Organic Chemistry
Organic Chemistry
7th Edition
ISBN: 9780321803221
Author: Paula Y. Bruice
Publisher: Prentice Hall
Question
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Chapter 18, Problem 79P

(a)

Interpretation Introduction

Interpretation:

The one equivalent of the malonic ester reacted with one equivalent of 1,5dibromopentane and two equivalents of base has to be predicted formed the unknown carboxylic acid.

Concept introduction:

In first case, base initiates the reaction by abstraction of a proton from the malonic ester. Enolate anion is formed which attacks 1,5dibromopentane.  The second equivalent of base abstracts a proton from the intermediate compound and a nucleophilic center is generated.  The nucleophilic carbon attacks another end of 1,5dibromopentane and a cyclic compound is formed.  On hydrolysis and heating, the carboxylic acid is formed.

In second case, base initiates the reaction by abstraction of a proton from the malonic ester.  Enolate anion is formed which attacks 1,5dibromopentane.  The second equivalent of base abstracts a proton from the second equivalent of malonic ester and a nucleophilic center is generated.  The nucleophilic carbon attacks the previously formed compound.  On hydrolysis and heating, the carboxylic acid is formed.

(b)

Interpretation Introduction

Interpretation:

The one equivalent of the malonic ester reacted with one equivalent of 1,5dibromopentane and two equivalents of base has to be predicted formed the unknown carboxylic acid.

Concept introduction:

In first case, base initiates the reaction by abstraction of a proton from the malonic ester. Enolate anion is formed which attacks 1,5dibromopentane.  The second equivalent of base abstracts a proton from the intermediate compound and a nucleophilic center is generated.  The nucleophilic carbon attacks another end of 1,5dibromopentane and a cyclic compound is formed.  On hydrolysis and heating, the carboxylic acid is formed.

In second case, base initiates the reaction by abstraction of a proton from the malonic ester.  Enolate anion is formed which attacks 1,5dibromopentane.  The second equivalent of base abstracts a proton from the second equivalent of malonic ester and a nucleophilic center is generated.  The nucleophilic carbon attacks the previously formed compound. On hydrolysis and heating, the carboxylic acid is formed.

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Chapter 18 Solutions

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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