ORGANIC CHEMISTRY-PACKAGE >CUSTOM<
10th Edition
ISBN: 9781260028355
Author: Carey
Publisher: MCG CUSTOM
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Chapter 22.10, Problem 13P
Interpretation Introduction
Interpretation:
The way in which each of the given compounds can be prepared from benzaldehyde by reductive amination is to be explained.
Concept Introduction:
Aldehyde compounds can be reduced to
The conversion of
The first step is the formation of imines using aldehydes or ketones and amines.
The second step involves the reduction of imine to form amines.
The best reagent for this reaction is sodiumborohydride.
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Maraviroc, a drug used to treat HIV, is prepared by reductive amination of aldehyde A with amine B. What is the structure of maraviroc, if the most basic N atom of amine B is used in reductive amination?
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
CI
acetoacetic
ester
synthesis
HC
7
MeO
MeO
1
8
2-Methoxynaphthalene
Nabumetone
(a) Account for the regioselectivity of chloromethylation at carbon 6 rather than at
carbon 5 or 7.
(b) Show steps in the acetoacetic ester synthesis by which the synthesis of nabum-
etone is completed.
Chapter 22 Solutions
ORGANIC CHEMISTRY-PACKAGE >CUSTOM<
Ch. 22.1 - Prob. 1PCh. 22.1 - Prob. 2PCh. 22.1 - Prob. 3PCh. 22.2 - Prob. 4PCh. 22.4 - Prob. 5PCh. 22.4 - Prob. 6PCh. 22.4 - Prob. 7PCh. 22.4 - Prob. 8PCh. 22.4 - Prob. 9PCh. 22.7 - Prob. 10P
Ch. 22.8 - Problem 22.11 Three of the following amines can be...Ch. 22.9 - Prob. 12PCh. 22.10 - Prob. 13PCh. 22.13 - Prob. 14PCh. 22.14 - Prob. 15PCh. 22.15 - Prob. 16PCh. 22.15 - Prob. 17PCh. 22.17 - Prob. 18PCh. 22.17 - Prob. 19PCh. 22.17 - Prob. 20PCh. 22.17 - Prob. 21PCh. 22.18 - Prob. 22PCh. 22 - Prob. 23PCh. 22 - Prob. 24PCh. 22 - Prob. 25PCh. 22 - Prob. 26PCh. 22 - Prob. 27PCh. 22 - Arrange the following compounds or anions in each...Ch. 22 - Prob. 29PCh. 22 - Prob. 30PCh. 22 - The compound shown is a somewhat stronger base...Ch. 22 - Prob. 32PCh. 22 - Prob. 33PCh. 22 - Prob. 34PCh. 22 - Prob. 35PCh. 22 - Prob. 36PCh. 22 - Write the structure of the product formed on...Ch. 22 - Prob. 38PCh. 22 - Prob. 39PCh. 22 - Prob. 40PCh. 22 - Prob. 41PCh. 22 - Prob. 42PCh. 22 - Prob. 43PCh. 22 - Prob. 44PCh. 22 - Devise efficient syntheses of each of the...Ch. 22 - Prob. 46PCh. 22 - Prob. 47PCh. 22 - Prob. 48PCh. 22 - Prob. 49PCh. 22 - Prob. 50PCh. 22 - Prob. 51PCh. 22 - Prob. 52PCh. 22 - Prob. 53PCh. 22 - Prob. 54PCh. 22 - Prob. 55PCh. 22 - Prob. 56DSPCh. 22 - Prob. 57DSPCh. 22 - Prob. 58DSPCh. 22 - Prob. 59DSPCh. 22 - Synthetic Applications of Enamines The formation...Ch. 22 - Prob. 61DSP
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- Arrange the members of each group in order of decreasing basicity: (a) Ammonia, aniline, methylamine (b) Acetanilide, aniline, N-methylaniline (c) 2,4-Dichloroaniline, 2,4-dimethylaniline, 2,4-dinitroaniline (d) 3,4-Dichloroaniline, 4-chloro-2-nitroaniline, 4-chloro-3-nitroaniline (e) Dimethylamine, diphenylamine, N-methylanilinearrow_forwarda. b. 22.16 Using ammonia as your source of nitrogen, show the reagents you would use to prepare each of the following amines: C. d. e. O f. PRACTICE the skill H Answer xi -N -NH₂ H O 1) [H*] NaBH₂CN NH3 2) [H*] NaBH3CN CH3CHOarrow_forwardA carbonyl compound on reaction with lodine in presence of sodium hydroxide followed by hydrolysis results in formation of iodoform and sodium salt of butanoic acid. Give the structure of the compound and reactions. A M A ::arrow_forward
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