Organic Chemistry
Organic Chemistry
7th Edition
ISBN: 9780321803221
Author: Paula Y. Bruice
Publisher: Prentice Hall
Question
Book Icon
Chapter 18.18, Problem 39P

(a)

Interpretation Introduction

Interpretation: The reason behind the given carboxylic acids cannot be prepared by a malonic ester synthesis has to be explained.

Concept introduction: Malonic ester synthesis is used to prepare carboxylic acids of the desired length.  The malonic ester is reacted with an alkoxide base which removes a alpha hydrogen.

The anion so formed is reacted with an alkyl halide.  The anion abstracts the alkyl group from the alkyl halide.  On heating, decarboxylation takes place which gives the desired carboxylic acid.

(b)

Interpretation Introduction

Interpretation: The reason behind the given carboxylic acids cannot be prepared by a malonic ester synthesis has to be explained.

Concept introduction: Malonic ester synthesis is used to prepare carboxylic acids of the desired length.  The malonic ester is reacted with an alkoxide base which removes a alpha hydrogen.

The anion so formed is reacted with an alkyl halide.  The anion abstracts the alkyl group from the alkyl halide.  On heating, decarboxylation takes place which gives the desired carboxylic acid.

(c)

Interpretation Introduction

Interpretation: The reason behind the given carboxylic acids cannot be prepared by a malonic ester synthesis has to be explained.

Concept introduction: Malonic ester synthesis is used to prepare carboxylic acids of the desired length.  The malonic ester is reacted with an alkoxide base which removes a alpha hydrogen.

The anion so formed is reacted with an alkyl halide.  The anion abstracts the alkyl group from the alkyl halide.  On heating, decarboxylation takes place which gives the desired carboxylic acid.

Blurred answer
Students have asked these similar questions
What compounds are obtained from the following hydrolysis reactions?
Explain why each of the following carboxylic acids cannot be prepared by a malonic ester synthesis: (a) (CH3CCH;COOH; (b) C,H;CH2COOH; (c) (CHa)CCOOH.
What reactions and reagents can be used to make phenol from benzene if electrophilic aromatic substitution reactions are excluded and benzene is the only source of carbon?

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:
Knowledge Booster
Background pattern image
Similar questions
SEE MORE QUESTIONS
Recommended textbooks for you
Text book image
Introduction to General, Organic and Biochemistry
Chemistry
ISBN:9781285869759
Author:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar Torres
Publisher:Cengage Learning