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
Topic: Nomenclature of alcohols Section: 13.1 Difficulty Level: Easy 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
Topic: Nomenclature of alcohols Section: 13.1 Difficulty Level: Easy
3. What is the IUPAC name for the following compound? 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
Topic: Nomenclature of alcohols 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
Topic: Nomenclature of alcohols Section: 13.1 Difficulty Level: Medium 5. What is the IUPAC name for the following compound? OH
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
Topic: Nomenclature of alcohols Section: 13.1 Difficulty Level: Medium
6. What is the correct structure for 1-chloro-3-ethyl-2-pentanol? CH2CH3
CH2CH3
CH3CH2CCH2CH2Cl OH
A) B) C) D) E)
CH3CHCHCH2CH2Cl OH
I
II
CH3CH2CHCH2CHCl CH3CH2CHCHCH2Cl III
I II III IV None of these Ans: D
Topic: Nomenclature of alcohols Section: 13.1 Difficulty Level: Medium 7. What is the IUPAC name for the following compound? Br
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
Topic: Nomenclature of alcohols Section: 13.1 Difficulty Level: Hard
CH2CH3
CH2CH3
OH
IV
OH
8. What is the IUPAC name for the following compound? 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
Topic: Nomenclature of alcohols Section: 13.1 Difficulty Level: Hard 9. What is the IUPAC name for the following compound? OH
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
Topic: Nomenclature of alcohols Section: 13.1 Difficulty Level: Hard 10. What is the IUPAC name for the following compound? 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
Topic: Nomenclature of alcohols Section: 13.1 Difficulty Level: Medium 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
V
I II III IV V Ans: D
Topic: Nomenclature of alcohols Section: 13.1 Difficulty Level: Hard 12. What is the correct structure for (E)-5,5-dimethyl-3-hepten-1-ol? OH HO
I
III
II OH
HO OH
A) B) C) D) E)
I II III IV V Ans: E
IV
V
Topic: Nomenclature of alcohols Section: 13.1 Difficulty Level: Medium 13. What is the IUPAC name for the following compound?
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
16. What is the IUPAC name for the following compound? OH
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
Topic: Nomenclature of alcohols Section: 13.1 Difficulty Level: Hard 18. Provide the structure for 5-chloro-2-propyl-1-heptanol. Cl Ans:
OH
Topic: Nomenclature of alcohols Section: 13.1 Difficulty Level: Hard 19. Provide the structure for 6-sec-butyl-7,7-dimethyl-4-decanol. Ans:
OH
Topic: Nomenclature of alcohols Section: 13.1 Difficulty Level: Hard
20. What is the IUPAC name for the following compound? 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
Topic: Nomenclature of alcohols Section: 13.1 Difficulty Level: Easy 24. What is the correct structure for 2-methylphenol? HO
A) B) C) D) E)
OH
OH
I
II
OH
OH
III
IV
V
I II III IV V Ans: A
Topic: Nomenclature of alcohols Section: 13.1 Difficulty Level: Medium 25. What is the correct structure for 2-bromo-5-isopropylphenol? OH
Br
OH
OH
OH
Br
IV
V
Br
Br
Br
I
A) B) C) D) E)
I II III IV V Ans: B
Topic: Nomenclature of alcohols Section: 13.1 Difficulty Level: Medium
II
III
OH
26. What is the IUPAC name for the following compound? 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
Topic: Nomenclature of alcohols Section: 13.1 Difficulty Level: Medium 27. What is the IUPAC name for the following compound? OH
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
295. What is the IUPAC name for the following compound? 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
Topic: Nomenclature of alcohols Section: 13.5 Difficulty Level: Hard 3026. What is the IUPAC name for the following compound?
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
Topic: Acidity of alcohols and phenols Section: 13.2 Difficulty Level: Hard
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
Topic: Acidity of alcohols and phenols Section: 13.2 Difficulty Level: Medium 3329. Rank the following alcohols in decreasing order of acidity.
Br
I
Ans: II>I>III Topic: Acidity of alcohols and phenols Section: 13.2 Difficulty Level: Medium
OH
OH
OH
F
II
I
III
340. Which one of the following alcohols is most acidic? O
OH
O
OH
OH
III
II
I
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
F
OH
OH
OH F
F
III
II
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.
Topic: Acidity of alcohols and phenols Section: 13.2 Difficulty Level: Medium 362. Rank the following alcohols in decreasing order of acidity. O2 N
OH
I
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
Topic: Acidity of alcohols and phenols Section: 13.2 Difficulty Level: Medium 38. Predict the product(s) for the following reaction. OH
Li
Ans:
O Li
+
1 H2 2
Topic: Acidity of alcohols and phenols Section: 13.2 Difficulty Level: Medium 394. Predict the product for the following reaction. OH
1. NaH 2. CH3CH2Br
Ans:
Topic: Preparation of Alcohols Section: 13.3 Difficulty Level: Medium
O
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
Topic: Preparation of Alcohols Section: 13.3 Difficulty Level: Medium 4136. Predict the product(s) for the following reaction. 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
Topic: Preparation of Alcohols Section: 13.3 Difficulty Level: Medium
OH
+ enantiomer II
III
IV
4237. Predict the product for the following reaction.
1. Hg(OAc)2, H2O 2. NaBH4 CH2OH
OH
OH
II
I
A) B) C) D) E)
OH
III
IV
I II III IV None of these Ans: C
Topic: Preparation of Alcohols Section: 13.3 Difficulty Level: Medium 3843. Provide the reagents necessary to carry out the following conversion. (E)-3-methyl-3-hexene
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
Topic: Preparation of Alcohols Section: 13.3 Difficulty Level: Medium 450. Predict the product for the following reaction.
1. Hg(OAc)2, H2O 2. NaBD4
OH OH
I
A) B) C) D) E)
OH
OH
D
III
II
D
D
OH
IV
V
I II III IV V Ans: C
Topic: Preparation of Alcohols Section: 13.3 Difficulty Level: Medium 461. Provide the reagents necessary to carry out the following conversion. Br
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
Topic: Oxidation states Section: 13.4 Difficulty Level: Easy 483. What is the oxidation state of the carbon atoms I and II in the following reactioncompound? O
II
H
I
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
Topic: Oxidation states Section: 13.4 Difficulty Level: Easy
O
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)
O
CH3COH II
I. +1, II. +2 I. +2, II. +2 I. +1, II. +3 I. +3, II. +2 I. +2, II. +1 Ans: C
Topic: Oxidation states Section: 13.4 Difficulty Level: Medium 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. 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
Difficulty Level: Medium 4752. For the following conversion, identify if the starting material has been oxidized, reduced or neither. Explain your answer. OH
O
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
O
A) B) C) D)
reduced oxidized neither A& B Ans: B
Topic: Oxidation states Section: 13.4 Difficulty Level: Hard 54. For the following conversion, identify if the starting material has been oxidized, reduced or neither. OH
O
A) B) C) D)
reduced oxidized neither A& B Ans: C
Topic: Preparation of Alcohols via Reduction Section: 13.4
O
O
Difficulty Level: Easy 4955. Predict the product for the following reaction. O
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
H
NaBH4/CH3OH
O
OH
A) B) C) D)
I II III IV Ans: A
I
OH
OH
OH
II
Topic: Preparation of Alcohols via Reduction Section: 13.4 Difficulty Level: Medium
III
OH
IV
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
A) B) C) D) E)
I II III IV V Ans: A
IV
V
Topic: Preparation of Alcohols via Reduction Section: 13.4 Difficulty Level: Hard 582. Provide the reagents necessary to carry out the following conversion. OH HC
CCH2CH2CH3
CH3CHCH2CH2CH3
+
Ans: 1. H3O / HgSO4 2. NaBH4/CH3OH OR 1. H2/Ni2B (OR Na, NH3) 2. H3O+ Topic: Preparation of Alcohols via Reduction Section: 13.4 Difficulty Level: Hard
593. Predict the product for the following reaction. O
H
H2.Pd
O
OH
A) B) C) D)
I II III IV Ans: C
OH
II
I
Topic: Preparation of Alcohols via Reduction Section: 13.4 Difficulty Level: Hard 5460. Predict the product for the following reaction. O COCH3
NaBH4 / H2O
O
O
Ans:
OH
OH
COCH3
H HO
Topic: Preparation of Alcohols via Reduction Section: 13.4 Difficulty Level: Hard
III
OH
IV
5561. Predict the product for the following reaction. O COCH3
1. LiAlH4 excess 2. H2O O
CH2OH
Ans:
H HO
Topic: Preparation of Alcohols via Reduction Section: 13.4 Difficulty Level: Hard 5662. Predict the product for the following reaction. H2O / H2SO4 HgSO4
Ans: OH
Topic: Preparation of Alcohols via Reduction Section: 13.4 Difficulty Level: Medium
NaBH4/CH3OH
5763. Provide the reactant (A) for the following reaction 1. LiAlH4 5-methyl-3-heptanol A 2. H2O O
O O H
I
II O
O
III
H
IV
A) B) C) D) E)
V
I II III IV V Ans: A
Topic: Preparation of Diols Section: 13.5 Difficulty Level: Easy 5864. Provide the reagents necessary to carry out the following conversion. A) B) C) D) E)
cyclohexene KMnO4, NaOHcold KMnO4, H3O+, 75oC H2SO4, heat 1. mCPBA 2. H3O+ none of these Ans: A
Topic: Preparation of Diols Section: 13.5 Difficulty Level: Medium
cis-1,2-cyclohexanediol
5965. Predict the product(s) for the following reaction sequence. H2/Ni2B 1. OsO4 3-hexyne 2. NaHSO3 H
H
HO
A) B) C) D) E)
HO
OH
HO
I
HO
H
H
H
II
OH
H
III
I II III Both I & II None of these Ans: BA
Topic: Preparation of Diols Section: 13.5 Difficulty Level: Medium 660. Provide the reagents necessary to carry out the following conversion. 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
Topic: Preparation of Diols Section: 13.5 Difficulty Level: Medium 671. Provide the structure(s) of the each product (A-D)(s) in the following reaction sequence. CH3CH2ONa A B
Br2 h
mCPBA
Ans:
C
NaOH/H2O
D CH3
CH3 Br
OH
O
OH
A
B
C
+ enantiomer
+ enantiomer D
H
Topic: Preparation of Diols Section: 13.5 Difficulty Level: Hard 682. Predict the product for the following reaction. O
O
excess H
OH
NaBH4/CH3OH
OH
O
O
OH
OH
H
II
I OH
III OH
OH
OH
OH
IV
A) B) C) D) E)
I II III IV V Ans: C
Topic: Preparation of Diols Section: 13.5 Difficulty Level: Medium
V
693. Predict the product(s) for the following reaction. O
H3O+
OH
OH
H O
OH
A) B) C) D) E)
OH
OH
II
I
IV
III
I II III IV none of these Ans: C
Topic: Preparation of Diols Section: 13.5 Difficulty Level: Medium 7064. Provide the reagent(s) necessary to carry out the following conversion. OH
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
Topic: Preparation of Diols Section: 13.5 Difficulty Level: Hard 6672. Predict the product(s) for the following reaction. O
O
1. excess LiAlH4 2. H2O
O
Ans:
OH OH
OH
Topic: Preparation of Alcohols via Grignard Reagents Section: 13.6 Difficulty Level: Easy 6773. Predict the product for the following reaction sequence. O
1. CH3CH2MgBr 2. H2O
Ans:
HO
Topic: Preparation of Alcohols via Grignard Reagents Section: 13.6 Difficulty Level: Medium
6874. Predict the product for the following reaction sequence. O
1.
Mg/ether
H
Br
2. H2O
Ans:
OH
Topic: Preparation of Alcohols via Grignard Reagents Section: 13.6 Difficulty Level: Medium 6975. Provide the reagent(s) necessary to carry out the following conversion. O
O
Ans: 1. excess CH3MgBr/ether 2. H2O Topic: Preparation of Alcohols via Grignard Reagents Section: 13.6 Difficulty Level: Medium
OH
760. Predict the product for the following reaction. O
1. CH3CH2CH2MgBr/ether 2. H2O
OH
OH
HO
OH
I
A) B) C) D) E)
III
II
I II III IV None of these Ans: A
Topic: Preparation of Alcohols via Grignard Reagents Section: 13.6 Difficulty Level: Medium 771. Predict the product for the following reaction. O
Br
1.
Mg/ether
H
H
2. H2O
Ans:
OH
Topic: Preparation of Alcohols via Grignard Reagents Section: 13.6 Difficulty Level: Medium
IV
78. Using Grignard reaction, show how you could prepare the following alcohol. OH
Ans:
MgBr
1.
O C H
H
2. H2O
Topic: Preparation of Alcohols via Grignard Reagents Section: 13.6 Difficulty Level: Medium 79. Using Grignard reaction, show how you could prepare the following alcohol.
OH
Ans: 1. MgBr 2. H2O
O
OR 1.
MgBr
O
2. H2O
Topic: Preparation of Alcohols via Grignard Reagents Section: 13.6 Difficulty Level: Hard
80. Using Grignard reaction, show how you could prepare the following alcohol.
HO
Ans: MgBr
1. O
2. H2O
OR 1.
O
MgBr
2. H2O
OR
1. O
MgBr
2. H2O
Topic: Preparation of Alcohols via Grignard Reagents Section: 13.6 Difficulty Level: Hard 7281. Provide the reagent(s) necessary to carry out the following conversion. HO
Ans: 1. HBr 2. Mg/ether O
3. H 4. H2O
H
Topic: Preparation of Alcohols via Grignard Reagents Section: 13.6 Difficulty Level: Hard
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 Difficulty Level: Medium 7483. Predict the product for the following reaction. O
OCH3
excess 1. CH3CH2CH2MgBr 2. H2O
Ans:
OH
Topic: Preparation of alcohols via Grignard Reagents Section: 13.6 Difficulty Level: Hard 84. Predict the product for the following reaction. O
O
excess 1. CH3CH2MgBr 2. H2O
Ans: OH
OH
Topic: Preparation of alcohols via Grignard Reagents Section: 13.6 Difficulty Level: Hard
85. Predict the product for the following reaction. excess 1. CH3CH2MgBr
O
O
2. H2O
O
Ans: OH
Topic: Preparation of alcohols via Grignard Reagents Section: 13.6 Difficulty Level: Hard 86. Predict the product for the following reaction and provide a curved arrow mechanism for the formation of the product. excess 1. CH3CH2MgBr
O
O
2. H2O
O
Ans: OH
Mechanism O
O
O
CH3CH2MgBr O
O
O
CH3CH2MgBr
O
O
+ CH3OMgBr O
O
CH3CH2MgBr O
+ CH3OMgBr
O O
H
H HO
+ OH
Topic: Protection of alcohols Section: 13.7 Difficulty Level: Hard
7587. Provide the reagent(s) necessary to carry out the following conversion. OH HO
Br
HO
Ans: 1. (CH3)3SiCl / (CH3CH2)3N 2. Mg/ether O
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
O
HO
HO
Ans: 1. CH3)3SiCl / (CH3CH2)3N 2. MgBr
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
A
Mg/ ether
(CH3CH2)3N
B
2. H2O
C
Ans: OSi(CH3)3
OSi(CH3)3
MgBr
Br
A
B
OH
OSi(CH3)3
HO
HO
D
C
Topic: Protection of alcohols Section: 13.7 Difficulty Level: Medium 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
Topic: Protection of alcohols Section: 13.7 Difficulty Level: Medium
(CH3CH2)3N
Mg/ ether
H
O H
2. H2O
TBAF
TBAF
D
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
Topic: Reactions of Alcohols Section: 13.9 Difficulty Level: Easy 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
Topic: Reactions of Alcohols Section: 13.9 Difficulty Level: Easy 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 Topic: Reactions of Alcohols Section: 13.9 Difficulty Level: Medium
8194. Predict the product for the following reaction. OH
PBr3
Br
Ans:
Topic: Reactions of Alcohols Section: 13.9 Difficulty Level: Hard 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
Br Br
Topic: Reactions of Alcohols Section: 13.9 Difficulty Level: Hard
+ H2O
8396. Predict the major product for the following reaction.
OH
HCl
Ans: Cl
Topic: Reactions of Alcohols Section: 13.9 Difficulty Level: Medium 8497. Predict the product for the following reaction. SOCl2/pyridine OH
Ans:
Cl
Topic: Reactions of Alcohols Section: 13.9 Difficulty Level: Medium
8598. Predict the major product for the following reaction. H OH
CH3 H
1. TsCl /pyridine 2. NaI
H
H I
CH3
I
A) B) C) D) E)
H
II
H
I
H
OTs
H
Ts
CH3
CH3
CH3
III
H
IV
H
I II III IV both I and III Ans: C
Topic: Reactions of Alcohols Section: 13.9 Difficulty Level: Medium 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 Topic: Reactions of Alcohols Section: 13.9 Difficulty Level: Medium 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
Topic: Reactions of Alcohols Section: 13.9 Difficulty Level: Medium 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. 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:
Topic: Reactions of Alcohols Section: 13.9 Difficulty Level: Medium
90103 Predict the major product for the following reaction. OH . H2SO4
Ans:
Topic: Reactions of Alcohols Section: 13.9 Difficulty Level: Medium 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.
Topic: Reactions of Alcohols Section: 13.9 Difficulty Level: Medium
92105 Provide a stepwise curved arrow mechanism for the following reaction. HO . CH2CH3 CH2CH3
CH2CH3 CH2CH3
H2SO4 O
Ans: HO
CH2CH3 CH2CH3
H
O
S
O
H2O
H
CH2CH3 O CH2CH3
O
O
+
S
O
H
O
H
O H3CH2C
H3CH2C CH2CH3
H
O
CH2CH3
O
CH2CH3
CH2CH3
+ H2O CH2CH3
+ H2SO4 CH2CH3
Topic: Reactions of Alcohols Section: 13.9 Difficulty Level: Hard
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
O
S
O
H OH2
OH
O
O OH
+
O
S
O
H
O O H
O OH
+ H2O
Topic: Reactions of Alcohols Section: 13.10 Difficulty Level: Easy
H
O
S
O O
H
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)
O
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
Topic: Reactions of Alcohols Section: 13.10 Difficulty Level: Easy
96109 Predict the product for the following reaction. OH . Na2Cr2O7/H2SO4/H2O
Ans:
O
Topic: Reactions of Alcohols Section: 13.10 Difficulty Level: Easy 97110 Predict the product for the following reaction. OH . PCC CH2Cl2 H
Ans: O
Topic: Reactions of Alcohols Section: 13.10 Difficulty Level: Easy 98111 Provide the reagents necessary to carry out the following conversion. . O
OH
A) B) C) D) E)
KMnO4/NaOH/H2O Na2Cr2O7CrO3/H2SO4/H2O PCC/CH2Cl2 Br2, CCl4 None of these Ans: C
Topic: Reactions of Alcohols Section: 13.10 Difficulty Level: Medium
H
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
Topic: Reactions of Alcohols Section: 13.10 Difficulty Level: Medium 11300 Predict the product for the following reaction. . OH
excess PCC/CH2Cl2
Ans:
CH2OH OH
CH O
Topic: Reactions of Alcohols Section: 13.10 Difficulty Level: Medium 11401 Predict the product for the following reaction. .
OH
PCC CH2Cl2
Ans: No reaction. Tertiary alcohols do not undergo oxidation reactions.
Topic: Reactions of Alcohols Section: 13.10 Difficulty Level: Medium 11502 Predict the product for the following reaction. PCC . cis-4-methylcyclohexanol
CH2Cl2
Ans:
O
. Topic: Oxidation of Phenols Section: 13.12 Difficulty Level: Medium 116. Predict the product for the following reaction. OH
Na2Cr2O7/H2SO4/H2O
Ans:
O
O
.
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
A
Mg ether
H3C
H
B
C
H2O
D
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
A
Mg ether
CH3
B
H3C
H
C 2. H2O OH
Ans: Br
A
Topic: Synthesis Section: 13.13 Difficulty Level: Hard
MgBr
B
C
11904 Provide the structure for the final product (E), in the following reaction sequence. O . PBr3
OH
Mg
A
B
ether
H
H
H2O
C
D
PCC
OH
O H
OH
II
I
A) B) C) D) E)
E
CH2Cl2
III
V
IV O
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
A
ether
B
O
H
H
2. H2O
PCC
C
D
CH2Cl2
Ans:
A
Topic: Synthesis Section: 13.13 Difficulty Level: Medium
O
OH
Br
MgBr
B
C
D
10512 Provide the structure for product (A), in the following reaction sequence. 1. OH
PBr3
Mg
D2O
A
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
10712 Provide a stepwise synthesis for the following. 3.
Cl
Ans: Cl2
OH
CH3CH2ONa
H3O+
PCC
h
CH2Cl2
O
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
I
O
IV
A) B) C) D) E)
I II III IV V Ans: C
H2O
K2Cr2O7/H2SO4/H2O
H2O
ether
ether
O
OH
MgBr
HO
III
II
V
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.
H
CrO3/ H2SO4/H2O
2. H3O+ O
OH
III
II
I
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
O
OH
H
V
O
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
O
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
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
PCC O
CH2Cl2
CH3
1. CH3MgBr 2. H2O
H2SO4
OH
heat
H2/Pd
Br
Br2
CH3CH2ONa
h
2. H2O2/NaOH/H2O
PCC CH2Cl2
H2/Pd
Topic: Synthesis Section: 13.13 Difficulty Level: Hard
1. BH3
O
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
O
1. O H
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?
SDBS: National Institute of Advanced Industrial Science and Technology
OH
I
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
C
IV
N
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
I
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
O
O
OH
III
IV
OH
V
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
I
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
0
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
I
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
0
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
2
2
2
1 exchanges with D2O
7
6
O
I
A) B) C) D) E)
I II III IV V Ans: C
Topic: Spectroscopy Section: 13, 16.11 & 16.12 Difficulty Level: Hard
5
4 PPM
3
1
OH
OH
II
2
III OH
IV
0 OH
V
137. A compound with a molecular formula C6H14O displays the following 1HNMR and 13 CNMR spectra. Propose astructure for this compound.
9
3 2
90
80
70
Ans:
OH
60
50
PPM
40
1
30
20
10
0
