(a) Interpretation: The structure of brevicomin is to be drawn. Concept introduction: The acid-catalyzed cyclization of 6 , 7 − dihydroxy − 2 − nonanone gives brevicomin.

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Answer 1

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Chapter 21, Problem 21.89P

Interpretation Introduction

(a)

Interpretation: The structure of brevicomin is to be drawn.

Concept introduction: The acid-catalyzed cyclization of 6,7−dihydroxy−2−nonanone gives brevicomin.

Interpretation Introduction

(b)

Interpretation: The synthesis of 6,7−dihydroxynonan−2−one from 6−bromohexan−2−one is to be stated.

Concept introduction: The nucleophilic addition reactions are the common reactions, which form products like imines, diols, alcohols, cyanohydrins, and alkenes. In nucleophilic reaction, an electron rich species attack the species that is deficient in electrons. The electrophile and the leaving group together form a substrate. The nucleophile attacks over the substrate and there occurs the removal of leaving group from the substrate.

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Brevicomin, the aggregation pheromone of the western pine bark beetle, contains a bicyclic bridged ring system and is prepared by the acidcatalyzed cyclization of 6,7-dihydroxy-nonan-2-one. a. Suggest a structure for brevicomin. b. Devise a synthesis of 6,7-dihydroxynonan-2-one from 6-bromohexan-2- one. You may also use three-carbon alcohols and any required organic or inorganic reagents.

VI. VII. X. IX. o-chlorocyanobenzene p-chlorocyanobenzene C. mixture of o-and p-chlorocyanobenzene D. m-chlorocyanobenzene E. mixture of m-and o-chlorocyanobenzene VIII. The nitration reaction of acetophenone provides: o-nitroacetophenone p-nitroacetophenone mixture of o-and p-nitroacetophenone D. m-nitroacetophenone No reaction occurred During the reaction of benzene with n-propyl chloride and aluminum chloride as catalyst, the electrophilic species undergoing reaction with benzene is: A. B. C. iso-propyl carbocation D. sec-butyl carbocation E. iso-butyl carbocation The reaction of benzonitrile with chlorine in the presence of iron(III) chloride as a catalyst provides: A. B. ARCDE A. B. C. E. Conversion of benzene into m-bromoaniline is achieved with the following sets of reagents arranged in right order: A. C. B. D. A. B. C. n-propyl carbocation tert-butyl carbocation bromine and iron(III) bromide, nitric acid and sulfuric acid, tin, hydrochloric acid, heat nitric acid and sulfuric…

What alkyl halide reacts with lithium divinylcuprate [(CH2=CH)2CuLi] for the synthesis of each of the following compounds?

Answer 2

Question

Chapter 21, Problem 21.89P

Interpretation Introduction

(a)

Interpretation: The structure of brevicomin is to be drawn.

Concept introduction: The acid-catalyzed cyclization of 6,7−dihydroxy−2−nonanone gives brevicomin.

Interpretation Introduction

(b)

Interpretation: The synthesis of 6,7−dihydroxynonan−2−one from 6−bromohexan−2−one is to be stated.

Concept introduction: The nucleophilic addition reactions are the common reactions, which form products like imines, diols, alcohols, cyanohydrins, and alkenes. In nucleophilic reaction, an electron rich species attack the species that is deficient in electrons. The electrophile and the leaving group together form a substrate. The nucleophile attacks over the substrate and there occurs the removal of leaving group from the substrate.

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Answer 3

Question

Chapter 21, Problem 21.89P

Interpretation Introduction

(a)

Interpretation: The structure of brevicomin is to be drawn.

Concept introduction: The acid-catalyzed cyclization of 6,7−dihydroxy−2−nonanone gives brevicomin.

Interpretation Introduction

(b)

Interpretation: The synthesis of 6,7−dihydroxynonan−2−one from 6−bromohexan−2−one is to be stated.

Concept introduction: The nucleophilic addition reactions are the common reactions, which form products like imines, diols, alcohols, cyanohydrins, and alkenes. In nucleophilic reaction, an electron rich species attack the species that is deficient in electrons. The electrophile and the leaving group together form a substrate. The nucleophile attacks over the substrate and there occurs the removal of leaving group from the substrate.

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Answer 4

Question

Chapter 21, Problem 21.89P

Interpretation Introduction

(a)

Interpretation: The structure of brevicomin is to be drawn.

Concept introduction: The acid-catalyzed cyclization of 6,7−dihydroxy−2−nonanone gives brevicomin.

Interpretation Introduction

(b)

Interpretation: The synthesis of 6,7−dihydroxynonan−2−one from 6−bromohexan−2−one is to be stated.

Concept introduction: The nucleophilic addition reactions are the common reactions, which form products like imines, diols, alcohols, cyanohydrins, and alkenes. In nucleophilic reaction, an electron rich species attack the species that is deficient in electrons. The electrophile and the leaving group together form a substrate. The nucleophile attacks over the substrate and there occurs the removal of leaving group from the substrate.

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Answer 5

Chapter 21, Problem 21.89P

Interpretation Introduction

(a)

Interpretation: The structure of brevicomin is to be drawn.

Concept introduction: The acid-catalyzed cyclization of 6,7−dihydroxy−2−nonanone gives brevicomin.

Interpretation Introduction

(b)

Interpretation: The synthesis of 6,7−dihydroxynonan−2−one from 6−bromohexan−2−one is to be stated.

Concept introduction: The nucleophilic addition reactions are the common reactions, which form products like imines, diols, alcohols, cyanohydrins, and alkenes. In nucleophilic reaction, an electron rich species attack the species that is deficient in electrons. The electrophile and the leaving group together form a substrate. The nucleophile attacks over the substrate and there occurs the removal of leaving group from the substrate.

Answer 6

Chapter 21, Problem 21.89P

Interpretation Introduction

(a)

Interpretation: The structure of brevicomin is to be drawn.

Concept introduction: The acid-catalyzed cyclization of 6,7−dihydroxy−2−nonanone gives brevicomin.

Answer 7

Chapter 21, Problem 21.89P

Interpretation Introduction

(a)

Interpretation: The structure of brevicomin is to be drawn.

Concept introduction: The acid-catalyzed cyclization of 6,7−dihydroxy−2−nonanone gives brevicomin.

Answer 8

Interpretation Introduction

(b)

Interpretation: The synthesis of 6,7−dihydroxynonan−2−one from 6−bromohexan−2−one is to be stated.

Concept introduction: The nucleophilic addition reactions are the common reactions, which form products like imines, diols, alcohols, cyanohydrins, and alkenes. In nucleophilic reaction, an electron rich species attack the species that is deficient in electrons. The electrophile and the leaving group together form a substrate. The nucleophile attacks over the substrate and there occurs the removal of leaving group from the substrate.

Answer 9

Interpretation Introduction

(b)

Interpretation: The synthesis of 6,7−dihydroxynonan−2−one from 6−bromohexan−2−one is to be stated.

Concept introduction: The nucleophilic addition reactions are the common reactions, which form products like imines, diols, alcohols, cyanohydrins, and alkenes. In nucleophilic reaction, an electron rich species attack the species that is deficient in electrons. The electrophile and the leaving group together form a substrate. The nucleophile attacks over the substrate and there occurs the removal of leaving group from the substrate.

Answer 10

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Answer 11

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Answer 12

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Answer 13

Ch. 21 - Rank the following compounds in order of...Ch. 21 - Prob. 21.2P Ch. 21 - Give the IUPAC name for each aldehyde.Ch. 21 - Prob. 21.4P Ch. 21 - Give the IUPAC name for each ketone.Ch. 21 - Prob. 21.6P Ch. 21 - Prob. 21.7P Ch. 21 - The boiling point of is significantly higher than...Ch. 21 - Which carbonyl group in each pair absorbs at a...Ch. 21 - Problem 21.10 Draw the structure of all...

(a) Interpretation: The structure of brevicomin is to be drawn. Concept introduction: The acid-catalyzed cyclization of 6 , 7 − dihydroxy − 2 − nonanone gives brevicomin.

Solution Summary: The author explains the structure of brevicomin, which is a bicyclic compound.

(a)

Interpretation: The structure of brevicomin is to be drawn.

Concept introduction: The acid-catalyzed cyclization of 6,7−dihydroxy−2−nonanone gives brevicomin.

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Chapter 21 Solutions

(a) Interpretation: The structure of brevicomin is to be drawn. Concept introduction: The acid-catalyzed cyclization of 6 , 7 − dihydroxy − 2 − nonanone gives brevicomin.

Solution Summary: The author explains the structure of brevicomin, which is a bicyclic compound.

(a) Interpretation: The structure of brevicomin is to be drawn. Concept introduction: The acid-catalyzed cyclization of 6,7−dihydroxy−2−nonanone gives brevicomin.

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Chapter 21 Solutions

(a)

Interpretation: The structure of brevicomin is to be drawn.

Concept introduction: The acid-catalyzed cyclization of 6,7−dihydroxy−2−nonanone gives brevicomin.