Chapter 8.6, Problem 12CC

(a)

Interpretation Introduction

Interpretation:

The products of acid-catalysed hydration and oxymercuration-demercuration of given reactants have to be identified.

Concept Introduction:

• Simple hydration in acidic media gives the addition product through carbocation intermediate and follows Markovnikov’s addition.
• An acid-catalysed hydration is shown below.

  

• Markovnikov’s rule: An unsymmetrical alkene reacts with hydrogen halide in which halide ions goes to the more substitution position of carbon-carbon double bond which provides alkyl halides.

• Oxymercuration-Demercuration:  In this reaction, alkene undergoes oxymercuration to form mercurinium ion intermediate.  This intermediate reacts with nucleophile and mercury can be removed by sodium borohydride.

  

(b)

Interpretation Introduction

Interpretation:

The products of acid-catalysed hydration and oxymercuration-demercuration of given reactants have to be identified.

Concept Introduction:

• Simple hydration in acidic media gives the addition product through carbocation intermediate and follows Markovnikov’s addition.
• An acid-catalysed hydration is shown below.

  

• Markovnikov’s rule: An unsymmetrical alkene reacts with hydrogen halide in which halide ions goes to the more substitution position of carbon-carbon double bond which provides alkyl halides.

• Oxymercuration-Demercuration:  In this reaction, alkene undergoes oxymercuration to form mercurinium ion intermediate.  This intermediate reacts with nucleophile and mercury can be removed by sodium borohydride.

  

(c)

Interpretation Introduction

Interpretation:

The products of acid-catalysed hydration and oxymercuration-demercuration of given reactants have to be identified.

Concept Introduction:

• Simple hydration in acidic media gives the addition product through carbocation intermediate and follows Markovnikov’s addition.
• An acid-catalysed hydration is shown below.

  

• Markovnikov’s rule: An unsymmetrical alkene reacts with hydrogen halide in which halide ions goes to the more substitution position of carbon-carbon double bond which provides alkyl halides.

• Oxymercuration-Demercuration:  In this reaction, alkene undergoes oxymercuration to form mercurinium ion intermediate.  This intermediate reacts with nucleophile and mercury can be removed by sodium borohydride.