Chapter E, Problem E.23P

Interpretation Introduction

(a)

Interpretation:

The structure is to be drawn, and the correct IUPAC name for the given trivial name is to be provided.

Concept introduction:

Ketones consist of two alkyl or aryl groups attached to a carbonyl group, and their trivial names consist of identifying the alkyl or aryl groups and listing them both before the word ketone. Alkyl groups can be alkenes, alkynes, or benzene derivatives. Some of the most common names for alkenes and alkynes are vinyl, allyl, or propargyl. Their structures are as follows:

Trivial names such as iso and neo, sec, tert are used to indicate the alkyl groups and their structure as shown below:

The root names of ketones are derived from those of the parent alkanes, defined by the longest continuous chain of carbon atoms that contains the functional group. For a ketone, drop the -e from the alkane name and add the ending one. To indicate the position of a substituent on a ketone, number the chain in the manner that gives the carbonyl carbon atom the lowest possible locator number. In cyclic ketones, it is understood that the carbonyl carbon atom is C1.

Answer to Problem E.23P

The correct IUPAC name for the given trivial name $\text{divinyl ketone}$ is $\text{penta-1, 4-diene-3-one}$, and its structure is

Explanation of Solution

The name for the given molecule is $\text{divinyl ketone}$. The vinyl in the trivial name indicates the ethenyl group attached to the carbonyl group. The structure for the vinyl (ethenyl) group is

The prefix di represents that there are two vinyl groups attached to the carbonyl carbon atom in ketone. Thus, the structure for $\text{divinyl ketone}$ is

While writing the IUPAC name for ketones, the longest continuous carbon chain containing the ketone functional group is to be determined, and it is numbered such that the carbonyl carbon receives the lowest possible numbering. Using this rule, the numbering for the above structure is

The longest continuous carbon chain has five carbon atoms, and the carbonyl carbon is at number 3. Thus, the root name for this will be $\text{pentan-3-one}$. At C1 and C4 carbon atoms of the root, $\text{C=C}$ groups are present as substituents. The prefix di is used to indicate the two $\text{C=C}$ groups present. Thus, the complete IUPAC name for the compound is $\text{penta-1, 4-diene-3-one}$.

Conclusion

The structure of the molecule is drawn and the correct IUPAC name is written for the given trivial name.

Interpretation Introduction

(b)

Interpretation:

The structure is to be drawn, and the correct IUPAC name for the given trivial name is to be provided.

Concept introduction:

Ketones consist of two alkyl or aryl groups attached to a carbonyl group, and their trivial names consist of identifying the alkyl or aryl groups and listing them both before the word ketone. Alkyl groups can be alkenes, alkynes, or benzene derivatives. Some of the most common names for alkenes and alkynes are vinyl, allyl, or propargyl. Their structures are as follows:

Trivial names such as iso and neo, sec, tert are used to indicate the alkyl groups and their structure as shown below:

The root names of ketones are derived from those of the parent alkanes, defined by the longest continuous chain of carbon atoms that contains the functional group. For a ketone, drop the -e from the alkane name and add the ending one. To indicate the position of a substituent on a ketone, number the chain in the manner that gives the carbonyl carbon atom the lowest possible locator number. In cyclic ketones, it is understood that the carbonyl carbon atom is C1.

Answer to Problem E.23P

The correct IUPAC name for the given trivial name $\text{benzyl isopropyl ketone}$ is $\text{3-methyl-1-phenylbutan-2-one}$, and its structure is

Explanation of Solution

The name for the given molecule is $\text{benzyl isopropyl ketone}$. The two groups on either sides of the carbonyl carbon are benzyl and isopropyl. There is no other substituent present; thus, the structure for the compound is

While writing the IUPAC name for ketones, the longest continuous carbon chain containing the ketone functional group is to be determined, and it is numbered such that the carbonyl carbon receives the lowest possible numbering. Using this rule, the numbering for the above structure is

The longest continuous carbon chain has four carbon atoms, and the carbonyl carbon is at number 2. Thus, the root name for this will be $\text{butan-2-one}$. At C1 carbon atom of the root, one phenyl group is attached. At C3 carbon atom of the root, a methyl group is attached. Thus, the complete IUPAC name for the compound is $\text{3-methyl-1-phenylbutan-2-one}$.

Conclusion

The structure of the molecule is drawn, and the correct IUPAC name is written for the given trivial name.

Interpretation Introduction

(c)

Interpretation:

The structure is to be drawn, and the correct IUPAC name for the given trivial name is to be provided.

Concept introduction:

Ketones consist of two alkyl or aryl groups attached to a carbonyl group, and their trivial names consist of identifying the alkyl or aryl groups and listing them both before the word ketone. Alkyl groups can be alkenes, alkynes, or benzene derivatives. Some of the most common names for alkenes and alkynes are vinyl, allyl, or propargyl. Their structures are as follows:

Trivial names such as iso and neo, sec, tert are used to indicate the alkyl groups and their structure as shown below:

The root names of ketones are derived from those of the parent alkanes, defined by the longest continuous chain of carbon atoms that contains the functional group. For a ketone, drop the -e from the alkane name and add the ending one. To indicate the position of a substituent on a ketone, number the chain in the manner that gives the carbonyl carbon atom the lowest possible locator number. In cyclic ketones, it is understood that the carbonyl carbon atom is C1.

Answer to Problem E.23P

The correct IUPAC name for the given trivial name $\text{cyclohexyl methyl ketone}$ is $\text{cyclohexylethanone}$, and its structure is

Explanation of Solution

The name for the given molecule is $\text{cyclohexyl methyl ketone}$. The two groups on either sides of the carbonyl carbon are cyclohexyl and methyl. There is no other substituent present; thus, the structure for the compound is

While writing the IUPAC name for ketones, the longest continuous carbon chain containing the ketone functional group is to be determined, and it is numbered such that the carbonyl carbon receives the lowest possible numbering. Using this rule, the numbering for the above structure is

The longest continuous carbon chain has two carbon atoms, and the carbonyl carbon is at number 1. Thus, the root name for this will be $\text{ethanone}$. At C1 carbon atom of the root, one cyclohexyl group is attached. Thus, the complete IUPAC name of the compound is $\text{cyclohexylethanone}$.

Conclusion

The structure of the molecule is drawn, and the correct IUPAC name is written for the given trivial name.

Interpretation Introduction

(d)

Interpretation:

The structure is to be drawn, and the correct IUPAC name for the given trivial name is to be provided.

Concept introduction:

Ketones consist of two alkyl or aryl groups attached to a carbonyl group, and their trivial names consist of identifying the alkyl or aryl groups and listing them both before the word ketone. Alkyl groups can be alkenes, alkynes, or benzene derivatives. Some of the most common names for alkenes and alkynes are vinyl, allyl, or propargyl. Their structures are as follows:

Trivial names such as iso and neo, sec, tert are used to indicate the alkyl groups and their structure as shown below:

The root names of ketones are derived from those of the parent alkanes, defined by the longest continuous chain of carbon atoms that contains the functional group. For a ketone, drop the -e from the alkane name and add the ending one. To indicate the position of a substituent on a ketone, number the chain in the manner that gives the carbonyl carbon atom the lowest possible locator number. In cyclic ketones, it is understood that the carbonyl carbon atom is C1.

Answer to Problem E.23P

The correct IUPAC name for the given trivial name $\text{diisopropylketone}$ is $\text{2, 4-dimethylpentan-3-one}$, and its structure is

Explanation of Solution

The name for the given molecule is $\text{diisopropylketone}$. The two groups on either sides of the carbonyl carbon are isopropyl groups. The structure for an isopropyl group is

There is no other substituent present; thus, the structure for the compound is

While writing the IUPAC name for ketones, the longest continuous carbon chain containing the ketone functional group is to be determined, and it is numbered such that the carbonyl carbon receives the lowest possible numbering. Using this rule, the numbering for the above structure is

The longest continuous carbon chain has five carbon atoms, and the carbonyl carbon is at number 3. Thus, the root name for this will be $\text{pentan-3-one}$. At C2 and C4 carbon atoms of the root, methyl substituent is attached. Thus, the complete IUPAC name for the compound is $\text{2, 4-dimethylpentan-3-one}$.

Conclusion

The structure of the molecule is drawn, and the correct IUPAC name is written for the given trivial name.

Interpretation Introduction

(e)

Interpretation:

The structure is to be drawn, and the correct IUPAC name for the given trivial name is to be provided.

Concept introduction:

Ketones consist of two alkyl or aryl groups attached to a carbonyl group, and their trivial names consist of identifying the alkyl or aryl groups and listing them both before the word ketone. Alkyl groups can be alkenes, alkynes, or benzene derivatives. Some of the most common names for alkenes and alkynes are vinyl, allyl, or propargyl. Their structures are as follows:

Trivial names such as iso and neo, sec, tert are used to indicate the alkyl groups and their structure as shown below:

The root names of ketones are derived from those of the parent alkanes, defined by the longest continuous chain of carbon atoms that contains the functional group. For a ketone, drop the -e from the alkane name and add the ending one. To indicate the position of a substituent on a ketone, number the chain in the manner that gives the carbonyl carbon atom the lowest possible locator number. In cyclic ketones, it is understood that the carbonyl carbon atom is C1.

Answer to Problem E.23P

The correct IUPAC name for the given trivial name $\text{isobutyl phenyl ketone}$ is $\text{3-methyl-1-phenylbutan-1-one}$, and its structure is

Explanation of Solution

The name for the given molecule is $\text{isobutyl phenyl ketone}$. The two groups on either sides of the carbonyl carbon are isobutyl and phenyl groups. Isobutyl is a branched alkyl group with four carbon atoms. The structure for an iso group is

There is no other substituent present; thus, the structure for the compound is

While writing the IUPAC name for ketones, the longest continuous carbon chain containing the ketone functional group is to be determined, and it is numbered such that the carbonyl carbon receives the lowest possible numbering. Using this rule, the numbering for the above structure is

The longest continuous carbon chain has four carbon atoms, and the carbonyl carbon is at number 1. Thus, the root name for this will be $\text{butan-1-one}$. At C3 carbon atom of the root, one methyl substituent is attached. Thus, the complete IUPAC name for the compound is $\text{3-methyl-1-phenylbutan-1-one}$.

Conclusion

The structure of the molecule is drawn, and the correct IUPAC name is written for the given trivial name.