Chapter Thirteen: CH CH

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 CH3
A) 4-isopropyl-3,4-dimethyl-2-butanol
B) 2,3,4-trimethyl-4-pentanol
C) 1,1,2,3-tetramethyl-4-pentanol
D) 3,4,5-trimethyl-2-hexanol
E) 3,4,5,5-tetramethyl-2-pentanol
Ans: D

Section: 13.1
2. What is the IUPAC name for isobutyl alcohol?

A) 2-methyl-1-propanol
B) 2-methyl-1-butanol
C) 1-methyl-1-propanol
D) 1,1-dimethyl-1-ethanol
E) 3-methyl-1-propanol
Ans: A

Section: 13.1
CH2CH3
CH3CH2CCH2CH3
OH
A) 1,1,1-triethylmethanol
B) 1,1-diethyl-1-propanol
C) 2-ethyl-3-pentanol
D) 3-ethyl-3-pentanol
E) t-heptanol
Ans: D

Section: 13.1
Difficulty Level: Medium
4. What is the IUPAC name for t-butyl alcohol?

A) 1-butanol
B) 2-methyl-1-propanol
C) 2-methyl-2-propanol
D) 2-butanol
E) 1,1-dimethyl-1-ethanol
Ans: C

Section: 13.1
OH
A) 1-isopropyl-4-cyclopentanol
B) 3-isopropyl-1-cyclopentanol
C) 1-isopropyl-3-cyclopentanol
D) 1-isopropyl-4-hydroxycyclopentane
E) None of these
Ans: B

Section: 13.1
6. What is the correct structure for 1-chloro-3-ethyl-2-pentanol?
CH2CH3 CH2CH3 CH2CH3 CH2CH3
CH3CH2CCH2CH2Cl CH3CHCHCH2CH2Cl CH3CH2CHCH2CHCl CH3CH2CHCHCH2Cl
OH OH OH IV OH
I II III
A) I
B) II
C) III
D) IV
E) None of these
Ans: D

Section: 13.1

Br
HO
A) 2-methyl-5-bromocyclohexanol
B) 3-bromo-2-methylcyclohexanol
C) 1-bromo-4-methylcyclohexanol
D) 4-bromo-6-methylcyclohexanol
E) 4-bromo-2-methylcyclohexanol
Ans: E

Section: 13.1
Difficulty Level: Hard
CH2CH2OH
CH3CH2C=CCH2CH3
CH3
A) 3-methyl-4-ethyl-3-hexen-6-ol
B) 4-ethyl-3-methyl-3,6-hexenol
C) 3-ethyl-4-methyl-3-hexen-1-ol
D) 3-methyl-4-(2-hydroxyethyl)-3-hexene
E) 3-(2-hydroxyethyl)- 3-methyl-3-hexene
Ans: C

Section: 13.1

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

Section: 13.1
CH3
C
H
C
HO
CC
H
2 CH
3
A) (R)-3-hexyn-2-ol
B) (S)-3-hexyn-2-ol
C) (R)-2-hexyn-4-ol
D) (S)-2-hexyn-4-ol
E) (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 CH3
Br Br
CH3CH2CH2CH2CCH(CH3)OH CH3CCH2CH2CH2CHOH
Br
I Br
III
OH II OH
Br Br
Br Br
IV V
A) I
B) II
C) III
D) IV
E) V
Ans: D

Section: 13.1
12. What is the correct structure for (E)-5,5-dimethyl-3-hepten-1-ol?

OH
HO
I
III
II
OH
HO
OH IV V
A) I
B) II
C) III
D) IV
E) V
Ans: E
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.

Ans: Cl
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
OH OH OH
OH
I II III IV V
A) I
B) II
C) III
D) IV
E) V
Ans: A

Section: 13.1
25. What is the correct structure for 2-bromo-5-isopropylphenol?

Br
OH OH OH OH Br OH
Br
Br Br
I II III IV V
A) I
B) II
C) III
D) IV
E) V
Ans: B

Section: 13.1
OH
Br
Br
A) 3,4-dibromophenol
B) 2,4-dibromophenol
C) 2,5-dibromophenol
D) 3,6-dibromophenol
E) 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) cis-1,2-cyclopentanediol
B) meso-1,2-cyclopentanediol
C) (1R,2R)-1,2-cyclopentanediol
D) (1R,2S)-1,2-cyclopentanediol
E) (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 O O
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.

OH OH
OH
F II I III
Br I
Ans: II>I>III

Section: 13.2
340. Which one of the following alcohols is most acidic?
O OH O
OH OH
II III
I
Ans: I

Section: 13.2
351. Rank the following alcohols in decreasing order of acidity. Explain your answer.
F F
OH
OH OH
F
F
II III
I
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.
O2N OH OH NC OH
I II III
Ans: I>III>II

Section: 13.2
373. Predict the product(s) for the following reaction.

OH
Na
Ans: ONa
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: O
Topic: Preparation of Alcohols

Section: 13.3
3540. Provide the reagents necessary to carry out the following conversion.
CH3CH2CH2CHCH3 CH3CH2CH2CH2CH2OH
Br
Ans: 1. (CH3)3COK
2. BH3
3. •THF
4. H2O2/NaOH/H2O

Section: 13.3

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

Section: 13.3
1. Hg(OAc)2, H2O
2. NaBH4
CH2OH
OH
OH
I II III IV
OH
A) I
B) II
C) III
D) IV
E) 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 D D OH
OH D OH
I II III IV V
A) I
B) II
C) III
D) IV
E) V
Ans: C

Section: 13.3
Br OH
Ans: NaOH

Section: 13.3
OH
Cl
A) NaOH/H2O
B) 1. NaOCH3, 2. H3O+
C) 1. (CH3)3COK, 2. BH3, •THF, 3. H2O2/NaOH/H2O
D) 1. (CH3)3COK, 2. H3O+
E) 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
I O
A) I. +1, II. +2
B) I. +2, II. +2
C) I. +1, II. +3
D) I. +3, II. +2
E) 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 O
CH3CH CH3COH
I II
A) I. +1, II. +2
B) I. +2, II. +2
C) I. +1, II. +3
D) I. +3, II. +2
E) 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 O
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 O
Ans: Neither.
The oxidation state of the carbon atoms is not changed.

Section: 13.4
or neither.
O
A) reduced
B) oxidized
C) neither
D) A&B
Ans: B

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

Section: 13.4

O
NaBH4/CH3OH
CH3CCH2CH2CH3
Ans: OH
CH3CHCH2CH2CH3

Section: 13.4

O
H
NaBH4/CH3OH
O OH
OH OH OH OH
IV
I II III
A) I
B) II
C) III
D) IV
Ans: A

Section: 13.4
571. Which one of the following compounds gives 5-methyl-3-heptanol with LiAlH4
followed by water?
O O
O
H
I II
O O
III
H
IV V
A) I
B) II
C) III
D) IV
E) V
Ans: A

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

Section: 13.4

O
COCH3
NaBH4 / H2O
O
O
Ans:
COCH3
HO

Section: 13.4
O
COCH3
1. LiAlH4 excess
2. H2O
O
CH2OH
Ans:
HO

Section: 13.4

H2O / H2SO4
NaBH4/CH3OH
HgSO4
Ans:
OH

Section: 13.4
5763. Provide the reactant (A) for the following reaction
1. LiAlH4
A 5-methyl-3-heptanol
2. H2O
O O
O
H
I II
O O III
H
IV V
A) I
B) II
C) III
D) IV
E) V
Ans: A
Topic: Preparation of Diols

Section: 13.5
cyclohexene cis-1,2-cyclohexanediol
A) KMnO4, NaOHcold
B) KMnO4, H3O+, 75oC
C) H2SO4, heat
D) 1. mCPBA 2. H3O+
E) none of these
Ans: A

Section: 13.5
5965. Predict the product(s) for the following reaction sequence.
H2/Ni2B 1. OsO4
3-hexyne
2. NaHSO3
H HO HO OH
OH H
H H H H
HO HO II III
I
A) I
B) II
C) III
D) Both I & II
E) None of these
Ans: BA

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

Section: 13.5
671. Provide the structure(s) of the each product (A-D)(s) in the following reaction sequence.
Br2 CH3CH2ONa mCPBA NaOH/H2O

A B C D
h
Ans: CH3 CH3
Br
OH
O
OH
+ enantiomer + enantiomer
C D H
A B
Section: 13.5

O O
excess
NaBH4/CH3OH
H
OH O O OH
H OH OH
II III
I
OH
OH OH
OH
OH
IV V
A) I
B) II
C) III
D) IV
E) V
Ans: C

Section: 13.5
O
H3O+
OH OH
H
O
OH OH
OH
I II III IV
A) I
B) II
C) III
D) IV
E) 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. O3
2. (CH3)2S
3. excess NaBH4/CH3OH
4.
Section: 13.5

O
1. excess LiAlH4
O
2. H2O
O
OH
Ans:
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 H
Br
2. H2O
Ans:
OH

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

2. H2O

Section: 13.6
O
1. CH3CH2CH2MgBr/ether
2. H2O
OH
OH
HO
OH
I II III IV
A) I
B) II
C) III
D) IV
E) None of these
Ans: A

Section: 13.6

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

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

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

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

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

Section: 13.6
7382. Provide the reagent(s) necessary to prepare 1-isopropylcyclopentanol using a Grignard
reaction.
Ans: O
MgBr
1.
2. H2O
Topic: Preparation of alcohols via Grignard Reagents

Section: 13.6

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

Section: 13.6

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

Section: 13.6
O excess
1. CH3CH2MgBr
O O 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.
O excess
1. CH3CH2MgBr
O O 2. H2O
Ans:
OH
Mechanism
O
O O
CH3CH2MgBr CH3CH2MgBr
O O O O O
+ CH3OMgBr
O O
CH3CH2MgBr
O
+ CH3OMgBr
O
H H
O 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
O
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
1. O
Br
(CH3)3SiCl Mg/ ether TBAF
A B C D
(CH3CH2)3N 2. H2O
Ans:
OSi(CH3)3 OSi(CH3)3
Br MgBr
A B
OSi(CH3)3 OH
HO HO
C D

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

OH 1. O
H H
(CH3)3SiCl Mg/ ether TBAF
Br (CH3CH2)3N 2. H2O
A) 2,4-heptanediol
B) 1,4-heptanediol
C) 2,5-octanediol
D) 1,5-octanediol
E) none of these
Ans: B

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

2. NaNH2
3. CH3CH2CH2Br
4. TBAF
Topic: Reactions of Alcohols

Section: 13.9
7992. Which of the following could be used to synthesize 1-bromopentane?
A) CH3CH2CH2CH=CH2 + HBr 

B) CH3CH2CH2CH2CH2OH + PBr3 
C) CH3CH2CH2CH2CH2OH + NaBr 
D) CH3CH2CH2CH2CH2OH + Br2 
E) CH3CH2CH2CH=CH2 + Br2 
Ans: B

Section: 13.9
8093. Provide the reagents necessary to convert 3-methyl-2-butanol to 2-bromo-3-

methylbutane.
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 H Br OH2
+ Br
H + H2O
Br
Br

Section: 13.9
OH
HCl
Ans:
Cl

Section: 13.9
SOCl2/pyridine
OH
Ans:
Cl

Section: 13.9
H
OH
1. TsCl /pyridine
CH3
2. NaI
H
H H I H
I OTs H Ts
CH3 CH3 CH3 CH3

H H III H IV H
II
I
A) I
B) II
C) III
D) IV
E) 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) SN1 mechanism
B) SN2 mechanism
C) E1 mechanism
D) E2 mechanism
E) 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 H2SO4 CH2CH3
Ans: O
H2O
HO H O S O H CH2CH3
CH2CH3 O
O CH2CH3
CH2CH3
O S O H
+
O
H3CH2C H3CH2C
H O
CH2CH3 CH2CH3
O S O H
CH2CH3 CH2CH3 O
+ H2O
CH2CH3
+ H2SO4
CH2CH3

Section: 13.9
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 O S O H
OH2
O
OH O OH
O S O H
+
O
O
O
H O H
O S O H
OH
O
+ H2O
+ H2SO4

Section: 13.10
94107 Predict the product for the following reaction.
. PCC
2-hexanol
CH2Cl2
A) O
CH3COH
O
B)
CH3CH2CH2CH2COH
O
C)
CH3(CH2)3CCH3
O
D)
CH3CH2CH2CH2CH2COH
E) O
CH3CH2CH2CH2CH2CH
Ans: C

Section: 13.10
95108 Provide the reagents necessary to carry out the following conversion.
. OH O
A) KMnO4/NaOH/H2O
B) Na2Cr2CrOO73/H2SO4/H2O
C) H2, Pt
D) Br2, CCl4
E) None of these
Ans: B

Section: 13.10
. OH
Na2Cr2O7/H2SO4/H2O
Ans: O

Section: 13.10

. OH
PCC
CH2Cl2
Ans: H

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

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

Section: 13.10

.
OH
excess
PCC/CH2Cl2
CH2OH
OH
Ans:
CH

Section: 13.10

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

Section: 13.10

. PCC
cis-4-methylcyclohexanol
CH2Cl2
Ans: O
Topic: Oxidation of Phenols

Section: 13.12

OH
Na2Cr2O7/H2SO4/H2O
Ans: O
O .
Topic: Synthesis
Section: 13.13
11703 Provide the structure for the final product (D), in the following reaction sequence.
. O
PBr3 Mg H3C H H2O

CH3CH2CHOH A B C D
ether
CH3
Ans: OH
Topic: Synthesis
Section: 13.13
118. Provide the structure for each product (A-C) in the following reaction sequence.
1. O
PBr3 Mg H3C H
CH3CH2CHOH A B C
ether
2. H2O
CH3
Ans: OH
Br MgBr
A B C
Topic: Synthesis
Section: 13.13
11904 Provide the structure for the final product (E), in the following reaction sequence.
. O
PBr3 Mg H H H2O PCC

OH A B C D E
ether CH2Cl2
OH O
H
OH
I II
III V
O IV O
A) I
B) II
C) III
D) IV
E) V
Ans: C
Topic: Synthesis
Section: 13.13
120. Provide the structure for each product (A-D) in the following reaction sequence.
O
1.
PBr3 Mg H H PCC
OH A B C D
ether 2. H2O CH2Cl2
Ans:
OH O
Br MgBr
A B C D
Topic: Synthesis
Section: 13.13
10512 Provide the structure for product (A), in the following reaction sequence.
1.
OH
PBr3 Mg D2O
A
ether
A) CH3CH2CH2CH3
B) CH3CH2CHDCH3
C) CH3CH2CHODCH3
D) CH3CH2CH2CH2OD
E) CH3CH2CH2CH2D
Ans: B
Topic: Synthesis
Section: 13.13
O
2.
OH
Ans: 1. PBr3
2. Mg/ether
O
3. H
4. H2O
5. PCC/CH2Cl2
Topic: Synthesis
Section: 13.13
10712 Provide a stepwise synthesis for the following.
3.
Cl
Ans: OH
Cl2 CH3CH2ONa H3O+ PCC

h
CH2Cl2
O OH
1. CH3MgBr H2SO4
2. H2O heat
Topic: Synthesis
Section: 13.13
10812 Provide the product for the following reaction sequence:

MgBr
4. MgBr
OH K2Cr2O7/H2SO4/H2O H2O
PCC H2O
CH2Cl2 ether ether
OH O HO
I II III
O
IV V
A) I
B) II
C) III
D) IV
E) V
Ans: C
Topic: Synthesis
Section: 13.13
Difficulty Level: MediumHard
10912 Predict the product, for the following reaction sequence,

O
5.
1.
SOCl2 Mg/ether H CrO3/ H2SO4/H2O
3,4-dimethyl-1-hexanol
pyridine 2. H3O+
OH O
II III
I OH
OH H
IV O V O
A) 6,7-dimethyl-3-nonanolI
B) 6,7-dimethyl-3-nonanoneII
C) 6,7-dimethyl-3-nonanalIII
D) 3,4-dimethyl-7-nonanolIV
E) 3,4-dimethyl-7-nonanoneV
Ans: B
Topic: Synthesis
Section: 13.13
11012 Provide a stepwise synthesis for the following.
6.
O
Ans:
Cl
OH
CH3CH2ONa 1. BH3 THF PCC

Br2
2. H2O2/NaOH/H2O CH2Cl2
h
Topic: Synthesis
Section: 13.13
O
7.
O
Ans: 1. Cl2/h
2. CCONa
3. KMnO4/NaOH/H2O
4. excess PCC/CH2Cl2
5.
Topic: Synthesis
Section: 13.13
8. O HO
HO HO
Ans: 1. (CH3)3SiCl/ (CH3CH2)3N

2. CH3MgBr
3. H3O+
4.
Topic: Synthesis
Section: 13.13
9. O
Br OH
Ans: 1. NaOH
2. Na2Cr2O7/H2SO4/H2O
3.
Topic: Synthesis
Section: 13.13
11413 Provide a stepwise synthesis to carry out the following conversion.
0.
Ans:
Br
Br2 1. BH3 THF
CH3CH2ONa
h OH
2. H2O2/NaOH/H2O
CH3
PCC
1. CH3MgBr H2SO4
CH2Cl2 O
2. H2O OH heat
H2/Pd
Br
Br2 1. BH3
CH3CH2ONa
h OH
2. H2O2/NaOH/H2O
CH3
PCC
1. CH3MgBr H2SO4
CH2Cl2 O
2. H2O OH heat
H2/Pd
Topic: Synthesis
Section: 13.13
131. Provide a stepwise synthesis to carry out the following conversion.
O
OH
OH
Ans:
OH PBr3 Br Mg/ether MgBr
1. O O
H H CrO3/H2SO4/H2O
OH OH
2. H2O
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
OH OH O
C HO C
I II N III IV N
A) I
B) II
C) III
D) IV
E) V
Ans: A
Topic: Spectroscopy
Section: 13 & 15.6
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 O O OH
OH OH
I II III IV V
A) I
B) II
C) III
D) IV
E) V
Ans: E
Topic: Spectroscopy
Section: 13, 16.11 & 16.12
134. Which of the following compounds is consistent with the following proton decoupled
13
C NMR spectrum?
80 70 60 50 40 30 20 10 0
PPM
OH OH OH
HO
I II IV
III
A) I
B) II
C) III
D) IV
E) none of these
Ans: B
Topic: Spectroscopy
Section: 13, 16.11 & 16.12
135. Which of the following compounds is consistent with the following proton decoupled
13
C NMR spectrum?
70 60 50 40 30 20 10 0
PPM
OH OH
HO
I II IV
III OH
A) I
B) II
C) III
D) IV
E) none of these
Ans: A
Topic: Spectroscopy
Section: 13, 16.11 & 16.12
136. A compound with a molecular formula C9H12O has the following 1HNMR spectrum.
Which of the following structures is consistent with this spectrum?
2 2 2 2
1
exchanges with D2O
7 6 5 4 3 2 1 0
PPM
O OH OH OH
I II III OH IV V
A) I
B) II
C) III
D) IV
E) V
Ans: C
Topic: Spectroscopy
Section: 13, 16.11 & 16.12
137. A compound with a molecular formula C6H14O displays the following 1HNMR and
13
CNMR spectra. Propose astructure for this compound.
2 1
90 80 70 60 50 40 30 20 10 0
PPM
Ans:
OH

Chapter Thirteen: CH CH

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Chapter Thirteen: CH CH

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Chapter Thirteen

Topic: Nomenclature of alcohols

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

Topic: Nomenclature of alcohols

2. What is the IUPAC name for isobutyl alcohol?

Topic: Nomenclature of alcohols

Topic: Nomenclature of alcohols

4. What is the IUPAC name for t-butyl alcohol?

Topic: Nomenclature of alcohols

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

Topic: Nomenclature of alcohols

CH3CH2CCH2CH2Cl CH3CHCHCH2CH2Cl CH3CH2CHCH2CHCl CH3CH2CHCHCH2Cl

Topic: Nomenclature of alcohols

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

Topic: Nomenclature of alcohols

Topic: Nomenclature of alcohols

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

Topic: Nomenclature of alcohols

11. What is the correct structure for 2,2-dibromo-1-methylcyclohexanol?

Topic: Nomenclature of alcohols

12. What is the correct structure for (E)-5,5-dimethyl-3-hepten-1-ol?

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

Topic: Nomenclature of alcohols

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

Topic: Nomenclature of alcohols

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

Topic: Nomenclature of alcohols

Topic: Nomenclature of alcohols

17. Provide the structure for (E)-4,5,5-trimethyl-3-hepten-1-ol?

Topic: Nomenclature of alcohols

18. Provide the structure for 5-chloro-2-propyl-1-heptanol.

Topic: Nomenclature of alcohols

19. Provide the structure for 6-sec-butyl-7,7-dimethyl-4-decanol.

Topic: Nomenclature of alcohols

Topic: Nomenclature of alcohols

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

Topic: Nomenclature of alcohols

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

Topic: Nomenclature of alcohols

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

24. What is the correct structure for 2-methylphenol?

Topic: Nomenclature of alcohols

25. What is the correct structure for 2-bromo-5-isopropylphenol?

Topic: Nomenclature of alcohols

Topic: Nomenclature of alcohols

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

Topic: Nomenclature of alcohols

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

Topic: Nomenclature of alcohols

Topic: Nomenclature of alcohols

3026. What is the IUPAC name for the following compound?

Topic: Nomenclature of alcohols

3127. Provide the structure for (2R, 3S)- 2-bromo-1,3-pentanediol.

Topic: Acidity of alcohols and phenols

The conjugate base of cyclohexanol has no resonance stabilization and the

Topic: Acidity of alcohols and phenols

3329. Rank the following alcohols in decreasing order of acidity.

Topic: Acidity of alcohols and phenols

Topic: Acidity of alcohols and phenols

The negative charge on the conjugate base of compound I is stabilized by three

Topic: Acidity of alcohols and phenols

362. Rank the following alcohols in decreasing order of acidity.

Topic: Acidity of alcohols and phenols