Chapter F, Problem F.12P

Interpretation Introduction

(a)

Interpretation:

The structure of the molecule is to be drawn and the IUPAC name is to be provided that corresponds to the given trivial name.

Concept introduction:

Carboxylic acids are the compounds containing $\text{RCOOH}$ group. They include both monocarboxylic acids as well as dicarboxylic acids. Trivial names for many mono and dicarboxylic acids are widely accepted by IUPAC and they are:

The carbonyl carbon atom is always numbered as C1 and the numbering continues. The substituents, if any, attached to the carbon chain are names according to the alphabetical order and the lowest locator number.

The trivial names of carboxylic acids are in the general form alkionic acid, while the IUPAC names are in the general form alkanoic acid. The suffix ‘ionic’ is replaced by ‘noic’ in the IUPAC name.

Answer to Problem F.12P

The structure of the molecule that corresponds to the given trivial name $\text{trichloroacetic acid}$ is:

The IUPAC name of $\text{trichloroacetic acid}$ is $\text{trichloroethanoic acid}$.

Explanation of Solution

The given IUPAC name is $\text{trichloroacetic acid}$. The name suggests that it is a monocarboxylic substituted acid. The acetic acid is a trivial name of the carboxylic acid of two carbon atoms. The IUPAC name of acetic acid is ethanoic acid, however the name acetic acid is accepted widely in the IUPAC nomenclature. The structure of acetic acid is:

The portion ‘$\text{trichloro}$’ indicates that there are three chlorine atoms attached to the carbon atom in the acetic acid. Carbon atom C2 is the only carbon atom in the acetic acid where the substituents can be attached. Thus, the structure of $\text{trichloroacetic acid}$ is:

The IUPAC name of $\text{trichloroacetic acid}$ is $\text{trichloroethanoic acid}$.

Conclusion

The structure of the compound is drawn and the IUPAC name of the compound is written that corresponds to the given trivial name.

Interpretation Introduction

(b)

Interpretation:

The structure of the molecule is to be drawn and the IUPAC name is to be provided that corresponds to the given trivial name.

Concept introduction:

Carboxylic acids are the compounds containing $\text{RCOOH}$ group. They include both monocarboxylic acids as well as dicarboxylic acids. Trivial names for many mono and dicarboxylic acids are widely accepted by IUPAC and they are:

The carbonyl carbon atom is always numbered as C1 and the numbering continues. The substituents, if any, attached to the carbon chain are names according to the alphabetical order and the lowest locator number.

The trivial names of carboxylic acids are in the general form alkionic acid, while the IUPAC names are in the general form alkanoic acid. The suffix ‘ionic’ is replaced by ‘noic’ in the IUPAC name.

Answer to Problem F.12P

The structure of the molecule that corresponds to the given trivial name $\text{2, 2-dimethylbutyric acid}$ is:

The IUPAC name of $\text{2, 2-dimethylbutyric acid}$ is $\text{2, 2-dimethylbutanoic acid}$.

Explanation of Solution

The given IUPAC name is $\text{2, 2-dimethylbutyric acid}$. The name suggests that it is a monocarboxylic substituted acid. Butyric acid is the trivial name of the carboxylic acid containing four carbon atoms. The carbonyl carbon of the carboxylic acid is always numbered as C1. The structure of butyric acid is:

The prefix ‘2, 2-dimethyl’ indicates that the methyl group is attached at C2, and C2 carbon atoms of the butyric acid. The structure of $\text{2, 2-dimethylbutyric acid}$ is:

The trivial names of carboxylic acids are in the general form alkionic acid while the IUPAC names are in the general form alkanoic acid. The suffix ‘ionic’ is replaced by ‘noic’ in the IUPAC name.

The butyric acid is the trivial name, its IUPAC name is butanoic acid. Thus, the IUPAC name of

$\text{2, 2-dimethylbutyric acid}$ is $\text{2, 2-dimethylbutanoic acid}$.

Conclusion

The structure of the compound is drawn and the IUPAC name of the compound is written that corresponds to the given trivial name.

Interpretation Introduction

(c)

Interpretation:

The structure of the molecule is to be drawn and the IUPAC name is to be provided that corresponds to the given trivial name.

Concept introduction:

Carboxylic acids are the compounds containing $\text{RCOOH}$ group. They include both monocarboxylic acids as well as dicarboxylic acids. Trivial names for many mono and dicarboxylic acids are widely accepted by IUPAC, and they are:

The carbonyl carbon atom is always numbered as C1 and the numbering continues. The substituents, if any, attached to the carbon chain are names according to the alphabetical order and the lowest locator number.

The trivial names of carboxylic acids are in the general form alkionic acid, while the IUPAC names are in the general form alkanoic acid. The suffix ‘ionic’ is replaced by ‘noic’ in the IUPAC name.

Answer to Problem F.12P

The structure of the molecule that corresponds to the given trivial name $\text{2-aminopropionic acid}$ is:

The IUPAC name of $\text{2-aminopropionic acid}$ is $\text{2-aminopropanoic acid}$.

Explanation of Solution

The given IUPAC name is $\text{2-aminopropionic acid}$. The name suggests that it is a monocarboxylic substituted acid. Propionic acid is the trivial name of the carboxylic acid containing three carbon atoms. The carbonyl carbon of the carboxylic acid is always numbered as C1. The structure of propionic acid is:

The prefix ‘2-amino’ indicates that amine group (${\text{NH}}_2$) is attached at C2 carbon atom of the propionic acid. The structure of $\text{2-aminopropionic acid}$ is:

The trivial names of carboxylic acids are in the general form alkionic acid while the IUPAC names are in the general form alkanoic acid. The suffix ‘ionic’ is replaced by ‘noic’ in the IUPAC name.

The propionic acid is the trivial name; its IUPAC name is propanoic acid. Thus, the IUPAC name of $\text{2-aminopropionic acid}$ is $\text{2-aminopropanoic acid}$.

Conclusion

The structure of the compound is drawn and the IUPAC name of the compound is written that corresponds to the given trivial name.

Interpretation Introduction

(d)

Interpretation:

The structure of the molecule is to be drawn and the IUPAC name is to be provided that corresponds to the given trivial name.

Concept introduction:

Carboxylic acids are the compounds containing $\text{RCOOH}$ group. They include both monocarboxylic acids as well as dicarboxylic acids. Trivial names for many mono and dicarboxylic acids are widely accepted by IUPAC and they are:

The carbonyl carbon atom is always numbered as C1 and the numbering continues. The substituents, if any, attached to the carbon chain are names according to the alphabetical order and the lowest locator number.

The trivial names of carboxylic acids are in the general form alkionic acid, while the IUPAC names are in the general form alkanoic acid. The suffix ‘ionic’ is replaced by ‘noic’ in the IUPAC name.

Answer to Problem F.12P

The structure of the molecule that corresponds to the given trivial name $\text{dimethylmaleic acid}$ is:

The IUPAC name of $\text{dimethylmaleic acid}$ is $\text{(Z)-2, 3-dimethylbutenedioic acid}$.

Explanation of Solution

The given IUPAC name is $\text{dimethylmaleic acid}$. Maleic acid is a four carbon chain containing two $\text{RCOOH}$ groups and a $\text{C=C}$ between C2 and C3 carbon atoms. The two $\text{RCOOH}$ groups are located at each end. The numbering would start from any one carbonyl carbon. The structure of maleic acid is:

Note the stereochemistry about the doubly bonded carbon atoms. The two high-priority groups are on the same side of the double bond making it (Z) stereoisomer.

The prefix $\text{dimethyl}$ indicates that the methyl group is attached at C2 and C3 carbon atoms of maleic acid. The locator numbers 2 and 3 are not included in the trivial name explicitly because there are only C2 and C3 carbon atoms to which any substituent can be attached. Thus, the complete structure of $\text{dimethylmaleic acid}$ is:

As the longest carbon chain has four atoms, the root name for carboxylic acid is $\text{(Z)-butenedione}$. The prefix (Z) denotes the stereochemistry of the groups around the doubly bonded carbon atoms. Also, the ‘ane’ has been changed to ‘ene’ as there is one double bond between C2 and C3 carbon atoms, the locator numbers are explicitly written in the IUPAC name, albeit the substituents can get attached only at those two carbon atoms. Hence, the IUPAC name of $\text{dimethylmaleic acid}$ is $\text{(Z)-2, 3-dimethylbutenedioic acid}$.

Conclusion

The structure of the compound is drawn and the IUPAC name of the compound is written that corresponds to the given trivial name.

Interpretation Introduction

(e)

Interpretation:

The structure of the molecule is to be drawn and the IUPAC name is to be provided that corresponds to the given trivial name.

Concept introduction:

Carboxylic acids are the compounds containing $\text{RCOOH}$ group. They include both monocarboxylic acids as well as dicarboxylic acids. Trivial names for many mono and dicarboxylic acids are widely accepted by IUPAC and they are:

The carbonyl carbon atom is always numbered as C1 and the numbering continues. The substituents, if any, attached to the carbon chain are names according to the alphabetical order and the lowest locator number.

The trivial names of carboxylic acids are in the general form alkionic acid, while the IUPAC names are in the general form alkanoic acid. The suffix ‘ionic’ is replaced by ‘noic’ in the IUPAC name.

Answer to Problem F.12P

The structure of the molecule that corresponds to the given trivial name $\text{diethylmalonic acid}$ is:

The IUPAC name of $\text{diethylmalonic acid}$ is $\text{2, 2-diethylpropanedionic acid}$.

Explanation of Solution

The given IUPAC name is $\text{diethylmalonic acid}$. Malonic acid is a three carbon chain carboxylic acid with two $\text{RCOOH}$ groups. The two $\text{RCOOH}$ groups are located at each end. The numbering would start from any one carbonyl carbon. The structure of malonic acid is:

The prefix ‘diethyl’ in the name suggests that an ethyl group is attached at C2 carbon atom of the root. The locator numbers 2 and 2 are not included in the name because there is only one carbon atom to which any substituent could get attached. Thus, the complete structure of $\text{diethylmalonic acid}$ is:

As the longest carbon chain has three atoms, the root name for this dicarboxylic acid is $\text{propanedionic acid}$. The alkyl group is written as it is and suffix ‘dionic’ is added. There are ethyl substituents attached at C2, and C2 carbon atoms. Thus, the complete IUPAC name of $\text{diethylmalonic acid}$ is $\text{2, 2-diethylpropanedionic acid}$.

Conclusion

The structure of the compound is drawn and the IUPAC name of the compound is written that corresponds to the given trivial name.