JEE MAIN - Chemistry (2019 - 12th January Evening Slot - No. 11)

The increasing order of the reactivity of the following with LiAlH4 is

JEE Main 2019 (Online) 12th January Evening Slot Chemistry - Compounds Containing Nitrogen Question 181 English
A < B < C < D
B < A < C < D
B < A < D < C
A < B < D < C

Explanation

All the given compounds are acid derivatives, thus contain carbonyl group in them. LiAlH4 reduces these compounds through nucleophilic substitution via addition elimination (SNAE) reaction. The rate of reaction depends upon the following factors:

(i) Size of alkyl group.

(ii) Steric hinderance around the > C == O group.

(iii) (+) ve charge on the C-atom of > C == O group.

The alkyl groups are more or less same in the given compounds. Thus, the reactivity order of given compounds depends upon 2nd and 3rd factor written above. The cumulative effect of these two factors results to leaving group ability (LGA) of the substituents in the following order :

JEE Main 2019 (Online) 12th January Evening Slot Chemistry - Compounds Containing Nitrogen Question 181 English Explanation 1

This leaving group ability (weak conjugate base) corresponds directly to the reactivity order.

Hence, the correct reactivity order is:

JEE Main 2019 (Online) 12th January Evening Slot Chemistry - Compounds Containing Nitrogen Question 181 English Explanation 2

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