Chapter 7.SE, Problem 27MP

Interpretation Introduction

a)

Interpretation:

The product and the complete arrow-pushing mechanism for the electrophilic reaction given which involves a carbocation rearrangement.

Concept introduction:

In electrophilic addition reactions, the first step is the attack of the π electrons of the double bond on the hydrogen of the alkyl halide to yield a carbocation. One of the carbon in C=C gets attached to hydrogen while the other acquires a positive charge. In the second step, the carbocation formed can rearrange to give another more stable carbocation either by a hydride shift (shift of hydrogen atom with its electron pair) or by an alkyl shift (shift of an alkyl group with its electron pair) between neighboring carbons. In the last step the carbocation produced reacts with the halide ion to give the alkyl halide.

To predict:

The product and to show the complete arrow-pushing mechanism for the electrophilic reaction given which involves a carbocation rearrangement.

Interpretation Introduction

b)

Interpretation:

The product and the complete arrow-pushing mechanism for the electrophilic reaction given which involves a carbocation rearrangement.

Concept introduction:

In electrophilic addition reactions, the first step is the attack of the π electrons of the double bond on the hydrogen of the alkyl halide to yield a carbocation. One of the carbon in C=C gets attached to hydrogen while the other acquires a positive charge. In the second step, the carbocation formed can rearrange to give another more stable carbocation either by a hydride shift (shift of hydrogen atom with its electron pair) or by an alkyl shift (shift of an alkyl group with its electron pair) between neighboring carbons. In the last step the carbocation produced reacts with the halide ion to give the alkyl halide.

To predict:

The product and to show the complete arrow-pushing mechanism for the electrophilic reaction given which involves a carbocation rearrangement.

Interpretation Introduction

c)

Interpretation:

The product and the complete arrow-pushing mechanism for the electrophilic reaction given which involves a carbocation rearrangement.

Concept introduction:

In electrophilic addition reactions, the first step is the attack of the π electrons of the double bond on the H+ of the acid to yield a carbocation. One of the carbon in C=C gets attached to hydrogen while the other acquires a positive charge. In the second step, the carbocation formed can rearrange to give a more stable carbocation either by a hydride shift (shift of hydrogen atom with its electron pair) or by an alkyl shift (shift of an alkyl group with its electron pair) between neighboring carbons. In the last step the carbocation produced reacts with the halide ion to give the alkyl halide.

To predict:

The product and to show the complete arrow-pushing mechanism for the electrophilic reaction given which involves a carbocation rearrangement.