III
IV
both I and III
Ans: C
SN1 mechanism
SN2 mechanism
E1 mechanism
E2 mechanism
None of these.
Ans: C
OH
NaOH
not produced
Ans: The tertiary halide is too sterically hindered for an SN2 reaction with hydroxide as
nucleophile. Instead, the hydroxide ion is a strong base and will react with the
alkyl chloride to form alkene via an E2 mechanism.
Topic: Reactions of Alcohols
Section: 13.9
Difficulty Level: Medium
89102 Predict the major product for the following reaction.
.
OH
1. TsCl/pyridine
2. CH3CH2ONa
Ans:
Ans:
92105 Provide a stepwise curved arrow mechanism for the following reaction.
HO
.
CH2CH3
CH2CH3
CH2CH3
CH2CH3
H2SO4
Ans:
HO
CH2CH3
CH2CH3
H2O
CH2CH3
O
CH2CH3
O
H3CH2C
H3CH2C
CH2CH3
CH2CH3
CH2CH3
CH2CH3
+ H2O
CH2CH3
+ H2SO4
CH2CH3
S
O
93106 Predict the product and provide a stepwise curved arrow mechanism for the following
. reaction.
OH
OH
H2SO4
heat
Ans:
O
Mechanism
O
OH
H
OH2
OH
O
OH
O
O
H
O
OH
+ H2O
O
O
+ H2SO4
B)
CH3CH2CH2CH2COH
O
C)
CH3(CH2)3CCH3
D)
CH3CH2CH2CH2CH2COH
O
E)
CH3CH2CH2CH2CH2CH
Ans: C
Topic: Reactions of Alcohols
Section: 13.10
Difficulty Level: Medium
95108 Provide the reagents necessary to carry out the following conversion.
O
OH
.
A)
B)
C)
D)
E)
KMnO4/NaOH/H2O
Na2Cr2CrOO73/H2SO4/H2O
H2, Pt
Br2, CCl4
None of these
Ans: B
Ans:
Ans:
O
OH
A)
B)
C)
D)
E)
KMnO4/NaOH/H2O
Na2Cr2O7CrO3/H2SO4/H2O
PCC/CH2Cl2
Br2, CCl4
None of these
Ans: C
99112 Provide the reagents necessary to carry out the following conversion.
.
O
OH
A)
B)
C)
D)
E)
OH
KMnO4/NaOH/H2O
Na2Cr2O7CrO3/H2SO4/H2O
PCC/CH2Cl2
Br2, CCl4
None of these
Ans: B
excess
PCC/CH2Cl2
Ans:
CH2OH
OH
CH
O
OH
PCC
CH2Cl2
CH2Cl2
Ans:
.
Topic: Oxidation of Phenols
Section: 13.12
Difficulty Level: Medium
116. Predict the product for the following reaction.
OH
Na2Cr2O7/H2SO4/H2O
Ans:
Topic: Synthesis
Section: 13.13
Difficulty Level: Medium
11703 Provide the structure for the final product (D), in the following reaction sequence.
O
.
CH3CH2CHOH
PBr3
Mg
ether
H3C
H2O
CH3
OH
Ans:
Topic: Synthesis
Section: 13.13
Difficulty Level: Medium
118. Provide the structure for each product (A-C) in the following reaction sequence.
1. O
CH3CH2CHOH
PBr3
Mg
ether
CH3
H3C
C
2. H2O
OH
Ans:
Br
Topic: Synthesis
Section: 13.13
Difficulty Level: Hard
MgBr
11904 Provide the structure for the final product (E), in the following reaction sequence.
O
.
PBr3
OH
Mg
ether
H2O
PCC
OH
O
H
OH
II
A)
B)
C)
D)
E)
CH2Cl2
III
IV O
I
II
III
IV
V
Ans: C
Topic: Synthesis
Section: 13.13
Difficulty Level: Hard
120. Provide the structure for each product (A-D) in the following reaction sequence.
1.
PBr3
OH
Mg
ether
2. H2O
PCC
CH2Cl2
Ans:
Topic: Synthesis
Section: 13.13
Difficulty Level: Medium
OH
Br
MgBr
10512 Provide the structure for product (A), in the following reaction sequence.
1.
OH
PBr3
Mg
D2O
ether
A)
B)
C)
D)
E)
CH3CH2CH2CH3
CH3CH2CHDCH3
CH3CH2CHODCH3
CH3CH2CH2CH2OD
CH3CH2CH2CH2D
Ans: B
Topic: Synthesis
Section: 13.13
Difficulty Level: Medium
10612 Provide the reagents necessary to carry out the following conversion.
O
2.
OH
Ans:
1.
2.
PBr3
Mg/ether
O
H
3.
4.
5.
H2O
PCC/CH2Cl2
Topic: Synthesis
Section: 13.13
Difficulty Level: Hard
Cl
Ans:
Cl2
OH
CH3CH2ONa
H3O+
PCC
CH2Cl2
OH
H2SO4
1. CH3MgBr
2. H2O
heat
Topic: Synthesis
Section: 13.13
Difficulty Level: Hard
10812 Provide the product for the following reaction sequence:
MgBr
4.
OH
PCC
CH2Cl2
IV
A)
B)
C)
D)
E)
I
II
III
IV
V
Ans: C
H2O
K2Cr2O7/H2SO4/H2O
H2O
ether
ether
OH
MgBr
HO
III
II
Topic: Synthesis
Section: 13.13
Difficulty Level: MediumHard
10912 Predict the product, for the following reaction sequence,
O
5.
3,4-dimethyl-1-hexanol
SOCl2
Mg/ether
pyridine
1.
CrO3/ H2SO4/H2O
2. H3O+
O
OH
III
II
OH
IV
A)
B)
C)
D)
E)
6,7-dimethyl-3-nonanolI
6,7-dimethyl-3-nonanoneII
6,7-dimethyl-3-nonanalIII
3,4-dimethyl-7-nonanolIV
3,4-dimethyl-7-nonanoneV
Ans: B
Topic: Synthesis
Section: 13.13
Difficulty Level: Hard
OH
Ans:
Cl
OH
CH3CH2ONa
Br2
h
1. BH3 THF
PCC
2. H2O2/NaOH/H2O
CH2Cl2
Topic: Synthesis
Section: 13.13
Difficulty Level: Hard
11112 Provide the reagents necessary to carry out the following conversion.
O
7.
O
Ans:
1.
2.
3.
4.
Cl2/h
CCONa
KMnO4/NaOH/H2O
excess PCC/CH2Cl2
5.
Topic: Synthesis
Section: 13.13
Difficulty Level: Hard
11212 Provide the reagents necessary to carry out the following conversion.
O
HO
8.
HO
HO
Ans:
1.
2.
3.
(CH3)3SiCl/ (CH3CH2)3N
CH3MgBr
H3O+
4.
Topic: Synthesis
Section: 13.13
Difficulty Level: Medium
11312 Provide the reagents necessary to carry out the following conversion.
O
9.
Br
Ans: 1. NaOH
2. Na2Cr2O7/H2SO4/H2O
3.
Topic: Synthesis
Section: 13.13
Difficulty Level: Hard
OH
Ans:
Br
Br2
1. BH3 THF
CH3CH2ONa
OH
2. H2O2/NaOH/H2O
PCC
O
CH2Cl2
CH3
1. CH3MgBr
2. H2O
H2SO4
OH
heat
H2/Pd
Br
Br2
CH3CH2ONa
2. H2O2/NaOH/H2O
PCC
CH2Cl2
H2/Pd
Topic: Synthesis
Section: 13.13
Difficulty Level: Hard
1. BH3
1. CH3MgBr
2. H2O
CH3
OH
H2SO4
heat
OH
Ans:
OH
PBr3
Br
Mg/ether
MgBr
1. O
H
OH
2. H2O
CrO3/H2SO4/H2O
OH
Topic: Spectroscopy
Section: 13 & 15.6
Difficulty Level: Medium
132. Which one of the following compounds is consistent with the following IR spectrum?
OH
A)
B)
C)
D)
E)
I
II
III
IV
V
Ans: A
Topic: Spectroscopy
Section: 13 & 15.6
Difficulty Level: Medium
OH
II
OH
C
N
III
O
HO
IV
133. Which one of the following compounds is consistent with the following IR spectrum?
OH
OH
A)
B)
C)
D)
E)
I
II
III
IV
V
Ans: E
Topic: Spectroscopy
Section: 13, 16.11 & 16.12
Difficulty Level: Hard
II
OH
OH
III
IV
OH
134. Which of the following compounds is consistent with the following proton decoupled
13
C NMR spectrum?
80
70
60
50
40
PPM
OH
OH
30
20
OH
HO
A)
B)
C)
D)
E)
I
II
III
IV
none of these
Ans: B
Topic: Spectroscopy
Section: 13, 16.11 & 16.12
Difficulty Level: Hard
II
III
IV
10
135. Which of the following compounds is consistent with the following proton decoupled
13
C NMR spectrum?
70
60
50
40
PPM
30
20
10
OH
OH
HO
A)
B)
C)
D)
E)
I
II
III
IV
none of these
Ans: A
Topic: Spectroscopy
Section: 13, 16.11 & 16.12
Difficulty Level: Hard
II
III
IV
OH
136. A compound with a molecular formula C9H12O has the following 1HNMR spectrum.
Which of the following structures is consistent with this spectrum?
3
2
1
exchangeswithD2O
A)
B)
C)
D)
E)
I
II
III
IV
V
Ans: C
Topic: Spectroscopy
Section: 13, 16.11 & 16.12
Difficulty Level: Hard
4
PPM
OH
OH
II
III OH
IV
0
OH
137. A compound with a molecular formula C6H14O displays the following 1HNMR and
13
CNMR spectra. Propose astructure for this compound.
3
2
90
80
70
Ans:
OH
60
50
PPM
40
30
20
10