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Organic And Biological Chemistry

7th Edition
STOKER + 1 other
ISBN: 9781305081079

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Chapter
Section
BuyFindarrow_forward

Organic And Biological Chemistry

7th Edition
STOKER + 1 other
ISBN: 9781305081079
Textbook Problem

Draw a condensed structural formula for the organic product of the reaction of each of the following compounds with water.

  1. a. Butanoyl chloride
  2. b. Butanoic anhydride

(a)

Interpretation Introduction

Interpretation:

Condensed structural formula for the organic product that is formed when butanoyl chloride reacts with water has to be drawn.

Concept Introduction:

Acid chlorides are organic derivatives of carboxylic acid.  The difference between carboxylic acid and acid chloride structure is that the OH portion present in the carboxyl group is replaced by a Cl atom.  This gives the structure of acid chlorides as,

Organic And Biological Chemistry, Chapter 5, Problem 5.150EP , additional homework tip  1

Acid chlorides react with water to give carboxylic acid and hydrogen chloride.  The carboxylic acid formed from acid chloride is the parent carboxylic acid.  The general reaction scheme of acid chloride reaction with water can be given as,

Organic And Biological Chemistry, Chapter 5, Problem 5.150EP , additional homework tip  2

Explanation

Given name of the compound is butanoyl chloride.  The structure of butanoyl chloride is,

Acid chlorides react with water to give carboxylic acid and hydrogen chloride...

(b)

Interpretation Introduction

Interpretation:

Condensed structural formula for the organic product that is formed when butanoic anhydride reacts with water has to be drawn.

Concept Introduction:

Acid anhydrides are organic derivatives of carboxylic acid.  The difference between carboxylic acid and acid anhydride structure is that the OH portion present in the carboxyl group is replaced by a OCOR group.  This gives the structure of acid anhydride as,

Organic And Biological Chemistry, Chapter 5, Problem 5.150EP , additional homework tip  3

Acid anhydride on reaction with water undergoes hydrolysis to form two carboxylic acid molecules.  If the acid anhydride is a symmetric one, then two molecules of same carboxylic acid is obtained on hydrolysis.  If the acid anhydride is an asymmetric one, the two molecules of two different carboxylic acid molecules are obtained.  The general reaction can be given as,

Organic And Biological Chemistry, Chapter 5, Problem 5.150EP , additional homework tip  4

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