Chapter 23, Problem 23.16P

(a)

Interpretation Introduction

Interpretation:

Structural formula of N,N-dimethylaniline has to be given.

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 23.16P

Explanation of Solution

Given amine is N,N-dimethylaniline.

From the name it is clear that,

• It is a tertiary amine since the name has prefix “N, N-“
• The parent name is aniline and hence a benzene ring attached to an amine group is present.
• Two methyl groups are present at the nitrogen atom of amine.

Therefore,

The structural formula of N,N-dimethylaniline is,

(b)

Interpretation Introduction

Interpretation:

Structural formula of triethylamine has to be given.

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.

Common name of amine:

Alkyl groups attached to nitrogen atom of amine group must follow alphabetical order with the suffix “-amine”.

Answer to Problem 23.16P

Explanation of Solution

Given amine is triethylamine.

From the name it is clear that, it is a tertiary amine where three ethyl groups are present at the nitrogen atom of amine.

Therefore,

The structural formula of triethylamine is,

(c)

Interpretation Introduction

Interpretation:

Structural formula of tert-butylamine has to be given.

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.

Common name of amine:

Alkyl groups attached to nitrogen atom of amine group must follow alphabetical order with the suffix “-amine”.

Answer to Problem 23.16P

Explanation of Solution

Given amine is tert-butylamine.

From the name it is clear that, it is a primary amine where one tert-butyl group is present at the nitrogen atom of amine.

Therefore,

The structural formula of tert-butylamine is,

(d)

Interpretation Introduction

Interpretation:

Structural formula of 1,4-benzenediamine has to be given.

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 23.16P

Explanation of Solution

Given amine is 1,4-benzenediamine.

From the name it is clear that,

• Two amine groups are present where both are primary amines.
• The parent name is benzene.
• One amine groups is present at the first and fourth position of benzene.

Therefore,

The structural formula of 1,4-benzenediamine is,

(e)

Interpretation Introduction

Interpretation:

Structural formula of 4-aminobutanoic acid has to be given.

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 $RCOOH$

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 23.16P

Explanation of Solution

Given amine is 4-aminobutanoic acid.

From the name it is clear that,

• It has both $N{H}_{2}and\text{ COOH}$ group. Comparing to amine, carboxylic acid has higher priority. Hence the prefix “amino” should be given for the compound
• The longest carbon chain has four carbon atoms with a $COOH$ group at the first carbon atom and hence the parent name is butanoic acid.
• Amino group is present at the fourth carbon atom.

Therefore,

The structural formula of 4-aminobutanoic acid is,

(f)

Interpretation Introduction

Interpretation:

Structural formula of (R)-2-butanamine has to be given.

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 23.16P

Explanation of Solution

Given amine is (R)-2-butanamine.

From the name it is clear that,

• It is a primary amine.
  • The longest carbon chain has four carbon atoms with a $N{H}_2$ group and hence the parent name is butanamine.
• $N{H}_2$ group is present at the second carbon atom of butanamine.

• The second carbon atom is chiral and the configuration is R. Hence, the numbering according to the decreasing atomic mass of atoms attached to chiral carbon must follows clockwise direction.

Therefore,

The structural formula of (R)-2-butanamine is,

(g)

Interpretation Introduction

Interpretation:

Structural formula of benzylamine has to be given.

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.

Common name of amine:

Alkyl groups attached to nitrogen atom of amine group must follow alphabetical order with the suffix “-amine”.

Answer to Problem 23.16P

Explanation of Solution

Given amine is benzylamine.

From the name it is clear that, it is a primary amine where one benzyl group is present at the nitrogen atom of amine.

Therefore,

The structural formula of benzylamine is,

(h)

Interpretation Introduction

Interpretation:

Structural formula of trans-2-aminocyclohexanol has to be given.

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.

Alcohol: It is an organic compound where it contains at least one $-OH$ group. It is represented as $ROH$.

The IUPAC name for alcohol is written by replacing the ‘e’ of alkane to ‘ol’.

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 23.16P

Explanation of Solution

Given amine is trans-2-aminocyclohexanol.

From the name it is clear that,

• It has both $N{H}_{2}and\text{ OH}$ groups. Comparing to amine, alcohol has higher priority. Hence the prefix “amino” should be given for the compound
• The parent name is cyclohexanol and thus it has six membered ring attached with the primary amine group ($N{H}_2$ ) and alcohol group
• Amino group is present at the second carbon atom.
• It is a trans isomer where amine and alcohol group be trans to each other (opposite side of the bond).

Therefore,

The structural formula of trans-2-aminocyclohexanol is,

(i)

Interpretation Introduction

Interpretation:

Structural formula of 1-phenyl-2-propanamine has to be given.

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 $RCOOH$

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 23.16P

Explanation of Solution

Given amine is 1-phenyl-2-propanamine.

From the name it is clear that,

• It is a primary 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 2-propanamine.
• One phenyl group is present at the second carbon atom of 1-propanamine.

Therefore,

The structural formula of 1-phenyl-2-propanamine is,

(j)

Interpretation Introduction

Interpretation:

Structural formula of lithium diisopropylamide has to be given.

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.

Common name of amine:

Alkyl groups attached to nitrogen atom of amine group must follow alphabetical order with the suffix “-amine”.

Answer to Problem 23.16P

Explanation of Solution

Given amine is lithium diisopropylamide.

From the name it is clear that, in the compound have an anion and a cation. Lithium is the cation. Anion is the amine where two isopropyl group present at the nitrogen atom of amine.

Therefore,

The structural formula of lithium diisopropylamide is,

(j)

Interpretation Introduction

Interpretation:

Structural formula of benzyltrimethylammonium hydroxide has to be given.

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.

Common name of amine:

Alkyl groups attached to nitrogen atom of amine group must follow alphabetical order with the suffix “-amine”.

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.

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 23.16P

Explanation of Solution

Given amine is benzyltrimethylammonium hydroxide.

From the name it is clear that, it is a hydroxide salt. The compound has an anion and a cation. Lithium is the cation. Cation is the benzyltrimethylammonium where three ethyl groups and a benzyl group are present at the nitrogen atom of amine. Anion is the hydroxide ion.

Therefore,

The structural formula of benzyltrimethylammonium hydroxide is,