Chapter 23, Problem 23.17P

(a)

Interpretation Introduction

Interpretation:

Given compound has to be named.

Concept introduction:

In chemistry Structure is the arrangement of chemical bonds between atoms in a molecule, specifically which atoms are chemically bonded to what other atoms with what kind of chemical bond.

Amines are the derivatives of ammonia $\left(N{H}_3\right)$ with one or more of the hydrogens replaced with a substituent such as an alkyl group.

Depending on the number of carbon side chain of the amide, different types of amides can form.

From the name of the compound its structure can be determined.

Primary amines can be named in the IUPAC system in several ways,

For simple amines the suffix – amine is added to the name of the alkyl substituent.

The suffix-amine can be used in place of the final –e in the name of the parent compound.

For a secondary amine an N prefixes the compound giving the shorter carbon chain and its chain prefix name.

For a tertiary amine an N, N prefixes the compound giving the two shorter carbon chains and their side chain prefix names.

Answer to Problem 23.17P

Name of the given compound is 3,4-Dimethoxyaniline.

Explanation of Solution

Given compound is,

From the structure it is clear that,

• It is a primary amine
• The parent name is aniline since a benzene ring attached to an amine group is present.
• One methoxy group is present at the third and fourth carbon of benzene ring.

Therefore,

Name of the given compound is 3,4-Dimethoxyaniline.

(b)

Interpretation Introduction

Interpretation:

Given compound has to be named.

Concept introduction:

According to IUPAC nomenclature, the naming of compound is determined by the priority of the functional group if more than one functional group is present. The carbon attached to the functional group having most priority should get the least number while naming the compound.

The order of priority is,

$\begin{array}{l}\text{carboxylic}\text{acid>esters>amides>aldehydes>ketones>}\text{alcolhols>thiols>}\text{amines}\text{>}\\ \text{ethers>alkenes>alkyl}\text{halides>alkanes}\end{array}$

Amines are the derivatives of ammonia $\left(N{H}_3\right)$ with one or more of the hydrogens replaced with a substituent such as an alkyl group.

Depending on the number of carbon side chain of the amide, different types of amides can form.

From the name of the compound its structure can be determined.

Primary amines can be named in the IUPAC system in several ways,

For simple amines the suffix – amine is added to the name of the alkyl substituent.

The suffix-amine can be used in place of the final –e in the name of the parent compound.

For a secondary amine an N prefixes the compound giving the shorter carbon chain and its chain prefix name.

For a tertiary amine an N, N prefixes the compound giving the two shorter carbon chains and their side chain prefix names.

The IUPAC name for the carboxylic acid is written by replacing the ‘e’ of alkane to ‘oic acid’.

If the compound contains amine and a functional group that has higher precedence than the amine group, then the amine group should be indicated with the prefix “amino”

Answer to Problem 23.17P

Name of the given compound is 1-aminomethylcyclohexanol.

Explanation of Solution

Given compound is,

From the structure it is clear that,

• It has both $N{H}_{2}and\text{ OH}$ group. Comparing to amine, alcohol has higher priority. Hence the prefix “amino” should be given for the compound
• The compound has a six membered ring and hence parent name is cyclohexanol.
• Amino group is present at the first carbon atom.

Therefore,

Name of the given compound is 1-Aminomethylcyclohexanol.

(c)

Interpretation Introduction

Interpretation:

Given compound has to be named.

Concept introduction:

According to IUPAC nomenclature, the naming of compound is determined by the priority of the functional group if more than one functional group is present. The carbon attached to the functional group having most priority should get the least number while naming the compound.

The order of priority is,

$\begin{array}{l}\text{carboxylic}\text{acid>esters>amides>aldehydes>ketones>}\text{alcolhols>thiols>}\text{amines}\text{>}\\ \text{ethers>alkenes>alkyl}\text{halides>alkanes}\end{array}$

Amines are the derivatives of ammonia $\left(N{H}_3\right)$ with one or more of the hydrogens replaced with a substituent such as an alkyl group.

Depending on the number of carbon side chain of the amide, different types of amides can form.

From the name of the compound its structure can be determined.

Primary amines can be named in the IUPAC system in several ways,

For simple amines the suffix – amine is added to the name of the alkyl substituent.

The suffix-amine can be used in place of the final –e in the name of the parent compound.

For a secondary amine an N prefixes the compound giving the shorter carbon chain and its chain prefix name.

For a tertiary amine an N, N prefixes the compound giving the two shorter carbon chains and their side chain prefix names.

Answer to Problem 23.17P

Name of the given compound is 1-Naphthylamine.

Explanation of Solution

Given compound is,

From the structure it is clear that, the compound is a primary amine where a naphthyl group is attached to the nitrogen atom of amine.

Therefore,

Name of the given compound is 1-Naphthylamine.

(d)

Interpretation Introduction

Interpretation:

Given compound has to be named.

Concept introduction:

In chemistry Structure is the arrangement of chemical bonds between atoms in a molecule, specifically which atoms are chemically bonded to what other atoms with what kind of chemical bond.

Amines are the derivatives of ammonia $\left(N{H}_3\right)$ with one or more of the hydrogens replaced with a substituent such as an alkyl group.

Depending on the number of carbon side chain of the amide, different types of amides can form.

From the name of the compound its structure can be determined.

Primary amines can be named in the IUPAC system in several ways,

For simple amines the suffix – amine is added to the name of the alkyl substituent.

The suffix-amine can be used in place of the final –e in the name of the parent compound.

For a secondary amine an N prefixes the compound giving the shorter carbon chain and its chain prefix name.

For a tertiary amine an N, N prefixes the compound giving the two shorter carbon chains and their side chain prefix names.

Answer to Problem 23.17P

Name of the given compound is N-methylpropylamine.

Explanation of Solution

Given compound is,

From the structure it is clear that,

• It is a secondary amine with a methyl group and a propyl group present in the nitrogen atom of amine.
• The longest carbon chain has three carbon atoms with a $N{H}_2$ group at the second carbon atom and hence the parent name is 1-propanamine.

Therefore,

Name of the given compound is N-methylpropylamine.

(e)

Interpretation Introduction

Interpretation:

Given compound has to be named.

Concept introduction:

In chemistry Structure is the arrangement of chemical bonds between atoms in a molecule, specifically which atoms are chemically bonded to what other atoms with what kind of chemical bond.

Amines are the derivatives of ammonia $\left(N{H}_3\right)$ with one or more of the hydrogens replaced with a substituent such as an alkyl group.

Depending on the number of carbon side chain of the amide, different types of amides can form.

From the name of the compound its structure can be determined.

Primary amines can be named in the IUPAC system in several ways,

For simple amines the suffix – amine is added to the name of the alkyl substituent.

The suffix-amine can be used in place of the final –e in the name of the parent compound.

For a secondary amine an N prefixes the compound giving the shorter carbon chain and its chain prefix name.

For a tertiary amine an N, N prefixes the compound giving the two shorter carbon chains and their side chain prefix names.

If nitrogen atom in amine group is attached with four atoms or group of atoms then the compound can be named as the salt of the corresponding amine. Amines react with $HCl$ to form a hydrochloride salt.

For the naming of the salt, ending of the corresponding amine “-amine (pyridine, aniline)” is replaced by “ammonium (pyridinium, anilinium)” and anion name is given as suffix.

Answer to Problem 23.17P

Name of the given compound is anilinium chloride.

Explanation of Solution

Given compound is,

From the structure it is clear that,

• It is a hydrochloride salt.
• The compound has cation part where nitrogen atom of amine is bonded with a benzene ring. The parent name is written by replacing the ‘aniline’ to ‘anilinium’.
• The anion is chloride.

Therefore,

Name of the given compound is anilinium chloride.

(f)

Interpretation Introduction

Interpretation:

Given compound has to be named.

Concept introduction:

In chemistry Structure is the arrangement of chemical bonds between atoms in a molecule, specifically which atoms are chemically bonded to what other atoms with what kind of chemical bond.

Amines are the derivatives of ammonia $\left(N{H}_3\right)$ with one or more of the hydrogens replaced with a substituent such as an alkyl group.

Depending on the number of carbon side chain of the amide, different types of amides can form.

From the name of the compound its structure can be determined.

Primary amines can be named in the IUPAC system in several ways,

For simple amines the suffix – amine is added to the name of the alkyl substituent.

The suffix-amine can be used in place of the final –e in the name of the parent compound.

For a secondary amine an N prefixes the compound giving the shorter carbon chain and its chain prefix name.

For a tertiary amine an N, N prefixes the compound giving the two shorter carbon chains and their side chain prefix names.

Diazonium compounds are organic compounds having $R-N_2{}^{+}{X}^{-}$ as functional group where R can be an alkyl or aryl group and X can be an organic or inorganic anion.

Answer to Problem 23.17P

Name of the given compound is Benzenediazonium chloride.

Explanation of Solution

Given compound is,

From the structure it is clear that,

• It is a diazonium salt.
• The compound has cation part where alkyl group attached to $-N_2$ is a benzene ring and hence the parent name is benzenediazonium
• The anion is chloride.

Therefore,

Name of the given compound is Benzenediazonium chloride.

(g)

Interpretation Introduction

Interpretation:

Given compound has to be named.

Concept introduction:

In chemistry Structure is the arrangement of chemical bonds between atoms in a molecule, specifically which atoms are chemically bonded to what other atoms with what kind of chemical bond.

Amines are the derivatives of ammonia $\left(N{H}_3\right)$ with one or more of the hydrogens replaced with a substituent such as an alkyl group.

Depending on the number of carbon side chain of the amide, different types of amides can form.

From the name of the compound its structure can be determined.

Primary amines can be named in the IUPAC system in several ways,

For simple amines the suffix – amine is added to the name of the alkyl substituent.

The suffix-amine can be used in place of the final –e in the name of the parent compound.

For a secondary amine an N prefixes the compound giving the shorter carbon chain and its chain prefix name.

For a tertiary amine an N, N prefixes the compound giving the two shorter carbon chains and their side chain prefix names.

R and S nomenclature: it is used to assign the molecule using CIP rules.

According to Cahn-Ingold-Prelog system,

The group attached to asymmetric center should be ranked based on the atomic number of atom which directly connected to asymmetric center. The higher the atomic number of atom, higher the priority. If there is tie, then consider the next atoms attached to the connected atom and so on.

Check the direction of arrow drawn in the direction of decreasing priority. If the arrow points clockwise direction, then the atom has R configuration. If the arrow points counterclockwise direction, then the atom has S configuration. If the group with lowest priority is not bonded by a hatched wedge, then interchange this group (lowest priority) by group bonded to hatched wedge and draw the arrow in priority order but the configuration is assigned as just reverse.

Answer to Problem 23.17P

Name of the given compound is (R)-2-Hexanamine.

Explanation of Solution

Given compound is,

From the structure it is clear that,

• It is a primary amine.
• The longest carbon chain has six carbon atoms with a $N{H}_2$ group and hence the parent name is hexanamine.
• $N{H}_2$ group is present at the second carbon atom of hexanamine.
• The second carbon atom is chiral. The numbering according to the decreasing atomic mass of atoms attached to chiral carbon follows clockwise direction. Hence, the configuration is R.

Therefore,

Name of the given compound is (R)-2-Hexanamine.

(c)

Interpretation Introduction

Interpretation:

Given compound has to be named.

Concept introduction:

According to IUPAC nomenclature, the naming of compound is determined by the priority of the functional group if more than one functional group is present. The carbon attached to the functional group having most priority should get the least number while naming the compound.

The order of priority is,

$\begin{array}{l}\text{carboxylic}\text{acid>esters>amides>aldehydes>ketones>}\text{alcolhols>thiols>}\text{amines}\text{>}\\ \text{ethers>alkenes>alkyl}\text{halides>alkanes}\end{array}$

Amines are the derivatives of ammonia $\left(N{H}_3\right)$ with one or more of the hydrogens replaced with a substituent such as an alkyl group.

Depending on the number of carbon side chain of the amide, different types of amides can form.

From the name of the compound its structure can be determined.

Primary amines can be named in the IUPAC system in several ways,

For simple amines the suffix – amine is added to the name of the alkyl substituent.

The suffix-amine can be used in place of the final –e in the name of the parent compound.

For a secondary amine an N prefixes the compound giving the shorter carbon chain and its chain prefix name.

For a tertiary amine an N, N prefixes the compound giving the two shorter carbon chains and their side chain prefix names.

Carboxylic acid: One $-OH$ group is attached to the carbonyl carbon atom of the compound. It is represented as $RCOOH$

Answer to Problem 23.17P

Name of the given compound is Pyridine-3-carboxylic acid.

Explanation of Solution

Given compound is,

From the structure it is clear that, the compound is a pyridine where a carboxylic acid group is attached to the third carbon atom of pyridine.

Therefore,

Name of the given compound is Pyridine-3-carboxylic acid.