CH 13

Chapter Thirteen
Topic: Nomenclature of alcohols

Section: 13.1
Difficulty Level: Easy
1. What is the IUPAC name for the following compound?
CH3
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

Section: 13.1
2.
A)
B)
C)
D)
E)
What is the IUPAC name for isobutyl alcohol?

2-methyl-1-propanol
2-methyl-1-butanol
1-methyl-1-propanol
1,1-dimethyl-1-ethanol
3-methyl-1-propanol
Ans: A

Section: 13.1

CH2CH3
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

Section: 13.1
Difficulty Level: Medium
4.
A)
B)
C)
D)
E)
What is the IUPAC name for t-butyl alcohol?

1-butanol
2-methyl-1-propanol
2-methyl-2-propanol
2-butanol
1,1-dimethyl-1-ethanol
Ans: C

Section: 13.1
OH
A)
B)
C)
D)
E)
1-isopropyl-4-cyclopentanol
1-isopropyl-4-hydroxycyclopentane
None of these
Ans: B

Section: 13.1
6. What is the correct structure for 1-chloro-3-ethyl-2-pentanol?

CH2CH3
CH2CH3
CH3CH2CCH2CH2Cl
OH
A)
B)
C)
D)
E)
CH3CHCHCH2CH2Cl
OH
II
CH3CH2CHCH2CHCl CH3CH2CHCHCH2Cl
III
I
II
III
IV
None of these
Ans: D

Section: 13.1
Br
HO
A)
B)
C)
D)
E)
2-methyl-5-bromocyclohexanol
3-bromo-2-methylcyclohexanol
Ans: E

Section: 13.1
Difficulty Level: Hard
CH2CH3
CH2CH3
OH
IV
OH

CH2CH2OH
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

Section: 13.1
OH
A)
B)
C)
D)
E)
4-penten-2-methyl-2-ol
4-methyl-1-penten-2-ol
4-hydroxy-4-methyl-1-pentene
Ans: C

Section: 13.1
CH3
H
HO
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

Section: 13.1
11. What is the correct structure for 2,2-dibromo-1-methylcyclohexanol?
OH
Br
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

Section: 13.1
12. What is the correct structure for (E)-5,5-dimethyl-3-hepten-1-ol?
OH
HO
III
II
OH
HO
OH
A)
B)
C)
D)
E)
I
II
III
IV
V
Ans: E
IV

Section: 13.1
OH
Ans: 7-ethyl-8-methyl-4-nonanol
Section: 13.1
HO
Ans: (R)-3-ethyl-2-methyl-3-heptanol
Section: 13.1
Br
OH
Ans: (1R,2S)-2-bromo-1-methylcyclopentanol
Section: 13.1

OH
Ans: 7-cyclohexyl-2,8-dimethyl-3-decanol
Section: 13.1
17. Provide the structure for (E)-4,5,5-trimethyl-3-hepten-1-ol?
Ans:
OH

Section: 13.1
18. Provide the structure for 5-chloro-2-propyl-1-heptanol.
Cl
Ans:
OH

Section: 13.1
19. Provide the structure for 6-sec-butyl-7,7-dimethyl-4-decanol.
Ans:
OH

Section: 13.1

OH
Ans: 4-isobutyl-2-methyl-3-octanol
Section: 13.1
HO
H
C
CH3(CH2)4
C
C
H
Ans: (S)-1-octyn-3-ol
Section: 13.1
HO
Ans: 4,5,6-tripropyl-4-decanol
Section: 13.1
HO
Ans: 3-ethyl-3-cyclohexen-1-ol

Section: 13.1
24. What is the correct structure for 2-methylphenol?
HO
A)
B)
C)
D)
E)
OH
OH
II
OH
OH
III
IV
I
II
III
IV
V
Ans: A

Section: 13.1
25. What is the correct structure for 2-bromo-5-isopropylphenol?
OH
Br
OH
OH
OH
Br
IV
Br
Br
Br
A)
B)
C)
D)
E)
I
II
III
IV
V
Ans: B

Section: 13.1
II
III
OH

OH
Br
Br
A)
B)
C)
D)
E)
3,4-dibromophenol
2,4-dibromophenol
2,5-dibromophenol
3,6-dibromophenol
2,6-dibromophenol
Ans: C

Section: 13.1
OH
Ans: 2-sec-butyl-5-ethylphenol
Section: 13.5
HOCH2CH2CH2OH
A) 1,2-butanediol
B) isopropanol
C) 1-propanol
D) 1,3-propanediol
E) 1,2-ethanediol
Ans: D
Section: 13.5

OH
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

Section: 13.5
OH
OH
Ans: 3,5-dimethyl-2,4-heptanediol
Section: 13.5
3127. Provide the structure for (2R, 3S)- 2-bromo-1,3-pentanediol.
Ans:
OH
OH
Br
Topic: Acidity of alcohols and phenols

Section: 13.2
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
The conjugate base of cyclohexanol has no resonance stabilization and the

negative charge on oxygen is localized, making it a stronger base, and
cyclohexanol a weaker acid
O

Section: 13.2
3329. Rank the following alcohols in decreasing order of acidity.
Br
Ans: II>I>III
Section: 13.2
OH
OH
OH
II
III
340. Which one of the following alcohols is most acidic?

O
OH
OH
OH
III
II
Ans: I
Section: 13.2
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.

Section: 13.2
362. Rank the following alcohols in decreasing order of acidity.
O2 N
OH
Ans: I>III>II
OH
II
NC
OH
III
Section: 13.2
373. Predict the product(s) for the following reaction.
OH
Na
ONa
Ans:
1
H2
2

Section: 13.2
OH
Li
Ans:
O Li
1
H2
2

Section: 13.2
394. Predict the product for the following reaction.
OH
1. NaH
2. CH3CH2Br
Ans:
Topic: Preparation of Alcohols

Section: 13.3
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

Section: 13.3
1. BH3 THF
2. H2O2/NaOH/H2O
CH2OH
OH
OH
+ enantiomer
I
A)
B)
C)
D)
E)
I
II
III
IV
None of these
Ans: B

Section: 13.3
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

Section: 13.3
(E)-3-methyl-3-hexene
3-methyl-3-hexanol
Ans: H3O+
OR
1. Hg(OAc)2, H2O
2. NaBH4
Section: 13.3
3944. Predict the major product for the following reaction.
H3O+
Ans:
OH

Section: 13.3
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

Section: 13.3
Br
Ans: NaOH
Section: 13.3
OH
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
Topic: Oxidation states

Section: 13.4
483. What is the oxidation state of the carbon atoms I and II in the following
reactioncompound?
O
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

Section: 13.4
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

Section: 13.4
450. For the following conversion, identify if the starting material has been oxidized, reduced
or neither. Explain your answer.
OH
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.
Section: 13.4
or neither.
Cl
Cl
Ans: Oxidized.
Section: 13.4

or neither. Explain your answer.
OH
Ans: Neither.
The oxidation state of the carbon atoms is not changed.
Section: 13.4
or neither.
O
H
A)
B)
C)
D)
reduced
oxidized
neither
A& B
Ans: B

Section: 13.4
or neither.
OH
A)
B)
C)
D)
reduced
oxidized
neither
A& B
Ans: C
Topic: Preparation of Alcohols via Reduction

Section: 13.4

O
CH3CCH2CH2CH3
NaBH4/CH3OH
OH
Ans:
CH3CHCH2CH2CH3
Section: 13.4
O
NaBH4/CH3OH
OH
A)
B)
C)
D)
I
II
III
IV
Ans: A
OH
OH
OH
II

Section: 13.4
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

Section: 13.4
OH
HC
CCH2CH2CH3
CH3CHCH2CH2CH3
Ans: 1. H3O / HgSO4

2. NaBH4/CH3OH
OR
1. H2/Ni2B (OR Na, NH3)
2. H3O+
Section: 13.4

O
H2.Pd
OH
A)
B)
C)
D)
I
II
III
IV
Ans: C
OH
II

Section: 13.4
O
COCH3
NaBH4 / H2O
Ans:
OH
OH
COCH3
H
HO

Section: 13.4
III
OH
IV

O
COCH3
1. LiAlH4 excess
2. H2O
O
CH2OH
Ans:
H
HO

Section: 13.4
H2O / H2SO4
HgSO4
Ans:
OH

Section: 13.4
NaBH4/CH3OH
5763. Provide the reactant (A) for the following reaction

1. LiAlH4
5-methyl-3-heptanol
A
2. H2O
O
O
O
H
II
O
III
IV
A)
B)
C)
D)
E)
I
II
III
IV
V
Ans: A
Topic: Preparation of Diols

Section: 13.5
A)
B)
C)
D)
E)
cyclohexene
KMnO4, NaOHcold
KMnO4, H3O+, 75oC
H2SO4, heat
1. mCPBA 2. H3O+
none of these
Ans: A

Section: 13.5
cis-1,2-cyclohexanediol
5965. Predict the product(s) for the following reaction sequence.

H2/Ni2B
1. OsO4
3-hexyne
2. NaHSO3
H
HO
A)
B)
C)
D)
E)
HO
OH
HO
HO
II
OH
III
I
II
III
Both I & II
None of these
Ans: BA

Section: 13.5
A)
B)
C)
D)
E)
cyclohexene
KMnO4, NaOH
KMnO4, H3O+, 75oC
H2SO4, heat
1. mCPBA 2. H3O+
none of these
Ans: D
trans-1,2-cyclohexanediol

Section: 13.5
671. Provide the structure(s) of the each product (A-D)(s) in the following reaction sequence.
CH3CH2ONa
A
B
Br2
h
mCPBA
Ans:
NaOH/H2O
D
CH3
CH3
Br
OH
OH
+ enantiomer
+ enantiomer
D

Section: 13.5
O
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

Section: 13.5

O
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

Section: 13.5
7064. Provide the reagent(s) necessary to carry out the following conversion.
OH
OH
Ans: 1. mCPBA
2. H3O+ OR NaOH/H2O
Section: 13.5
OH
OH
Ans:
1.
2.
3.
4.
O3
(CH3)2S
excess NaBH4/CH3OH

Section: 13.5
O
1. excess LiAlH4
2. H2O
Ans:
OH
OH
OH
Topic: Preparation of Alcohols via Grignard Reagents

Section: 13.6
6773. Predict the product for the following reaction sequence.
O
1. CH3CH2MgBr
2. H2O
Ans:
HO

Section: 13.6
6874. Predict the product for the following reaction sequence.

O
1.
Mg/ether
Br
2. H2O
Ans:
OH

Section: 13.6
O
Ans: 1. excess CH3MgBr/ether

2. H2O
Section: 13.6
OH

O
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

Section: 13.6
O
Br
1.
Mg/ether
2. H2O
Ans:
OH

Section: 13.6
IV
78. Using Grignard reaction, show how you could prepare the following alcohol.
OH
Ans:
MgBr
1.
O
C
H
2. H2O

Section: 13.6
OH
Ans:
1. MgBr
2. H2O
OR
1.
MgBr
2. H2O

Section: 13.6
HO
Ans:
MgBr
1.
O
2. H2O
OR
1.
MgBr
2. H2O
OR
1.
O
MgBr
2. H2O

Section: 13.6
HO
Ans: 1. HBr
2. Mg/ether
O
3. H
4. H2O

Section: 13.6
7382. Provide the reagent(s) necessary to prepare 1-isopropylcyclopentanol using a Grignard

reaction.
O
Ans:
MgBr
1.
2. H2O
Topic: Preparation of alcohols via Grignard Reagents

Section: 13.6
O
OCH3
excess
1. CH3CH2CH2MgBr
2. H2O
Ans:
OH

Section: 13.6
O
excess
1. CH3CH2MgBr
2. H2O
Ans:
OH
OH

Section: 13.6

excess
1. CH3CH2MgBr
2. H2O
Ans:
OH

Section: 13.6
86. Predict the product for the following reaction and provide a curved arrow mechanism
for the formation of the product.
excess
1. CH3CH2MgBr
2. H2O
Ans:
OH
Mechanism
O
CH3CH2MgBr
O
CH3CH2MgBr
+ CH3OMgBr
O
CH3CH2MgBr
O
+ CH3OMgBr
O
O
H
HO
+ OH
Topic: Protection of alcohols

Section: 13.7
OH
HO
Br
HO
Ans: 1. (CH3)3SiCl / (CH3CH2)3N

2. Mg/ether
O
3.
4. H2O
5. TBAF
Section: 13.7
OH
HO
HO
Ans: 1. CH3)3SiCl / (CH3CH2)3N

2.
MgBr
3. H2O
4. TBAF
Section: 13.7
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

Section: 13.7
7790. Predict the product(s) for the following reaction sequence.
1.
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

Section: 13.7
(CH3CH2)3N
Mg/ ether
O
H
2. H2O
TBAF
TBAF
HO
HO
Ans:
1.
2.
3.
4.
(CH3)3SiCl / (CH3CH2)3N
NaNH2
CH3CH2CH2Br
TBAF
Topic: Reactions of Alcohols

Section: 13.9
7992. Which of the following could be used to synthesize 1-bromopentane?
A)
B)
C)
D)
E)
CH3CH2CH2CH=CH2 +
CH3CH2CH2CH2CH2OH
CH3CH2CH2CH2CH2OH
CH3CH2CH2CH2CH2OH
CH3CH2CH2CH=CH2 +
Ans: B
HBr
+ PBr3
+ NaBr
+ Br2
Br2

Section: 13.9
8093. Provide the reagents necessary to convert 3-methyl-2-butanol to 2-bromo-3methylbutane.
A) conc. HBr
B) Br2
C) NaBr, H2SO4
D) PBr3
E) HBr, peroxide
Ans: D
Section: 13.9

OH
PBr3
Br
Ans:

Section: 13.9
8295. Predict the major product for the following reaction and provide a curved arrow
mechanism for the formation of the product.
OH
HBr
Ans:
Br
Mechanism
OH
Br
OH2
+ Br
H
Br
Br

Section: 13.9
+ H2O
OH
HCl
Ans:
Cl

Section: 13.9
SOCl2/pyridine
OH
Ans:
Cl

Section: 13.9

H
OH
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

Section: 13.9
8699. Predict the product when cis-3-methylcyclopentanol is treated with TsCl/pyridine,
followed by sodium bromide.
A) trans-1-bromo-3-methylcyclopentane
B) cis-1-bromo-3-methylcyclopentane
C) 1-methylcyclopentene
D) 2-mMethylcyclopentene
E) 3-mMethylcyclopentene
Ans: A
Section: 13.9
87100 The reaction between 2-methyl-2-pentanol and sulfuric acid to yield 2-methyl-2-pentene
. goes via a(n) _____.
A)
B)
C)
D)
E)
SN1 mechanism
SN2 mechanism
E1 mechanism
E2 mechanism
None of these.
Ans: C

Section: 13.9
88101 Explain why the following reaction will not produce an alcohol as product.
.
Cl
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.
Section: 13.9
89102 Predict the major product for the following reaction.
.
OH
1. TsCl/pyridine
2. CH3CH2ONa
Ans:

Section: 13.9
90103 Predict the major product for the following reaction.

OH
.
H2SO4
Ans:

Section: 13.9
91104 Provide the reagent(s) necessary to convert cyclohexanol to cyclohexane.
. .
Ans: 1. H2SO4, heat
2. H2/Pd
OR
OR
1. TsCl/pyridine
2. CH3CH2ONa
3. H2/Pd
4.

Section: 13.9
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

Section: 13.9
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

Section: 13.10
O
O
+ H2SO4
94107 Predict the product for the following reaction.

PCC
.
2-hexanol
CH2Cl2
O
A)
CH3COH
O
B)
CH3CH2CH2CH2COH
O
C)
CH3(CH2)3CCH3
D)
CH3CH2CH2CH2CH2COH
O
E)
CH3CH2CH2CH2CH2CH
Ans: C
Section: 13.10
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

Section: 13.10

OH
.
Na2Cr2O7/H2SO4/H2O
Ans:

Section: 13.10
OH
.
PCC
CH2Cl2
H
Ans:
O

Section: 13.10
.
O
OH
A)
B)
C)
D)
E)
KMnO4/NaOH/H2O
Na2Cr2O7CrO3/H2SO4/H2O
PCC/CH2Cl2
Br2, CCl4
None of these
Ans: C

Section: 13.10
.
O
OH
A)
B)
C)
D)
E)
OH
KMnO4/NaOH/H2O
Na2Cr2O7CrO3/H2SO4/H2O
PCC/CH2Cl2
Br2, CCl4
None of these
Ans: B

Section: 13.10
.
OH
excess
PCC/CH2Cl2
Ans:
CH2OH
OH
CH
O

Section: 13.10
.
OH
PCC
CH2Cl2
Ans: No reaction. Tertiary alcohols do not undergo oxidation reactions.

Section: 13.10
PCC
.
cis-4-methylcyclohexanol
CH2Cl2
Ans:
.
Topic: Oxidation of Phenols
Section: 13.12
OH
Na2Cr2O7/H2SO4/H2O
Ans:
Topic: Synthesis
Section: 13.13
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
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
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
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
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
O
2.
OH
Ans:
1.
2.
PBr3
Mg/ether
O
H
3.
4.
5.
H2O
PCC/CH2Cl2
Topic: Synthesis
Section: 13.13
10712 Provide a stepwise synthesis for the following.

3.
Cl
Ans:
Cl2
OH
CH3CH2ONa
H3O+
PCC
CH2Cl2
OH
H2SO4
1. CH3MgBr
2. H2O
heat
Topic: Synthesis
Section: 13.13
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
OH
11012 Provide a stepwise synthesis for the following.

6.
O
Ans:
Cl
OH
CH3CH2ONa
Br2
h
1. BH3 THF
PCC
2. H2O2/NaOH/H2O
CH2Cl2
Topic: Synthesis
Section: 13.13
O
7.
O
Ans:
1.
2.
3.
4.
Cl2/h
CCONa
KMnO4/NaOH/H2O
excess PCC/CH2Cl2
5.
Topic: Synthesis
Section: 13.13
O
HO
8.
HO
HO
Ans:
1.
2.
3.
(CH3)3SiCl/ (CH3CH2)3N
CH3MgBr
H3O+
4.
Topic: Synthesis
Section: 13.13
O
9.
Br
Ans: 1. NaOH
2. Na2Cr2O7/H2SO4/H2O
3.
Topic: Synthesis
Section: 13.13
OH
11413 Provide a stepwise synthesis to carry out the following conversion.

0.
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
1. BH3
1. CH3MgBr
2. H2O
CH3
OH
H2SO4
heat
OH
131. Provide a stepwise synthesis to carry out the following conversion.

O
OH
OH
Ans:
OH
PBr3
Br
Mg/ether
MgBr
1. O
H
OH
2. H2O
CrO3/H2SO4/H2O
OH
Topic: Spectroscopy
Section: 13 & 15.6
132. Which one of the following compounds is consistent with the following IR spectrum?
SDBS: National Institute of Advanced Industrial Science and Technology
OH
A)
B)
C)
D)
E)
I
II
III
IV
V
Ans: A
Topic: Spectroscopy
Section: 13 & 15.6
OH
II
OH
C
N
III
O
HO
IV
133. Which one of the following compounds is consistent with the following IR spectrum?
SDBS: National Institute of Advanced Industrial Science and Technology
OH
OH
A)
B)
C)
D)
E)
I
II
III
IV
V
Ans: E
Topic: Spectroscopy
Section: 13, 16.11 & 16.12
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
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
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
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

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Chapter Thirteen

Topic: Nomenclature of alcohols

Topic: Nomenclature of alcohols

What is the IUPAC name for isobutyl alcohol?

Topic: Nomenclature of alcohols

3. What is the IUPAC name for the following compound?

Topic: Nomenclature of alcohols

What is the IUPAC name for t-butyl alcohol?

Topic: Nomenclature of alcohols

Topic: Nomenclature of alcohols

6. What is the correct structure for 1-chloro-3-ethyl-2-pentanol?

Topic: Nomenclature of alcohols

Topic: Nomenclature of alcohols

8. What is the IUPAC name for the following compound?

Topic: Nomenclature of alcohols

Topic: Nomenclature of alcohols

Topic: Nomenclature of alcohols

Topic: Nomenclature of alcohols

Topic: Nomenclature of alcohols

16. What is the IUPAC name for the following compound?

Topic: Nomenclature of alcohols

Topic: Nomenclature of alcohols

Topic: Nomenclature of alcohols

20. What is the IUPAC name for the following compound?

Topic: Nomenclature of alcohols

Topic: Nomenclature of alcohols

Topic: Nomenclature of alcohols

26. What is the IUPAC name for the following compound?

Topic: Nomenclature of alcohols

295. What is the IUPAC name for the following compound?

Topic: Nomenclature of alcohols

Topic: Acidity of alcohols and phenols

The conjugate base of cyclohexanol has no resonance stabilization and the

Topic: Acidity of alcohols and phenols

340. Which one of the following alcohols is most acidic?

Topic: Acidity of alcohols and phenols

Topic: Acidity of alcohols and phenols

Topic: Acidity of alcohols and phenols

Topic: Preparation of Alcohols

Topic: Preparation of Alcohols

Topic: Preparation of Alcohols

4237. Predict the product for the following reaction.

Topic: Preparation of Alcohols

Topic: Preparation of Alcohols

Topic: Preparation of Alcohols

Topic: Oxidation states

Topic: Oxidation states

Topic: Oxidation states

Difficulty Level: Medium

Topic: Oxidation states

Topic: Preparation of Alcohols via Reduction

Difficulty Level: Easy

Topic: Preparation of Alcohols via Reduction

Topic: Preparation of Alcohols via Reduction

Ans: 1. H3O / HgSO4

593. Predict the product for the following reaction.

Topic: Preparation of Alcohols via Reduction

Topic: Preparation of Alcohols via Reduction

5561. Predict the product for the following reaction.

Topic: Preparation of Alcohols via Reduction

Topic: Preparation of Alcohols via Reduction

5763. Provide the reactant (A) for the following reaction