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Chapter 17.10, Problem 33P

(a)

Interpretation Introduction

Interpretation:

The mechanisms for the following reactions should be determined.

  1. 1. The acid-base catalyzed hydrolysis of an imine to a carbonyl compound and a primary amine.
  2. 2. The acid-base catalyzed hydrolysis of an enamine to a carbonyl compounds and a secondary amine.

Concept introduction:

The chemical compound containing carbon and nitrogen double bond is known as imine.

Enamine is derived by the condensation of an aldehyde or ketone with secondary amine.

Organic Chemistry; Modified MasteringChemistry with Pearson eText -- ValuePack Access Card;  Study Guide and Student Solutions Manual for Organic Chemistry, Books a la Carte Edition (7th Edition), Chapter 17.10, Problem 33P , additional homework tip  1

(b)

Interpretation Introduction

Interpretation:

The reason for the difference in mechanism of two reactions should be given.

Concept introduction:

The chemical compound containing carbon and nitrogen double bond is known as imine.

Enamine is derived by the condensation of an aldehyde and ketone with secondary amine.

Organic Chemistry; Modified MasteringChemistry with Pearson eText -- ValuePack Access Card;  Study Guide and Student Solutions Manual for Organic Chemistry, Books a la Carte Edition (7th Edition), Chapter 17.10, Problem 33P , additional homework tip  2

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Chapter 17 Solutions

Organic Chemistry; Modified MasteringChemistry with Pearson eText -- ValuePack Access Card; Study Guide and Student Solutions Manual for Organic Chemistry, Books a la Carte Edition (7th Edition)

Ch. 17.4 - Show how the following compounds can be...Ch. 17.5 - Prob. 13PCh. 17.5 - Prob. 14PCh. 17.6 - In the mechanism for cyanohydrin formation, why is...Ch. 17.6 - Prob. 16PCh. 17.6 - Prob. 17PCh. 17.6 - Show two ways to convert an alkyl halide into a...Ch. 17.7 - Prob. 20PCh. 17.7 - Prob. 21PCh. 17.7 - Prob. 22PCh. 17.7 - Prob. 23PCh. 17.8 - Prob. 24PCh. 17.9 - What reducing agents should be used to obtain the...Ch. 17.9 - Prob. 26PCh. 17.9 - Prob. 27PCh. 17.10 - Prob. 28PCh. 17.10 - Prob. 29PCh. 17.10 - Prob. 30PCh. 17.10 - The pKa of protonated acetone is about 7.5. and...Ch. 17.10 - Prob. 32PCh. 17.10 - Prob. 33PCh. 17.10 - Prob. 34PCh. 17.10 - Excess ammonia must be used when a primary amine...Ch. 17.10 - The compounds commonly known as amino acids are...Ch. 17.11 - Hydration of an aldehyde is also catalyzed by...Ch. 17.11 - Which ketone forms the most hydrate in an aqueous...Ch. 17.11 - When trichloroacetaldehyde is dissolved in water,...Ch. 17.12 - Which of the following are a. hermiacetals? b....Ch. 17.12 - Prob. 41PCh. 17.12 - Explain why an acetal can be isolated but most...Ch. 17.13 - Prob. 43PCh. 17.13 - Prob. 44PCh. 17.13 - What products would be formed from the proceedings...Ch. 17.13 - a. In a six-step synthesis, what is the yield of...Ch. 17.13 - Show how each of the following compounds could be...Ch. 17.15 - Prob. 48PCh. 17.17 - Prob. 50PCh. 17.18 - Prob. 51PCh. 17.19 - Prob. 52PCh. 17 - Draw the structure for each of the following: a....Ch. 17 - Prob. 54PCh. 17 - Prob. 55PCh. 17 - a. Show the reagents required to form the primary...Ch. 17 - Prob. 57PCh. 17 - Using cyclohexanone as the starting material,...Ch. 17 - Prob. 59PCh. 17 - 60. Show how each of the following compounds could...Ch. 17 - Fill in the boxes:Ch. 17 - Prob. 62PCh. 17 - Identify A through O:Ch. 17 - Prob. 64PCh. 17 - Prob. 65PCh. 17 - Prob. 66PCh. 17 - How many signals would the product of the...Ch. 17 - Prob. 68PCh. 17 - Prob. 69PCh. 17 - Prob. 70PCh. 17 - Prob. 71PCh. 17 - Prob. 72PCh. 17 - Prob. 73PCh. 17 - Prob. 74PCh. 17 - Prob. 75PCh. 17 - Prob. 76PCh. 17 - Prob. 77PCh. 17 - A compound gives the following IR spectrum. Upon...Ch. 17 - a. Propose a mechanism for the following reaction:...Ch. 17 - Prob. 80PCh. 17 - Prob. 81PCh. 17 - Prob. 82PCh. 17 - Prob. 83PCh. 17 - Prob. 84PCh. 17 - In the presence of an acid catalyst, acetaldehyde...Ch. 17 - Prob. 86PCh. 17 - Prob. 87PCh. 17 - Prob. 88PCh. 17 - A compound reacts with methylmagnesium bromide...Ch. 17 - Show how each of the following compounds can be...Ch. 17 - Prob. 91PCh. 17 - Prob. 92PCh. 17 - The pKa values of the carboxylic acid groups of...Ch. 17 - The Baylis-Hillman reaction is a DABCO...Ch. 17 - Prob. 95PCh. 17 - Prob. 96P
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