Chapter F, Problem F.21P

Interpretation Introduction

(a)

Interpretation:

The structure of the molecule hexanedinitrile is to be drawn.

Concept introduction:

The structure of a nitrile can be drawn on the basis of its IUPAC name as follows. The name consists of three parts, a prefix, a root, and a suffix. The suffix is ‘nitrile’. The root, which is the middle part of the name, shows the number of carbons in the longest continuous carbon chain that also contains the nitrile group. The nitrile carbon is a part of this chain. If the nitrile is attached to a ring, the nitrile carbon is not considered a part of the root. Any lower priority functional groups attached to this chain or ring are named in the prefix with their locants. The numbering of the carbons in the root starts at the nitrile carbon if the root is an open chain. If the root is a ring, the carbon with the nitrile group is numbered 1, and the numbering continues in the direction that will give the lowest possible numbers to any substituent groups.

Interpretation Introduction

(b)

Interpretation:

The structure of the molecule, $\text{(S)-4-nitroheptanenitrile}$ is to be drawn.

Concept introduction:

The structure of a nitrile can be drawn on the basis of its IUPAC name as follows. The name consists of three parts, a prefix, a root, and a suffix. The suffix is ‘nitrile’. The root, the middle part of the name shows the number of carbons in the longest continuous carbon chain that also contains the nitrile group. The nitrile carbon is a part of this chain. If the nitrile is attached to a ring, the nitrile carbon is not considered a part of the root. Any lower priority functional groups attached to this chain or ring are named in the prefix, with their locants. The numbering of the carbons in the root starts at the nitrile carbon if the root is an open chain. If the root is a ring, the carbon with the nitrile group is numbered 1, and the numbering continues in the direction that will give the lowest possible numbers to any substituent groups.

If the molecule contains a chiral carbon, the absolute configuration is specified at the start of the name. The configuration is shown using a dash/wedge representation so that the priority groups 1 to 3 are arranged in a clockwise direction with the lowest priority group pointing away from the observer for an R configuration. The three groups are arranged in counterclockwise direction with the lowest priority group pointing away from the observer for an S configuration. The respective directions are reversed if the lowest priority group is pointing toward the observer.

Interpretation Introduction

(c)

Interpretation:

The structure of $\text{4, 4-diethylcyclohexanecarbonitrile}$ is to be drawn.

Concept introduction:

The structure of a nitrile can be drawn on the basis of its IUPAC name as follows. The name consists of three parts, a prefix, a root, and a suffix. The suffix is ‘nitrile’. The root, the middle part of the name shows the number of carbons in the longest continuous carbon chain that also contains the nitrile group. The nitrile carbon is a part of this chain. If the nitrile is attached to a ring, the nitrile carbon is not considered a part of the root. Any lower priority functional groups attached to this chain or ring are named in the prefix, with their locants. The numbering of the carbons in the root starts at the nitrile carbon if the root is an open chain. If the root is a ring, the carbon with the nitrile group is numbered 1, and the numbering continues in the direction that will give the lowest possible numbers to any substituents.