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 .

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Answer 1

Question

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.

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Classify each of the following molecules as aromatic, antiaromatic, or nonaromatic. ZI NH Explanation Check O aromatic O antiaromatic O nonaromatic O aromatic O antiaromatic H O nonaromatic O aromatic O antiaromatic O nonaromatic ×

Part I. Draw the stepwise reaction mechanism of each product (a, b, c, d, e, f) HO HO OH НОН,С HO OH Sucrose HO CH₂OH H N N HO -H H -OH KMnO4, Heat H OH CH₂OH (d) Phenyl Osatriazole OH НОН,С HO HO + Glacial HOAC HO- HO CH₂OH OH HO Fructose (a) Glucose OH (b) H₂N HN‍ (c) CuSO4-5H2O, ethanol H N N N HO ·H H OH H OH N CH₂OH OH (f) Phenyl Osazone H (e) Carboxy phenyl osatriazole Figure 2.1. Reaction Scheme for the Total Synthesis of Fine Chemicals

Answer 2

Question

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.

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Answer 3

Question

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.

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Answer 4

Question

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.

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Answer 5

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.

Answer 6

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.

Answer 7

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.

Answer 8

(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.

Answer 9

(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.

Answer 10

(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.

Answer 11

(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.

Answer 12

(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.

Answer 13

(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.

Answer 14

(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.

Answer 15

(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.

Answer 16

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Answer 17

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Answer 18

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Answer 19

Ch. 23.2 - Prob. 23.1P Ch. 23.3A - Prob. 23.2P Ch. 23.3A - Prob. 23.3P Ch. 23.3B - Draw and name the enantiomers of the sugars shown...Ch. 23.3B - Prob. 23.5P Ch. 23.3C - Prob. 23.6P Ch. 23.4 - Draw the Haworth projection for the cyclic...Ch. 23.4 - Prob. 23.8P Ch. 23.4 - Prob. 23.9P Ch. 23.4 - Prob. 23.10P

Solution Summary: The author analyzes the relative configurations of the stereoisomers of tartaric acid established from the given synthesis.

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