Chapter 16, Problem 16.97EP

(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,

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

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”.

Answer to Problem 16.97EP

IUPAC name of the ester formed is ethyl ethanoate.

Explanation of Solution

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,

Alkyl group contains only two carbon atoms.  Hence alkyl group is named as ethyl.  The acyl group contains two carbon atoms.  The IUPAC name of carboxylic acid that contains three carbon atoms is ethanoic acid.  For naming acyl group in ester the suffix “-ic acid” is converted into “-ate”.  This gives the name of acyl part as ethanoate.  Therefore IUPAC name of the given ester is ethyl ethanoate.

Conclusion

IUPAC name of the formed ester is assigned.

(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,

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

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”.

Answer to Problem 16.97EP

IUPAC name of the ester formed is methyl ethanoate.

Explanation of Solution

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,

Alkyl group contains only one carbon atom.  Hence alkyl group is named as methyl.  The acyl group contains two carbon atoms.  The IUPAC name of carboxylic acid that contains three carbon atoms is ethanoic acid.  For naming acyl group in ester the suffix “-ic acid” is converted into “-ate”.  This gives the name of acyl part as ethanoate.  Therefore IUPAC name of the given ester is methyl ethanoate.

Conclusion

IUPAC name of the formed ester is assigned.

(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,

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

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”.

Answer to Problem 16.97EP

IUPAC name of the ester formed is ethyl butanoate.

Explanation of Solution

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,

Alkyl group contains only two carbon atoms.  Hence alkyl group is named as ethyl.  The acyl group contains four carbon atoms.  The IUPAC name of carboxylic acid that contains three carbon atoms is butanoic acid.  For naming acyl group in ester the suffix “-ic acid” is converted into “-ate”.  This gives the name of acyl part as butanoate.  Therefore IUPAC name of the given ester is ethyl butanoate.

Conclusion

IUPAC name of the formed ester is assigned.

(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,

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

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”.

Answer to Problem 16.97EP

IUPAC name of the ester formed is 1-methylpropyl hexanoate.

Explanation of Solution

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,

Alkyl group contains a total of four carbon atoms.  In that alkyl group (propyl) a methyl group is substituted in the first carbon atom.  Hence alkyl group is named as 1-methylpropyl.  The acyl group contains six carbon atoms.  The IUPAC name of carboxylic acid that contains three carbon atoms is hexanoic acid.  For naming acyl group in ester the suffix “-ic acid” is converted into “-ate”.  This gives the name of acyl part as hexanoate.  Therefore IUPAC name of the given ester is 1-methylpropyl hexanoate.

Conclusion

IUPAC name of the formed ester is assigned.