Chapter 19 Carbonyl Reactions & Enolates Complete Test Bank - Organic Chemistry 13e | Test Bank by Solomons by Graham Solomons. DOCX document preview.
Package Title: Solomons Test Bank
Course Title: Solomons 12e
Chapter Number: 19
Question type: Multiple Choice
1) The Claisen condensation produces which of these?
a) An -keto ester
b) A -keto ester
c) A -hydroxy ester
d) A -hydroxyaldehyde
e) A -diketone
Topic: General Information
Section: 19.2
Difficulty Level: Easy
2) Cyclization reactions, such as the Dieckmann condensation, are best carried out using fairly dilute solutions of the compound to be cyclized. Why is this so?
a) It then is possible to use less base.
b) The reagents generally are expensive.
c) A smaller amount of the compound to be cyclized can be used.
d) Intermolecular condensation is minimized at low concentration.
e) The concentration factor is unimportant.
Topic: General Information
Section: 19.2
Difficulty Level: Easy
3) Why is CH3ONa not used in the Claisen condensation of ethyl acetate?
a) CH3O– is a weaker base than the CH3CH2O– which is used.
b) CH3O–Na+ is more difficult to prepare than CH3CH2O–Na+.
c) CH3O– would abstract a proton from the ethyl group of the ester.
d) Use of CH3O–Na+ would result in transesterification.
e) CH3O–Na+ can be used as well as CH3CH2O–Na+.
Topic: General Information
Section: 19.2
Difficulty Level: Easy
4) Which of these combinations is not one which would result in the formation of essentially one Claisen condensation product when one compound is added slowly to the mixture of the other and the base employed?
a) HCO2Et + CH3CH2CO2Et
b) PhCO2Et + CH3CO2Et
c) (CO2Et)2 + PhCH2CO2Et
d) (CH3)3CCO2Et + CH3CO2Et
e) PhCH2CO2Et + CH3CO2Et
Topic: General Information
Section: 19.2
Difficulty Level: Medium
5) What would be the major product of the following reaction?
a) I
b) II
c) III
d) IV
e) V
Topic: Reaction Products
Section: 19.2
Difficulty Level: Easy
6) What product is formed during the following reaction?
a) I
b) II
c) III
d) IV
e) V
Topic: Reaction Products
Section: 19.2
Difficulty Level: Easy
7) The product(s) of the reaction of 2 mol of ethyl butanoate with sodium ethoxide is(are):
a) 
b)
c)
d)
e)
Topic: Reaction Products
Section: 19.2
Difficulty Level: Easy
8) The reaction of diethyl heptanedioate with sodium ethoxide would give as the product:
a) I
b) II
c) III
d) IV
e) V
Topic: Reaction Products
Section: 19.2
Difficulty Level: Medium
9) The reaction of diethyl hexanedioate with sodium ethoxide would give as the product:
a) I
b) II
c) III
d) IV
e) V
Topic: Reaction Products
Section: 19.2
Difficulty Level: Medium
10) What is the product of the Dieckmann condensation of this diester,
a) I
b) II
c) III
d) I and II
e) I, II, and III
Topic: Reaction Products
Section: 19.2
Difficulty Level: Medium
11) What is the product of the Dieckmann condensation of this diester,
a) I
b) II
c) III
d) IV
e) V
Topic: Reaction Products
Section: 19.2
Difficulty Level: Medium
12) What is the product of the Dieckmann condensation of this diester,
a) I
b) II
c) III
d) IV
e) V
Topic: Reaction Products
Section: 19.2
Difficulty Level: Medium
13) What is the product of the Dieckmann condensation of this diester,
a) I
b) II
c) III
d) IV
e) V
Topic: Reaction Products
Section: 19.2
Difficulty Level: Medium
14) What is the product of the Dieckmann condensation of this diester,
a) I
b) II
c) III
d) IV
e) V
Topic: Reaction Products
Section: 19.2
Difficulty Level: Medium
15) What is the product of the Dieckmann condensation of this diester,
a) I
b) II
c) III
d) IV
e) V
Topic: Reaction Products
Section: 19.2
Difficulty Level: Medium
16) What is the product of the Dieckmann condensation of this diester,
a) I
b) II
c) III
d) IV
e) V
Topic: Reaction Products
Section: 19.2
Difficulty Level: Medium
17) What is the product of the reaction sequence:
a) I
b) II
c) III
d) IV
e) V
Topic: Reaction Products
Section: 19.2
Difficulty Level: Medium
18) What is the product of the reaction sequence:
a) I
b) II
c) III
d) IV
e) V
Topic: Reaction Products
Section: 19.2
Difficulty Level: Medium
19) What is the product of the reaction sequence:
a) I
b) II
c) III
d) IV
e) V
Topic: Reaction Products
Section: 19.2
Difficulty Level: Medium
20) What is the product of the reaction sequence:
a) I
b) II
c) III
d) IV
e) V
Topic: Reaction Products
Section: 19.2
Difficulty Level: Medium
21) What is the product of the reaction:
a) I
b) II
c) III
d) IV
e) V
Topic: Reaction Products
Section: 19.5
Difficulty Level: Medium
22) What is the product of the reaction:
a) I
b) II
c) III
d) IV
e) V
Topic: Reaction Products
Section: 19.5
Difficulty Level: Medium
23) What is the product of the reaction sequence:
a) I
b) II
c) III
d) IV
e) V
Topic: Reaction Products
Section: 19.5
Difficulty Level: Medium
24) What is the product of the reaction sequence:
a) I
b) II
c) III
d) IV
e) V
Topic: Reaction Products
Section: 19.5
Difficulty Level: Medium
25) What is the product of the reaction sequence:
a) I
b) II
c) III
d) IV
e) V
Topic: Reaction Products
Section: 19.2
Difficulty Level: Medium
26) What is the product of the reaction sequence:
a) I
b) II
c) III
d) IV
e) V
Topic: Reaction Products
Section: 19.2
Difficulty Level: Medium
27) What is the product of the Dieckmann condensation of this diester,
a) I
b) II
c) III
d) IV
e) V
Topic: Reaction Products
Section: 19.2
Difficulty Level: Medium
28) What is the product of the Dieckmann condensation of this diester,
a) I
b) II
c) III
d) IV
e) V
Topic: Reaction Products
Section: 19.2
Difficulty Level: Medium
29) What is the product of the reaction sequence:
a) I
b) II
c) III
d) IV
e) V
Topic: Reaction Products
Section: 19.2
Difficulty Level: Medium
30) What is the product of the reaction sequence:
a) I
b) II
c) III
d) IV
e) V
Topic: Reaction Products
Section: 19.2
Difficulty Level: Medium
31) What is the product of the reaction sequence:
a) I
b) II
c) III
d) IV
e) V
Topic: Reaction Products
Section: 19.2
Difficulty Level: Medium
32) What is the product of the reaction sequence:
a) I
b) II
c) III
d) IV
e) V
Topic: Reaction Products
Section: 19.2
Difficulty Level: Medium
33) What product(s) is (are) likely to be obtained upon Dieckmann condensation of the following substance?
a) I and II
b) II and III
c) III and IV
d) I and III
e) II and IV
Topic: Reaction Products
Section: 19.2
Difficulty Level: Medium
34) What would be the product of the following sequence?
a) I
b) II
c) III
d) IV
e) V
Topic: Reaction Products
Section: 19.2
Difficulty Level: Medium
35) What is the expected product from the following reaction sequence? 
a) I
b) II
c) III
d) IV
e) V
Topic: Reaction Products
Section: 19.2
Difficulty Level: Medium
36) What would be the major product of the following reaction?
a) CH3CH2CH2OH + CH3CH2COO–
b) 
c) 
d) 
e) 
Topic: Reaction Product
Section: 19.4
Difficulty Level: Medium
37) The aldol reaction of cyclohexanone produces which of these self-condensation products?
a) I
b) II
c) III
d) IV
e) V
Topic: Reaction Product
Section: 19.4
Difficulty Level: Medium
38) The aldol reaction of cyclopentanone produces which of these self-condensation products?
a) I
b) II
c) III
d) IV
e) V
Topic: Reaction Product
Section: 19.4
Difficulty Level: Medium
39) The aldol reaction of cyclobutanone produces which of these self-condensation products?
a) I
b) II
c) III
d) IV
e) V
Topic: Reaction Product
Section: 19.4
Difficulty Level: Medium
40) The aldol reaction of cycloheptanone produces which of these self-condensation products
a) I
b) II
c) III
d) IV
e) V
Topic: Reaction Product
Section: 19.4
Difficulty Level: Medium
41) What is the product of the Dieckmann-like condensation of this ketoester,
a) I
b) II
c) III
d) IV
e) V
Topic: Reaction Products
Section: 19.2 and 19.4
Difficulty Level: Medium
42) What is the product of the Dieckmann-like condensation of this ketoester,
a) I
b) II
c) III
d) IV
e) V
Topic: Reaction Products
Section: 19.2 and 19.4
Difficulty Level: Medium
43) What is the product of the Dieckmann-like condensation of this ketoester,
a) I
b) II
c) III
d) IV
e) V
Topic: Reaction Products
Section: 19.2 and 19.4
Difficulty Level: Medium
44) Predict the product of the following reaction sequence:
a) I
b) II
c) III
d) IV
e) V
Topic: Reaction Products
Section: 19.2 and 19.4
Difficulty Level: Medium
45) What would be the major product of the following reaction?
a) I
b) II
c) III
d) IV
e) V
Topic: Reaction Product
Section: 19.5
Difficulty Level: Medium
46) What would be the major product of the following reaction?
a) I
b) II
c) III
d) IV
e) V
Topic: Reaction Product
Section: 19.5
Difficulty Level: Medium
47) What would be the major product of the following reaction?
a) I
b) II
c) III
d) IV
e) V
Topic: Reaction Product
Section: 19.5
Difficulty Level: Medium
48) What would be the major product of the following reaction?
a) I
b) II
c) III
d) IV
e) V
Topic: Reaction Product
Section: 19.5
Difficulty Level: Medium
49) What would be the major product of the following reaction?
a) I
b) II
c) III
d) IV
e) V
Topic: Reaction Product
Section: 19.5
Difficulty Level: Medium
50) What would be the major product of the following reaction?
a) I
b) II
c) III
d) IV
e) V
Topic: Reaction Product
Section: 19.5
Difficulty Level: Medium
51) What is the product of the Dieckmann-like condensation of this ketoester,
IV V
a) I
b) II
c) III
d) IV
e) V
Topic: Reaction Products
Section: 19.2 and 19.4
Difficulty Level: Medium
52) Predict the product of the following reaction sequence:
a) I
b) II
c) III
d) IV
e) V
Topic: Reaction Products
Section: 19.2 and 19.4
Difficulty Level: Medium
53) What would be the major product of the following reaction?
a) 
b) 
c) 
d) 
e) 
Topic: Reaction Product
Section: 19.5
Difficulty Level: Medium
54) What would be the major product of the following reaction?
a) I
b) II
c) III
d) IV
e) V
Topic: Reaction Product
Section: 19.5
Difficulty Level: Medium
55) The product of the following reaction is:
a) I
b) II
c) III
d) IV
e) V
Topic: Reaction Products
Section: 19.5
Difficulty Level: Medium
56) The product of the following reaction is:
a) I
b) II
c) III
d) IV
e) V
Topic: Reaction Products
Section: 19.5
Difficulty Level: Medium
57) What is the major product of the following reaction?
a) I
b) II
c) III
d) IV
e) V
Topic: Reaction Products
Section: 19.5
Difficulty Level: Medium
58) What product is formed during the following reaction?
a) I
b) II
c) III
d) IV
e) V
Topic: Reaction Products
Section: 19.6
Difficulty Level: Medium
59) When 
cyclizes in basic solution, which of these compounds will be formed?
a) I
b) II
c) III
d) IV
e) V
Topic: Reaction Product
Section: 19.6
Difficulty Level: Medium
60) What is the missing reagent?
a) 
b) 
c) 
d) 
e) 
Topic: Predict Reactants
Section: 19.6
Difficulty Level: Medium
61) What product results from the intramolecular aldol reaction of 2,5-hexanedione?
a) I
b) II
c) III
d) IV
e) V
Topic: Reaction Product
Section: 19.6
Difficulty Level: Medium
62) What would be the product of the following reaction?
a)
b) CH3CHCHCO2CN
c) CH3CHCHCN
d) 
e) 
Topic: Reaction Product
Section: 19.7
Difficulty Level: Medium
63) What would be the major product of the following reaction?
a) 
b) 
c) 
d) 
e) 
Topic: Reaction Product
Section: 19.7
Difficulty Level: Medium
64) Which of these is a product of the reaction of C6H5MgBr with
a) 
b) 
c) 
d) 
e) 
Topic: Predicting Reactants
Section: 19.7
Difficulty Level: Medium
65) What product(s) result from the Claisen condensation carried out with an equimolar mixture of ethyl acetate and ethyl propanoate?
a) I
b) II
c) III
d) IV
e) All of these choices.
Topic: Reaction Products
Section: 19.2
Difficulty Level: Hard
66) What is the expected product from the following reaction sequence?
a) I
b) II
c) III
d) IV
e) V
Topic: Reaction Products
Section: 19.2
Difficulty Level: Hard
67) What final product is obtained when 2,8-nonanedione is treated with base, followed by reaction with sodium borohydride?
a) I
b) II
c) III
d) IV
e) V
Topic: Reaction Product
Section: 19.6
Difficulty Level: Hard
68) What final product is obtained when 2,8-nonanedione is treated with base, followed by reaction with lithium aluminum hydride?
a) I
b) II
c) III
d) IV
e) V
Topic: Reaction Product
Section: 19.6
Difficulty Level: Hard
69) Predict the major product from the following reaction:
a) I
b) II
c) III
d) IV
e) V
Topic: Reaction Product
Section: 19.6
Difficulty Level: Hard
70) What would be the product of the following reaction?
a) I
b) II
c) III
d) IV
e) V
Topic: Reaction Product
Section: 19.5 and 19.6
Difficulty Level: Hard
71) What would be the product of the following reaction sequence?
a) I
b) II
c) III
d) IV
e) V
Topic: Reaction Product
Section: 19.5 and 19.6
Difficulty Level: Hard
72) What would be the product of the following reaction?
a) I
b) II
c) III
d) IV
e) V
Topic: Reaction Product
Section: 19.5 and 19.6
Difficulty Level: Hard
73) What would be the product of the following reaction sequence?
a) I
b) II
c) III
d) IV
e) V
Topic: Reaction Product
Section: 19.5 and 19.6
Difficulty Level: Hard
74) Predict the major product of the following reaction:
a) I
b) II
c) III
d) IV
e V
Topic: Reaction Product
Section: 19.5
Difficulty Level: Hard
75) In the Claisen-Schmidt condensation of 1 mole of acetone with 2 moles of 4-methylbenzaldehyde how many products are possible?
a) 1
b) 2
c) 3
d) 4
e) 5
Topic: Reaction Product
Section: 19.5
Difficulty Level: Hard
76) In the Claisen-Schmidt condensation of 1 mole of acetone with 2 moles of 4-methylbenzaldehyde what is the relationship between the products formed?
a) enantiomers
b) conformational isomers
c) constitutional isomers
d) diastereomers
e) unrelated
Topic: Reaction Product
Section: 19.5
Difficulty Level: Hard
77) What would be the product of the following reaction?
a) C6H5CHCHCH2CN
b) 
c) 
d) 
e) 
Topic: Reaction Product
Section: 19.5
Difficulty Level: Hard
78) What would be the product of the following reaction?
a) I
b) II
c) III
d) IV
e) V
Topic: Reaction Product
Section: 19.5
Difficulty Level: Hard
79) What would be the product of the following reaction?
a) I
b) II
c) III
d) IV
e) V
Topic: Reaction Product
Section: 19.5
Difficulty Level: Hard
80) What would be the product of the following reaction?
a) I
b) II
c) III
d) IV
e) V
Topic: Reaction Product
Section: 19.5
Difficulty Level: Hard
81) Predict the product of the following reaction sequence.
a) I
b) II
c) III
d) IV
e) V
Topic: Reaction Products
Section: 19.7
Difficulty Level: Hard
82) Consider the synthesis below: What is compound X?
a) O=C(OEt)2
b) HCO2Et
c) EtO-CO-CO-OEt
d) CH3CO2Et
e) BrCH2CO2Et
Topic: Synthesis Products and Reactants
Section: 19.2
Difficulty Level: Medium
83) What would be the product of the following sequence?
a) I
b) II
c) III
d) IV
e) V
Topic: Reaction Sequence
Section: 19.2
Difficulty Level: Medium
84) What would be the product of the following sequence?
a) I
b) II
c) III
d) IV
e) V
Topic: Reaction Sequence
Section: 19.2
Difficulty Level: Medium
85) What would be the product of the following sequence?
a) I
b) II
c) III
d) IV
e) V
Topic: Reaction Sequence
Section: 19.2
Difficulty Level: Medium
86) What would be the product of the following sequence?
a) I
b) II
c) III
d) IV
e) V
Topic: Reaction Sequence
Section: 19.2
Difficulty Level: Medium
87) What would be the product of the following sequence?
a) I
b) II
c) III
d) IV
e) V
Topic: Reaction Sequence
Section: 19.2
Difficulty Level: Medium
88) What is the expected product from the following reaction sequence? 
a) I
b) II
c) III
d) IV
e) V
Topic: Reaction Sequence
Section: 19.2
Difficulty Level: Medium
89) What is the expected product from the following reaction sequence? 
a) I
b) II
c) III
d) IV
e) V
Topic: Reaction Sequence
Section: 19.2
Difficulty Level: Medium
90) Predict the product from the following sequence:
a) I
b) II
c) III
d) IV
e) V
Topic: Reaction Sequence
Section: 19.4
Difficulty Level: Medium
91) What would be the major product of the following reaction?
a) 
b) 
c) 
d) 
e) 
Topic: Reaction Sequence:
Section: 19.5
Difficulty Level: Medium
92) The product, C, of the following sequence of reactions,
would be:
a) 
b) 
c) 
d) 
e) 
Topic: Reaction Sequence
Section: 19.5
Difficulty Level: Medium
93) Predict the product from the following sequence:
a) I
b) II
c) III
d) IV
e) V
Topic: Reaction Sequence
Section: 19.5
Difficulty Level: Medium
94) Predict the product from the following sequence:
a) I
b) II
c) III
d) IV
e) V
Topic: Reaction Sequence
Section: 19.5
Difficulty Level: Medium
95) Predict the product from the following sequence:
a) I
b) II
c) III
d) IV
e) V
Topic: Reaction Sequence
Section: 19.5
Difficulty Level: Medium
96) Predict the product from the following sequence:
a) I
b) II
c) III
d) IV
e) V
Topic: Reaction Sequence
Section: 19.5
Difficulty Level: Medium
97) What would be the major product of the following reaction?
a) I
b) II
c) III
d) IV
e) V
Topic: Reaction Sequence
Section: 19.5
Difficulty Level: Medium
98) What would be the major product of the following reaction?
a) I
b) II
c) III
d) IV
e) V
Topic: Reaction Sequence
Section: 19.5
Difficulty Level: Medium
99) What would be the major product of the following reaction?
a) I
b) II
c) III
d) IV
e) V
Topic: Reaction Sequence
Section: 19.5
Difficulty Level: Medium
100) What would be the major product, B, of the following reaction sequence?
a) I
b) II
c) III
d) IV
e) V
Topic: Reaction Sequence
Section: 19.5
Difficulty Level: Medium
101) What would be the major product, B, of the following reaction sequence?
a) I
b) II
c) III
d) IV
e) V
Topic: Reaction Sequence
Section: 19.5
Difficulty Level: Medium
102) What is the expected product from the following reaction sequence? 
a) I
b) II
c) III
d) IV
e) V
Topic: Reaction Sequence
Section: 19.2
Difficulty Level: Medium
103) What would be the final product of the following reaction sequence?
a) C6H5CH2CH2CH2CH3
b) 
c) 
d) 
e) 
Topic: Reaction Sequence
Section: 19.5
Difficulty Level: Medium
104) What would be the product, C, of the following reaction sequence?
a) (CH3)3CCH2CH2CH2OH
b) 
c) 
d) 
e) 
Topic: Reaction Sequence
Section: 19.5
Difficulty Level: Medium
105) What would be the product, C, of the following reaction sequence?
a) (CH3)3CCH2CH2CH2OH
b) 
c) 
d) 
e) 
Topic: Reaction Sequence
Section: 19.5
Difficulty Level: Medium
106) What would be the product of the following reaction sequence?
a) I
b) II
c) III
d) IV
e) V
Topic: Reaction Sequence
Section: 19.5
Difficulty Level: Hard
107) What would be the product of the following reaction sequence?
a) I
b) II
c) III
d) IV
e) V
Topic: Reaction Sequence
Section: 19.5
Difficulty Level: Hard
108) What would be the product, B, of the following reaction sequence?
a) C6H5CHCHCO2H
b) 
c) C6H5CH2CH2CO2H
d) 
e) 
Topic: Reaction Sequence
Section: 19.5
Difficulty Level: Hard
109) What would be the product, C, of the following reaction sequence?
a) 
b) 
c) 
d) 
e) 
hi
Topic: Reaction Sequence
Section: 19.5
Difficulty Level: Hard
110) What would be the product, C, of the following reaction sequence?
a) 
b) 
c) 
d) 
e) 
Topic: Reaction Sequence
Section: 19.5
Difficulty Level: Hard
111) Which of the following statements is true about the anion formed from the reaction of diethyl malonate with sodium ethoxide?
a) It can react with an ,-unsaturated ester by conjugate addition.
b) It can condense with aldehydes and ketones.
c) It can be alkylated with an alkyl halide.
d) It is resonance stabilized.
e) All of these statements are true.
Topic: Synthesis
Section: 18.1, 18.7, 19.2, 19.4 and 19.7
Difficulty Level: Easy
112) Which compound could be prepared via Dieckmann condensation?
a) I
b) II
c) III
d) IV
e) V
Topic: Synthesis
Section: 19.2
Difficulty Level: Medium
113) Which of the following would afford the best synthesis of diethyl phenylmalonate, 
a)
b)
c) 
e)
Topic: Synthesis
Section: 19.2
Difficulty Level: Medium
114) Which reagents would you use to prepare the following substance from ethyl acetoacetate?
a) i) NaH/DMSO; ii) PhCOCl; iii) OH–/H2O, heat; iv) H3O+; v) heat
b) i) NaOEt/EtOH; ii) PhCOCH2Br; iii) OH–/H2O, heat; iv) H3O+; v) heat
c) i) heat; ii) NaOEt/EtOH; iii) PhCOCH2Br
d) i) NaOEt/EtOH; ii) PhCl
e) i) NaOEt/EtOH; ii) PhCOCl; iii) OH–/H2O, heat; iv) H3O+; v) heat
Topic: Synthesis
Section: 19.2
Difficulty Level: Medium
115) 2-Methylcyclohexane-1,3-dione can be synthesized from:
a) I
b) II
c) III
d) IV
e) V
Topic: Synthesis
Section: 19.2 and 19.4
Difficulty Level: Medium
116) 2-Phenylcyclohexane-1,3-dione can be synthesized from:
a) I
b) II
c) III
d) IV
e) V
Topic: Synthesis
Section: 19.2 and 19.4
Difficulty Level: Medium
117) Which of the following might be used to synthesize the following substance?
a)
b)
c)
d) Two of these choices.
e) All of these choices.
Topic: Synthesis
Section: 19.2
Difficulty Level: Hard
118) Which compound could be prepared using a Michael reaction?
a) I
b) II
c) III
d) IV
e) V
Topic: Synthesis
Section: 19.7
Difficulty Level: Hard
119) Which compound may be prepared using a Mannich reaction?
a) I
b) II
c) III
d) IV
e) V
Topic: Synthesis
Section: 19.8
Difficulty Level: Hard
120) Which compound may be prepared using a Mannich reaction?
a) I
b) II
c) III
d) IV
e) V
Topic: Synthesis
Section: 19.8
Difficulty Level: Hard
121) Which reagents would be used in a Mannich reaction to synthesize
a) I
b) II
c) III
d) IV
e) V
Topic: Synthesis
Section: 19.8
Difficulty Level: Hard
122) Which reagents would be used in a Mannich reaction to synthesize
a) I
b) II
c) III
d) IV
e) V
Topic: Synthesis
Section: 19.8
Difficulty Level: Hard
123) Which is the only one of these compounds which cannot self-condense in the presence of dilute aqueous alkali?
a) Phenylethanal
b) Propanal
c) 2-Methylpropanal
d) 3-Methylpentanal
e) 2,2-Dimethylpropanal
Topic: Aldol Reaction
Section: 19.4
Difficulty Level: Medium
124) Which of these compounds cannot self-condense in the presence of dilute aqueous alkali?
a) 3-(4-Nitrophenyl)propanal
b) 2-Methyl-3-pentanone
c) 2-(4-Nitrophenyl)propanal
d) 3-(4-Nitrophenyl)-2-butanone
e) All of these compounds can self-condense.
Topic: Aldol Reaction
Section: 19.4
Difficulty Level: Medium
125) Which of these is not among the reaction products when a crossed aldol addition occurs between ethanal and butanal?
a) 
b) 
c) 
d) 
e) 
Topic: Aldol Reaction
Section: 19.5
Difficulty Level: Medium
126) The aldol condensation product formed from 3-pentanone in the presence of base has the IUPAC name:
a) 5-Ethyl-4-methyl-4-hepten-3-one
b) 5-Ethyl-4-methyl-5-hepten-3-one
c) 4-Methyl-4-nonen-3,7-dione
d) 3-Ethyl-4-methyl-3-hepten-5-one
e) 3-Ethyl-4-methyl-2-hepten-5-one
Topic: Aldol Reaction
Section: 19.4
Difficulty Level: Hard
127) What compound results from the aldol cyclization of
a) I
b) II
c) III
d) IV
e) Both III and IV
Topic: Aldol Reaction
Section: 19.6
Difficulty Level: Medium
128) The aldol cyclization of 
produces which of these?
a) I
b) II
c) III
d) IV
e) V
Topic: Aldol Reaction
Section: 19.6
Difficulty Level: Medium
129) The reaction of 
with base affords which of these products?
a) I
b) II
c) III
d) IV
e) V
Topic: Aldol Reaction
Section: 19.6
Difficulty Level: Medium
130) If butanal is added slowly to an aqueous solution of sodium hydroxide and 2,2-dimethylpropanal at 25 C, the principal product is which of these?
a) 
b) 
c) 
d) 
e) 
Topic: Aldol Reaction
Section: 19.5
Difficulty Level: Hard
131) Which of these is not a reversible process?
a) Base-promoted ester hydrolysis
b) Acid-catalyzed ester hydrolysis
c) Aldol addition
d) Claisen condensation
e) Acetal formation
Topic: General Reactions of Carbonyl Compounds
Sections: 19.2 and 19.4
Difficulty Level: Medium
132) Which reagents would you use to synthesize this compound by an aldol condensation?
a) 
b) 
c) 
d) 
e) 
Topic: Predicting Reactants
Section: 19.5
Difficulty Level: Medium
133) Which reagents would you use to synthesize this compound by an aldol condensation?
a) 
b) 
c) 
d) 
e) 
Topic: Predicting Reactants
Section: 19.5
Difficulty Level: Medium
134) What starting compound(s) would you use in an aldol reaction to prepare
a) I
b) II
c) III
d) IV
e) V
Topic: Predicting Reactants
Section: 19.6
Difficulty Level: Medium
135) What starting compound(s) would you use in an aldol reaction to prepare as the major product:
a) I
b) II
c) III
d) IV
e) V
Topic: Predicting Reactants
Section: 19.6
Difficulty Level: Medium
136) What starting compound(s) would you use in an aldol reaction to prepare as the major product:
a) I
b) II
c) III
d) IV
e) V
Topic: Predicting Reactants
Section: 19.6
Difficulty Level: Medium
137) What starting compound(s) would you use in an aldol reaction to prepare as the major product:
a) I
b) II
c) III
d) IV
e) V
Topic: Predicting Reactants
Section: 19.6
Difficulty Level: Medium
138) What starting compound(s) would you use in an aldol reaction to prepare as the major product:
a) I
b) II
c) III
d) IV
e) V
Topic: Predicting Reactants
Section: 19.6
Difficulty Level: Medium
139) What starting compound(s) would you use in an aldol reaction to prepare as the major product:
a) I
b) II
c) III
d) IV
e) V
Topic: Predicting Reactants
Section: 19.6
Difficulty Level: Medium
140) What starting compound(s) would you use in an aldol reaction to prepare as the major product:
a) I
b) II
c) III
d) IV
e) V
Topic: Predicting Reactants
Section: 19.6
Difficulty Level: Medium
141) What starting compound(s) would you use in an aldol reaction to prepare as the major product:
a) I
b) II
c) III
d) IV
e) V
Topic: Predicting Reactants
Section: 19.6
Difficulty Level: Medium
142) What starting compound(s) would you use in an aldol reaction to prepare as the major product:
a) I
b) II
c) III
d) IV
e) V
Topic: Predicting Reactants
Section: 19.6
Difficulty Level: Medium
143) The Robinson annulation reaction which produces
uses which of the following as starting materials?
a) I
b) II
c) III
d) IV
e) V
Topic: Predicting Reactants
Section: 19.7
Difficulty Level: Hard
144) Which of these compounds can react with 4-methylhexanal to afford good yields of the crossed aldol product?
a) 3-(4-Nitrophenyl)propanal
b) 2-Methyl-3-pentanone
c) 2-(4-Nitrophenyl)propanal
d) 3-(4-Nitrophenyl)-2-butanone
e) None of the above compounds will give good yields of the crossed aldol product with 4-methylhexanal.
Topic: Crossed Aldol Reaction
Section: 19.5
Difficulty Level: Medium
145) Which of these compounds can react with 4-methylpentanal to afford good yields of the crossed aldol product?
a) 3-(4-Nitrophenyl)propanal
b) 2-Ethyl-2-methylheptanal
c) 2-(4-Nitrophenyl)propanal
d) 3-(4-Nitrophenyl)-2-butanone
e) None of the above compounds will give good yields of the crossed aldol product with 4-methylhexanal.
Topic: Crossed Aldol Reaction
Section: 19.5
Difficulty Level: Medium
146) Consider the synthesis above in answering this question. What is compound A?
a) Butanone
b) Butanal
c) Propanal
d) 1-Butanol
e) 2-Methylpropanal
Topic: Reagents, Intermediates, and Spectroscopy
Section: 19.5
Difficulty Level: Medium
147) What is the intermediate B in the synthesis shown above?
a) I
b) II
c) III
d) IV
e) V
Topic: Reagents, Intermediates, and Spectroscopy
Section: 19.5
Difficulty Level: Medium
Question type: fill-in-the-blank
148) When planning a reaction with an ester and an alkoxide ion, it is important to use an alkoxide that has the same alkyl group as the ester in order to avoid ___.
Topic: General Information
Section: 19.2
Difficulty Level: Easy
149) An aldol reaction that starts with two different carbonyl compounds is called a ___.
Topic: General
Section: 19.5
Difficulty Level: Easy
Question type: Essay
150) When ,-unsaturated aldehydes and ketones react with nucleophiles, they do so in one of two ways. What are the two ways?
Topic: General
Section: 19.7
Difficulty Level: Easy
Question type: fill-in-the-blank
151) When ,-unsaturated aldehydes and ketones react with nucleophiles, simple addition is favored when ___ nucleophiles are used, while conjugate addition is preferred by ___ nucleophiles.
Topic: General
Section: 19.7
Difficulty Level: Easy
152) The sequence of a Michael addition followed by an intramolecular aldol condensation is known as a ___.
Topic: General
Section: 19.7
Difficulty Level: Medium
153) Esters frequently react in the presence of alkoxides by a reaction called the ___ condensation.
Topic: Claisen condensation
Section: 19.2
Difficulty Level: Easy
Question type: Essay
154) Explain why ethyl 2-methylpropanoate does not undergo the usual Claisen condensation.
Topic: Claisen Condensation
Section: 19.2
Difficulty Level: Medium
155) Suggest a reasonable synthetic strategy to carry out the following transformation.
Topic: Synthetic Strategy
Section: 19.2
Difficulty Level: Medium
156) Suggest a reasonable synthetic strategy to carry out the following transformation.
Topic: Synthetic Strategy
Section: 19.2
Difficulty Level: Medium
157) An intramolecular Claisen condensation is known as a ___.
Topic: Dieckmann Condensation
Section: 19.2
Difficulty Level: Easy
158) Explain why diethyl pentanedioate does not undergo a Dieckmann condensation.
Topic: Dieckmann Condensation
Section: 19.2
Difficulty Level: Medium
159) Predict what is likely to happen when ethyl 6-oxooctanoate is treated with NaOEt, followed by acid work-up.
Topic: Dieckmann Condensation
Section: 19.2
Difficulty Level: Hard
160) What is the final product of the following reaction sequence? Give structural details of all significant intermediates.
Topic: Multistep Reaction Sequence
Section: 19.2
Difficulty Level: Medium
161) What is the final product of the following reaction sequence? Give structural details of all significant intermediates.
Topic: Multistep Reaction Sequence
Section: 19.2
Difficulty Level: Hard
162) What is the final product of the following reaction sequence? Give structural details of all significant intermediates.
Topic: Multistep Reaction Sequence
Section: 19.2
Difficulty Level: Hard
163) What is the final product of the following reaction sequence? Give structural details of all significant intermediates.
Topic: Multistep Reaction Sequence
Section: 19.2
Difficulty Level: Hard
164) What is the final product of the following reaction sequence? Give structural details of all significant intermediates.
Topic: Multistep Reaction Sequence
Section: 18.6 and 19.2
Difficulty Level: Hard
165) What is the final product of the following reaction sequence? Give structural details of all significant intermediates.
Topic: Multistep Reaction Sequence
Section: 8.17 and 19.6
Difficulty Level: Hard
166) What is the final product of the following reaction sequence? Give structural details of all significant intermediates.
Topic: Multistep Reaction Sequence
Section: 8.17 and 19.6
Difficulty Level: Hard
167) What is the product of the following reaction sequence? Give structural details of all significant intermediates.
Topic: Multistep Reaction Sequence
Section: 13.11 and 19.6
Difficulty Level: Hard
168) What is the product of the following reaction sequence? Give structural details of all significant intermediates.
Topic: Multistep Reaction Sequence
Section: 13.11 and 19.6
Difficulty Level: Hard
169) What is the product of the following reaction sequence? Give structural details of all significant intermediates.
Topic: Multistep Reaction Sequence
Section: 13.11 and 19.6
Difficulty Level: Hard
170) What is the final product of the following reaction sequence? Give structural details of all significant intermediates.
Topic: Multistep Reaction Sequence
Section: 19.7
Difficulty Level: Hard
171) Suggest a reasonable synthetic strategy to carry out the following transformation.
Topic: Reaction Sequence and Predicting Reagents
Section: 19.5
Difficulty Level: Medium
172) When acetaldehyde is reacted with 3 equivalents of formaldehyde under alkaline conditions, followed by treatment with sodium borohydride, the product formed shows the following spectra data:
IR: broad peak at 3326 cm−1
1H NMR: singlet at 3.45 δ
singlet at 4.78 δ (found to be exchangeable)
Predict a reasonable structure for this product.
Topic: Reaction Products and Spectroscopy
Section: 19.5
Difficulty Level: Hard
173) What is the final product of the following reaction sequence? Give structural details of all significant intermediates.
Topic: Reaction Sequence
Section: 19.5
Difficulty Level: Hard
174) What is the final product of the following reaction sequence? Give structural details of all significant intermediates.
Topic: Reaction Sequence
Section: 19.6 and 19.7
Difficulty Level: Hard
175) What is the final product of the following reaction sequence? Give structural details of all significant intermediates.
Topic: Multistep Reaction Sequence
Section: 19.2, 19.4, 19.6 and 19.7
Difficulty Level: Hard
176) In the Claisen-Schmidt condensation of 1 mole of acetone with 2 moles of 4-methylbenzaldehyde draw the possible products that form.
Topic: Reaction Sequence
Section: 19.5
Difficulty Level: Hard
177) What is the product of the following reaction?
Topic: Reaction Products
Section: 19.6
Difficulty Level: Medium
178) There are several possible cyclization products that might be formed when 5-methyl-6-oxoheptanal undergoes intramolecular aldol condensation in presence of ethoxide. Draw the structures of all these possible products. Comment on which of these is likely to be the major product, clearly explaining your rationale.
Topic: Reaction Products
Section: 19.6
Difficulty Level: Hard
179) Predict the major product from the following reaction:
Topic: Reaction Product
Section: 19.6
Difficulty Level: Hard
180) In the aldol cyclization reaction of the following compound, predict the major product formed and explain your choice.
Of the two possible products formed, shown below as 1 and 2, 2 is the major product expected since condensation occurs with the more reactive aldehyde carbon acting as the electrophile.
Topic: Reaction Product
Section: 19.6
Difficulty Level: Hard
181) What is the product of the following reaction?
Topic: Reaction Products
Section: 19.7
Difficulty Level: Hard
182) Suggest a reasonable mechanism for the following reaction.
Topic: Reaction Mechanisms
Section: 19.7
Difficulty Level: Hard
183) What final product is obtained when 5-methyl-7-oxooctanal is treated with base, followed by reaction with sodium borohydride?
a) I
b) II
c) III
d) IV
e) V
Topic: Reaction Product
Section: 19.6
Difficulty Level: Hard
184) What final product is obtained when 5-methyl-7-oxooctanal is treated with base, followed by reaction with lithium aluminum hydride?
a) I
b) II
c) III
d) IV
e) V
Topic: Reaction Product
Section: 19.6
Difficulty Level: Hard
185) What would be the product, B, of the following reaction sequence?
a) (CH3)3CCH2CH2CH2OH
b)
c)
d)
e)
Topic: Reaction Sequence
Section: 19.5
Difficulty Level: Medium
186) What would be the product, A, of the following reaction sequence?
a) C6H5CHCHCO2H
b)
c) C6H5CH2CH2CO2H
d)
e)
Topic: Reaction Sequence
Section: 19.5
Difficulty Level: Hard
187) What would be the product, A, of the following reaction sequence?
a)
b)
c)
d)
e) hi
Topic: Reaction Sequence
Section: 19.5
Difficulty Level: Hard
188) What would be the product, B, of the following reaction sequence?
a)
b)
c)
d)
e) hi
Topic: Reaction Sequence
Section: 19.5
Difficulty Level: Hard
189) What would be the product, B, of the following reaction sequence?
a)
b)
c)
d)
e)
Topic: Reaction Sequence
Section: 19.5
Difficulty Level: Hard
190) Starting from ethyl acetoacetate, what is the product of the following reaction sequence?
i) NaH/DMSO; ii) PhCOCl; iii) OH–/H2O, heat; iv) H3O+; v) heat
a) 1-phenyl-1,3-butadione
b) 1-phenyl-1,4-pentadione
c) 1-phenyl-1,3-pentadione
d) 1-phenyl-1,4-hexadione
e) None of these choices
i) NaH/DMSO; ii) PhCOCl; iii) OH–/H2O, heat; iv) H3O+; v) heat
b) i) NaOEt/EtOH; ii) PhCOCH2Br; iii) OH–/H2O, heat; iv) H3O+; v) heat
c) i) heat; ii) NaOEt/EtOH; iii) PhCOCH2Br
d) i) NaOEt/EtOH; ii) PhCl
e) i) NaOEt/EtOH; ii) PhCOCl; iii) OH–/H2O, heat; iv) H3O+; v) heat
Topic: Synthesis
Section: 19.2
Difficulty Level: Medium
191) Starting from ethyl acetoacetate, what is the product of the following reaction sequence?
i) NaOEt/EtOH; ii) PhCOCH2Br; iii) OH–/H2O, heat; iv) H3O+; v) heat
a) 1-phenyl-1,3-butadione
b) 1-phenyl-1,4-pentadione
c) 1-phenyl-1,3-pentadione
d) 1-phenyl-1,4-hexadione
e) None of these choices
c) i) heat; ii) NaOEt/EtOH; iii) PhCOCH2Br
d) i) NaOEt/EtOH; ii) PhCl
e) i) NaOEt/EtOH; ii) PhCOCl; iii) OH–/H2O, heat; iv) H3O+; v) heat
Topic: Synthesis
Section: 19.2
Difficulty Level: Medium