EBK ORGANIC CHEMISTRY
EBK ORGANIC CHEMISTRY
7th Edition
ISBN: 9780133556186
Author: Bruice
Publisher: VST
Question
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Chapter 18.19, Problem 40P

(a)

Interpretation Introduction

Interpretation: Alkyl bromide used in the acetoacetic ester synthesis of each methyl ketone has to be stated.

Concept introduction: Acetoacetic ester synthesis is used to prepare methyl ketone of the desired length.  The acetoacetic ester is reacted with an alkoxide base which removes a α hydrogen atom.  The anion so formed is reacted with an alkyl bromide.  The anion abstracts the alkyl group from the alkyl bromide.  Acidic hydrolysis of the intermediate so formed on heating undergo decarboxylation which gives the desired methyl ketone.

(b)

Interpretation Introduction

Interpretation: Alkyl bromide used in the acetoacetic ester synthesis of each methyl ketone is to be stated.

Concept introduction: Acetoacetic ester synthesis is used to prepare methyl ketone of the desired length.  The acetoacetic ester is reacted with an alkoxide base which removes a α hydrogen atom.  The anion so formed is reacted with an alkyl bromide.  The anion abstracts the alkyl group from the alkyl bromide.  Acidic hydrolysis of the intermediate so formed on heating undergo decarboxylation which gives the desired methyl ketone.

(c)

Interpretation Introduction

Interpretation: Alkyl bromide used in the acetoacetic ester synthesis of each methyl ketone has to be stated.

Concept introduction: Acetoacetic ester synthesis is used to prepare methyl ketone of the desired length.  The acetoacetic ester is reacted with an alkoxide base which removes a α hydrogen atom.  The anion so formed is reacted with an alkyl bromide.  The anion abstracts the alkyl group from the alkyl bromide.  Acidic hydrolysis of the intermediate so formed on heating undergo decarboxylation which gives the desired methyl ketone.

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Chapter 18 Solutions

EBK ORGANIC CHEMISTRY

Ch. 18.5 - Show how the following compounds can be prepared...Ch. 18.6 - What compound is formed when a dilute solution of...Ch. 18.7 - Prob. 13PCh. 18.7 - Prob. 14PCh. 18.7 - How many stereoisomers are obtained from each of...Ch. 18.7 - Prob. 16PCh. 18.8 - Prob. 17PCh. 18.9 - Prob. 18PCh. 18.9 - Prob. 19PCh. 18.10 - Prob. 20PCh. 18.10 - What aldehyde or ketone would be obtained when...Ch. 18.11 - Prob. 22PCh. 18.12 - Prob. 24PCh. 18.12 - What two carbonyl compound are required for the...Ch. 18.12 - Propose a mechanism for the following reaction:Ch. 18.13 - Draw the products of the following reactions:Ch. 18.13 - Prob. 28PCh. 18.13 - Prob. 29PCh. 18.14 - Prob. 30PCh. 18.15 - Write the mechanism for the reaction of a...Ch. 18.15 - Prob. 32PCh. 18.15 - Prob. 33PCh. 18.15 - Draw the product of the reaction of each of the...Ch. 18.16 - Draw the product obtained by heating each pair of...Ch. 18.16 - Prob. 36PCh. 18.17 - Prob. 37PCh. 18.18 - Prob. 38PCh. 18.18 - Prob. 39PCh. 18.19 - Prob. 40PCh. 18.20 - Prob. 42PCh. 18.21 - Propose a mechanism for the formation of...Ch. 18.21 - Prob. 44PCh. 18.21 - a. If the biosynthesis of palmitic acid were...Ch. 18.21 - Prob. 46PCh. 18 - Prob. 47PCh. 18 - Prob. 48PCh. 18 - Number the following compounds in order of...Ch. 18 - The 1H NMR chemical shifts of nitromethane,...Ch. 18 - Prob. 51PCh. 18 - Draw the products of the following reactions: a....Ch. 18 - A racemic mixture of 2-methyl-1-phenyl-1-butanone...Ch. 18 - Prob. 54PCh. 18 - Prob. 55PCh. 18 - Prob. 56PCh. 18 - Prob. 57PCh. 18 - Identify A-L. (Hint: A shows three singles in its...Ch. 18 - Using cyclopentanone as the reactant, show the...Ch. 18 - Show how the following compounds can be prepared...Ch. 18 - Prob. 61PCh. 18 - Prob. 62PCh. 18 - Prob. 63PCh. 18 - The ketone whose 1H NMR spectrum is shown here was...Ch. 18 - Prob. 65PCh. 18 - Compound A with molecular formula C6H10 has two...Ch. 18 - Indicate how each of the following compounds can...Ch. 18 - Draw the products of the following reactions:Ch. 18 - Prob. 69PCh. 18 - a. Show how the amino acid alanine can be...Ch. 18 - Prob. 71PCh. 18 - Show how the following compounds can be...Ch. 18 - Explain why the following bromoketone forms...Ch. 18 - Prob. 74PCh. 18 - What carbonyl compounds are required to prepare a...Ch. 18 - Prob. 76PCh. 18 - A carboxylic arid is formed when an -haloketone...Ch. 18 - An , -unsaturated carbonyl compound can be...Ch. 18 - Prob. 79PCh. 18 - A Cannizzaro reaction is the reaction of an...Ch. 18 - Propose a mechanism for each of the following...Ch. 18 - The following reaction is known as the benzoni...Ch. 18 - Prob. 83PCh. 18 - Prob. 84PCh. 18 - Prob. 85PCh. 18 - Prob. 86PCh. 18 - Propose a mechanism for the following reaction:
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