The correct order of reactivity of the following benzyl halides towards reaction with KCN is : [figure]
- a > b > c > d
- b > a > d > c
- b > a > c > d
- a > b > d > c
Answer
(2) b > a > d > c
Solution
Benzyl halides undergo nucleophilic substitution with KCN in a polar (protic) medium mainly through the SN1 path, i.e. via a benzylic carbocation Ar CH2.
Rate stability of the benzylic carbocation.
Electron-releasing (+R) groups at the para position stabilise the carbocation; electron-withdrawing groups destabilise it.
b: p-NH2 – strongest +R effect (N is less electronegative than O) most stable carbocation
a: p-OH – +R effect, weaker than –NH2
d: m-NO2 – only –I effect (–R does not operate from the meta position)
c: p-NO2 – both –R and –I effects least stable carbocation
Reactivity: b > a > d > c
Answer: (2)