Chapter 17, Problem 17.7P

Write the IUPAC name of each compound, showing stereochemistry where relevant.

Interpretation Introduction

Interpretation: The IUPAC name for the compound has to be given and its configuration should be specified.

Concept introduction:

Carboxylic acids contain a carbonyl group attached to a hydroxyl group as shown below,

Nomenclature of carboxylic acid:

• Find the Parent hydrocarbon chain.
• Carboxyl carbon must be numbered first.
• Replace the –e in the alkane name with –oic acid.

Naming of compounds with two functional groups;

If a compound has two functional groups, the one with lower priority is indicated by a prefix and another with the higher priority by a suffix.

  $\begin{array}{ccc}\text{Class}& \text{Suffix name}& \text{Prefix name}\\ \text{Carboxylic acid}& \text{-oic acid}& \text{Carboxy}\\ \text{Ester}& \text{-oate}& \text{Alkoxy carbonyl}\\ \text{Amide}& \text{-amide}& \text{Amido}\\ \text{Nitrile}& \text{-ntrile}& \text{Cyano}\\ \text{Aldehyde}& \text{-al}& \text{Oxo(=O)}\\ \text{Aldehyde}& \text{-al}& \text{Formyl(-CH=O)}\\ \text{Ketone}& \text{-one}& \text{Oxo(=O)}\\ \text{Alcohol}& \text{-ol}& \text{Hydroxy}\\ \text{Amine}& \text{-amine}& \text{Amino}\\ \text{Alkene}& \text{-ene}& \text{Alkenyl}\\ \text{Alkyne}& \text{-yne}& \text{Alkynyl}\\ \text{Alkane}& \text{-ane}& \text{Alkyl}\\ \text{Ether}& \text{---}& \text{Alkoxy}\\ \text{Alkylhalide}& \text{---}& \text{Halo}\end{array}$

R and S nomenclature: it is used to assign the molecule using CIP (Cahn-Ingold-Prelog) rules.

The CIP rules are as follows:

Select the chiral carbon and assign the numbers according to the decreasing atomic mass of atoms attached to it.

If the numbering follows clockwise direction then the molecule is termed as R and if it follows anti-clockwise direction then molecule is termed as S.

Explanation of Solution

Given carboxylic acid is,

Let’s given numbering to this compound as follows,

The parent hydrocarbon ring has 6 carbon atoms, one $C=C$ bond and a carboxylic acid group are attached to the first carbon atom.

Thus, according to IUPAC the compound can be named as, 1-Cyclohexenecarboxylic acid.

Interpretation Introduction

Interpretation: The IUPAC name for the compound has to be given and its configuration should be specified.

Concept introduction:

Carboxylic acids contain a carbonyl group attached to a hydroxyl group as shown below,

Nomenclature of carboxylic acid:

• Find the Parent hydrocarbon chain.
• Carboxyl carbon must be numbered first.
• Replace the –e in the alkane name with –oic acid. If two or more carboxylic functional groups are present in the same compound then its number should be taken in to consideration and the prefix di, tri, tetra.. must be used.

Naming of compounds with two functional groups;

If a compound has two functional groups, the one with lower priority is indicated by a prefix and another with the higher priority by a suffix.

  $\begin{array}{ccc}\text{Class}& \text{Suffix name}& \text{Prefix name}\\ \text{Carboxylic acid}& \text{-oic acid}& \text{Carboxy}\\ \text{Ester}& \text{-oate}& \text{Alkoxy carbonyl}\\ \text{Amide}& \text{-amide}& \text{Amido}\\ \text{Nitrile}& \text{-ntrile}& \text{Cyano}\\ \text{Aldehyde}& \text{-al}& \text{Oxo(=O)}\\ \text{Aldehyde}& \text{-al}& \text{Formyl(-CH=O)}\\ \text{Ketone}& \text{-one}& \text{Oxo(=O)}\\ \text{Alcohol}& \text{-ol}& \text{Hydroxy}\\ \text{Amine}& \text{-amine}& \text{Amino}\\ \text{Alkene}& \text{-ene}& \text{Alkenyl}\\ \text{Alkyne}& \text{-yne}& \text{Alkynyl}\\ \text{Alkane}& \text{-ane}& \text{Alkyl}\\ \text{Ether}& \text{---}& \text{Alkoxy}\\ \text{Alkylhalide}& \text{---}& \text{Halo}\end{array}$

R and S nomenclature: it is used to assign the molecule using CIP (Cahn-Ingold-Prelog) rules.

The CIP rules are as follows:

Select the chiral carbon and assign the numbers according to the decreasing atomic mass of atoms attached to it.

If the numbering follows clockwise direction then the molecule is termed as R and if it follows anti-clockwise direction then molecule is termed as S.

Explanation of Solution

Given carboxylic acid is,

Let’s given numbering to this compound as follows,

The parent hydrocarbon chain has five carbon atoms, there are two functional groups, one is –OH (which is attached to the fourth carbon atom) and the other one is –COOH. But, carboxylic acid has higher priority than the -OH, thus –OH will appeared in the name of the compound as the prefix – hydroxy.

Here, this compound has a chiral center (it is highlighted as *); its configuration can be specified as follows,

The numbering follows a clock wise direction and so molecule is in as R- configuration.

Thus, according to IUPAC the compound can be named as, (R)-4-hydroxypentanoic acid.

Interpretation Introduction

Interpretation: The IUPAC name for the compound has to be given and its configuration should be specified.

Concept introduction:

Carboxylic acids contain a carbonyl group attached to a hydroxyl group as shown below,

Nomenclature of carboxylic acid:

• Find the Parent hydrocarbon chain.
• Carboxyl carbon must be numbered first.
• Replace the –e in the alkane name with –oic acid.

Naming of compounds with two functional groups;

If a compound has two functional groups, the one with lower priority is indicated by a prefix and another with the higher priority by a suffix.

  $\begin{array}{ccc}\text{Class}& \text{Suffix name}& \text{Prefix name}\\ \text{Carboxylic acid}& \text{-oic acid}& \text{Carboxy}\\ \text{Ester}& \text{-oate}& \text{Alkoxy carbonyl}\\ \text{Amide}& \text{-amide}& \text{Amido}\\ \text{Nitrile}& \text{-ntrile}& \text{Cyano}\\ \text{Aldehyde}& \text{-al}& \text{Oxo(=O)}\\ \text{Aldehyde}& \text{-al}& \text{Formyl(-CH=O)}\\ \text{Ketone}& \text{-one}& \text{Oxo(=O)}\\ \text{Alcohol}& \text{-ol}& \text{Hydroxy}\\ \text{Amine}& \text{-amine}& \text{Amino}\\ \text{Alkene}& \text{-ene}& \text{Alkenyl}\\ \text{Alkyne}& \text{-yne}& \text{Alkynyl}\\ \text{Alkane}& \text{-ane}& \text{Alkyl}\\ \text{Ether}& \text{---}& \text{Alkoxy}\\ \text{Alkylhalide}& \text{---}& \text{Halo}\end{array}$

E-Z designators are used as like cis-trans terminology for non-similar groups attached alkenes.

In E-Z designations, the groups attached to vinylic positions are checked by their priority on the basis of higher molecular weight. If the higher priority groups are on the same sides, then the configuration is designated as Z. If the higher priority groups are on the opposite sides, then the configuration is designated as E.

Explanation of Solution

Given carboxylic acid is,

Let’s given numbering to this compound as follows,

The parent hydrocarbon chain has eight carbon atoms, two methyl groups were attached to the third and seventh carbon atoms and these branches has lower priority over the carboxylic acid part.

The higher priority group (-COOH) are on the opposite sides, thus the configuration is designated as E.

Thus, according to IUPAC the compound can be named as, (E)-3,7-Dimethyl-2,6-octadienoic acid.

Interpretation Introduction

Interpretation: The IUPAC name for the compound has to be given and its configuration should be specified.

Concept introduction:

Carboxylic acids contain a carbonyl group attached to a hydroxyl group as shown below,

Nomenclature of carboxylic acid:

• Find the Parent hydrocarbon chain.
• Carboxyl carbon must be numbered first.
• Replace the –e in the alkane name with –oic acid.

Naming of compounds with two functional groups;

If a compound has two functional groups, the one with lower priority is indicated by a prefix and another with the higher priority by a suffix.

  $\begin{array}{ccc}\text{Class}& \text{Suffix name}& \text{Prefix name}\\ \text{Carboxylic acid}& \text{-oic acid}& \text{Carboxy}\\ \text{Ester}& \text{-oate}& \text{Alkoxy carbonyl}\\ \text{Amide}& \text{-amide}& \text{Amido}\\ \text{Nitrile}& \text{-ntrile}& \text{Cyano}\\ \text{Aldehyde}& \text{-al}& \text{Oxo(=O)}\\ \text{Aldehyde}& \text{-al}& \text{Formyl(-CH=O)}\\ \text{Ketone}& \text{-one}& \text{Oxo(=O)}\\ \text{Alcohol}& \text{-ol}& \text{Hydroxy}\\ \text{Amine}& \text{-amine}& \text{Amino}\\ \text{Alkene}& \text{-ene}& \text{Alkenyl}\\ \text{Alkyne}& \text{-yne}& \text{Alkynyl}\\ \text{Alkane}& \text{-ane}& \text{Alkyl}\\ \text{Ether}& \text{---}& \text{Alkoxy}\\ \text{Alkylhalide}& \text{---}& \text{Halo}\end{array}$

E-Z designators are used as like cis-trans terminology for non-similar groups attached alkenes.

In E-Z designations, the groups attached to vinylic positions are checked by their priority on the basis of higher molecular weight. If the higher priority groups are on the same sides, then the configuration is designated as Z. If the higher priority groups are on the opposite sides, then the configuration is designated as E.

Explanation of Solution

Given carboxylic acid is,

Let’s given numbering to this compound as follows,

The parent hydrocarbon ring has five carbon atoms, one methyl groups is attached to the first carbon atom  to this same carbon atom carboxylic acid is attached.

Thus, according to IUPAC the compound can be named as, 1-methylcyclopentane carboxylic acid.

Interpretation Introduction

Interpretation: The IUPAC name for the compound has to be given and its configuration should be specified.

Concept introduction:

Carboxylic acids contain a carbonyl group attached to a hydroxyl group as shown below,

Nomenclature of carboxylic acid:

• Find the Parent hydrocarbon chain.
• Carboxyl carbon must be numbered first.
• Replace the –e in the alkane name with –oic acid.

Naming of compounds with two functional groups;

If a compound has two functional groups, the one with lower priority is indicated by a prefix and another with the higher priority by a suffix.

  $\begin{array}{ccc}\text{Class}& \text{Suffix name}& \text{Prefix name}\\ \text{Carboxylic acid}& \text{-oic acid}& \text{Carboxy}\\ \text{Ester}& \text{-oate}& \text{Alkoxy carbonyl}\\ \text{Amide}& \text{-amide}& \text{Amido}\\ \text{Nitrile}& \text{-ntrile}& \text{Cyano}\\ \text{Aldehyde}& \text{-al}& \text{Oxo(=O)}\\ \text{Aldehyde}& \text{-al}& \text{Formyl(-CH=O)}\\ \text{Ketone}& \text{-one}& \text{Oxo(=O)}\\ \text{Alcohol}& \text{-ol}& \text{Hydroxy}\\ \text{Amine}& \text{-amine}& \text{Amino}\\ \text{Alkene}& \text{-ene}& \text{Alkenyl}\\ \text{Alkyne}& \text{-yne}& \text{Alkynyl}\\ \text{Alkane}& \text{-ane}& \text{Alkyl}\\ \text{Ether}& \text{---}& \text{Alkoxy}\\ \text{Alkylhalide}& \text{---}& \text{Halo}\end{array}$

Explanation of Solution

Given compound of acid is,

Let’s given numbering to this compound as follows,

The parent hydrocarbon chain has six carbon atoms; an ammonium ion is attached with the carboxyl part of this compound.

Thus, according to IUPAC the compound can be named as, Ammonium hexanoate.

Interpretation Introduction

Interpretation: The IUPAC name for the compound has to be given and its configuration should be specified.

Concept introduction:

Carboxylic acids contain a carbonyl group attached to a hydroxyl group as shown below,

Nomenclature of carboxylic acid:

• Find the Parent hydrocarbon chain.
• Carboxyl carbon must be numbered first.
• Replace the –e in the alkane name with –oic acid. If two or more carboxylic functional groups are present in the same compound then its number should be taken in to consideration and the prefix di, tri, tetra.. must be used.

Naming of compounds with two functional groups;

If a compound has two functional groups, the one with lower priority is indicated by a prefix and another with the higher priority by a suffix.

  $\begin{array}{ccc}\text{Class}& \text{Suffix name}& \text{Prefix name}\\ \text{Carboxylic acid}& \text{-oic acid}& \text{Carboxy}\\ \text{Ester}& \text{-oate}& \text{Alkoxy carbonyl}\\ \text{Amide}& \text{-amide}& \text{Amido}\\ \text{Nitrile}& \text{-ntrile}& \text{Cyano}\\ \text{Aldehyde}& \text{-al}& \text{Oxo(=O)}\\ \text{Aldehyde}& \text{-al}& \text{Formyl(-CH=O)}\\ \text{Ketone}& \text{-one}& \text{Oxo(=O)}\\ \text{Alcohol}& \text{-ol}& \text{Hydroxy}\\ \text{Amine}& \text{-amine}& \text{Amino}\\ \text{Alkene}& \text{-ene}& \text{Alkenyl}\\ \text{Alkyne}& \text{-yne}& \text{Alkynyl}\\ \text{Alkane}& \text{-ane}& \text{Alkyl}\\ \text{Ether}& \text{---}& \text{Alkoxy}\\ \text{Alkylhalide}& \text{---}& \text{Halo}\end{array}$

R and S nomenclature: it is used to assign the molecule using CIP (Cahn-Ingold-Prelog) rules.

The CIP rules are as follows:

Select the chiral carbon and assign the numbers according to the decreasing atomic mass of atoms attached to it.

If the numbering follows clockwise direction then the molecule is termed as R and if it follows anti-clockwise direction then molecule is termed as S.

Explanation of Solution

Given carboxylic acid is,

Let’s given numbering to this compound as follows,

The parent hydrocarbon chain has four carbon atoms, there are three functional groups, one is –OH (which is attached to the second carbon atom) and the other two is –COOH. But, carboxylic acid has higher priority than the -OH, thus –OH will appeared in the name of the compound as the prefix – hydroxy.

Here, this compound has a chiral center (it is highlighted as *); its configuration can be specified as follows,

The numbering follows a clock wise direction and so molecule is in as R- configuration.

Thus, according to IUPAC the compound can be named as, (R)-2-hydroxybutanedioic acid.