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:

Question

Want to see the full answer?

Answer 1

Question

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:

Expert Solution & Answer

Want to see the full answer?

Check out a sample textbook solution

See solution

Students have asked these similar questions

Rank the labeled protons (Ha-Hd) in order of increasing acidity, starting with the least acidic. НОН НЬ OHd Онс

Can the target compound at right be efficiently synthesized in good yield from the unsubstituted benzene at left? ? starting material target If so, draw a synthesis below. If no synthesis using reagents ALEKS recognizes is possible, check the box under the drawing area. Be sure you follow the standard ALEKS rules for submitting syntheses. + More... Note for advanced students: you may assume that you are using a large excess of benzene as your starting material. C :0 T Add/Remove step G

The following equations represent the formation of compound MX. What is the AH for the electron affinity of X (g)? X₂ (g) → 2X (g) M (s) → M (g) M (g) M (g) + e- AH = 60 kJ/mol AH = 22 kJ/mol X (g) + e-X (g) M* (g) +X (g) → MX (s) AH = 118 kJ/mol AH = ? AH = -190 kJ/mol AH = -100 kJ/mol a) -80 kJ b) -30 kJ c) -20 kJ d) 20 kJ e) 156 kJ