ORGANIC CHEMISTRY-PRINT (LL)-W/WILEY
ORGANIC CHEMISTRY-PRINT (LL)-W/WILEY
4th Edition
ISBN: 9781119761105
Author: Klein
Publisher: WILEY
Question
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Chapter 12.3, 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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