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Chapter Thirteen
Topic: Nomenclature of alcohols Section: 13.1 Difficulty Level: Easy
1. What is the IUPAC name for the following compound?
CH3CHCHCHCHCH3
OH
CH3
CH3
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 Topic: Nomenclature of alcohols Section: 13.1 Difficulty Level: Easy
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 Topic: Nomenclature of alcohols Section: 13.1 Difficulty Level: Easy
3.
What is the IUPAC name for the following compound?
CH3CH2CCH2CH3
CH2CH3
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 Topic: Nomenclature of alcohols 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 Topic: Nomenclature of alcohols Section: 13.1 Difficulty Level: Medium
5. What is the IUPAC name for the following compound?
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 Topic: Nomenclature of alcohols Section: 13.1 Difficulty Level: Medium
6. What is the correct structure for 1-chloro-3-ethyl-2-pentanol?
CH3CH2CCH2CH2Cl
CH2CH3
OH
CH3CHCHCH2CH2Cl
CH2CH3
OH
CH3CH2CHCHCH2Cl
CH2CH3
OH
CH3CH2CHCH2CHCl
CH2CH3
OHI II III IV
A) I B) II C) III D) IV E) 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) 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 Topic: Nomenclature of alcohols Section: 13.1 Difficulty Level: Hard
8. What is the IUPAC name for the following compound?
CH3CH2C=CCH2CH3
CH3
CH2CH2OH
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 Topic: Nomenclature of alcohols Section: 13.1 Difficulty Level: Hard
9. What is the IUPAC name for the following compound? 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 Topic: Nomenclature of alcohols Section: 13.1 Difficulty Level: Hard
10. What is the IUPAC name for the following compound? CH3
C
HOH
CCCH
2 CH3
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
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
OH
Br Br
Br
Br
OH
CH3CH2CH2CH2CCH(CH3)OH
Br
Br
II
IV V
I
CH3CCH2CH2CH2CHOH
Br
Br
CH3
III
A) I B) II C) III D) IV E) 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?
VIV
III
HO
HO
OH
OH
III
OH
A) I B) II C) III D) IV E) V
Ans: E
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? H Br
CH3
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. Ans: Cl
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?
CC
CCH3(CH2)4
HO H
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: 13.5 Difficulty Level: Medium
24. 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
25. What is the IUPAC name for the following compound? 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 Topic: Nomenclature of alcohols Section: 13.5 Difficulty Level: Hard
26. 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
27. 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
28.
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
29.
Rank the following alcohols in decreasing order of acidity. OH
Br
OH
F
OH
II II III
Ans: II>I>III Topic: Acidity of alcohols and phenols Section: 13.2 Difficulty Level: Medium
30.
Which one of the following alcohols is most acidic? O
OH
O
OH
OH
I II III Ans: I
Topic: Acidity of alcohols and phenols Section: 13.2 Difficulty Level: Medium
31.
Rank the following alcohols in decreasing order of acidity. Explain your answer.
FOH F
OHOH
IIIIII
F F
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
32.
Rank the following alcohols in decreasing order of acidity.
O2N OH NC OHOHI II III
Ans: I>III>II Topic: Acidity of alcohols and phenols Section: 13.2 Difficulty Level: Medium
33.
Predict the product(s) for the following reaction. OH Na
Ans: ONa
+ H212
Topic: Acidity of alcohols and phenols Section: 13.2 Difficulty Level: Medium
34.
Predict the product for the following reaction. OH 1. NaH
2. CH3CH2Br
Ans: O
Topic: Preparation of Alcohols Section: 13.3 Difficulty Level: Medium
35. Provide the reagents necessary to carry out the following conversion.
CH3CH2CH2CHCH3
Br
CH3CH2CH2CH2CH2OH
Ans: 1. (CH3)3COK 2. BH3 3. H2O2/NaOH/H2O
Topic: Preparation of Alcohols Section: 13.3 Difficulty Level: Medium
36. Predict the product(s) for the following reaction.
1. BH3
2. H2O2/NaOH/H2O
OH OH
OHCH2OH
I IIIII IV+ enantiomer + enantiomer
A) I B) II C) III D) IV E) None of these
Ans: B Topic: Preparation of Alcohols Section: 13.3 Difficulty Level: Medium
37. Predict the product for the following reaction.
1. Hg(OAc)2, H2O
2. NaBH4
OH
OH
OH CH2OH
I II III IV
A) I B) II C) III D) IV E) None of these
Ans: C Topic: Preparation of Alcohols Section: 13.3 Difficulty Level: Medium
38. 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
39. Predict the major product for the following reaction.
H3O+
Ans: OH
Topic: Preparation of Alcohols Section: 13.3 Difficulty Level: Medium
40. Predict the product for the following reaction.
1. Hg(OAc)2, H2O
2. NaBD4
OH
OH D
OH D
OH
D OH
I II III IV V
A) I B) II C) III D) IV E) V
Ans: C Topic: Preparation of Alcohols Section: 13.3 Difficulty Level: Medium
41. Provide the reagents necessary to carry out the following conversion. Br OH
Ans: NaOH
Topic: Preparation of Alcohols Section: 13.3 Difficulty Level: Hard
42. Provide the reagents necessary to carry out the following conversion. OH
Cl
A) NaOH/H2O B) 1. NaOCH3, 2. H3O+
C) 1. (CH3)3COK, 2. BH3, 3. H2O2/NaOH/H2O D) 1. (CH3)3COK, 2. H3O+ E) B & D
Ans: D Topic: Oxidation states Section: 13.4 Difficulty Level: Easy
43. What is the oxidation state of the carbon atoms I and II in the following reaction?
I
O
O
H
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: E Topic: Oxidation states Section: 13.4 Difficulty Level: Easy
44. What is the oxidation state of the carbon atoms I and II in the following reaction?
CH3CH
O
CH3COH
O
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
Topic: Oxidation states Section: 13.4 Difficulty Level: Medium
45. 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 in starting compound has a zero oxidation state and the carbon atom in the product has an oxidation state of +2.
Topic: Oxidation states Section: 13.4 Difficulty Level: Medium
46. 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
47. 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
48. For the following conversion, identify if the starting material has been oxidized, reduced or neither.
O
O
H
A) reduced B) oxidized C) neither D) A & B
Ans: B Topic: Preparation of Alcohols Section: 13.4 Difficulty Level: Easy
49. Predict the product for the following reaction.
CH3CCH2CH2CH3
O
NaBH4/CH3OH
Ans:
CH3CHCH2CH2CH3
OH
Topic: Preparation of Alcohols Section: 13.4 Difficulty Level: Medium
50. Predict the product for the following reaction.
H
O
NaBH4/CH3OH
OH OHOH
O
OH
OH
I II IIIIV
A) I B) II C) III D) IV
Ans: A
Topic: Preparation of Alcohols Section: 13.4 Difficulty Level: Medium
51. Which one of the following compounds gives 5-methyl-3-heptanol with LiAlH4 followed by water?
O
H
O
H
O O
O
I II III
IV V A) I B) II C) III D) IV E) V
Ans: A Topic: Preparation of Alcohols Section: 13.4 Difficulty Level: Hard
52. Provide the reagents necessary to carry out the following conversion.
HC CCH2CH2CH3 CH3CHCH2CH2CH3
OH
Ans: 1. H3O+/ HgSO4 2. NaBH4/CH3OH
Topic: Preparation of Alcohols Section: 13.4 Difficulty Level: Hard
53. Predict the product for the following reaction.
H
O
H2.Pd
OH OHOH
O
OH
OH
I II III IV A) I B) II C) III D) IV
Ans: C Topic: Preparation of Alcohols Section: 13.4 Difficulty Level: Hard
54. Predict the product for the following reaction.
COCH3
O
O
NaBH4 / H2O
Ans:
COCH3
O
H
HO Topic: Preparation of Alcohols Section: 13.4 Difficulty Level: Hard
55. Predict the product for the following reaction.
COCH3
O
O
1. LiAlH4
2. H2O
excess
Ans: CH2OH
H
HO Topic: Preparation of Alcohols Section: 13.4 Difficulty Level: Hard
56. Predict the product for the following reaction.
HgSO4
H2O / H2SO4NaBH4/CH3OH
Ans:
OH
Topic: Preparation of Alcohols Section: 13.4 Difficulty Level: Medium
57. Provide the reactant (A) for the following reaction 1. LiAlH4
2. H2O5-methyl-3-heptanolA
O
H
O
H
O O
O
I IIIII
IV V A) I B) II C) III D) IV E) V
Ans: A Topic: Preparation of Diols Section: 13.5 Difficulty Level: Easy
58. Provide the reagents necessary to carry out the following conversion. cyclohexene cis-1,2-cyclohexanediol
A) KMnO4, NaOH, Η2Ο B) KMnO4, H3O+, 75oC C) H2SO4, heat D) 1. mCPBA 2. H3O+
E) none of these Ans: A
Topic: Preparation of Diols Section: 13.5 Difficulty Level: Medium
59. Predict the product(s) for the following reaction sequence.
3-hexyne
H2/Ni2B 1. OsO42. NaHSO3
HO
H OH
HHO
HO H
H H
HO OH
HI II III
A) I B) II C) III D) Both I & II E) None of these
Ans: B Topic: Preparation of Diols Section: 13.5 Difficulty Level: Medium
60. Provide the reagents necessary to carry out the following conversion. cyclohexene trans-1,2-cyclohexanediol
A) KMnO4, NaOH, Η2Ο B) KMnO4, H3O+, 75oC C) H2SO4, heat D) 1. mCPBA 2. H3O+
E) none of these Ans: D
Topic: Preparation of Diols Section: 13.5 Difficulty Level: Medium
61. Provide the structure(s) of the product(s) in the following reaction sequence.
ACH3CH2ONa
B Br2
hν
mCPBA NaOH/H2OC D
Ans:
Br
O
CH3 CH3
OH
OH
HA B C D+ enantiomer+ enantiomer
Topic: Preparation of Diols Section: 13.5 Difficulty Level: Hard
62. Predict the product for the following reaction.
NaBH4/CH3OH
O
H
O
excess
OH
H
O O
OH
OH
OH
OH
OH
OH
III III
IV
OH
OH
V
A) I B) II C) III D) IV E) V
Ans: C Topic: Preparation of Diols Section: 13.5 Difficulty Level: Medium
63. Predict the product(s) for the following reaction.
OH3O
+
OH OH
OH
OH
OH
O
H
I II III IV
A) I B) II C) III D) IV E) none of these
Ans: C Topic: Preparation of Diols Section: 13.5 Difficulty Level: Medium
64. 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
65. Provide the reagent(s) necessary to carry out the following conversion.
OH
OH
Ans: 1. O3 2. (CH3)2S 3. excess NaBH4/CH3OH
Topic: Preparation of Diols Section: 13.5 Difficulty Level: Hard
66. Predict the product(s) for the following reaction.
O
O
2. H2O
1. excess LiAlH4
O
Ans: OH
OH
OH Topic: Preparation of Alcohols Section: 13.6 Difficulty Level: Easy
67. Predict the product for the following reaction sequence. O
2. H2O
1. CH3CH2MgBr
Ans: HO
Topic: Preparation of Alcohols Section: 13.6 Difficulty Level: Medium
68. Predict the product for the following reaction sequence.
BrH
O
Mg/ether
2. H2O
1.
Ans:
OH Topic: Preparation of Alcohols Section: 13.6 Difficulty Level: Medium
69. Provide the reagent(s) necessary to carry out the following conversion.
COCH3
O
OH
Ans: 1. excess CH3MgBr/ether 2. H2O
Topic: Preparation of Alcohols Section: 13.6 Difficulty Level: Medium
70. Predict the product for the following reaction.
1. CH3CH2CH2MgBr/ether
2. H2O
O
OH
HO
I II
OH
IVIIIOH
A) I B) II C) III D) IV E) None of these
Ans: A Topic: Preparation of Alcohols Section: 13.6 Difficulty Level: Medium
71. Predict the product for the following reaction. Br
Mg/ether H H
O
1.
2. H2O
Ans: OH
Topic: Preparation of Alcohols Section: 13.6 Difficulty Level: Hard
72. Provide the reagent(s) necessary to carry out the following conversion. HO
Ans: 1. HBr 2. Mg/ether
3. H H
O
4. H2O
Topic: Preparation of Alcohols Section: 13.6 Difficulty Level: Hard
73. Provide the reagent(s) necessary to prepare 1-isopropylcyclopentanol using a Grignard reaction.
Ans: OMgBr
1.
2. H2O Topic: Preparation of alcohols Section: 13.6 Difficulty Level: Medium
74. Predict the product for the following reaction.
OCH3
O
2. H2O
1. CH3CH2CH2MgBrexcess
Ans:
OH
Topic: Protection of alcohols Section: 13.7 Difficulty Level: Hard
75. Provide the reagent(s) necessary to carry out the following conversion. HO Br HO
OH
Ans: 1. (CH3)3SiCl / (CH3CH2)3N 2. Mg/ether
3.
O
4. H2O 5. TBAF
Topic: Protection of alcohols Section: 13.7 Difficulty Level: Medium
76. Predict the product(s) for the following reaction sequence.
Br
OH
A B
O
CTBAF
D (CH3)3SiCl
(CH3CH2)3N
Mg/ ether
1.
2. H2O
Ans: OSi(CH3)3
Br
OSi(CH3)3
MgBr
A B OSi(CH3)3
HO
C
OH
HO
D Topic: Protection of alcohols Section: 13.7 Difficulty Level: Medium
77. Predict the product(s) for the following reaction sequence.
Br
OH
H H
O
TBAF (CH3)3SiCl
(CH3CH2)3N
Mg/ ether
1.
2. H2O
A) 2,4-heptanediol B) 1,4-heptanediol C) 2,5-octanediol D) 1,5-octanediol E) none of these
Ans: B Topic: Protection of alcohols Section: 13.7 Difficulty Level: Medium
78. Provide the reagents necessary to carry out the following conversion.
HO HO
Ans: 1. (CH3)3SiCl / (CH3CH2)3N 2. NaNH2 3. CH3CH2CH2Br 4. TBAF
Topic: Reactions of Alcohols Section: 13.9 Difficulty Level: Easy
79. 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 Topic: Reactions of Alcohols Section: 13.9 Difficulty Level: Easy
80. 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 Topic: Reactions of Alcohols Section: 13.9 Difficulty Level: Medium
81. Predict the product for the following reaction. OH
PBr3
Ans: Br
Topic: Reactions of Alcohols Section: 13.9 Difficulty Level: Hard
82. 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
83. Predict the major product for the following reaction.
OH
HCl
Ans:
Cl
Topic: Reactions of Alcohols Section: 13.9 Difficulty Level: Medium
84. Predict the product for the following reaction.
SOCl2/pyridine
OH Ans:
Cl Topic: Reactions of Alcohols Section: 13.9 Difficulty Level: Medium
85. Predict the major product for the following reaction. H
H
OH
CH3
1. TsCl /pyridine
2. NaI
H
H
I
CH3
H
H
OTsI
CH3
I
H
H
CH3
H
H
Ts
CH3
I II III IV
A) I B) II C) III D) IV E) both I and III
Ans: C Topic: Reactions of Alcohols Section: 13.9 Difficulty Level: Medium
86. 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-Methylcyclopentene E) 3-Methylcyclopentene
Ans: A Topic: Reactions of Alcohols Section: 13.9 Difficulty Level: Medium
87. The reaction between 2-methyl-2-pentanol and sulfuric acid to yield 2-methyl-2-pentene goes via_____.
A) SN1 mechanism B) SN2 mechanism C) E1 mechanism D) E2 mechanism E) None of these.
Ans: C Topic: Reactions of Alcohols Section: 13.9 Difficulty Level: Medium
88. Explain why the following reaction will not produce alcohol as product.
Cl
NaOHOH
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
89. 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
90. Predict the major product for the following reaction. OH
H2SO4
Δ Ans:
Topic: Reactions of Alcohols Section: 13.9 Difficulty Level: Medium
91. Provide the reagent(s) necessary to convert cyclohexanol to cyclohexane. . Ans: 1. H2SO4, heat
2. H2/Pd OR 1. TsCl/pyridine 2. CH3CH2ONa 3. H2/Pd
Topic: Reactions of Alcohols Section: 13.9 Difficulty Level: Medium
92. Provide a stepwise curved arrow mechanism for the following reaction. HO
CH2CH3
CH2CH3 H2SO4Δ
CH2CH3
CH2CH3
Ans:
CH2CH3
HOCH2CH3
H O S O H
O
O
CH2CH3
H2O CH2CH3
O S O H
O
O
+
CH2CH3
H3CH2C
CH2CH3
CH2CH3
CH2CH3
CH2CH3
CH2CH3
H3CH2C H
O S O H
O
O
+ H2SO4
+ H2O
Topic: Reactions of Alcohols Section: 13.9 Difficulty Level: Hard
93. Predict the product and provide a stepwise curved arrow mechanism for the following reaction.
H2SO4heat
OH
OH
Ans:
O
Mechanism
OH H O S O H
O
O
O S O H
O
O
+
OH
OHOH2
OH
HO S O H
O
O
O HO
+ H2SO4+ H2O
Topic: Reactions of Alcohols Section: 13.10 Difficulty Level: Easy
94. Predict the product for the following reaction. PCC
2-hexanolCH2Cl2
A)
CH3COH
O
B)
CH3CH2CH2CH2COH
O
C)
CH3(CH2)3CCH3
O
D)
CH3CH2CH2CH2CH2COH
O
E)
CH3CH2CH2CH2CH2CH
O
Ans: C
Topic: Reactions of Alcohols Section: 13.10 Difficulty Level: Medium
95. Provide the reagents necessary to carry out the following conversion. OH O
A) KMnO4/NaOH/H2O B) CrO3/H2SO4/H2O C) H2, Pt D) Br2, CCl4 E) None of these
Ans: B Topic: Reactions of Alcohols Section: 13.10 Difficulty Level: Easy
96. Predict the product for the following reaction. OH
Na2Cr2O7/H2SO4/H2O
Ans: O
Topic: Reactions of Alcohols Section: 13.10 Difficulty Level: Easy
97. Predict the product for the following reaction. OH
CH2Cl2
PCC
Ans: H
O
Topic: Reactions of Alcohols Section: 13.10 Difficulty Level: Easy
98. Provide the reagents necessary to carry out the following conversion.
OH H
O
A) KMnO4/NaOH/H2O B) CrO3/H2SO4/H2O C) PCC/CH2Cl2 D) Br2, CCl4 E) None of these
Ans: C Topic: Reactions of Alcohols Section: 13.10 Difficulty Level: Medium
99. Provide the reagents necessary to carry out the following conversion.
OH OH
O
A) KMnO4/NaOH/H2O B) CrO3/H2SO4/H2O C) PCC/CH2Cl2 D) Br2, CCl4 E) None of these
Ans: B Topic: Reactions of Alcohols Section: 13.10 Difficulty Level: Medium
100. Predict the product for the following reaction.
OH
CH2OH
PCC/CH2Cl2excess
Ans: OH
CH
O Topic: Reactions of Alcohols Section: 13.10 Difficulty Level: Medium
101. 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
102. Predict the product for the following reaction. PCC
CH2Cl2cis-4-methylcyclohexanol
Ans: O
. Topic: Synthesis Section: 13.13 Difficulty Level: Medium
103. Provide the structure for the final product (D), in the following reaction sequence.
CH3CH2CHOH
CH3
PBr3A
MgBH3C H
O
CH2O D
ether
Ans: OH
Topic: Synthesis Section: 13.13 Difficulty Level: Hard
104. Provide the structure for the final product (E), in the following reaction sequence.
OHPBr3 A
MgB C
H2OD
PCC
CH2Cl2
O
O
IV V
etherE
H H
O
OH
OHI II
H
OIII
A) I B) II C) III D) IV E) V
Ans: C Topic: Synthesis Section: 13.13 Difficulty Level: Medium
105. Provide the structure for product (A), in the following reaction sequence.
PBr3
OH
Mg D2O Aether
A) CH3CH2CH2CH3 B) CH3CH2CHDCH3
C) CH3CH2CHODCH3
D) CH3CH2CH2CH2OD E) CH3CH2CH2CH2D
Ans: B Topic: Synthesis Section: 13.13 Difficulty Level: Medium
106. Provide the reagents necessary to carry out the following conversion.
OH
O
Ans: 1. PBr3
2. Mg/ether
3. H
O
4. H2O 5. PCC/CH2Cl2
Topic: Synthesis Section: 13.13 Difficulty Level: Hard
107. Provide a stepwise synthesis for the following.
Ans:
O
Cl2
1. CH3MgBr
Cl
OH
CH3CH2ONa
H2SO4
H3O+
OH
PCC
CH2Cl2hν
2. H2O heat
Topic: Synthesis Section: 13.13 Difficulty Level: Hard
108. Provide the product for the following reaction sequence: MgBr
H2O
MgBr
H2O
ether
K2Cr2O7/H2SO4/H2O
ether
OH PCCCH2Cl2
OH O HO
OI II III
IV V
A) I B) II C) III D) IV E) V
Ans: C Topic: Synthesis Section: 13.13 Difficulty Level: Medium
109. Predict the product, for the following reaction sequence,
OHSOCl2 H
O
CrO3/ H2SO4/H2OMg/ether
2. H3O+
1.
pyridine
A) 6,7-dimethyl-3-nonanol B) 6,7-dimethyl-3-nonanone C) 6,7-dimethyl-3-nonanal D) 3,4-dimethyl-7-nonanol E) 3,4-dimethyl-7-nonanone
Ans: B Topic: Synthesis Section: 13.13 Difficulty Level: Hard
110. Provide a stepwise synthesis for the following.
O
Ans:
Cl2 CH3CH2ONa PCC
CH2Cl2hν
1. BH3
2. H2O2/NaOH/H2O
ClOH
O
Topic: Synthesis Section: 13.13 Difficulty Level: Hard
111. Provide the reagents necessary to carry out the following conversion. O
O
Ans: 1. Cl2/hν
2. CΗ3CΗ2ONa 3. KMnO4/NaOH/H2O 4. excess PCC/CH2Cl2
Topic: Synthesis Section: 13.13 Difficulty Level: Hard
112. Provide the reagents necessary to carry out the following conversion.
HO
O
HO
HO
Ans: 1. (CH3)3SiCl/ (CH3CH2)3N
2. CH3MgBr 3. H3O+
Topic: Synthesis Section: 13.13 Difficulty Level: Medium
113. Provide the reagents necessary to carry out the following conversion.
Br OH
O
Ans: 1. NaOH
2. Na2Cr2O7/H2SO4/H2O
Topic: Synthesis Section: 13.13 Difficulty Level: Hard
114. Provide a stepwise synthesis to carry out the following conversion.
Ans:
Br2
Br
CH3CH2ONa
PCC
CH2Cl2 OOH
CH3H2SO4
OH1. BH3
2. H2O2/NaOH/H2Ohν
1. CH3MgBr
2. H2O heat
H2/Pd