Chapter 23, Problem 23.51SP

(a)

Interpretation Introduction

To determine: The relative configurations of the stereoisomers of tartaric acid established from the given synthesis.

Interpretation: The relative configurations of the stereoisomers of tartaric acid established from the given synthesis are to be stated.

Concept introduction: Nucleophilic addition takes place when hydrogen cyanide reacts with aldehyde or ketones. Hydrogen cyanide attacks the carbonyl group of aldehydes and ketones to form cyanohydrin. It undergoes acidic hydrolysis to give carboxylic acid.

(b)

Interpretation Introduction

To determine: The relative configurations of the stereoisomers of tartaric acid established from the given synthesis.

Interpretation: The relative configurations of the stereoisomers of tartaric acid established from the given synthesis are to be stated.

Concept introduction: Nucleophilic addition takes place when hydrogen cyanide reacts with aldehyde or ketones. Hydrogen cyanide attacks the carbonyl group of aldehydes and ketones to form cyanohydrin. It undergoes acidic hydrolysis to give carboxylic acid.

(c)

Interpretation Introduction

To determine: The relative configurations of the stereoisomers of tartaric acid established from the given synthesis.

Interpretation: The relative configurations of the stereoisomers of tartaric acid established from the given synthesis are to be stated.

Concept introduction: Nucleophilic addition takes place when hydrogen cyanide reacts with aldehyde or ketones. Hydrogen cyanide attacks the carbonyl group of aldehydes and ketones to form cyanohydrin. It undergoes acidic hydrolysis to give carboxylic acid.

(d)

Interpretation Introduction

To determine: The absolute configuration of A, B, C and D.

Interpretation: The absolute configuration of A, B, C and D is to be shown.

Concept introduction: Nucleophilic addition takes place when hydrogen cyanide reacts with aldehyde or ketones. Hydrogen cyanide attacks the carbonyl group of aldehydes and ketones to form cyanohydrin. It undergoes acidic hydrolysis to give carboxylic acid.

(e)

Interpretation Introduction

To determine: The absolute configuration of $(+)$-tartaric acid, $(-)$-tartaric acid and meso-tartaric acid.

Interpretation: The absolute configuration of $(+)$-tartaric acid, $(-)$-tartaric acid and meso-tartaric acid is to be shown.

Concept introduction: Nucleophilic addition takes place when hydrogen cyanide reacts with aldehyde or ketones. Hydrogen cyanide attacks the carbonyl group of aldehydes and ketones to form cyanohydrin. It undergoes acidic hydrolysis to give carboxylic acid.