Chapter 16, Problem 16.15P

(a)

Interpretation Introduction

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

Concept introduction:

The Structural formula of a compound shows how the atoms are arranged in a molecule and, in particular, shows which functional groups are present.

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

Naming Aldehydes:

Aldehyde has 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

Name of the given compound is 1-Chloro-2-propanone.

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

• ✓  The given compound is a ketone compound with three carbon atoms.
• ✓  Chlorine is attached as the substituent in the first carbon atom of the parent chain.

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:

The Structural formula of a compound shows how the atoms are arranged in a molecule and, in particular, shows which functional groups are present.

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

Naming Aldehydes:

Aldehyde has 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

Name of the given compound is 3-Hydroxybutanal.

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

• ✓  The given compound is an aldehyde compound with four carbon atoms including aldehyde functional group.
• ✓  A hydroxy substituent is attached to the third 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:

The Structural formula of a compound shows how the atoms are arranged in a molecule and, in particular, shows which functional groups are present.

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

Naming Aldehydes:

Aldehyde has 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

Name of the given compound is 4-Hydroxy-4-methyl-2-pentanone.

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

• ✓  The given compound is a ketone compound with five carbon atoms including the functional group.
• ✓  A hydroxy substituent is attached to the fourth carbon atom in the parent chain.
• ✓  A methyl group was attached to the fourth carbon atom in the parent chain.

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:

The Structural formula of a compound shows how the atoms are arranged in a molecule and, in particular, shows which functional groups are present.

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

Naming Aldehydes:

Aldehyde has 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.

  

Explanation of Solution

Name of the given compound is 3-Methyl-3-phenylbutanal.

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

• ✓  The given compound is an aldehyde compound with four carbon atoms including aldehyde functional group.
• ✓  A hydroxy substituent and a phenyl substituent are attached to the third carbon atom in the parent chain.

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:

The Structural formula of a compound shows how the atoms are arranged in a molecule and, in particular, shows which functional groups are present.

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

Naming Aldehydes:

Aldehyde has 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

Name of the given compound is 1, 3-Cyclohexanedione.

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

• ✓  The given compound is a ketone compound and it has six membered carbon ring.
• ✓  Two ketone groups are there in first and third carbon atom in the parent ring.

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:

The Structural formula of a compound shows how the atoms are arranged in a molecule and, in particular, shows which functional groups are present.

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

Naming Aldehydes:

Aldehyde has 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

Name of the given compound is 3-Methyl-3-buten-2-one.

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

• ✓  The given compound is a ketone compound and it will have four membered carbon chain.
• ✓  A methyl group is attached to the third carbon atom in the parent chain and also there is a $C=C$ bond between third and fourth carbon.

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:

The Structural formula of a compound shows how the atoms are arranged in a molecule and, in particular, shows which functional groups are present.

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

Naming Aldehydes:

Aldehyde has 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

Name of the given compound is 5-Oxohexanal.

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

• ✓  The given compound contains both the aldehyde and ketone functional groups but the aldehyde has more priority over ketone, and so the ketone will consider as the substituent.
• ✓  Ketone group is in fifth carbon of the parent chain.

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:

The Structural formula of a compound shows how the atoms are arranged in a molecule and, in particular, shows which functional groups are present.

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

Naming Aldehydes:

Aldehyde has 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

Name of the given compound is 2,2-Dimethylcyclohexanecarbaldehyde.

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

• ✓  The given compound contains an aldehyde functional group.
• ✓  Aldehyde included to the cyclohexane ring and also two methyl groups are attached to the second carbon atom of the ring.

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:

The Structural formula of a compound shows how the atoms are arranged in a molecule and, in particular, shows which functional groups are present.

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-Oxobutanoic acid.

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

• ✓  The given compound is an acid and which contains four carbon atoms including the COOH functional group.
• ✓  A ketone group was attached as a substituent in the third carbon atom in the parent carbon chain.

Thus,

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