Structure of ( + ) - α -naphthylurethane of ( – ) -isopinocampheol should be written. Concept introduction: Hydroboration-oxidation involves a sequence of two reactions. The hydroboration stage involves the treatment of alkene with diborane that generates alkyl borane. In second stage hydrogen peroxide in alkaline medium is used to oxidize the alkyl borane produced in step 1 that leads to the synthesis of alcohols from alkenes . Hydroboration of ( + ) - α -Pinene occurs as illustrated as below. Since structure I have BH 2 added from backside so stereospecific nature of syn addition reaction suggests that OH must add from the same backside as the side of BH 2 to result in exclusive syn product II.

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Answer 1

Question

Chapter 10.8, Problem 12E

Interpretation Introduction

Interpretation:Structure of (+)-α-naphthylurethane of (–)-isopinocampheol should be written.

Concept introduction:Hydroboration-oxidation involves a sequence of two reactions. The hydroboration stage involves the treatment of alkene with diborane that generates alkyl borane. In second stage hydrogen peroxide in alkaline medium is used to oxidize the alkyl borane produced in step 1 that leads to the synthesis of alcohols from alkenes.

Hydroboration of (+)-α-Pinene occurs as illustrated as below.

Since structure I have BH2 added from backside so stereospecific nature of syn addition reaction suggests that OH must add from the same backside as the side of BH2 to result in exclusive syn product II.

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Answer 2

Question

Chapter 10.8, Problem 12E

Interpretation Introduction

Interpretation:Structure of (+)-α-naphthylurethane of (–)-isopinocampheol should be written.

Concept introduction:Hydroboration-oxidation involves a sequence of two reactions. The hydroboration stage involves the treatment of alkene with diborane that generates alkyl borane. In second stage hydrogen peroxide in alkaline medium is used to oxidize the alkyl borane produced in step 1 that leads to the synthesis of alcohols from alkenes.

Hydroboration of (+)-α-Pinene occurs as illustrated as below.

Since structure I have BH2 added from backside so stereospecific nature of syn addition reaction suggests that OH must add from the same backside as the side of BH2 to result in exclusive syn product II.

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Answer 3

Question

Chapter 10.8, Problem 12E

Interpretation Introduction

Interpretation:Structure of (+)-α-naphthylurethane of (–)-isopinocampheol should be written.

Concept introduction:Hydroboration-oxidation involves a sequence of two reactions. The hydroboration stage involves the treatment of alkene with diborane that generates alkyl borane. In second stage hydrogen peroxide in alkaline medium is used to oxidize the alkyl borane produced in step 1 that leads to the synthesis of alcohols from alkenes.

Hydroboration of (+)-α-Pinene occurs as illustrated as below.

Since structure I have BH2 added from backside so stereospecific nature of syn addition reaction suggests that OH must add from the same backside as the side of BH2 to result in exclusive syn product II.

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Answer 4

Question

Chapter 10.8, Problem 12E

Interpretation Introduction

Interpretation:Structure of (+)-α-naphthylurethane of (–)-isopinocampheol should be written.

Concept introduction:Hydroboration-oxidation involves a sequence of two reactions. The hydroboration stage involves the treatment of alkene with diborane that generates alkyl borane. In second stage hydrogen peroxide in alkaline medium is used to oxidize the alkyl borane produced in step 1 that leads to the synthesis of alcohols from alkenes.

Hydroboration of (+)-α-Pinene occurs as illustrated as below.

Since structure I have BH2 added from backside so stereospecific nature of syn addition reaction suggests that OH must add from the same backside as the side of BH2 to result in exclusive syn product II.

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Answer 5

Chapter 10.8, Problem 12E

Interpretation Introduction

Interpretation:Structure of (+)-α-naphthylurethane of (–)-isopinocampheol should be written.

Concept introduction:Hydroboration-oxidation involves a sequence of two reactions. The hydroboration stage involves the treatment of alkene with diborane that generates alkyl borane. In second stage hydrogen peroxide in alkaline medium is used to oxidize the alkyl borane produced in step 1 that leads to the synthesis of alcohols from alkenes.

Hydroboration of (+)-α-Pinene occurs as illustrated as below.

Since structure I have BH2 added from backside so stereospecific nature of syn addition reaction suggests that OH must add from the same backside as the side of BH2 to result in exclusive syn product II.

Answer 6

Chapter 10.8, Problem 12E

Interpretation Introduction

Interpretation:Structure of (+)-α-naphthylurethane of (–)-isopinocampheol should be written.

Concept introduction:Hydroboration-oxidation involves a sequence of two reactions. The hydroboration stage involves the treatment of alkene with diborane that generates alkyl borane. In second stage hydrogen peroxide in alkaline medium is used to oxidize the alkyl borane produced in step 1 that leads to the synthesis of alcohols from alkenes.

Hydroboration of (+)-α-Pinene occurs as illustrated as below.

Since structure I have BH2 added from backside so stereospecific nature of syn addition reaction suggests that OH must add from the same backside as the side of BH2 to result in exclusive syn product II.

Answer 7

Chapter 10.8, Problem 12E

Interpretation Introduction

Interpretation:Structure of (+)-α-naphthylurethane of (–)-isopinocampheol should be written.

Concept introduction:Hydroboration-oxidation involves a sequence of two reactions. The hydroboration stage involves the treatment of alkene with diborane that generates alkyl borane. In second stage hydrogen peroxide in alkaline medium is used to oxidize the alkyl borane produced in step 1 that leads to the synthesis of alcohols from alkenes.

Hydroboration of (+)-α-Pinene occurs as illustrated as below.

Since structure I have BH2 added from backside so stereospecific nature of syn addition reaction suggests that OH must add from the same backside as the side of BH2 to result in exclusive syn product II.

Answer 8

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Answer 9

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Answer 10

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Answer 11

Ch. 10.2 - Prob. 1E Ch. 10.2 - Prob. 2E Ch. 10.2 - Prob. 3E Ch. 10.2 - Prob. 4E Ch. 10.2 - Prob. 5E Ch. 10.2 - Prob. 6E Ch. 10.2 - Prob. 7E Ch. 10.2 - Prob. 8E Ch. 10.2 - Prob. 9E Ch. 10.2 - Prob. 10E

Solution Summary: The author explains that hydroboration-oxidation involves a sequence of two reactions. The first involves the treatment of alkene with diborane, and the second involves hydrogen peroxide in alkaline medium.

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