In 1 HNMR, Disparlure, C 19 H 38 O, shows a large absorption in the alkane region, 1 to 2 δ and a triplet at 2.8 δ. Treatment of Disparlure first with aqueous acid and then with KMnO4 yielded undecanoic acid and 6-methylheptanoic acid. A structure for disparlure is to be proposed neglecting stereochemistry. Its structure also is to be given with stereochemistry if the actual compound is a chiral molecule with 7R, 8S stereochemistry. Concept introduction: In 1 HNMR, the epoxides absorb in the region 2.5 -3.5 δ and alkanes in the range 1 to 2 δ. Epoxides get protonated in the presence of acids and the nucleophilic attack of water opens the epoxide ring to give a diol . The diol is oxidized by KMnO 4 to carboxylic acids with less number of carbon atoms. To propose: A structure for disparlure neglecting stereochemistry, satisfying the 1 HNMR data and the chemical reactions given. If the actual compound is a chiral molecule with 7R, 8S stereochemistry its structure with stereochemistry also is to be given.

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Answer 1

Question

Chapter 18.SE, Problem 63GP

Interpretation Introduction

Interpretation:

In ¹HNMR, Disparlure, C₁₉H₃₈O, shows a large absorption in the alkane region, 1 to 2 δ and a triplet at 2.8 δ. Treatment of Disparlure first with aqueous acid and then with KMnO4 yielded undecanoic acid and 6-methylheptanoic acid. A structure for disparlure is to be proposed neglecting stereochemistry. Its structure also is to be given with stereochemistry if the actual compound is a chiral molecule with 7R, 8S stereochemistry.

Concept introduction:

In ¹HNMR, the epoxides absorb in the region 2.5 -3.5 δ and alkanes in the range 1 to 2 δ.

Epoxides get protonated in the presence of acids and the nucleophilic attack of water opens the epoxide ring to give a diol. The diol is oxidized by KMnO₄ to carboxylic acids with less number of carbon atoms.

To propose:

A structure for disparlure neglecting stereochemistry, satisfying the ¹HNMR data and the chemical reactions given. If the actual compound is a chiral molecule with 7R, 8S stereochemistry its structure with stereochemistry also is to be given.

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Answer 2

Question

Chapter 18.SE, Problem 63GP

Interpretation Introduction

Interpretation:

In ¹HNMR, Disparlure, C₁₉H₃₈O, shows a large absorption in the alkane region, 1 to 2 δ and a triplet at 2.8 δ. Treatment of Disparlure first with aqueous acid and then with KMnO4 yielded undecanoic acid and 6-methylheptanoic acid. A structure for disparlure is to be proposed neglecting stereochemistry. Its structure also is to be given with stereochemistry if the actual compound is a chiral molecule with 7R, 8S stereochemistry.

Concept introduction:

In ¹HNMR, the epoxides absorb in the region 2.5 -3.5 δ and alkanes in the range 1 to 2 δ.

Epoxides get protonated in the presence of acids and the nucleophilic attack of water opens the epoxide ring to give a diol. The diol is oxidized by KMnO₄ to carboxylic acids with less number of carbon atoms.

To propose:

A structure for disparlure neglecting stereochemistry, satisfying the ¹HNMR data and the chemical reactions given. If the actual compound is a chiral molecule with 7R, 8S stereochemistry its structure with stereochemistry also is to be given.

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Answer 3

Question

Chapter 18.SE, Problem 63GP

Interpretation Introduction

Interpretation:

In ¹HNMR, Disparlure, C₁₉H₃₈O, shows a large absorption in the alkane region, 1 to 2 δ and a triplet at 2.8 δ. Treatment of Disparlure first with aqueous acid and then with KMnO4 yielded undecanoic acid and 6-methylheptanoic acid. A structure for disparlure is to be proposed neglecting stereochemistry. Its structure also is to be given with stereochemistry if the actual compound is a chiral molecule with 7R, 8S stereochemistry.

Concept introduction:

In ¹HNMR, the epoxides absorb in the region 2.5 -3.5 δ and alkanes in the range 1 to 2 δ.

Epoxides get protonated in the presence of acids and the nucleophilic attack of water opens the epoxide ring to give a diol. The diol is oxidized by KMnO₄ to carboxylic acids with less number of carbon atoms.

To propose:

A structure for disparlure neglecting stereochemistry, satisfying the ¹HNMR data and the chemical reactions given. If the actual compound is a chiral molecule with 7R, 8S stereochemistry its structure with stereochemistry also is to be given.

Expert Solution & Answer

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Answer 4

Question

Chapter 18.SE, Problem 63GP

Interpretation Introduction

Interpretation:

In ¹HNMR, Disparlure, C₁₉H₃₈O, shows a large absorption in the alkane region, 1 to 2 δ and a triplet at 2.8 δ. Treatment of Disparlure first with aqueous acid and then with KMnO4 yielded undecanoic acid and 6-methylheptanoic acid. A structure for disparlure is to be proposed neglecting stereochemistry. Its structure also is to be given with stereochemistry if the actual compound is a chiral molecule with 7R, 8S stereochemistry.

Concept introduction:

In ¹HNMR, the epoxides absorb in the region 2.5 -3.5 δ and alkanes in the range 1 to 2 δ.

Epoxides get protonated in the presence of acids and the nucleophilic attack of water opens the epoxide ring to give a diol. The diol is oxidized by KMnO₄ to carboxylic acids with less number of carbon atoms.

To propose:

A structure for disparlure neglecting stereochemistry, satisfying the ¹HNMR data and the chemical reactions given. If the actual compound is a chiral molecule with 7R, 8S stereochemistry its structure with stereochemistry also is to be given.

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Answer 5

Chapter 18.SE, Problem 63GP

Interpretation Introduction

Interpretation:

In ¹HNMR, Disparlure, C₁₉H₃₈O, shows a large absorption in the alkane region, 1 to 2 δ and a triplet at 2.8 δ. Treatment of Disparlure first with aqueous acid and then with KMnO4 yielded undecanoic acid and 6-methylheptanoic acid. A structure for disparlure is to be proposed neglecting stereochemistry. Its structure also is to be given with stereochemistry if the actual compound is a chiral molecule with 7R, 8S stereochemistry.

Concept introduction:

In ¹HNMR, the epoxides absorb in the region 2.5 -3.5 δ and alkanes in the range 1 to 2 δ.

Epoxides get protonated in the presence of acids and the nucleophilic attack of water opens the epoxide ring to give a diol. The diol is oxidized by KMnO₄ to carboxylic acids with less number of carbon atoms.

To propose:

A structure for disparlure neglecting stereochemistry, satisfying the ¹HNMR data and the chemical reactions given. If the actual compound is a chiral molecule with 7R, 8S stereochemistry its structure with stereochemistry also is to be given.

Answer 6

Chapter 18.SE, Problem 63GP

Interpretation Introduction

Interpretation:

In ¹HNMR, Disparlure, C₁₉H₃₈O, shows a large absorption in the alkane region, 1 to 2 δ and a triplet at 2.8 δ. Treatment of Disparlure first with aqueous acid and then with KMnO4 yielded undecanoic acid and 6-methylheptanoic acid. A structure for disparlure is to be proposed neglecting stereochemistry. Its structure also is to be given with stereochemistry if the actual compound is a chiral molecule with 7R, 8S stereochemistry.

Concept introduction:

In ¹HNMR, the epoxides absorb in the region 2.5 -3.5 δ and alkanes in the range 1 to 2 δ.

Epoxides get protonated in the presence of acids and the nucleophilic attack of water opens the epoxide ring to give a diol. The diol is oxidized by KMnO₄ to carboxylic acids with less number of carbon atoms.

To propose:

A structure for disparlure neglecting stereochemistry, satisfying the ¹HNMR data and the chemical reactions given. If the actual compound is a chiral molecule with 7R, 8S stereochemistry its structure with stereochemistry also is to be given.

Answer 7

Chapter 18.SE, Problem 63GP

Interpretation Introduction

Interpretation:

In ¹HNMR, Disparlure, C₁₉H₃₈O, shows a large absorption in the alkane region, 1 to 2 δ and a triplet at 2.8 δ. Treatment of Disparlure first with aqueous acid and then with KMnO4 yielded undecanoic acid and 6-methylheptanoic acid. A structure for disparlure is to be proposed neglecting stereochemistry. Its structure also is to be given with stereochemistry if the actual compound is a chiral molecule with 7R, 8S stereochemistry.

Concept introduction:

In ¹HNMR, the epoxides absorb in the region 2.5 -3.5 δ and alkanes in the range 1 to 2 δ.

Epoxides get protonated in the presence of acids and the nucleophilic attack of water opens the epoxide ring to give a diol. The diol is oxidized by KMnO₄ to carboxylic acids with less number of carbon atoms.

To propose:

A structure for disparlure neglecting stereochemistry, satisfying the ¹HNMR data and the chemical reactions given. If the actual compound is a chiral molecule with 7R, 8S stereochemistry its structure with stereochemistry also is to be given.

Answer 8

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Answer 10

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Answer 11

Ch. 18.1 - Name the following ethers:Ch. 18.2 - Why do you suppose only symmetrical ethers are...Ch. 18.2 - How would you prepare the following ethers using a...Ch. 18.2 - Review the mechanism of oxymercuration shown in...Ch. 18.2 - How would you prepare the following ethers? Use...Ch. 18.2 - Prob. 6P Ch. 18.3 - Prob. 7P Ch. 18.3 - Write the mechanism of the acid-induced cleavage...Ch. 18.3 - Why are HI and HBr more effective than HCl in...Ch. 18.4 - What product would you expect from Claisen...

Solution Summary: The author proposes a structure for disparlure neglecting stereochemistry, satisfying the 1 HNMR data and the chemical reactions given.

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