Chapter 17, Problem 17.8P

(a)

Interpretation Introduction

Interpretation: The structural formula for the given compound has to be drawn.

Concept introduction:

Carboxylic acids contain a carbonyl 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

Name of the given compound is phenyl acetic acid.

From the name, we will get the following facts about the structure of the compound.

• ✓ The given compound is a carboxylic acid.
• ✓ A phenyl substituent is attached to the acetic acid; Acetic acid is the common name of ethanoic acid.

Thus,

The structural formula for this compound can be drawn as shown below,

(b)

Interpretation Introduction

Interpretation: The structural formula for the given compound has to be drawn.

Concept introduction:

Carboxylic acids contain a carbonyl 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.

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

Explanation of Solution

Name of the given compound is 4-Aminobutanoic acid

From the name, we will get the following facts about the structure of the compound.

• ✓ The given compound is a carboxylic acid.
• ✓ Parent chain contains four carbon atoms including the carboxylic acid functional group.
• ✓ An amino substituent is attached to the fourth carbon atom in the parent chain.

Thus,

The structural formula for this compound can be drawn as shown below,

(c)

Interpretation Introduction

Interpretation: The structural formula for the given compound has to be drawn.

Concept introduction:

Carboxylic acids contain a carbonyl 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

Name of the given compound is 3-Chloro-4-phenylbutanoic acid.

From the name, we will get the following facts about the structure of the compound.

• ✓ The given compound is a carboxylic acid.
• ✓ Parent chain contains four carbon atoms including the carboxylic acid functional group.
• ✓ One chlorine atom and a phenyl ring substituents are attached to the third and fourth carbon atoms in the parent chain respectively.

Thus,

The structural formula for this compound can be drawn as shown below,

(d)

Interpretation Introduction

Interpretation: The structural formula for the given compound has to be drawn.

Concept introduction:

Carboxylic acids contain a carbonyl 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

Name of the given compound is Propenoic acid (acrylic acid).

From the name, we will get the following facts about the structure of the compound.

• ✓ The given compound is a carboxylic acid.
• ✓ Parent chain contains three carbon atoms including the carboxylic acid functional group.
• ✓ There is a double bond in the compound.

Thus,

The structural formula for this compound can be drawn as shown below,

(e)

Interpretation Introduction

Interpretation: The structural formula for the given compound has to be drawn.

Concept introduction:

Carboxylic acids contain a carbonyl 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

Name of the given compound is (Z)-3-Hexenedioic acid.

From the name, we will get the following facts about the structure of the compound.

• ✓ The given compound is a dicarboxylic acid.
• ✓ Parent chain contains six carbon atoms including the carboxylic acid functional group.
• ✓ There is a double bond in the compound. The higher priority substituents are on same side; (Z)

Thus,

The structural formula for this compound can be drawn as shown below,

(f)

Interpretation Introduction

Interpretation: The structural formula for the given compound has to be drawn.

Concept introduction:

Carboxylic acids contain a carbonyl 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.

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

Explanation of Solution

Name of the given compound is 2-Pentynoic acid.

From the name, we will get the following facts about the structure of the compound.

• ✓ The given compound is a monocarboxylic acid.
• ✓ Parent chain contains five carbon atoms including the carboxylic acid functional group.
• ✓ There is a triple bond in between second and third carbon atoms in the compound.

Thus,

The structural formula for this compound can be drawn as shown below,

(g)

Interpretation Introduction

Interpretation: The structural formula for the given compound has to be drawn.

Concept introduction:

Carboxylic acids contain a carbonyl 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.

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

Explanation of Solution

Name of the given compound is Potassium phenylacetate.

From the name, we will get the following facts about the structure of the compound.

• ✓ The given compound is a potassium salt of phenyl acetic acid.
• ✓ A phenyl substituent is attached to the acetic acid; Acetic acid is the common name of ethanoic acid.

Thus,

The structural formula for this compound can be drawn as shown below,

(h)

Interpretation Introduction

Interpretation: The structural formula for the given compound has to be drawn.

Concept introduction:

Carboxylic acids contain a carbonyl 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.

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

Explanation of Solution

Name of the given compound is sodium oxalate.

From the name, we will get the following facts about the structure of the compound.

• ✓ The given compound is a sodium salt of oxalic acid.
• ✓ Two sodium atoms are attached to the both carboxyl group of oxalic acid.

Thus,

The structural formula for this compound can be drawn as shown below,

(i)

Interpretation Introduction

Interpretation: The structural formula for the given compound has to be drawn.

Concept introduction:

Carboxylic acids contain a carbonyl 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.

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

Explanation of Solution

Name of the given compound is 2-Oxocyclohexanecarboxylic acid.

From the name, we will get the following facts about the structure of the compound.

• ✓ The given compound is a monocarboxylic acid.
• ✓ Parent ring contains six carbon atoms including the carboxylic acid functional group.
• ✓ There is a ketone group on second carbon atom in the parent ring.

Thus,

The structural formula for this compound can be drawn as shown below,

(j)

Interpretation Introduction

Interpretation: The structural formula for the given compound has to be drawn.

Concept introduction:

Carboxylic acids contain a carbonyl 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.

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

Explanation of Solution

Name of the given compound is 2, 2-Dimethylpropanoic acid.

From the name, we will get the following facts about the structure of the compound.

• ✓ The given compound is a monocarboxylic acid.
• ✓ Parent chain contains three carbon atoms including the carboxylic acid functional group.
• ✓ Two methyl substituents are attached on the second carbon atom in the parent chain.

Thus,

The structural formula for this compound can be drawn as shown below,