Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
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Textbook Question
Chapter 23.11, Problem 20P
Show how you might use an enamine reaction to prepare each of the following compounds:
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Propose preparative routes to the following ketones using an enamine intermediate - you must make the bond highlighted in red:
Propose preparative routes to the following ketones using an enamine intermediate - you must make the bond in red.
Which of the following compounds would be used to prepare an enamine from 3-pentanone?
A. hydroxylamine
B. ammonia
C. diethylamine
D. hydrazine
Chapter 23 Solutions
Organic Chemistry
Ch. 23.1 - Prob. 1PCh. 23.1 - Prob. 2PCh. 23.3 - Prob. 3PCh. 23.3 - Prob. 4PCh. 23.4 - Prob. 5PCh. 23.4 - 1-Butanol is prepared commercially by a route that...Ch. 23.4 - Prob. 7PCh. 23.5 - Prob. 8PCh. 23.6 - Prob. 9PCh. 23.6 - What product would you Expect to obtain from base...
Ch. 23.7 - Show the products you would expect to obtain by...Ch. 23.7 - Prob. 12PCh. 23.8 - What product would you expect from the following...Ch. 23.9 - What product would you expect From the following...Ch. 23.9 - Prob. 15PCh. 23.10 - Prob. 16PCh. 23.10 - Prob. 17PCh. 23.10 - Prob. 18PCh. 23.11 - Prob. 19PCh. 23.11 - Show how you might use an enamine reaction to...Ch. 23.12 - Prob. 21PCh. 23.12 - How would you prepare the following compound using...Ch. 23.SE - Prob. 23VCCh. 23.SE - Prob. 24VCCh. 23.SE - Prob. 25VCCh. 23.SE - The following molecule was formed by a Robinson...Ch. 23.SE - Prob. 27MPCh. 23.SE - Prob. 28MPCh. 23.SE - Predict the product(s) and provide the mechanism...Ch. 23.SE - Predict the product(s) and provide the mechanism...Ch. 23.SE - Predict the product(s) and provide the mechanism...Ch. 23.SE - Knoevenagel condensation is a reaction involving...Ch. 23.SE - Azlactones are important starting materials used...Ch. 23.SE - Prob. 34MPCh. 23.SE - Isoleucine, another of the twenty amino acids...Ch. 23.SE - The first step in the citric acid cycle of food...Ch. 23.SE - Prob. 37MPCh. 23.SE - The Knoevenagel reaction is a carbonyl...Ch. 23.SE - The Darzens reaction invoIves a two-step,...Ch. 23.SE - The following reaction involves a hydrolysis...Ch. 23.SE - Prob. 41MPCh. 23.SE - Prob. 42MPCh. 23.SE - Prob. 43MPCh. 23.SE - Propose a mechanism for the following...Ch. 23.SE - Prob. 45MPCh. 23.SE - Prob. 46MPCh. 23.SE - Prob. 47MPCh. 23.SE - Prob. 48APCh. 23.SE - Prob. 49APCh. 23.SE - Prob. 50APCh. 23.SE - Prob. 51APCh. 23.SE - Prob. 52APCh. 23.SE - Prob. 53APCh. 23.SE - Prob. 54APCh. 23.SE - Prob. 55APCh. 23.SE - Prob. 56APCh. 23.SE - Prob. 57APCh. 23.SE - Prob. 58APCh. 23.SE - In the mixed Claisen reaction of cyclopentanone...Ch. 23.SE - Ethyl dimethylacetoacetate reacts instantly at...Ch. 23.SE - Prob. 61APCh. 23.SE - Prob. 62APCh. 23.SE - The so-called Wieland-Miescher ketone is a...Ch. 23.SE - Prob. 64APCh. 23.SE - Prob. 65APCh. 23.SE - Prob. 66APCh. 23.SE - What condensation products would you expect to...Ch. 23.SE - The following reactions are unlikely to provide...Ch. 23.SE - Fill in the missing reagents a-h in the following...Ch. 23.SE - Prob. 70APCh. 23.SE - Prob. 71APCh. 23.SE - Prob. 72APCh. 23.SE - Prob. 73AP
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- How would you prepare the following substances from pentanoic acid? a. Pentanamide b. Butylamine c. Pentylaminearrow_forwardWhat alkyl bromide would you use in a Gabriel synthesis to prepare each of the following amines? a. pentylamine b. isohexylamine c. benzylamine d. cyclohexylaminearrow_forwardShow how you would convert aniline to the following compounds. ) benzonitrilearrow_forward
- Show how you would accomplish the following syntheses using amides as intermediates.You may use any necessary reagents. ) pyrrolidine S N@ethylpyrrolidinearrow_forwardWhich of the following compounds is the most basic? A. p-nitroaniline B. p-chloroaniline C. N-methylaniline D. aniline E. p-methoxyanilinearrow_forwardHow can you prepare the following amine using a reductive amination reaction?arrow_forward
- Show how to synthesize the following amines from the indicated starting materials below. Each of the final products may require several sequential steps. Draw the structure for each of the steps and show the reagents required. Starting material Final product b) Benzene m-bromoaniline c) ethylbenzene p-ethylaniline + o-ethylaniline d) benzene p-bromoaniline + o-bromoanilinearrow_forwardWhat will be the right combination of reagents to be required for the synthesis of the following compound? a. Ethanal + n-Propylamine b. Ethanal + isopropylamine c. Propanal + Ethylamine d. Ethylamine + Ethanal .arrow_forwardShow how Gabriel syntheses are used to prepare the following amines. ) hexan-1-aminearrow_forward
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