Chapter 16, Problem 16.14P

(a)

Interpretation Introduction

Interpretation:

The given compound’s IUPAC name has to be determined and the relevant stereochemistry should be specified.

Concept introduction:

The functional group in the aldehydes and Ketones are carbonyl group.

Naming Aldehydes:

Aldehydes have at least one hydrogen attached to the carbonyl carbon atom.

The IUPAC naming of aldehydes is obtained by replacing the final "e" on the name of the parent hydrocarbon with "al".

For example:

Naming Ketones:

The IUPAC name of a ketones are obtained by replacing the "e" on the end of the parent hydrocarbon with "one".

Only few ketones have common name.

For example:

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

The given compound is as follows.

Let’s given numbering to this compound as follows,

The parent chain contains 9 carbon atoms; in the fifth carbon atom a ketone functional group is attached.

Thus, according to IUPAC this compound can be named as 5-Nonanone.

(b)

Interpretation Introduction

Interpretation:

The given compound’s IUPAC name has to be determined and the relevant stereochemistry should be specified.

Concept introduction:

The functional group in the aldehydes and Ketones are carbonyl group.

Naming Aldehydes:

Aldehydes have at least one hydrogen attached to the carbonyl carbon atom.

The IUPAC naming of aldehydes is obtained by replacing the final "e" on the name of the parent hydrocarbon with "al".

For example:

Naming Ketones:

The IUPAC name of a ketones are obtained by replacing the "e" on the end of the parent hydrocarbon with "one".

Only few ketones have common name.

For example:

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

The given compound is as follows.

Let’s write give the numbering to this compound.

This parent ring has five carbon atoms; a methyl group was attached to the second carbon atom.  Therefore, according to the IUPAC rules, the compound can be named as $\text{2-methylcyclopentanone}$

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

The numbering follows an anti-clock wise direction and so molecule is in as S configuration.

Thus, the compound name can be written as $\text{(S)-2-methylcyclopentanone}$

(c)

Interpretation Introduction

Interpretation:

The given compound’s IUPAC name has to be determined and the relevant stereochemistry should be specified.

Concept introduction:

The functional group in the aldehydes and Ketones are carbonyl group.

Naming Aldehydes:

Aldehydes have at least one hydrogen attached to the carbonyl carbon atom.

The IUPAC naming of aldehydes is obtained by replacing the final "e" on the name of the parent hydrocarbon with "al".

For example:

Naming Ketones:

The IUPAC name of a ketones are obtained by replacing the "e" on the end of the parent hydrocarbon with "one".

Only few ketones have common name.

For example:

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

The given compound is as follows.

Let’s give the numbering to the given compound.

The parent hydrocarbon chain has two functional groups and they are alkene ($-C=C-$) and aldehyde ($-CHO$). According to IUPAC the aldehyde group has higher priority. Thus the compound can be named as 2-Methyl-2-butenal.

(d)

Interpretation Introduction

Interpretation:

The given compound’s IUPAC name has to be determined and the relevant stereochemistry should be specified.

Concept introduction:

The functional group in the aldehydes and Ketones are carbonyl group.

Naming Aldehydes:

Aldehydes have at least one hydrogen attached to the carbonyl carbon atom.

The IUPAC naming of aldehydes is obtained by replacing the final "e" on the name of the parent hydrocarbon with "al".

For example:

Naming Ketones:

The IUPAC name of a ketones are obtained by replacing the "e" on the end of the parent hydrocarbon with "one".

Only few ketones have common name.

For example:

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

The given compound is as follows.

Let’s write give the numbering to this compound.

This parent chain has three carbon atoms; a methyl group was attached to the second carbon atom and hydroxyl group was attached to the third carbon atom.  Therefore, according to the IUPAC rules, the compound can be named as 3-Hydroxy-2-methyl-propanal.

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

The numbering of substituents on the chiral center follows clock wise direction and so molecule is in R configuration.

Thus, the compound name can be written as (R)-3-Hydroxy-2-methyl-propanal.

(e)

Interpretation Introduction

Interpretation:

The given compound’s IUPAC name has to be determined and the relevant stereochemistry should be specified.

Concept introduction:

The functional group in the aldehydes and Ketones are carbonyl group.

Naming Aldehydes:

Aldehydes have at least one hydrogen attached to the carbonyl carbon atom.

The IUPAC naming of aldehydes is obtained by replacing the final "e" on the name of the parent hydrocarbon with "al".

For example:

Naming Ketones:

The IUPAC name of a ketones are obtained by replacing the "e" on the end of the parent hydrocarbon with "one".

Only few ketones have common name.

For example:

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

The given compound is as follows.

Let’s give the numbering to the given compound.

A phenyl ring is attached to the first carbon atom in the three membered parent carbon chains. According to IUPAC the aldehyde group has higher priority. Thus the compound can be named as 1-phenyl-1-propanone.

(f)

Interpretation Introduction

Interpretation:

The given compound’s IUPAC name has to be determined and the relevant stereochemistry should be specified.

Concept introduction:

The functional group in the aldehydes and Ketones are carbonyl group.

Naming Aldehydes:

Aldehydes have at least one hydrogen attached to the carbonyl carbon atom.

The IUPAC naming of aldehydes is obtained by replacing the final "e" on the name of the parent hydrocarbon with "al".

For example:

Naming Ketones:

The IUPAC name of a ketones are obtained by replacing the "e" on the end of the parent hydrocarbon with "one".

Only few ketones have common name.

For example:

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

The given compound is as follows.

Let’s write give the numbering to this compound.

This parent ring has six carbon atoms; a hydroxyl (–OH) and a phenyl ring were attached to the first and fifth carbon atoms in the parent chain respectively.  Therefore, according to the IUPAC rules, the compound can be named as 5-Hydroxy-1-phenyl-3-hexanone.

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

The numbering follows an anti-clock wise direction and so molecule is in as S configuration.

Thus, the compound name can be written as (S)-5-Hydroxy-1-phenyl-3-hexanone.

(g)

Interpretation Introduction

Interpretation:

The given compound’s IUPAC name has to be determined and the relevant stereochemistry should be specified.

Concept introduction:

The functional group in the aldehydes and Ketones are carbonyl group.

Naming Aldehydes:

Aldehydes have at least one hydrogen attached to the carbonyl carbon atom.

The IUPAC naming of aldehydes is obtained by replacing the final "e" on the name of the parent hydrocarbon with "al".

For example:

Naming Ketones:

The IUPAC name of a ketones are obtained by replacing the "e" on the end of the parent hydrocarbon with "one".

Only few ketones have common name.

For example:

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

The given compound is as follows.

Let’s give the numbering to the given compound.

The parent hydrocarbon ring has five carbon atoms. A propyl group was attached to the second carbon atom in the ring and two ketone groups were present in first and third carbon atom respectively. Thus the compound can be named as $2-propyl-1,3-cyclopen\tan edione$.

(h)

Interpretation Introduction

Interpretation:

The given compound’s IUPAC name has to be determined and the relevant stereochemistry should be specified.

Concept introduction:

The functional group in the aldehydes and Ketones are carbonyl group.

Naming Aldehydes:

Aldehydes have at least one hydrogen attached to the carbonyl carbon atom.

The IUPAC naming of aldehydes is obtained by replacing the final "e" on the name of the parent hydrocarbon with "al".

For example:

Naming Ketones:

The IUPAC name of a ketones are obtained by replacing the "e" on the end of the parent hydrocarbon with "one".

Only few ketones have common name.

For example:

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

The given compound is as follows.

Let’s give the numbering to the given compound.

The parent hydrocarbon chain has five carbon atoms with two aldehydes on both ends. Thus according to IUPAC the compound can be named as pentanedial.

(i)

Interpretation Introduction

Interpretation:

The given compound’s IUPAC name has to be determined and the relevant stereochemistry should be specified.

Concept introduction:

The functional group in the aldehydes and Ketones are carbonyl group.

Naming Aldehydes:

Aldehydes have at least one hydrogen attached to the carbonyl carbon atom.

The IUPAC naming of aldehydes is obtained by replacing the final "e" on the name of the parent hydrocarbon with "al".

For example:

Naming Ketones:

The IUPAC name of a ketones are obtained by replacing the "e" on the end of the parent hydrocarbon with "one".

Only few ketones have common name.

For example:

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

The given compound is as follows.

Let’s give the numbering to the given compound.

The parent hydrocarbon chain has two functional groups and they are bromine and ketone. According to IUPAC the bromine has higher priority. Thus the compound can be named as 2-bromo-3-pentanone.

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 R configuration.

Thus, the compound name can be written as (R)-2-bromo-3-pentanone.