Question

What is the leaving group, degree of substituition, steric hinderance, stability of carbocation of the following alkyl halides:

1-chlorobutane, 1-bromobutane, 2-chlorobutane, 1-chloro-2-butene "crotyl chloride", 1-chloro-2-methyl propane, bromobenzene, 1-chloroadamantane, benzyl chloride

Answer 1

1-chloro butane

Leaving group - Cl-

Carbocation formed - CH2(+)-CH3-CH3-CH3 (1 degree carbocation)

Less steric hindrance

Not stable since primary carbocation

1-bromo butane

Leaving group - Br-

Carbocation formed - CH2(+)-CH3-CH3-CH3 (1 degree carbocation)

Less steric hindrance

Not stable since primary carbocation

2-chloro butane

Leaving group - Cl-

Carbocation formed - CH3-CH(+)-CH3-CH3 (2 degree carbocation)

Less steric hindrance

Little bit stable since secondary carbocation

1-chloro 2-butene

Leaving group - Cl-

Carbocation formed - CH2(+)-CH=CH3-CH2 (1 degree carbocation)

Less steric hindrance

Stable due to resonance

1-chloro 2-methyl propane

Leaving group - Cl-

Carbocation formed - CH+ - CH(CH3)-CH3

More steric hindrance

Not stable

Bromobenzene

Leaving group-Br-

Degree of substituton - secondary

steric hindrance - Not much

Stability of carbocation - stable due to resonance