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Organic And Biological Chemistry

7th Edition
STOKER + 1 other
ISBN: 9781305081079

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Section
BuyFindarrow_forward

Organic And Biological Chemistry

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

Assign IUPAC names to the esters that are produced from the reaction of the following carboxylic acids and alcohols.

  1. a. Acetic acid and ethanol
  2. b. Ethanoic acid and methanol
  3. c. Butyric acid and ethyl alcohol
  4. d. 2-Butanol and caproic acid

(a)

Interpretation Introduction

Interpretation:

The IUPAC name for the ester formed when acetic acid and ethanol react has to be assigned.

Concept Introduction:

Esters are prepared by condensation of carboxylic acid with an alcohol.  A molecule of water is lost on this reaction.  The reaction that takes place in producing esters is known as esterification reaction.

Esterification reaction is the one in which the carboxylic acid is condensed with an alcohol (or phenol) in presence of strong acid catalyst to produce ester.  The general reaction scheme can be given as,

Organic And Biological Chemistry, Chapter 5, Problem 5.97EP , additional homework tip  1

For naming an ester, it can be structurally viewed in a way that contains an acyl group and an alkyl group.

Organic And Biological Chemistry, Chapter 5, Problem 5.97EP , additional homework tip  2

Rules to obtain IUPAC name and common name for an ester:

  • Alkyl part appears first in the IUPAC name and it is followed by the acyl part of ester as a separate word.
  • Name of the alkyl part in the ester is just a name of R group.  It can be alkyl, cycloalkyl, or aryl group.
  • Acyl part present in the ester is named by considering the acid name and replacing the suffix “-ic acid” with “-ate”.
  • To obtain the common name the alkyl part name is the same while the acyl part name is derived from the common name of the acid by replacing the suffix “-ic acid” with “-ate”.
Explanation

Given carboxylic acid and alcohol structure is,

The reaction between two compounds that are shown above, result in the formation of ester.  The structure of the ester formed and the complete reaction can be given as shown below,

The structure of ester is,

The alkyl and acyl group is identified as shown below,

(b)

Interpretation Introduction

Interpretation:

The IUPAC name for the ester formed when ethanoic acid and methanol react has to be assigned.

Concept Introduction:

Esters are prepared by condensation of carboxylic acid with an alcohol.  A molecule of water is lost on this reaction.  The reaction that takes place in producing esters is known as esterification reaction.

Esterification reaction is the one in which the carboxylic acid is condensed with an alcohol (or phenol) in presence of strong acid catalyst to produce ester.  The general reaction scheme can be given as,

Organic And Biological Chemistry, Chapter 5, Problem 5.97EP , additional homework tip  3

For naming an ester, it can be structurally viewed in a way that contains an acyl group and an alkyl group.

Organic And Biological Chemistry, Chapter 5, Problem 5.97EP , additional homework tip  4

Rules to obtain IUPAC name and common name for an ester:

  • Alkyl part appears first in the IUPAC name and it is followed by the acyl part of ester as a separate word.
  • Name of the alkyl part in the ester is just a name of R group.  It can be alkyl, cycloalkyl, or aryl group.
  • Acyl part present in the ester is named by considering the acid name and replacing the suffix “-ic acid” with “-ate”.
  • To obtain the common name the alkyl part name is the same while the acyl part name is derived from the common name of the acid by replacing the suffix “-ic acid” with “-ate”.

(c)

Interpretation Introduction

Interpretation:

The IUPAC name for the ester formed when butyric acid and ethyl alcohol react has to be assigned.

Concept Introduction:

Esters are prepared by condensation of carboxylic acid with an alcohol.  A molecule of water is lost on this reaction.  The reaction that takes place in producing esters is known as esterification reaction.

Esterification reaction is the one in which the carboxylic acid is condensed with an alcohol (or phenol) in presence of strong acid catalyst to produce ester.  The general reaction scheme can be given as,

Organic And Biological Chemistry, Chapter 5, Problem 5.97EP , additional homework tip  5

For naming an ester, it can be structurally viewed in a way that contains an acyl group and an alkyl group.

Organic And Biological Chemistry, Chapter 5, Problem 5.97EP , additional homework tip  6

Rules to obtain IUPAC name and common name for an ester:

  • Alkyl part appears first in the IUPAC name and it is followed by the acyl part of ester as a separate word.
  • Name of the alkyl part in the ester is just a name of R group.  It can be alkyl, cycloalkyl, or aryl group.
  • Acyl part present in the ester is named by considering the acid name and replacing the suffix “-ic acid” with “-ate”.
  • To obtain the common name the alkyl part name is the same while the acyl part name is derived from the common name of the acid by replacing the suffix “-ic acid” with “-ate”.

(d)

Interpretation Introduction

Interpretation:

The IUPAC name for the ester formed when 2-butanol and caproic acid react has to be assigned.

Concept Introduction:

Esters are prepared by condensation of carboxylic acid with an alcohol.  A molecule of water is lost on this reaction.  The reaction that takes place in producing esters is known as esterification reaction.

Esterification reaction is the one in which the carboxylic acid is condensed with an alcohol (or phenol) in presence of strong acid catalyst to produce ester.  The general reaction scheme can be given as,

Organic And Biological Chemistry, Chapter 5, Problem 5.97EP , additional homework tip  7

For naming an ester, it can be structurally viewed in a way that contains an acyl group and an alkyl group.

Organic And Biological Chemistry, Chapter 5, Problem 5.97EP , additional homework tip  8

Rules to obtain IUPAC name and common name for an ester:

  • Alkyl part appears first in the IUPAC name and it is followed by the acyl part of ester as a separate word.
  • Name of the alkyl part in the ester is just a name of R group.  It can be alkyl, cycloalkyl, or aryl group.
  • Acyl part present in the ester is named by considering the acid name and replacing the suffix “-ic acid” with “-ate”.
  • To obtain the common name the alkyl part name is the same while the acyl part name is derived from the common name of the acid by replacing the suffix “-ic acid” with “-ate”.

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