Organic Chemistry - Standalone book
10th Edition
ISBN: 9780073511214
Author: Francis A Carey Dr., Robert M. Giuliano
Publisher: McGraw-Hill Education
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Chapter 20.12, Problem 21P
Interpretation Introduction
Interpretation:
The reason for the statement that an amide cannot be prepared by acid-catalyzed condensation of
Concept introduction:
The replacement or substitution of one
In a nucleophilic substitution reaction, nucleophile takes the position of leaving the group by attacking the electron-deficient carbon atom.
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MeO
22.55 One potential synthesis of the anti-inflammatory and analgesic drug nabumetone
is chloromethylation (Problem 22.48) of 2-methoxynaphthalene followed by an
acetoacetic ester synthesis (Section 19.6).
5
3
6
CH₂O
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acetoacetic
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HC
7
MeO
MeO
1
8
2-Methoxynaphthalene
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(b) Show steps in the acetoacetic ester synthesis by which the synthesis of nabum-
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22.47 Tertiary amines with three different alkyl groups are chiral but cannot be resolved because pyramidal
inversion causes racemization at room temperature. Nevertheless, chiral aziridines can be resolved and stored
at room temperature. Aziridine is a three-membered heterocycle containing a nitrogen atom. The following is
an example of a chiral aziridine. In this compound, the nitrogen atom is a chiral center. Suggest a reason why
chiral aziridines do not undergo racemization at room temperature.
17. Rank the acid derivatives with respect to their reactivity with water.
acid halide > ester > acid anhydride > amide
acid anhydride > amide > acid halide > ester
amide > ester > acid anhydride > acid halide
acid halide > acid anhydride > ester > amide
A)
B)
C)
D)
18. Disregarding
A) 3
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B) 1
C) 4
D) O
E) 2
Chapter 20 Solutions
Organic Chemistry - Standalone book
Ch. 20.1 - Prob. 1PCh. 20.2 - Prob. 2PCh. 20.3 - Prob. 3PCh. 20.4 - Prob. 4PCh. 20.5 - Prob. 5PCh. 20.8 - Prob. 6PCh. 20.8 - Prob. 7PCh. 20.8 - Prob. 8PCh. 20.9 - Prob. 9PCh. 20.9 - Prob. 10P
Ch. 20.9 - Prob. 11PCh. 20.9 - Prob. 12PCh. 20.10 - Prob. 13PCh. 20.10 - Prob. 14PCh. 20.11 - Prob. 15PCh. 20.11 - Prob. 16PCh. 20.11 - Prob. 17PCh. 20.12 - Prob. 18PCh. 20.12 - Prob. 19PCh. 20.12 - Prob. 20PCh. 20.12 - Prob. 21PCh. 20.13 - Prob. 22PCh. 20.13 - Prob. 23PCh. 20.14 - Prob. 24PCh. 20.15 - Prob. 25PCh. 20.16 - Prob. 26PCh. 20.17 - Prob. 27PCh. 20 - Prob. 28PCh. 20 - Prob. 29PCh. 20 - Prob. 30PCh. 20 - Write a structural formula for the principal...Ch. 20 - Prob. 32PCh. 20 - Prob. 33PCh. 20 - Prob. 34PCh. 20 - Prob. 35PCh. 20 - Prob. 36PCh. 20 - Prob. 37PCh. 20 - Prob. 38PCh. 20 - Prob. 39PCh. 20 - Prob. 40PCh. 20 - Prob. 41PCh. 20 - Prob. 42PCh. 20 - The preparation of the sex pheromone of the...Ch. 20 - Prob. 44PCh. 20 - Suggest a reasonable explanation for each of the...Ch. 20 - Prob. 46PCh. 20 - Prob. 47PCh. 20 - Prob. 48PCh. 20 - Prob. 49PCh. 20 - A compound has a molecular formula of C8H14O4, and...Ch. 20 - Prob. 51PCh. 20 - Prob. 52DSPCh. 20 - Prob. 53DSPCh. 20 - Prob. 54DSPCh. 20 - Prob. 55DSPCh. 20 - Prob. 56DSPCh. 20 - Thioesters Thioesters have the general formula ....Ch. 20 - Prob. 58DSP
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