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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 the condensed structural formula for each of the following compounds.

  1. a. propionyl chloride
  2. b. 3-Methylbutanoyl chloride
  3. c. Butyric anhydride
  4. d. Butanoic ethanoic anhydride

(a)

Interpretation Introduction

Interpretation:

Condensed structural formula for propionyl chloride has to be drawn.

Concept Introduction:

General structure of acid chloride can be represented as shown below,

Organic And Biological Chemistry, Chapter 5, Problem 5.145EP , additional homework tip  1

The structure of the acid chloride can be derived from the IUPAC name or common name.  “R” group present in the above structure is a part of the parent carboxylic acid from which the acid chloride is obtained.  Name of the acid chloride is obtained by replacing “-oic acid” in the parent carboxylic acid name with “-oyl chloride”.

Explanation

Given name of compound is propionyl chloride.  From the given name, the parent carboxylic acid is identified as propionic acid.  The structure of propionyl chloride can be obtained from the parent carboxylic acid by replacing the OH portion with Cl atom.  Structure of the parent carboxylic acid is

(b)

Interpretation Introduction

Interpretation:

Condensed structural formula for 3-methylbutanoyl chloride has to be drawn.

Concept Introduction:

General structure of acid chloride can be represented as shown below,

Organic And Biological Chemistry, Chapter 5, Problem 5.145EP , additional homework tip  2

The structure of the acid chloride can be derived from the IUPAC name or common name.  “R” group present in the above structure is a part of the parent carboxylic acid from which the acid chloride is obtained.  Name of the acid chloride is obtained by replacing “-oic acid” in the parent carboxylic acid name with “-oyl chloride”.

(c)

Interpretation Introduction

Interpretation:

Condensed structural formula for butyric anhydride has to be drawn.

Concept Introduction:

General structure of acid anhydride can be represented as shown below,

Organic And Biological Chemistry, Chapter 5, Problem 5.145EP , additional homework tip  3

The structure of the acid anhydride can be derived from the IUPAC name or common name.  “R, R1” group present in the above structure is a part of the parent carboxylic acid from which the acid anhydride is obtained.  If the acid anhydride is a symmetric one, then the name of acid anhydride is given by replacing the acid in the parent carboxylic acid name with anhydride.  If the acid anhydride is an asymmetric one, then the name of acid anhydride is given by using the name of individual carboxylic acid in an alphabetical order followed by anhydride.

(d)

Interpretation Introduction

Interpretation:

Condensed structural formula for butanoic ethanoic anhydride has to be drawn.

Concept Introduction:

General structure of acid anhydride can be represented as shown below,

Organic And Biological Chemistry, Chapter 5, Problem 5.145EP , additional homework tip  4

The structure of the acid anhydride can be derived from the IUPAC name or common name.  “R, R1” group present in the above structure is a part of the parent carboxylic acid from which the acid anhydride is obtained.  If the acid anhydride is a symmetric one, then the name of acid anhydride is given by replacing the acid in the parent carboxylic acid name with anhydride.  If the acid anhydride is an mixed one, then the name of acid anhydride is given by using the name of individual carboxylic acid in an alphabetical order followed by anhydride.

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