It is to be explained that the bicyclo [ 2 .2 .1 ] heptan-1-ol is relatively unreactive towards hydrogen halide. Concept introduction: The reaction of methyl and primary alcohols with hydrogen halide proceeds through S N 2 mechanism. The S N 2 reaction is the bimolecular nucleophilic substitution reaction whose rate determining step involves two reactants. The reaction of tertiary alcohol with hydrogen halide proceeds through S N 1 mechanism. The S N 1 reaction is the unimolecular nucleophilic substitution reaction, which means the rate determining step involves only one reactant. The slow step in the S N 1 mechanism is formation of carbocation and it is the rate determining step. The carbocation (positively charged carbon) is sp 2 hybridized and acquires planar structure. The carbocation at bridgehead carbon is unstable. The carbon atom which is a part of two or more rings in polycyclic compounds is as shown below:

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Chapter 5, Problem 39P

Interpretation Introduction

Interpretation:

It is to be explained that the bicyclo[2.2.1]heptan-1-ol is relatively unreactive towards hydrogen halide.

Concept introduction:

The reaction of methyl and primary alcohols with hydrogen halide proceeds through SN2 mechanism.

The SN2 reaction is the bimolecular nucleophilic substitution reaction whose rate determining step involves two reactants.

The reaction of tertiary alcohol with hydrogen halide proceeds through SN1 mechanism.

The SN1 reaction is the unimolecular nucleophilic substitution reaction, which means the rate determining step involves only one reactant.

The slow step in the SN1 mechanism is formation of carbocation and it is the rate determining step.

The carbocation (positively charged carbon) is sp2 hybridized and acquires planar structure.

The carbocation at bridgehead carbon is unstable.

The carbon atom which is a part of two or more rings in polycyclic compounds is as shown below:

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