The reagent for the given transformation should be identified. Concept introduction: 9-BBN (9-Borabicyclo[3.3.1]nonane) or diborane is used for the hydroboration of alkene . Boron addition to the double bond and subsequent oxidation of the new formed borane yields anti-Markovnikov alcohols. The role of dilute sulfuric acid is used for the hydration of alkene in organic synthesis . The oxymercuration reaction is an electrophilic addition reaction, an alkene undergoes oxymercuration and forms neutral alcohol. Anti-Markovnikov’s rule : unsymmetrical alkene reacts with hydrogen halide, halide ions (negative part) goes to the less substitution position of carbon-carbon double bond which provides alkyl halides. Markovnikov addition : unsymmetrical alkene reacts with hydrogen halide, halide ions (negative part) goes to the more substitution position of carbon-carbon double bond which provides alkyl halides.

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Answer 1

Question

Chapter 13.3, Problem 8CC

(a)

Interpretation Introduction

Interpretation:

The reagent for the given transformation should be identified.

Concept introduction:

9-BBN (9-Borabicyclo[3.3.1]nonane) or diborane is used for the hydroboration of alkene. Boron addition to the double bond and subsequent oxidation of the new formed borane yields anti-Markovnikov alcohols.

The role of dilute sulfuric acid is used for the hydration of alkene in organic synthesis.

The oxymercuration reaction is an electrophilic addition reaction, an alkene undergoes oxymercuration and forms neutral alcohol.

Anti-Markovnikov’s rule: unsymmetrical alkene reacts with hydrogen halide, halide ions (negative part) goes to the less substitution position of carbon-carbon double bond which provides alkyl halides.

Markovnikov addition: unsymmetrical alkene reacts with hydrogen halide, halide ions (negative part) goes to the more substitution position of carbon-carbon double bond which provides alkyl halides.

(b)

Interpretation Introduction

Interpretation:

The reagent for the given transformation should be identified.

Concept introduction:

9-BBN (9-Borabicyclo[3.3.1]nonane) or diborane is used for the hydroboration of alkene. Boron addition to the double bond and subsequent oxidation of the new formed borane yields anti-Markovnikov alcohols.

The role of dilute sulfuric acid is used for the hydration of alkene in organic synthesis.

The oxymercuration reaction is an electrophilic addition reaction, an alkene undergoes oxymercuration and forms neutral alcohol.

Anti-Markovnikov’s rule: unsymmetrical alkene reacts with hydrogen halide, halide ions (negative part) goes to the less substitution position of carbon-carbon double bond which provides alkyl halides.

Markovnikov addition: unsymmetrical alkene reacts with hydrogen halide, halide ions (negative part) goes to the more substitution position of carbon-carbon double bond which provides alkyl halides.

(c)

Interpretation Introduction

Interpretation:

The reagent for the given transformation should be identified.

Concept introduction:

9-BBN (9-Borabicyclo[3.3.1]nonane) or diborane is used for the hydroboration of alkene. Boron addition to the double bond and subsequent oxidation of the new formed borane yields anti-Markovnikov alcohols.

The role of dilute sulfuric acid is used for the hydration of alkene in organic synthesis.

The oxymercuration reaction is an electrophilic addition reaction, an alkene undergoes oxymercuration and forms neutral alcohol.

Anti-Markovnikov’s rule: unsymmetrical alkene reacts with hydrogen halide, halide ions (negative part) goes to the less substitution position of carbon-carbon double bond which provides alkyl halides.

Markovnikov addition: unsymmetrical alkene reacts with hydrogen halide, halide ions (negative part) goes to the more substitution position of carbon-carbon double bond which provides alkyl halides.

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Answer 2

Question

Chapter 13.3, Problem 8CC

(a)

Interpretation Introduction

Interpretation:

The reagent for the given transformation should be identified.

Concept introduction:

9-BBN (9-Borabicyclo[3.3.1]nonane) or diborane is used for the hydroboration of alkene. Boron addition to the double bond and subsequent oxidation of the new formed borane yields anti-Markovnikov alcohols.

The role of dilute sulfuric acid is used for the hydration of alkene in organic synthesis.

The oxymercuration reaction is an electrophilic addition reaction, an alkene undergoes oxymercuration and forms neutral alcohol.

Anti-Markovnikov’s rule: unsymmetrical alkene reacts with hydrogen halide, halide ions (negative part) goes to the less substitution position of carbon-carbon double bond which provides alkyl halides.

Markovnikov addition: unsymmetrical alkene reacts with hydrogen halide, halide ions (negative part) goes to the more substitution position of carbon-carbon double bond which provides alkyl halides.

(b)

Interpretation Introduction

Interpretation:

The reagent for the given transformation should be identified.

Concept introduction:

9-BBN (9-Borabicyclo[3.3.1]nonane) or diborane is used for the hydroboration of alkene. Boron addition to the double bond and subsequent oxidation of the new formed borane yields anti-Markovnikov alcohols.

The role of dilute sulfuric acid is used for the hydration of alkene in organic synthesis.

The oxymercuration reaction is an electrophilic addition reaction, an alkene undergoes oxymercuration and forms neutral alcohol.

Anti-Markovnikov’s rule: unsymmetrical alkene reacts with hydrogen halide, halide ions (negative part) goes to the less substitution position of carbon-carbon double bond which provides alkyl halides.

Markovnikov addition: unsymmetrical alkene reacts with hydrogen halide, halide ions (negative part) goes to the more substitution position of carbon-carbon double bond which provides alkyl halides.

(c)

Interpretation Introduction

Interpretation:

The reagent for the given transformation should be identified.

Concept introduction:

9-BBN (9-Borabicyclo[3.3.1]nonane) or diborane is used for the hydroboration of alkene. Boron addition to the double bond and subsequent oxidation of the new formed borane yields anti-Markovnikov alcohols.

The role of dilute sulfuric acid is used for the hydration of alkene in organic synthesis.

The oxymercuration reaction is an electrophilic addition reaction, an alkene undergoes oxymercuration and forms neutral alcohol.

Anti-Markovnikov’s rule: unsymmetrical alkene reacts with hydrogen halide, halide ions (negative part) goes to the less substitution position of carbon-carbon double bond which provides alkyl halides.

Markovnikov addition: unsymmetrical alkene reacts with hydrogen halide, halide ions (negative part) goes to the more substitution position of carbon-carbon double bond which provides alkyl halides.

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Answer 3

Question

Chapter 13.3, Problem 8CC

(a)

Interpretation Introduction

Interpretation:

The reagent for the given transformation should be identified.

Concept introduction:

9-BBN (9-Borabicyclo[3.3.1]nonane) or diborane is used for the hydroboration of alkene. Boron addition to the double bond and subsequent oxidation of the new formed borane yields anti-Markovnikov alcohols.

The role of dilute sulfuric acid is used for the hydration of alkene in organic synthesis.

The oxymercuration reaction is an electrophilic addition reaction, an alkene undergoes oxymercuration and forms neutral alcohol.

Anti-Markovnikov’s rule: unsymmetrical alkene reacts with hydrogen halide, halide ions (negative part) goes to the less substitution position of carbon-carbon double bond which provides alkyl halides.

Markovnikov addition: unsymmetrical alkene reacts with hydrogen halide, halide ions (negative part) goes to the more substitution position of carbon-carbon double bond which provides alkyl halides.

(b)

Interpretation Introduction

Interpretation:

The reagent for the given transformation should be identified.

Concept introduction:

9-BBN (9-Borabicyclo[3.3.1]nonane) or diborane is used for the hydroboration of alkene. Boron addition to the double bond and subsequent oxidation of the new formed borane yields anti-Markovnikov alcohols.

The role of dilute sulfuric acid is used for the hydration of alkene in organic synthesis.

The oxymercuration reaction is an electrophilic addition reaction, an alkene undergoes oxymercuration and forms neutral alcohol.

Anti-Markovnikov’s rule: unsymmetrical alkene reacts with hydrogen halide, halide ions (negative part) goes to the less substitution position of carbon-carbon double bond which provides alkyl halides.

Markovnikov addition: unsymmetrical alkene reacts with hydrogen halide, halide ions (negative part) goes to the more substitution position of carbon-carbon double bond which provides alkyl halides.

(c)

Interpretation Introduction

Interpretation:

The reagent for the given transformation should be identified.

Concept introduction:

9-BBN (9-Borabicyclo[3.3.1]nonane) or diborane is used for the hydroboration of alkene. Boron addition to the double bond and subsequent oxidation of the new formed borane yields anti-Markovnikov alcohols.

The role of dilute sulfuric acid is used for the hydration of alkene in organic synthesis.

The oxymercuration reaction is an electrophilic addition reaction, an alkene undergoes oxymercuration and forms neutral alcohol.

Anti-Markovnikov’s rule: unsymmetrical alkene reacts with hydrogen halide, halide ions (negative part) goes to the less substitution position of carbon-carbon double bond which provides alkyl halides.

Markovnikov addition: unsymmetrical alkene reacts with hydrogen halide, halide ions (negative part) goes to the more substitution position of carbon-carbon double bond which provides alkyl halides.

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Answer 4

Question

Chapter 13.3, Problem 8CC

(a)

Interpretation Introduction

Interpretation:

The reagent for the given transformation should be identified.

Concept introduction:

9-BBN (9-Borabicyclo[3.3.1]nonane) or diborane is used for the hydroboration of alkene. Boron addition to the double bond and subsequent oxidation of the new formed borane yields anti-Markovnikov alcohols.

The role of dilute sulfuric acid is used for the hydration of alkene in organic synthesis.

The oxymercuration reaction is an electrophilic addition reaction, an alkene undergoes oxymercuration and forms neutral alcohol.

Anti-Markovnikov’s rule: unsymmetrical alkene reacts with hydrogen halide, halide ions (negative part) goes to the less substitution position of carbon-carbon double bond which provides alkyl halides.

Markovnikov addition: unsymmetrical alkene reacts with hydrogen halide, halide ions (negative part) goes to the more substitution position of carbon-carbon double bond which provides alkyl halides.

(b)

Interpretation Introduction

Interpretation:

The reagent for the given transformation should be identified.

Concept introduction:

9-BBN (9-Borabicyclo[3.3.1]nonane) or diborane is used for the hydroboration of alkene. Boron addition to the double bond and subsequent oxidation of the new formed borane yields anti-Markovnikov alcohols.

The role of dilute sulfuric acid is used for the hydration of alkene in organic synthesis.

The oxymercuration reaction is an electrophilic addition reaction, an alkene undergoes oxymercuration and forms neutral alcohol.

Anti-Markovnikov’s rule: unsymmetrical alkene reacts with hydrogen halide, halide ions (negative part) goes to the less substitution position of carbon-carbon double bond which provides alkyl halides.

Markovnikov addition: unsymmetrical alkene reacts with hydrogen halide, halide ions (negative part) goes to the more substitution position of carbon-carbon double bond which provides alkyl halides.

(c)

Interpretation Introduction

Interpretation:

The reagent for the given transformation should be identified.

Concept introduction:

9-BBN (9-Borabicyclo[3.3.1]nonane) or diborane is used for the hydroboration of alkene. Boron addition to the double bond and subsequent oxidation of the new formed borane yields anti-Markovnikov alcohols.

The role of dilute sulfuric acid is used for the hydration of alkene in organic synthesis.

The oxymercuration reaction is an electrophilic addition reaction, an alkene undergoes oxymercuration and forms neutral alcohol.

Anti-Markovnikov’s rule: unsymmetrical alkene reacts with hydrogen halide, halide ions (negative part) goes to the less substitution position of carbon-carbon double bond which provides alkyl halides.

Markovnikov addition: unsymmetrical alkene reacts with hydrogen halide, halide ions (negative part) goes to the more substitution position of carbon-carbon double bond which provides alkyl halides.

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Answer 5

Chapter 13.3, Problem 8CC

(a)

Interpretation Introduction

Interpretation:

The reagent for the given transformation should be identified.

Concept introduction:

9-BBN (9-Borabicyclo[3.3.1]nonane) or diborane is used for the hydroboration of alkene. Boron addition to the double bond and subsequent oxidation of the new formed borane yields anti-Markovnikov alcohols.

The role of dilute sulfuric acid is used for the hydration of alkene in organic synthesis.

The oxymercuration reaction is an electrophilic addition reaction, an alkene undergoes oxymercuration and forms neutral alcohol.

Anti-Markovnikov’s rule: unsymmetrical alkene reacts with hydrogen halide, halide ions (negative part) goes to the less substitution position of carbon-carbon double bond which provides alkyl halides.

Markovnikov addition: unsymmetrical alkene reacts with hydrogen halide, halide ions (negative part) goes to the more substitution position of carbon-carbon double bond which provides alkyl halides.

(b)

Interpretation Introduction

Interpretation:

The reagent for the given transformation should be identified.

Concept introduction:

9-BBN (9-Borabicyclo[3.3.1]nonane) or diborane is used for the hydroboration of alkene. Boron addition to the double bond and subsequent oxidation of the new formed borane yields anti-Markovnikov alcohols.

The role of dilute sulfuric acid is used for the hydration of alkene in organic synthesis.

The oxymercuration reaction is an electrophilic addition reaction, an alkene undergoes oxymercuration and forms neutral alcohol.

Anti-Markovnikov’s rule: unsymmetrical alkene reacts with hydrogen halide, halide ions (negative part) goes to the less substitution position of carbon-carbon double bond which provides alkyl halides.

Markovnikov addition: unsymmetrical alkene reacts with hydrogen halide, halide ions (negative part) goes to the more substitution position of carbon-carbon double bond which provides alkyl halides.

(c)

Interpretation Introduction

Interpretation:

The reagent for the given transformation should be identified.

Concept introduction:

9-BBN (9-Borabicyclo[3.3.1]nonane) or diborane is used for the hydroboration of alkene. Boron addition to the double bond and subsequent oxidation of the new formed borane yields anti-Markovnikov alcohols.

The role of dilute sulfuric acid is used for the hydration of alkene in organic synthesis.

The oxymercuration reaction is an electrophilic addition reaction, an alkene undergoes oxymercuration and forms neutral alcohol.

Anti-Markovnikov’s rule: unsymmetrical alkene reacts with hydrogen halide, halide ions (negative part) goes to the less substitution position of carbon-carbon double bond which provides alkyl halides.

Markovnikov addition: unsymmetrical alkene reacts with hydrogen halide, halide ions (negative part) goes to the more substitution position of carbon-carbon double bond which provides alkyl halides.

Answer 6

Chapter 13.3, Problem 8CC

(a)

Interpretation Introduction

Interpretation:

The reagent for the given transformation should be identified.

Concept introduction:

9-BBN (9-Borabicyclo[3.3.1]nonane) or diborane is used for the hydroboration of alkene. Boron addition to the double bond and subsequent oxidation of the new formed borane yields anti-Markovnikov alcohols.

The role of dilute sulfuric acid is used for the hydration of alkene in organic synthesis.

The oxymercuration reaction is an electrophilic addition reaction, an alkene undergoes oxymercuration and forms neutral alcohol.

Anti-Markovnikov’s rule: unsymmetrical alkene reacts with hydrogen halide, halide ions (negative part) goes to the less substitution position of carbon-carbon double bond which provides alkyl halides.

Markovnikov addition: unsymmetrical alkene reacts with hydrogen halide, halide ions (negative part) goes to the more substitution position of carbon-carbon double bond which provides alkyl halides.

Answer 7

Chapter 13.3, Problem 8CC

(a)

Interpretation Introduction

Interpretation:

The reagent for the given transformation should be identified.

Concept introduction:

9-BBN (9-Borabicyclo[3.3.1]nonane) or diborane is used for the hydroboration of alkene. Boron addition to the double bond and subsequent oxidation of the new formed borane yields anti-Markovnikov alcohols.

The role of dilute sulfuric acid is used for the hydration of alkene in organic synthesis.

The oxymercuration reaction is an electrophilic addition reaction, an alkene undergoes oxymercuration and forms neutral alcohol.

Anti-Markovnikov’s rule: unsymmetrical alkene reacts with hydrogen halide, halide ions (negative part) goes to the less substitution position of carbon-carbon double bond which provides alkyl halides.

Markovnikov addition: unsymmetrical alkene reacts with hydrogen halide, halide ions (negative part) goes to the more substitution position of carbon-carbon double bond which provides alkyl halides.

Answer 8

(b)

Interpretation Introduction

Interpretation:

The reagent for the given transformation should be identified.

Concept introduction:

9-BBN (9-Borabicyclo[3.3.1]nonane) or diborane is used for the hydroboration of alkene. Boron addition to the double bond and subsequent oxidation of the new formed borane yields anti-Markovnikov alcohols.

The role of dilute sulfuric acid is used for the hydration of alkene in organic synthesis.

The oxymercuration reaction is an electrophilic addition reaction, an alkene undergoes oxymercuration and forms neutral alcohol.

Anti-Markovnikov’s rule: unsymmetrical alkene reacts with hydrogen halide, halide ions (negative part) goes to the less substitution position of carbon-carbon double bond which provides alkyl halides.

Markovnikov addition: unsymmetrical alkene reacts with hydrogen halide, halide ions (negative part) goes to the more substitution position of carbon-carbon double bond which provides alkyl halides.

Answer 9

(b)

Interpretation Introduction

Interpretation:

The reagent for the given transformation should be identified.

Concept introduction:

9-BBN (9-Borabicyclo[3.3.1]nonane) or diborane is used for the hydroboration of alkene. Boron addition to the double bond and subsequent oxidation of the new formed borane yields anti-Markovnikov alcohols.

The role of dilute sulfuric acid is used for the hydration of alkene in organic synthesis.

The oxymercuration reaction is an electrophilic addition reaction, an alkene undergoes oxymercuration and forms neutral alcohol.

Anti-Markovnikov’s rule: unsymmetrical alkene reacts with hydrogen halide, halide ions (negative part) goes to the less substitution position of carbon-carbon double bond which provides alkyl halides.

Markovnikov addition: unsymmetrical alkene reacts with hydrogen halide, halide ions (negative part) goes to the more substitution position of carbon-carbon double bond which provides alkyl halides.

Answer 10

(c)

Interpretation Introduction

Interpretation:

The reagent for the given transformation should be identified.

Concept introduction:

9-BBN (9-Borabicyclo[3.3.1]nonane) or diborane is used for the hydroboration of alkene. Boron addition to the double bond and subsequent oxidation of the new formed borane yields anti-Markovnikov alcohols.

The role of dilute sulfuric acid is used for the hydration of alkene in organic synthesis.

The oxymercuration reaction is an electrophilic addition reaction, an alkene undergoes oxymercuration and forms neutral alcohol.

Anti-Markovnikov’s rule: unsymmetrical alkene reacts with hydrogen halide, halide ions (negative part) goes to the less substitution position of carbon-carbon double bond which provides alkyl halides.

Markovnikov addition: unsymmetrical alkene reacts with hydrogen halide, halide ions (negative part) goes to the more substitution position of carbon-carbon double bond which provides alkyl halides.

Answer 11

(c)

Interpretation Introduction

Interpretation:

The reagent for the given transformation should be identified.

Concept introduction:

9-BBN (9-Borabicyclo[3.3.1]nonane) or diborane is used for the hydroboration of alkene. Boron addition to the double bond and subsequent oxidation of the new formed borane yields anti-Markovnikov alcohols.

The role of dilute sulfuric acid is used for the hydration of alkene in organic synthesis.

The oxymercuration reaction is an electrophilic addition reaction, an alkene undergoes oxymercuration and forms neutral alcohol.

Anti-Markovnikov’s rule: unsymmetrical alkene reacts with hydrogen halide, halide ions (negative part) goes to the less substitution position of carbon-carbon double bond which provides alkyl halides.

Markovnikov addition: unsymmetrical alkene reacts with hydrogen halide, halide ions (negative part) goes to the more substitution position of carbon-carbon double bond which provides alkyl halides.

Answer 12

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Answer 13

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Answer 14

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Answer 15

Ch. 13.1 - Prob. 1LTS Ch. 13.1 - Prob. 1PTS Ch. 13.1 - Prob. 2ATS Ch. 13.1 - Prob. 3CC Ch. 13.2 - Prob. 4CC Ch. 13.2 - Prob. 2LTS Ch. 13.2 - Prob. 5PTS Ch. 13.2 - Prob. 6ATS Ch. 13.3 - Prob. 7CC Ch. 13.3 - Prob. 8CC

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Chapter 13 Solutions