Ch12 Carbonyl, Alcohol, Redox Test Bank - Organic Chemistry 13e | Test Bank by Solomons by Graham Solomons. DOCX document preview.
Package title: Solomons Test Bank
Course Title: Solomons 13e
Chapter Number: 12
Question type: Multiple choice
1) Which of the following resonance structures is not a significant contributor to the hybrid for the carbonyl group?
a) I
b) II
c) III
d) Neither II nor III is important.
e) All are significant contributors.
Topic: General Carbonyl Information
Section: 12.1
Difficulty Level: Easy
2) When nucleophilic addition to a carbonyl group occurs, the carbon attacked undergoes this hybridization change:
a) sp2 sp3
b) sp sp2
c) sp sp3
d) sp3 sp2
e) sp2 sp
Topic: General Carbonyl Information
Section: 12.1
Difficulty Level: Easy
3) The following transformation would be considered a(n)?
a) Reduction
b) Oxidation
c) Addition
d) Elimination
e) Rearrangement
Topic: Oxidation-Reduction
Section: 12.2
Difficulty Level: Easy
4) The following transformation would be considered a(n)?
a) Reduction
b) Oxidation
c) Addition
d) Elimination
e) Rearrangement
Topic: Oxidation-Reduction
Section: 12.2
Difficulty Level: Easy
5) The following transformation would be considered a(n)?
a) Reduction
b) Oxidation
c) Addition
d) Elimination
e) Rearrangement
Topic: Oxidation-Reduction
Section: 12.2
Difficulty Level: Easy
6) The following transformation would be considered a(n)?
a) Reduction
b) Oxidation
c) Addition
d) Elimination
e) Rearrangement
Topic: Oxidation-Reduction
Section: 12.2
Difficulty Level: Easy
7) The following transformation would be considered a(n)?
a) Reduction
b) Oxidation
c) Addition
d) Elimination
e) Rearrangement
Topic: Oxidation-Reduction
Section: 12.2
Difficulty Level: Easy
8) The following transformation would be considered a(n)?
a) Reduction
b) Oxidation
c) Addition
d) Elimination
e) Rearrangement
Topic: Oxidation-Reduction
Section: 12.2
Difficulty Level: Easy
9) Which reaction is an oxidation?
a) RCHO RCO2H
b) RCH2OH RCHO
c) RCH2OH RCO2H
d) None of these choices.
e) All of these choices.
Topic: Oxidation-Reduction
Section: 12.2
Difficulty Level: Easy
10) Which of these transformations cannot be classified as a reduction?
a) RCH2Cl RCH3
b) RCH=CH2 RCH2CH3
c) RCOOH RCH2OH
d) 
e) All of these are reductions.
Section: 12.2
Difficulty Level: Easy
Topic: Oxidation-Reduction
11) List the following compounds in order of increasing level of oxidation:
a) I, II, III
b) I, III, II
c) II, I, III
d) III, II, I
e) III, I, II
Topic: Oxidation-Reduction
Section: 12.2
Difficulty Level: Medium
12) List the following compounds in order of increasing level of oxidation:
a) I, II, III
b) I, III, II
c) II, I, III
d) III, I, II
e) III, II, I
Topic: Oxidation-Reduction
Section: 12.2
Difficulty Level: Medium
13) List the following compounds in order of increasing level of oxidation:
a) I, II, III
b) III, II, I
c) II, I, III
d) III, I, II
e) I, III, II
Topic: Oxidation-Reduction
Section: 12.2
Difficulty Level: Medium
14) List the following compounds in order of increasing level of oxidation:
a) I, II, III
b) III, II, I
c) II, I, III
d) III, I, II
e) I, III, II
Topic: Oxidation-Reduction
Section: 12.2
Difficulty Level: Medium
15) List the following compounds in order of increasing level of oxidation:
a) I, II, III
b) III, II, I
c) II, I, III
d) III, I, II
e) I, III, II
Topic: Oxidation-Reduction
Section: 12.2
Difficulty Level: Medium
16) List the following compounds in order of increasing level of oxidation:
a) I, II, III
b) III, II, I
c) II, I, III
d) III, I, II
e) I, III, II
Topic: Oxidation-Reduction
Section: 12.2
Difficulty Level: Medium
17) List the following compounds in order of increasing level of oxidation:
a) I, II, III
b) III, II, I
c) II, I, III
d) III, I, II
e) I, III, II
Topic: Oxidation-Reduction
Section: 12.2
Difficulty Level: Medium
18) List the following compounds in order of increasing level of oxidation:
a) I, II, III
b) III, II, I
c) II, I, III
d) III, I, II
e) I, III, II
Topic: Oxidation-Reduction
Section: 12.2
Difficulty Level: Medium
19) List the following compounds in order of increasing level of oxidation:
a) I, II, III
b) III, II, I
c) II, I, III
d) III, I, II
e) I, III, II
Topic: Oxidation-Reduction
Section: 12.2
Difficulty Level: Medium
20) The following transformation would be considered a(n)?
a) reduction
b) oxidation
c) addition
d) elimination
e) rearrangement
Topic: Oxidation-Reduction
Section: 12.2
Difficulty Level: Medium
21) The following transformation would be considered a(n)?
a) reduction
b) oxidation
c) addition
d) elimination
e) rearrangement
Topic: Oxidation-Reduction
Section: 12.2
Difficulty Level: Medium
22) The following transformation would be considered a(n)?
a) reduction
b) oxidation
c) addition
d) elimination
e) rearrangement
Topic: Oxidation-Reduction
Section: 12.2
Difficulty Level: Medium
23) List the following alkyl halides in order of increasing ease of Grignard formation:
a) I, II, III, IV
b) III, I, II, IV
c) IV, II, I, III
d) III, I, IV, II
e) I, IV, III, II
Topic: Oxidation-Reduction
Section: 12.2
Difficulty Level: Medium
24) Which product is formed from the following transformation:
a)
b)
c)
d)
e)
Topic: Synthetic Strategy, Redox
Section: 12.2
Difficulty Level: Easy
25) Which of these compounds will not be reduced by LiAlH4?
a) CH3CH2CH2CH=CH2
b) 
c) 
d) 
e) 
Topic: Synthetic Strategy, Redox
Section: 12.3
Difficulty Level: Easy
26) Which reagent(s) is/are capable of reducing the following ester to a primary alcohol? 
a) LiAlH4 / ether
b) NaBH4 / H2O
c) Na / C2H5OH
d) H2 / Ni, atmospheric pressure
e) All can be used successfully.
Topic: Synthetic Strategy, Redox
Section: 12.3
Difficulty Level: Easy
27) Which of the reagents listed below would efficiently accomplish the transformation of 3-methyl-3-cyclopentenone into 3-methyl-3-cyclopentenol?
a) i) LiAlH4; ii) H2O
b) NaBH4,H2O
c) H2, Pd
d) More than one of these choices.
Topic: Synthetic Strategy, Redox
Section: 12.3
Difficulty Level: Easy
28) Which of the reagents listed below would efficiently accomplish the transformation of ethyl-3-pentenoate into 3-penten-1-ol?
a) i) LiAlH4; ii) H2O
b) NaBH4,H2O
c) H2, Pd
d) Two of these choices.
e) All of these choices.
Topic: Synthetic Strategy, Redox
Section: 12.3
Difficulty Level: Easy
29) Which reagent(s) would you use to convert CH3(CH2)6CO2H to CH3(CH2)6CH2OH?
a) NaBH4/H2O
b) LiAlH4/ether, then H3O+
c) PCC/CH2Cl2
d) Zn, H3O+
e) H2, Pt
Topic: Synthetic Strategy, Redox
Section: 12.3
Difficulty Level: Easy
30) Which of these compounds cannot be reduced by sodium borohydride?
a) 
b) 
c) 
d) 
e) Two of these choices cannot be reduced.
Topic: Synthetic Strategy, Redox
Section: 12.3
Difficulty Level: Easy
31) In the reaction of carbonyl compounds with LiAlH4, the effective reducing species is:
a) Li+
b) Al+3
c) AlH4–
d) AlH3
e) H–
Topic: Redox, Reaction Mechanisms
Section: 12.3
Difficulty Level: Easy
32) Which of the reagents listed below would efficiently accomplish the transformation of CH3CH2CH=CHCH2CH2CHO into CH3CH2CH=CHCH2CH2CH2OH?
a) KMnO4
b) NaBH4
c) Br2 in CCl4
d) H2, Ni
e) Two of these choices.
Topic: Synthetic Strategy, Redox
Section: 12.3
Difficulty Level: Easy
33) Which of the reagents listed below would efficiently accomplish the transformation of CH3CH2CH=CHCH2CH2CH2OH into CH3CH2CH=CHCH2CH2CHO?
a) KMnO4(aq, alkaline)
b) CrO3 / H2SO4
c) PCC in CH2Cl2
d) Br2, CCl4
e) Two of these choices.
Topic: Synthetic Strategy, Redox
Section: 12.4
Difficulty Level: Easy
34) Which of the reagents listed below would efficiently accomplish the transformation of CH3CH2CH=CHCH2CH2CH2OH into CH3CH2CH=CHCH2CH2CHO?
a) KMnO4, OH–
b) CrO3 / H2SO4
c) (i) (COCl)2, DMSO, –60 oC, (ii) Et3N
d) Br2, CCl4
e) Two of these choices.
Topic: Synthetic Strategy, Redox
Section: 12.4
Difficulty Level: Easy
35) Which of the reagents listed below would efficiently accomplish the transformation of CH3CH2CH=CHCH2CH2CH2OH into CH3CH2CH=CHCH2CH2CHO?
a) KMnO4, OH–
b) CrO3 / H2SO4
c) PCC in CH2Cl2
d) (i) (COCl)2, DMSO, –60 oC, (ii) Et3N
e) Two of these choices.
Topic: Synthetic Strategy, Redox
Section: 12.4
Difficulty Level: Easy
36) Which of the reagents listed below would efficiently accomplish the transformation of CH3CH2C≡CCH2CH2CHO into CH3CH2C≡CCH2CH2CH2OH?
a) KMnO4
b) NaBH4
c) Br2 in CCl4
d) H2, Ni
e) Two of these choices.
Topic: Synthetic Strategy, Redox
Section: 12.3
Difficulty Level: Easy
37) Which of the reagents listed below would efficiently accomplish the transformation of CH3CH2CH=CHCH2CH2CHO into CH3CH2CH2CH2CH2CH2CH2OH?
a) KMnO4
b) NaBH4
c) Br2 in CCl4
d) H2, Ni
e) Two of these choices.
Topic: Synthetic Strategy, Redox
Section: 12.2
Difficulty Level: Medium
38) Select the correct reagent(s) for the following reaction:
a) LiAlH4/ether; then H3O+
b) NaBH4; then H3O+
c) H2 with Pt/C
d) Two of these choices.
e) All of these choices.
Topic: Synthetic Strategy, Redox
Section: 12.3
Difficulty Level: Medium
39) Select the correct reagent(s) for the following reaction:
a) LiAlH4/ether; then H3O+
b) NaBH4; then H3O+
c) H2 with Pt/C
d) Two of these choices.
e) All of these choices.
Topic: Synthetic Strategy, Redox
Section: 12.3
Difficulty Level: Medium
40) Which of the reagents listed below would efficiently accomplish the transformation of 2-methyl-3-cyclopentenol into 2-methyl-3-cyclopentenone?
a) KMnO4(aq, alkaline)
b) CrO3/H2SO4
c) H2, Pt
d) Br2, CCl4
e) Two of these choices.
Topic: Synthetic Strategy, Redox
Section: 12.4
Difficulty Level: Medium
41) Which reagent(s) is/are capable of reducing the following ester to an aldehyde?
a) LiAlH4 / ether
b) NaBH4 / H2O
c) Na / C2H5OH
d) H2 / Ni, atmospheric pressure
e) None of these choices can be used successfully.
Topic: Synthetic Strategy, Redox
Section: 12.3
Difficulty Level: Medium
42) Which product is formed from the following transformation:
a)
b)
c)
d)
e) None of these choices.
Topic: Synthetic Strategy, Redox
Section: 12.8
Difficulty Level: Medium
43) Your task is to synthesize 
through a Grignard synthesis. Which pairs of compounds listed below would you choose as starting materials?
a) 
b) 
c) 
d) More than one of these choices.
e) None of these choices.
Topic: Synthetic Strategy
Section: 12.8
Difficulty Level: Medium
44) Your task is to synthesize 
through a Grignard synthesis. Which pairs of compounds listed below would you choose as starting materials?
a) 
b) 
c) 
d) 
e) None of these choices.
Topic: Synthetic Strategy
Section: 12.8
Difficulty Level: Medium
45) How could the following synthesis be accomplished?
a) (1) SOCl2, (2) Mg, ether, (3) 
then H3O+
b) (1) SOCl2, (2) Li, ether, (3) (CH3CH2)2CuLi, (4) KMnO4, OH–
c) 1) PBr3, (2) Mg, ether, (3) 
then H3O+ (4) PCC, CH2Cl2
d) More than one of these choices.
e) None of these choices.
Topic: Synthetic Strategy
Section: 12.8
Difficulty Level: Hard
46) Which of the following synthetic procedures would be employed most effectively to transform ethanol into ethyl propyl ether?
a) Ethanol + HBr, then Mg/ether, then H3O+, then NaH, then CH3CH2Br
b) Ethanol + HBr, then Mg/ether, then HCHO, then H3O+, then NaH, then CH3CH2Br
c) Ethanol + CH3CH2CH2OH + H2SO4/140 C
d) Ethanol + NaH, then HCHO, then H3O+, then HBr, then Mg/ether, then CH3CH2CH2Br
e) Ethanol + H2SO4/180 °C, then CH3CH2CH2Br
Topic: Synthetic Strategy
Section: 12.8
Difficulty Level: Hard
47) Which reaction leads to an optically active product?
a) 
b) 
c) 
d) 
e)
Topic: Synthetic Strategy, Stereochemistry
Section: 12.8
Difficulty Level: Hard
48) Which method would give 
a) 
b) 
c) 
d) More than one of these choices.
e) None of these choices.
Topic: Synthetic Strategy
Section: 12.4 and 12.8
Difficulty Level: Hard
49) Which combination of reagents id to be preferred for the synthesis of 2,4-dimethylhexane by the Corey-Posner, Whitesides-House procedure?
a) Lithium dimethylcuprate + 4-bromo-2-methylhexane
b) Lithium di(2-methylbutyl)cuprate + isopropyl bromide
c) Lithium diisobutylcuprate + sec-butyl bromide
d) Lithium diisopropylcuprate + 1-bromo-2-methylbutane
e) Lithium dimethylcuprate + 2-bromo-4-methylhexane
Topic: Reactions and Reduction Sequences (Redox)
Section 12.3
Difficulty Level: Easy
50) Which of these reduction reactions would be unsuccessful?
a) 
b) 
c) 
d) 
e) All of these are successful reductions.
51) What would be the product, A, of the following reaction?
a) 
b) 
c) 
d) 
e) 
Topic: Reactions and Reaction Sequences (Redox)
Section: 12.3
Difficulty Level: Easy
52) What is the major product from the reaction of 2-hexanol with PCC in CH2Cl2?
a) CH3CO2H
b) CH3(CH2)3CO2H
c) 
d) CH3(CH2)4CO2H
e) Two of these choices.
Topic: Reactions and Reaction Sequences (Redox)
Section: 12.4
Difficulty Level: Easy
53) What is the major product from the reaction of 2-hexanol with KMnO4?
a) CH3CO2H
b) CH3(CH2)3CO2H
c) 
d) CH3(CH2)4CO2H
e) Two of these choices.
Topic: Reactions and Reaction Sequences (Redox)
Section: 12.4
Difficulty Level: Easy
54) What is the major product from the reaction of 2-hexanol with Na2Cr2O7/H+?
a) CH3CO2H
b) CH3(CH2)3CO2H
c) 
d) CH3(CH2)4CO2H
e) Two of these choices.
Topic: Reactions and Reaction Sequences (Redox)
Section: 12.4
Difficulty Level: Easy
55) What is the major product from the reaction of 2-hexanol with H2CrO4?
a) CH3CO2H
b) CH3(CH2)3CO2H
c) 
d) CH3(CH2)4CO2H
e) Two of these choices.
Topic: Reactions and Reaction Sequences (Redox)
Section: 12.4
Difficulty Level: Easy
56) What is the major product from the reaction of toluene with KMnO4?
a) 
b) 
c) 
d) 
e) 
Topic: Reactions and Reaction Sequences (Redox)
Section: 12.4
Difficulty Level: Easy
57) What would be the product, O, of the following reaction sequence?
a) CH3CH2CH2CH3
b) 
c) 
d) CH3CH2CH2CH2OD
e) CH3CH2CH2CH2D
Topic: Reactions and Reaction Sequences
Section: 12.7
Difficulty Level: Easy
58) What compound(s) result(s) from the reaction of CH3CH2CH2MgBr with CH3CH2CH2CH2CO2H (1:1 mole ratio)?
a) 
b) 
c) 
d) CH3CH2CH3 + CH3CH2CH2CH2CO2MgBr
e) 
Topic: Reactions and Reaction Sequences
Section: 12.7
Difficulty Level: Easy
59) What is the principal product(s) formed when 1 mol of methylmagnesium iodide reacts with 1 mol of p-hydroxyacetophenone?
a) I
b) II
c) III
d) IV
e) V
Topic: Reactions and Reaction Sequences (Grignard)
Section: 12.7
Difficulty Level: Easy
60) What is the principal product(s) formed when 1 mol of methylmagnesium iodide reacts with 1 mol of p-acetylbenzoic acid?
a) I
b) II
c) III
d) IV
e) V
Topic: Reactions and Reaction Sequences (Grignard)
Section: 12.7
Difficulty Level: Easy
61) What would be the product, A, of the following reaction sequence?
a) CH3CH2CH2CH3
b) 
c) 
d) CH3CH2CH2CH2OD
e) CH3CH2CH2CH2D
Topic: Reactions and Reaction Sequences
Section: 12.7
Difficulty Level: Medium
62) What would be the product, A, of the following reaction sequence?
a) CH3CH2CH2CH3
b) 
c) 
d) CH3CH2CH2CH2OD
e) CH3CH2CH2CH2D
Topic: Reactions and Reaction Sequences
Section: 12.7
Difficulty Level: Medium
63) What would be the product, A, of the following reaction sequence?
a) CH3CH2CH2CH3
b) 
c) 
d) CH3CH2CH2CH2OD
e) CH3CH2CH2CH2D
Topic: Reactions and Reaction Sequences
Section: 12.7
Difficulty Level: Medium
64) What is (are) the principal product(s) formed when 1 mol of ethylmagnesium bromide reacts with 1 mol of 3-(N-methylamino)cyclopentanone?
a) I
b) II
c) III
d) IV
e) V
Topic: Reactions and Reaction Sequences (Grignard)
Section: 12.7
Difficulty Level: Medium
65) Predict the product(s) of the following reaction:
a) A mixture of I and II
b) A mixture of I and III
c) A mixture of II and III
d) A mixture of II and IV
e) A mixture of III and IV
Topic: Reactions and Reaction Sequences (Redox)
Section: 12.3
Difficulty Level: Medium
66). Predict the product(s) of the following reaction:
a) I
b) II
c) III
d) IV
e) A mixture of two or more of these choices.
Topic: Reactions and Reaction Sequences (Redox)
Section: 12.4
Difficulty Level: Medium
67) What product(s) is/are formed in the following reaction?
a) CH3CH2CH2CH2OD + CH3CH2OD
b) CH3CH2CH2CD2OD + CH3CH2OD
c) CH3CH2CH2CD2OH + CH3CH2OH
d) CH3CH2CH2CHDOD + CH3CH2OD
e) 
Topic: Reactions and Reaction Sequences
Section: 12.3
Difficulty Level: Medium
68) Predict the product(s) of the following reaction:
a) A mixture of I and II
b) A mixture of I and III
c) A mixture of II and III
d) A mixture of II and IV
e) A mixture of III and IV
Topic: Reactions and Reaction Sequences (Redox)
Section: 12.3
Difficulty Level: Medium
69) When 1-pentanol is treated with alkaline potassium permanganate,
a) the color changes from orange to blue.
b) the color changes from purple to colorless.
c) the color changes from blue to red.
d) the color changes from orange to green.
e) the color changes from green to orange.
Topic: Reactions and Reaction Sequences (Chemical Tests)
Section: 12.4
Difficulty Level: Medium
70) Predict the product(s) of the following reaction:
a) A mixture of I and II
b) A mixture of I and III
c) A mixture of II and III
d) A mixture of II and IV
e) A mixture of III and IV
Topic: Reactions and Reaction Sequences (Redox)
Section: 12.3
Difficulty Level: Medium
71) The final product, D, in the following reaction sequence,
, would be?
a) 
b) 
c) 
d) 
e) 
Topic: Reactions and Reaction Sequences
Section: 12.7
Difficulty Level: Medium
72) The final product, B, in the following reaction sequence,
,would be?
a) 
b) 
c) 
d) 
e) 
Topic: Reactions and Reaction Sequences
Section: 12.7
Difficulty Level: Medium
73) The final product, B, in the following reaction sequence,
,would be?
a) 
b) 
c) 
d) 
e) NNone of these choices.
Topic: Reactions and Reaction Sequences
Section: 12.7
Difficulty Level: Medium
74) The final product, D, in the following reaction sequence
,
would be:
a) 
b) 
c) 
d) 
e) 
Topic: Reactions and Reaction Sequences
Section: 12.7
Difficulty Level: Medium
75) What is the product, A, that would be obtained from the following reaction sequence?
a) I
b) II
c) III
d) IV
e) V
Topic: Reactions and Reaction Sequences
Section: 12.7
Difficulty Level: Medium
76) What is the principal product of the following reaction:
+ CH3CH2CH2CH2MgBr/ether; then H2O ?
a) 
b) 
c) 
d) 
e) 
Topic: Reactions and Reaction Sequences
Section: 12.7
Difficulty Level: Medium
77) What would be the final product, A, in the following reaction sequence?
a) I
b) II
c) III
d) IV
e) V
Topic: Reactions and Reaction Sequences
Section: 12.6 and 12.7
Difficulty Level: Medium
78) What would be the final product, A, in the following reaction sequence?
a) I
b) II
c) III
d) IV
e) V
Topic: Reactions and Reaction Sequences
Section: 12.6 and 12.7
Difficulty Level: Medium
79) What would be the final product, D, in the following reaction sequence?
a) I
b) II
c) III
d) IV
e) V
Topic: Reactions and Reaction Sequences
Section: 12.6 and 12.7
Difficulty Level: Medium
80) What would be the final product, D, in the following reaction sequence?
a) I
b) II
c) III
d) IV
e) V
Topic: Reactions and Reaction Sequences
Section: 12.6 and 12.7
Difficulty Level: Medium
81) What is the product, A, that would be obtained from the following reaction sequence?
a) I
b) II
c) III
d) IV
e) V
Topic: Reactions and Reaction Sequences
Section: 12.8
Difficulty Level: Medium
82) What is the product, A, that would be obtained from the following reaction sequence?
a) I
b) II
c) III
d) IV
e) V
Topic: Reactions and Reaction Sequences
Section: 12.8
Difficulty Level: Medium
83) What is the product, A, that would be obtained from the following reaction sequence?
a) I
b) II
c) III
d) IV
e) V
Topic: Reactions and Reaction Sequences
Section: 12.8
Difficulty Level: Medium
84) What is the product, A, that would be obtained from the following reaction sequence?
a) I
b) II
c) III
d) IV
e) V
Topic: Reactions and Reaction Sequences
Section: 12.8
Difficulty Level: Medium
85) Predict the product(s) of the following reaction:
a) A mixture of I and II
b) A mixture of I and III
c) A mixture of II and III
d) A mixture of II and IV
e) A mixture of III and IV
Topic: Reactions and Reaction Sequences (Grignard)
Section: 12.8
Difficulty Level: Medium
86) Predict the product(s) of the following reaction sequence:
a) A mixture of I and II
b) A mixture of I and III
c) A mixture of II and III
d) A mixture of II and IV
e) A mixture of III and IV
Topic: Reactions and Reaction Sequences (Grignard)
Section: 12.8
Difficulty Level: Medium
87) Predict the product(s) of the following reaction sequence:
a) A mixture of I and II
b) A mixture of I and III
c) A mixture of II and III
d) A mixture of II and IV
e) A mixture of III and IV
Topic: Reactions and Reaction Sequences (Grignard)
Section: 12.8
Difficulty Level: Medium
88) Predict the product(s) of the following reaction sequence:
a) A mixture of I and II
b) A mixture of I and III
c) A mixture of II and III
d) A mixture of II and IV
e) A mixture of III and IV
Topic: Reactions and Reaction Sequences (Grignard)
Section: 12.8
Difficulty Level: Medium
89) What is/are the principal product(s) formed when excess methylmagnesium iodide reacts with p-hydroxyacetophenone?
a) I
b) II
c) III
d) IV
e) V
Topic: Reactions and Reaction Sequences (Grignard)
Section: 12.7 and 12.8
Difficulty Level: Medium
90) Predict the product(s) of the following reaction sequence:
a) I
b) II
c) III
d) IV
e) V
Topic: Reactions and Reaction Sequences
Section: 12.6 and 12.8
Difficulty Level: Medium
91) What product(s) is/are produced in the 1:1 reaction of sec-butylmagnesium bromide with
a) 
b) 
c) 
d) 
e) 
Topic: Reactions and Reaction Sequences
Section: 12.8
Difficulty Level: Medium
92) What is the product, A, that would be obtained from the following reaction sequence?
a) I
b) II
c) III
d) IV
e) V
Topic: Reactions and Reaction Sequences
Section: 12.7 and 12.8
Difficulty Level: Medium
93) What is the product, A, that would be obtained from the following reaction sequence?
a) I
b) II
c) III
d) IV
e) V
Topic: Reactions and Reaction Sequences
Section: 12.7 and 12.8
Difficulty Level: Medium
94) What is the product, A, that would be obtained from the following reaction sequence?
a) I
b) II
c) III
d) IV
e) V
Topic: Reactions and Reaction Sequences
Section: 12.8
Difficulty Level: Medium
95) What is the product, A, that would be obtained from the following reaction sequence?
NaNH2
a) I
b) II
c) III
d) IV
e) V
Topic: Reactions and Reaction Sequences
Section: 12.8
Difficulty Level: Medium
96) What is the product, A, that would be obtained from the following reaction sequence?
Br
a) I
b) II
c) III
d) IV
e) V
Topic: Reactions and Reaction Sequences
Section: 12.8
Difficulty Level: Medium
97) What is the final product?
a) 
b) 
c) 
d) 
e) None of these choices.
Topic: Reactions and Reaction Sequences
Section: 12.8
Difficulty Level: Medium
98) What is/are the principal product(s) formed when excess methylmagnesium iodide reacts with p-hydroxyacetophenone?
a) I
b) II
c) III
d) IV
e) V
Topic: Reactions and Reaction Sequences (Grignard)
Section: 12.9
Difficulty Level: Hard
99) What is/are the principal product(s) formed when excess methylmagnesium iodide reacts with methyl 4-hydroxybenzoate?
a) I
b) II
c) III
d) IV
e) V
Topic: Reactions and Reaction Sequences (Grignard)
Section: 12.9
Difficulty Level: Hard
100) What would be the product, D, of the following reaction sequence?
a) I
b) II
c) III
d) IV
e) V
Topic: Reactions and Reaction Sequences
Section: 12.6 and 12.8
Difficulty Level: Medium
101) What would be the product, C, of the following reaction sequence?
a) 2,6-Dimethylheptane
b) 2,2-Dimethylpropane
c) 2-Methylpentane
d) 2,2,5-Trimethylhexane
e) 2,2,6-Trimethylheptane
Topic: Reactions and Reaction Sequences
Section: 12.6 and 12.8
Difficulty Level: Hard
102) What would be the product, D, of the following reaction sequence?
a) 2,6-Dimethylheptane
b) 2,2-Dimethylpropane
c) 2-Methylpentane
d) 2,2,5-Trimethylhexane
e) 2,2,6-Trimethylheptane
Topic: Reactions and Reaction Sequences
Section: 12.6 and 12.8
Difficulty Level: Hard
103) What would be the product, D, of the following reaction sequence?
a) I
b) II
c) III
d) IV
e) V
Topic: Reactions and Reaction Sequences
Section: 12.6 and 12.8
Difficulty Level: Hard
104) What would be the alkane C that is the product of the following reaction sequence?
a) 
b) 
c) 
d) 
e) 
Topic: Reactions and Reaction Sequences
Section: 12.6 and 12.8
Difficulty Level: Hard
105) What would be the major product of the following reaction?
a) (R)-3-ethyl-5-methylheptane
b) (R,S)-3-ethyl-5-methylheptane
c) (S)-3-ethyl-5-methylheptane
d) (3R,5S)-5-ethyl-3-methylheptane
e) (3S,5R)-5-ethyl-3-methylheptane
Topic: Reactions and Reaction Sequences
Section: 12.6 and 12.8
Difficulty Level: Hard
106) The reaction of lithium di-sec-butylcuprate with isopentyl bromide yields:
a) 2,5-Dimethylheptane
b) 2,6-Dimethylheptane
c) 3,5-Dimethylheptane
d) 3,4-Dimethylheptane
e) 3,6-Dimethylheptane
Topic: Reactions and Reaction Sequences
Section: 12.6 and 12.8
Difficulty Level: Hard
107) The reaction of lithium diethylcuprate with 1-bromo-4,4-dimethylhexane yields:
a) 3,3-Dimethylheptane
b) 3,3-Dimethyloctane
c) 1-Ethyl-4,4-dimethylhexane
d) Di-4,4-dimethylhexylcuprate
e) None of these choices.
Topic: Reactions and Reaction Sequences
Section: 12.6 and 12.8
Difficulty Level: Hard
108) What would be the major product of the following reaction?
a) I
b) II
c) III
d) IV
e) V
Topic: Reactions and Reaction Sequences
Section: 12.3
Difficulty Level: Hard
109) What would be the major product of the following reaction?
a) CH3CH2OCH(CH3)CH2CH2CH2CH3
b) (CH3CH2O)2CHCHOHCH2CH2CH3
c) (CH3CH2)2CHOHCH2CH2CHOHCH3
d) CH3OCH(C2H5)CH2CH2CH2CH3
e) CH3CH2CH(OCH3)CH2CH2CHOHCH3
Topic: Reactions and Reaction Sequences (Redox, SN2)
Section: 12.4, 12.6, and 12.7
Difficulty Level: Hard
110) The final product, E, in the following reaction sequence is,
a) I
b) II
c) III
d) IV
e) V
Topic: Reactions and Reaction Sequences
Section: 12.4, 12.6 and 12.7
Difficulty Level: Hard
111) The final product, E, in the following reaction sequence is,
a) I
b) II
c) III
d) IV
e) V
Topic: Reactions and Reaction Sequences
Section: 12.4, 12.6 and 12.7
Difficulty Level: Hard
112) The final product, E, in the following reaction sequence is,
a) I
b) II
c) III
d) IV
e) V
Topic: Reactions and Reaction Sequences
Section: 12.4, 12.6 and 12.7
Difficulty Level: Hard
113) The final product, E, in the following reaction sequence is,
a) I
b) II
c) III
d) IV
e) V
Topic: Reactions and Reaction Sequences
Section: 12.4, 12.6 and 12.7
Difficulty Level: Hard
114) The final product, E, in the following reaction sequence is,
a) I
b) II
c) III
d) IV
e) V
Topic: Reactions and Reaction Sequences
Section: 12.4, 12.6 and 12.7
Difficulty Level: Hard
115) The final product, E, in the following reaction sequence is,
a) I
b) II
c) III
d) IV
e) V
Topic: Reactions and Reaction Sequences
Section: 12.4, 12.6 and 12.7
Difficulty Level: Hard
116) The final product, E, in the following reaction sequence is,
a) I
b) II
c) III
d) IV
e) V
Topic: Reactions and Reaction Sequences
Section: 12.4, 12.6 and 12.7
Difficulty Level: Hard
117) The final product, E, in the following reaction sequence is,
a) I
b) II
c) III
d) IV
e) V
Topic: Reactions and Reaction Sequences
Section: 12.4, 12.6 and 12.7
Difficulty Level: Hard
118) The final product, E, in the following reaction sequence is,
a) I
b) II
c) III
d) IV
e) V
Topic: Reactions and Reaction Sequences
Section: 12.4, 12.6 and 12.7
Difficulty Level: Hard
119) What is the final product of the following reaction sequence?
a) I
b) II
c) III
d) IV
e) V
Topic: Reactions and Reaction Sequences
Section: 12.4, 12.6 and 12.7
Difficulty Level: Hard
120) The final product, E, in the following reaction sequence is,
a) I
b) II
c) III
d) IV
e) V
Topic: Reactions and Reaction Sequences
Section: 12.4, 12.6 and 12.7
Difficulty Level: Hard
121) The reagent PCC in dry methylene chloride is successful in the selective oxidation of primary alcohols to aldehydes because:
a) PCC is a relatively weak oxidizing agent.
b) primary alcohols cannot oxidize any further.
c) hydration of the intermediate aldehyde is unable to take place in dry methylene chloride.
d) methylene chloride is a reducing agent.
e) None of these choices.
Topic: Redox, Reaction Mechanisms
Section: 12.4
Difficulty Level: Easy
122) The Swern oxidation is a method successful for the selective oxidation of primary alcohols to aldehydes because:
a) oxalyl chloride is a weak oxidizing agent.
b) primary alcohols cannot oxidize any further.
c) hydration of the intermediate aldehyde is unable to take place under the conditions employed.
d) DMSO is a reducing agent.
e) None of these choices.
Topic: Redox, Reaction Mechanisms
Section: 12.4
Difficulty Level: Easy
123) Fundamentally, 2-methyl-2-pentanol does not undergo oxidation by H2CrO4 because:
a) the intermediate chromate ester is not formed.
b) the oxidant isn't in a sufficiently high oxidation state.
c) the alcohol undergoes dehydration.
d) the intermediate chromate ester cannot lose hydrogen.
e) Actually, this oxidation does occur.
Topic: Redox, Reaction Mechanisms
Section: 12.4
Difficulty Level: Easy
124) CrO3 in H2SO4/H2O will fail to give a positive test with which of these compounds?
a) CH3CH2CH2CH2OH
b) 
c) (CH3)3COH
d) 
e) More than one of these choices.
Topic: Functional Group Tests
Section: 12.4
Difficulty Level: Easy
125) Jones reagent will fail to give a positive test with?
a) 
b) 
c) 
d) 
e) All of these choices.
Topic: Functional Group Tests
Section: 12.4
Difficulty Level: Easy
126) Which reagent(s) will distinguish between cyclopentanol and cyclopentane?
a) Br2/CCl4
b) KMnO4 (cold)
c) CrO3/aqueous H2SO4
d) NaOH(aq)
e) Two of these choices
Topic: Functional Group Tests
Section: 12.4
Difficulty Level: Easy
127) Which reagent(s) will distinguish between 2-methylcyclopentanol and 1-methylcyclopentanol?
a) Br2/CCl4
b) KMnO4
c) CrO3/aqueous H2SO4
d) NaOH(aq)
e) Two of these choices.
Topic: Functional Group Tests
Section: 12.4
Difficulty Level: Easy
128) Which of the reagents listed below would serve as the basis for a simple chemical test to distinguish between (CH3)3COH and (CH3)2CHCH2OH?
a) NaH
b) NaOH/H2O
c) Br2 in CCl4
d) Cold conc. H2SO4
e) CrO3 in H2SO4
Topic: Functional Group Tests
Section: 12.4
Difficulty Level: Easy
129) Which of the reagents listed below would serve as the basis for a simple chemical test to distinguish between (CH3)3COH and (CH3)2CHCH2OH?
a) NaH
b) NaOH/H2O
c) Br2 in CCl4
d) Cold conc. H2SO4
e) Jones reagent
Topic: Functional Group Tests
Section: 12.4
Difficulty Level: Easy
130) Which of the following reagents might serve as the basis for a simple chemical test that would distinguish between CH3CH=CHCH3 and CH3CHOHCH2CH3?
a) CrO3 in H2SO4
b) KMnO4
c) Br2 in CCl4
d) Two of these choices.
e) All of these choices.
Topic: Functional Group Tests
Section: 12.4
Difficulty Level: Medium
131) Which of the reagents listed below would serve as the basis for a simple chemical test to distinguish between CH3CH=CHCH2OH and CH3CH2CH2CH2OH?
a) CrO3 in H2SO4
b) Cold conc. H2SO4
c) Br2 in CCl4
d) NaOH/H2O
e) NaBH4
Topic: Functional Group Tests
Section: 12.4
Difficulty Level: Medium
132) Which of the reagents listed below would serve as the basis for a simple chemical test to distinguish between (CH3)2C=CHCH2CH2OH and (CH3)2CHCH2CH2CH2OH?
a) CrO3 in H2SO4
b) Cold conc. H2SO4
c) Br2 in CCl4
d) NaOH/H2O
e) NaBH4
Topic: Functional Group Tests
Section: 12.4
Difficulty Level: Medium
133) Consider the molecule 
Which reagent will not give a positive test with this compound?
a) Cold conc. H2SO4
b) Br2/CCl4
c) NaOH(aq)
d) CrO3/H2SO4
e) Dilute KMnO4/H2O
Topic: Functional Group Tests
Section: 12.4
Difficulty Level: Medium
134) When 2-pentanol is treated with chromic acid,
a) the color changes from orange to blue.
b) the color changes from purple to colorless.
c) the color changes from blue to red.
d) the color changes from orange to green.
e) the color changes from green to orange.
Topic: Functional Group Tests
Section: 12.4
Difficulty Level: Medium
135) When 3-methyl-3-pentanol is treated with chromic acid,
a) the color changes from orange to blue.
b) the color changes from purple to colorless.
c) the purple color remains unchanged.
d) the color changes from orange to green.
e) the orange color remains unchanged.
Topic: Functional Group Tests
Section: 12.4
Difficulty Level: Medium
136) Which of the reagents/techniques listed below would serve as the basis for a simple chemical test to distinguish between 2-methyl-3-hexyn-2-ol and 2-methyl-5-hexyn-1-ol?
a) CrO3 in H2SO4
b) IR spectroscopy
c) Br2 in CCl4
d) Both CrO3 in H2SO4 and IR spectroscopy.
e) All of these choices.
Topic: Functional Group Tests
Section: 2.16 and 12.4
Difficulty Level: Medium
137) Which of the reagents/techniques listed below would serve as the basis for a simple chemical test to distinguish between 2-methyl-3-hexyn-1-ol and 2-methyl-5-hexyn-1-ol?
a) CrO3 in H2SO4
b) Cold conc. H2SO4
c) Br2 in CCl4
d) NaBH4
e) IR spectroscopy
Topic: Functional Group Tests
Section: 2.16 and 12.4
Difficulty Level: Medium
138) Which of the reagents/techniques listed below would serve as the basis for a simple chemical test to distinguish between CH3CH2CH=CHCH2CH2CHO and CH3CH2CH=CHCH2CH2CH2OH?
a) KMnO4
b) IR spectroscopy
c) Br2 in CCl4
d) Two of these choices.
e) All of these choices.
Topic: Functional Group Tests
Section: 2.16 and 12.4
Difficulty Level: Medium
139) Which of these is the least reactive type of organometallic compound?
a) RK
b) R2Hg
c) RLi
d) R2Zn
e) R3Al
Topic: Reactivity of Grignards and Other Organometallics
Section: 12.5
Difficulty Level: Easy
140) If the role of the solvent is to assist in the preparation and stabilization of the Grignard reagent by coordination with the magnesium, which of these solvents should be least effective?
a) I
b) II
c) III
d) IV
e) V
Topic: Synthesis of Grignards and Other Organometallics
Section: 12.6
Difficulty Level: Easy
141) Grignard reagents react with oxirane (ethylene oxide) to form 1 alcohols but can be prepared in tetrahydrofuran solvent. Why is this difference in behavior observed?
a) Steric hindrance in the case of tetrahydrofuran precludes reaction with the Grignard.
b) There is a better leaving group in the oxirane molecule.
c) The oxirane ring is the more highly strained.
d) It is easier to obtain tetrahydrofuran in anhydrous condition.
e) Oxirane is a cyclic ether, while tetrahydrofuran is a hydrocarbon.
Topic: Synthesis of Grignards and Other Organometallics
Section: 12.7
Difficulty Level: Easy
142) Which synthesis of a Grignard reagent would fail to occur as written?
a) 
b) 
c) 
d) 
e) All of these choices will succeed.
Topic: Synthetic Strategy
Section: 12.8
Difficulty Level: Easy
143) Which of these reactions will not produce a 1 alcohol?
a)
b) 
c) 
d) 
e) 
Topic: Synthetic Strategy
Section: 12.3 and 12.7
Difficulty Level: Medium
144) Which of the following would serve as a synthesis of racemic 2-methyl-1-phenyl-2-butanol?
a) I
b) II
c) III
d) All of these choices.
e) None of these choices.
Topic: Synthetic Strategy, Stereochemistry
Section: 12.8
Difficulty Level: Medium
145) Which of the following reactions would serve as a reasonable synthesis of the following racemic alcohol (2-phenyl-2-butanol)?
a)
b) 
c) 
d) Two of these choices.
e) All of these choices.
Topic: Synthetic Strategy, Stereochemistry
Section: 12.8
Difficulty Level: Medium
146) Which Grignard synthesis will produce an optically active product or product mixture?
a) 
b) 
c) 
d) 
e) 
Topic: Synthetic Strategy, Stereochemistry
Section: 12.8
Difficulty Level: Medium
147) Which of the following is the strongest base?
a) RMgX
b) Mg(OH)X
c) RH
d) H2O
e) NaOH
Topic: Acid/Base
Section: 12.8
Difficulty Level: Medium
148) In which of the following series are the compounds arranged in order of decreasing basicity?
a) CH3CH2MgBr > NaNH2 > HCCNa > NaOH > CH3CH2ONa
b) CH3CH2MgBr > NaNH2 > HCCNa > CH3CH2ONa > NaOH
c) HCCNa > CH3CH2MgBr > NaNH2 > CH3CH2ONa > NaOH
d) NaNH2 > CH3CH2MgBr > HCCNa > CH3CH2ONa > NaOH
e) None of these choices.
Topic: Acid/Base
Section: 12.8
Difficulty Level: Medium
149) Which of these compounds cannot be used to prepare the corresponding Grignard reagent?
a) CH3OCH2CH2CH2Br
b) (CH3)3CCl
c) CH2=CHCH2Br
d) (CH3)2NCH2CH2Br
e) 
Topic: Synthesis of Grignards and Other Organometallics
Section: 12.8
Difficulty Level: Easy
150) Which of these compounds can be used to prepare the corresponding Grignard reagent?
a) CH3CHOHCH2CH2CH2CH2Br
b) (CH3)3CHCHBrCH2CH2CO2H
c) BrCH=CHCH2CH2CH3
d) CH3NHCH2CH2Br
e) None of these choices can be used to prepare the corresponding Grignard reagent.
Topic: Synthesis of Grignards and Other Organometallics
Section: 12.8
Difficulty Level: Easy
Question type: fill-in-the-blank
151) Because the carbonyl carbon bears a partial positive charge, it is susceptible to ___ attack.
Topic: General
Section: 12.1
Difficulty Level: Easy
152) Because the carbonyl oxygen bears a partial negative charge, it is susceptible to ___ attack.
Topic: General
Section: 12.1
Difficulty Level: Easy
153) When nucleophilic addition to a carbonyl group occurs, the carbon attacked undergoes this hybridization change:
Topic: General
Section: 12.1
Difficulty Level: Easy
154) A reaction which increases the hydrogen content or decreases the oxygen content of an organic molecule is called a(n) ___.
Topic: General, Redox
Section: 12.2
Difficulty Level: Easy
155) A reaction which increases the oxygen content or decreases the hydrogen content of an organic molecule is called a(n) ___.
Topic: General, Redox
Section: 12.2
Difficulty Level: Easy
156) LAH is the abbreviation for the powerful reducing agent ___.
Topic: General, Redox
Section: 12.3
Difficulty Level: Easy
157) A negatively charged hydrogen atom is called a ___.
Topic: General, Redox
Section: 12.3
Difficulty Level: Easy
158) In the reaction of carbonyl compounds with LiAlH4, the effective reducing species is:
Topic: Redox Reactions
Section: 12.3
Difficulty Level: Easy
159) In the reaction of carbonyl compounds with NaBH4, the effective reducing species is:
Topic: Redox Reactions
Section: 12.3
Difficulty Level: Easy
160) A solution of CrO3 or Na2Cr2O7 in aqueous sulfuric acid is called the ___.
Topic: General, Redox Reagents
Section: 12.4
Difficulty Level: Easy
161) Upon reaction with a primary or secondary alcohol, the change in oxidation state of chromium ion in Jones reagent is from ___ to ___.
Topic: Redox Reactions
Section: 12.4
Difficulty Level: Easy
162) Upon reaction with a primary or secondary alcohol with CrO3 in H2SO4, the alcohol is ___ and the CrO3 is ___.
Topic: Redox Reactions
Section: 12.4
Difficulty Level: Easy
163) Upon oxidation of a 1° or 2° alcohol with Jones reagent, the chromium ion goes from ___ to ___.
Topic: General, Redox Reagents, Chemical Tests
Section: 12.4
Difficulty Level: Easy
164) The process of converting an alkyl halide to an alkane using LAH is a(n) ___ reaction.
Topic: General, Redox
Section: 12.5
Difficulty Level: Easy
165) Organomagnesium halides are known as ___.
Topic: General
Section: 12.6
Difficulty Level: Easy
166) Compounds that contain carbon-metal bonds are known as ___.
Topic: General
Section: 12.5
Difficulty Level: Easy
167) Key to the usefulness of PCC/CH2Cl2 as a selective oxidant for the production of aldehydes from 1° alcohols is ___.
Topic: General, Redox
Section: 12.4
Difficulty Level: Medium
168) The selective oxidation of a primary alcohol to an aldehyde using oxalyl chloride and DMSO at –60 °C, followed by triethylamine is referred to as the ___ oxidation.
Topic: General, Redox
Section: 12.4
Difficulty Level: Medium
169) Key to the usefulness of Swern oxidation as a selective oxidant for the production of aldehydes from primary alcohols is ___.
Topic: General, Redox
Section: 12.4
Difficulty Level: Medium
Question type: Essay
170) PCC and CrO3 are both Cr(VI) reagents. However, PCC/CH2Cl2 is useful in oxidizing primary alcohols to aldehydes, while the analogous reaction with CrO3/H2SO4 will typically produce carboxylic acids. Why?
Topic: General, Redox
Section: 12.4
Difficulty Level: Medium
Question type: Molecular Drawing
171) Draw the resonance structures that account for esters being less reactive toward NaBH4 than aldehydes or ketones.
Topic: Carbonyl Compounds Resonance Forms
Section: 12.1
Difficulty Level: Medium
172) What would be the major product, A, of the following reaction?
Topic: Multistep Reactions
Section: 12.3
Difficulty Level: Medium
173) Predict the product of the following reaction:
Topic: Reactions, Selective Redox Reactions
Section: 12.3
Difficulty Level: Medium
174) Predict the product(s) of the following reaction sequence:
and 
Topic: Reactions, Redox
Section: 12.3
Difficulty Level: Medium
175) Predict the product(s) of the following reaction sequence:
and
Topic: Reactions, Redox
Section: 12.3
Difficulty Level: Medium
176) For the ketone shown, indicate on the appropriate arrow which face is the re face, and which face is si?
si
Topic: Reactions, Redox
Section 12.3
Difficulty Level: Medium
177) Which of the following molecules, if any, contains a prochiral carbon?
a) I
b) II
c) III
d) IV
e) All of these choices.
Topic: Carbonyl Compounds, Prochirality, Stereochemistry
Section: 12.3
Difficulty Level: Hard
178) Which of the following molecules, if any, contains a prochiral carbon?
a) I
b) II
c) III
d) IV
e) None of these choices.
Topic: Carbonyl Compounds, Prochirality, Stereochemistry
Section: 12.3
Difficulty Level: Hard
179) For the ketone shown, indicate on the appropriate arrow which face is the re face, and which face is si?
re
Topic: Reactions, Redox
Section 12.3
Difficulty Level: Medium
180) For the aldehyde shown, indicate on the appropriate arrow which face is the re face, and which face is si?
si
Topic: Reactions, Redox
Section 12.3
Difficulty Level: Medium
181) For the aldehyde shown, indicate on the appropriate arrow which face is the re face, and which face is si?
re
Topic: Reactions, Redox
Section 12.3
Difficulty Level: Medium
Question type: fill-in-the-blank
182) Primary and secondary alcohols can be distinguished from most other compounds (with the exception of aldehydes) because they will react rapidly with a solution of CrO3 in aqueous sulfuric acid, causing a color change from ___ to ___.
Topic: Functional Group Tests
Section: 12.4
Difficulty Level: Easy
Question type: Essay
183) Diethyl ether, the most commonly used solvent for Grignard reactions, also acts as an ‘internal cooling agent’, preventing the overheating of the reaction mixture: what specific property of diethyl ether is exploited here and why is it important to prevent the overheating of the reaction mixture?
Topic: Synthesis of Grignards and Other Organometallics
Section: 12.6
Difficulty Level: Medium
184) Why can we not prepare a Grignard reagent from a molecule such as 4-bromo-1-butanol?
Topic: Synthesis of Grignards and Other Organometallics
Section: 12.8
Difficulty Level: Easy
Question type: fill-in-the-blank
185) The reactivity of organometallic compounds increases with the ___ of the carbon-metal bond.
Topic: Reactivity of Grignards and Other Organometallics
Section: 12.5
Difficulty Level: Easy
186) In a Grignard reagent, the carbon bonded to magnesium has a partial ___ charge and therefore behaves as a(n) ___.
Topic: Reactions of Grignards and Other Organometallics
Section: 12.7
Difficulty Level: Easy
187). A Grignard reagent will produce a primary alcohol when reacted with ___ or___.
Topic: Reactions of Grignards and Other Organometallics
Section: 12.8
Difficulty Level: Easy
188) A Grignard reagent will produce a secondary alcohol when reacted with ___.
Topic: Reactions of Grignards and Other Organometallics
Section: 12.8
Difficulty Level: Easy
189) Reaction of an alkyllithium with a ketone produces, after acid work-up, a ___ alcohol.
Topic: Reactions of Grignards and Other Organometallics
Section: 12.8
Difficulty Level: Easy
190) Reaction of excess methyllithium with ethyl acetate (CH3CO2C2H5) produces, after acid work-up, ___.
Topic: Reactions of Grignards and Other Organometallics
Section: 12.8
Difficulty Level: Easy
191) Reaction of excess ethyl magnesium bromide with ethyl benzoate (C6H5CO2C2H5) produces, after acid work-up, ___.
Topic: Reactions of Grignards and Other Organometallics
Section: 12.8
Difficulty Level: Easy
192) Reaction of excess ethyl magnesium iodide with ethyl acetate (CH3CO2C2H5) produces, after acid work-up, ___.
Topic: Reactions of Grignards and Other Organometallics
Section: 12.8
Difficulty Level: Easy
Question type: Essay
193) NH4Cl is sometimes preferred instead of HCl or H2SO4 for “acid” work-up after Grignard reactions, particularly when the expected and desired product is a tertiary alcohol: why?
Topic: Grignard Reactions
Section: 12.8
Difficulty Level: Easy
194) Predict the product(s) of the following reaction sequence:
and
Topic: Reactions, Grignard
Section: 12.8
Difficulty Level: Medium
195) Predict the product(s) of the following reaction sequence:
and
Topic: Reactions, Grignard
Section: 12.8
Difficulty Level: Hard
196) Suggest a reasonable synthetic strategy for the synthesis of 3-ethyl-3-heptanol from pentanoic acid, CH3CH2CH2CH2CO2H.
Topic: Multistep Synthetic Strategy
Section: 12.8
Difficulty Level: Hard
197) Suggest a reasonable synthetic strategy for the synthesis of 4-heptanol from 1-pentene.
Topic: Multistep Synthetic Strategy
Section: 12.7
Difficulty Level: Hard
198) Complete the following reaction sequence, giving structural details of all key intermediates.
4-methyl-1-hexene
i) BH3, THF
ii) H2O2,NaOH
iii) SOCl2
iv) Mg, Et2O
iv) ethylene oxide
v) NH4Cl
Topic: Multistep Reaction Sequence
Section: 12.7
Difficulty Level: Hard
199) Complete the following reaction sequence, giving structural details of all key intermediates.
1-hexene
i) HBr
ii) Li
iii) (CH3CH2)2C=O
iv) C2H5I
Topic: Multistep Reaction Sequence
Section: 12.8
Difficulty Level: Hard
200) Complete the following reaction sequence, giving structural details of all key intermediates.
1-hexene
i) HBr/ROOR
ii) Li
iii) (CH3CH2)2C=O
iv) C2H5I
Topic: Multistep Reaction Sequence
Section: 12.8
Difficulty Level: Hard
201) Complete the following reaction sequence, giving structural details of all key intermediates.
Topic: Multistep Reaction Sequence
Section: 12.8
Difficulty Level: Hard
202) Suggest a reasonable synthetic strategy for the synthesis of 3-methyl-3-hexanol from 3-hexanol.
Topic: Multistep Synthetic Strategy
Section: 12.4 and 12.8
Difficulty Level: Hard
203) Suggest a reasonable synthetic strategy for the synthesis of 2-methyl-3-hexanol from 1-butanol.
Topic: Multistep Synthetic Strategy
Section: 12.4 and 12.8
Difficulty Level: Hard
204) Predict the product(s) of the following reaction sequence:
and
Topic: Multistep Reactions, Grignard
Section: 12.6 and 12.8
Difficulty Level: Medium
205) Predict the product(s) of the following reaction sequence:
and
Topic: Multistep Reactions, Grignard
Section: 12.6 and 12.8
Difficulty Level: Medium
206) Predict the product(s) of the following reaction sequence:
Topic: Multistep Reactions, Grignard
Section: 12.6 and 12.8
Difficulty Level: Medium
207) Predict the product(s) of the following reaction sequence:
Topic: Multistep Reactions, Grignard
Section: 12.6 and 12.8
Difficulty Level: Medium
208) Predict the product(s) of the following reaction sequence:
Topic: Multistep Reactions, Grignard
Section: 12.6 and 12.8
Difficulty Level: Hard
209) Predict the major product(s) of the following reaction sequence:
Topic: Multistep Reactions, Grignard
Section: 12.6 and 12.8
Difficulty Level: Hard
210) Complete the following reaction sequence, giving structural details of all key intermediates.
2-methyl-1-pentene
i) BH3, THF
ii) H2O2,NaOH
iii) PCC, CH2Cl2
iv) CH3CH2C≡C:– Na+
v) NH4Cl
Topic: Multistep Reaction Sequence
Section: 12.8
Difficulty Level: Hard
211) Complete the following reaction sequence, giving structural details of all key intermediates.
2-methyl-1-pentene
i) BH3, THF
ii) H2O2,NaOH
iii) (COCl)2, DMSO, –60 °C
iv) Et3N
v) CH3CH2C≡C:– Na+
vi) NH4Cl
Topic: Multistep Reaction Sequence
Section: 12.8
Difficulty Level: Hard
212) Suggest a reasonable synthetic strategy for the synthesis of 4-methyl-1,4-pentanediol from methyl-4-hydroxybutanoate HOCH2CH2CH2COOCH3.
Topic: Multistep Synthetic Strategy (using protecting groups)
Section: 12.9
Difficulty Level: Hard
213) Suggest a reasonable synthetic strategy for the synthesis of 1,4-pentanediol from 4-hydroxybutanal HOCH2CH2CH2CHO.
Topic: Multistep Synthetic Strategy (using protecting groups)
Section: 12.9
Difficulty Level: Hard
214) Suggest a reasonable synthetic strategy for the synthesis of 4-methyl-1,4-pentanediol from 4-hydroxybutanone HOCH2CH2CH2COCH3.
Topic: Multistep Synthetic Strategy (using protecting groups)
Section: 12.9
Difficulty Level: Hard
215) Predict the product D of the following reaction sequence:
Topic: Multistep Reactions
Section:12.6A and 12.8C
Difficulty Level: Hard
216) Complete the following reaction sequence, giving structural details of all key intermediates.
Bromocyclohexane
i) Li
ii) CuI
iii) 4-methyl-1-bromohexane
Topic: Multistep Reaction Sequence
Section: 12.6 and 12.8
Difficulty Level: Hard
217) The following transformation would be considered a(n)?
RCHO RCO2H
a) Reduction
b) Oxidation
c) Addition
d) Elimination
e) Rearrangement
Topic: Oxidation-Reduction
Section: 12.2
Difficulty Level: Easy
218) The following transformation would be considered a(n)?
RCH2OH RCHO
a) Reduction
b) Oxidation
c) Addition
d) Elimination
e) Rearrangement
Topic: Oxidation-Reduction
Section: 12.2
Difficulty Level: Easy
219) The following transformation would be considered a(n)?
RCH2OH RCO2H
a) Reduction
b) Oxidation
c) Addition
d) Elimination
e) Rearrangement
Topic: Oxidation-Reduction
Section: 12.2
Difficulty Level: Easy
220) The following transformation would be considered a(n)?
RCH=CH2 RCH2CH3
a) Reduction
b) Oxidation
c) Addition
d) Elimination
e) Rearrangement
Topic: Oxidation-Reduction
Section: 12.2
Difficulty Level: Easy
221) The following transformation would be considered a(n)?
RCOOH RCH2OH
a) Reduction
b) Oxidation
c) Addition
d) Elimination
e) Rearrangement
Topic: Oxidation-Reduction
Section: 12.2
Difficulty Level: Easy
222) What is the major product of the following reaction?
a) 3-hexanol
b) 2-phenyl-2-pentanol
c) 2-ethylpentanoic acid
d) 2-methyl-3-pentanone
e) None of these choices.
Topic: Synthetic Strategy, Stereochemistry
Section: 12.8
Difficulty Level: Hard
223) What is the major product of the following reaction?
a) 3-hexanol
b) 2-phenyl-2-pentanol
c) 2-ethylpentanoic acid
d) 2-methyl-3-pentanone
e) None of these choices.
Topic: Synthetic Strategy, Stereochemistry
Section: 12.8
Difficulty Level: Hard
224) What is the major product of the following reaction?
a) 3-hexanol
b) 2-phenyl-2-pentanol
c) 2-ethylpentanoic acid
d) 2-methyl-3-pentanone
e) None of these choices.
Topic: Synthetic Strategy, Stereochemistry
Section: 12.8
Difficulty Level: Hard
225) What is the major product of the following reaction?
a) 3-hexanol
b) 2-phenyl-2-pentanol
c) 2-ethylpentanoic acid
d) 2-methyl-3-pentanone
e) None of these choices.
Topic: Synthetic Strategy, Stereochemistry
Section: 12.8
Difficulty Level: Hard
226) What is the major product of the following reaction?
a) 2-methylbut-3-yn-2-ol
b) 3-propanone
c) 2-propanol
d) but-3-yn-2-ol
e) None of these choices.
Topic: Synthetic Strategy
Section: 12.4 and 12.8
Difficulty Level: Hard
227) What is the major product of the following reaction?
a) 2-methylbut-3-yn-2-ol
b) 3-propanone
c) 2-propanol
d) but-3-yn-2-ol
e) None of these choices.
Topic: Synthetic Strategy
Section: 12.4 and 12.8
Difficulty Level: Hard
228) The reaction of lithium di-iso-butylcuprate with isopentyl bromide yields:
a) 2,5-Dimethylheptane
b) 2,6-Dimethylheptane
c) 3,5-Dimethylheptane
d) 3,4-Dimethylheptane
e) 3,6-Dimethylheptane
Topic: Reactions and Reaction Sequences
Section: 12.6 and 12.8
Difficulty Level: Hard
229) The reaction of lithium dimethylcuprate with 1-bromo-4,4-dimethylhexane yields:
a) 3,3-Dimethylheptane
b) 3,3-Dimethyloctane
c) 1-Ethyl-4,4-dimethylhexane
d) Di-4,4-dimethylhexylcuprate
e) None of these choices.
Topic: Reactions and Reaction Sequences
Section: 12.6 and 12.8
Difficulty Level: Hard
230) The reaction of lithium diethylcuprate with 1-bromo-4,4-dimethylpentane yields:
a) 3,3-Dimethylheptane
b) 3,3-Dimethyloctane
c) 1-Ethyl-4,4-dimethylhexane
d) Di-4,4-dimethylhexylcuprate
e) None of these choices.
Topic: Reactions and Reaction Sequences
Section: 12.6 and 12.8
Difficulty Level: Hard
231) What is the major product of the following reaction?
a) 4-methylpentanol
b) 5-methylhexanol
c) 1-phenylethanol
d) pentanol
e) heptanol
Topic: Synthetic Strategy
Section: 12.3 and 12.7
Difficulty Level: Medium
232) What is the major product of the following reaction?
a) 4-methylpentanol
b) 5-methylhexanol
c) 1-phenylethanol
d) pentanol
e) heptanol
Topic: Synthetic Strategy
Section: 12.3 and 12.7
Difficulty Level: Medium
233) What is the major product of the following reaction?
a) 4-methylpentanol
b) 5-methylhexanol
c) 1-phenylethanol
d) pentanol
e) heptanol
Topic: Synthetic Strategy
Section: 12.3 and 12.7
Difficulty Level: Medium
234) What is the major product of the following reaction?
a) 4-methylpentanol
b) 5-methylhexanol
c) 1-phenylethanol
d) pentanol
e) heptanol
Topic: Synthetic Strategy
Section: 12.3 and 12.7
Difficulty Level: Medium
235) What is the major product of the following reaction?
a) 4-methylpentanol
b) 5-methylhexanol
c) 1-phenylethanol
d) pentanol
e) heptanol
Topic: Synthetic Strategy
Section: 12.3 and 12.7
Difficulty Level: Medium
236) What is the major product of the following reaction?
a) 2-phenyl-2-butanol
b) 2-phenyl-1-butanol
c) 1-phenyl-2-butanol
d) 1-phenyl-1-butanol
e) None of these choices.
Topic: Synthetic Strategy, Stereochemistry
Section: 12.8
Difficulty Level: Medium
237) What is the major product of the following reaction?
a) 2-phenyl-2-butanol
b) 2-phenyl-1-butanol
c) 1-phenyl-2-butanol
d) 1-phenyl-1-butanol
e) None of these choices.
Topic: Synthetic Strategy, Stereochemistry
Section: 12.8
Difficulty Level: Medium
238) What is the major product of the following reaction?
a) 2-phenyl-2-butanol
b) 2-phenyl-1-butanol
c) 1-phenyl-2-butanol
d) 1-phenyl-1-butanol
e) None of these choices.
Topic: Synthetic Strategy, Stereochemistry
Section: 12.8
Difficulty Level: Medium
239) What is the major product of the following reaction?
a) 2-phenyl-2-hexanol
b) 3-phenyl-3-hexanol
c) 4-phenyl-4-heptanol
d) 7-methyl-4-octanol
e) 5-methyl-3-propyl-2-heptanol
Topic: Synthetic Strategy, Stereochemistry
Section: 12.8
Difficulty Level: Medium
240) What is the major product of the following reaction?
a) 2-phenyl-2-hexanol
b) 3-phenyl-3-hexanol
c) 4-phenyl-4-heptanol
d) 7-methyl-4-octanol
e) 5-methyl-3-propyl-2-heptanol
Topic: Synthetic Strategy, Stereochemistry
Section: 12.8
Difficulty Level: Medium
241) What is the major product of the following reaction?
a) 2-phenyl-2-hexanol
b) 3-phenyl-3-hexanol
c) 4-phenyl-4-heptanol
d) 7-methyl-4-octanol
e) 5-methyl-3-propyl-2-heptanol
Topic: Synthetic Strategy, Stereochemistry
Section: 12.8
Difficulty Level: Medium
242) What is the major product of the following reaction?
a) 2-phenyl-2-hexanol
b) 3-phenyl-3-hexanol
c) 4-phenyl-4-heptanol
d) 7-methyl-4-octanol
e) 5-methyl-3-propyl-2-heptanol
Topic: Synthetic Strategy, Stereochemistry
Section: 12.8
Difficulty Level: Medium
243) What is the major product of the following reaction?
a) 2-phenyl-2-hexanol
b) 3-phenyl-3-hexanol
c) 4-phenyl-4-heptanol
d) 7-methyl-4-octanol
e) 5-methyl-3-propyl-2-heptanol
Topic: Synthetic Strategy, Stereochemistry
Section: 12.8
Difficulty Level: Medium