JEE Advance - Chemistry (2014 - Paper 1 Offline - No. 12)

The reactivity of compound Z with different halogens under appropriate conditions is given below

JEE Advanced 2014 Paper 1 Offline Chemistry - Alcohols, Phenols and Ethers Question 19 English
The observed pattern of electrophilic substitution can be explained by
the steric effect on the halogen
the steric effect of the tert-butyl group
the electronic effect of the phenolic group
the electronic effect of the tert-butyl group

Explanation

Steric effect of halogens are as follows Cl2 < Br2 < I2

Electronic effect of phenolic group directs the approaching electrophile towards ortho and para positions. Tertiary butyl group has large size so it causes steric effect around aromatic nucleus. On the basis of above factors the products of the given reactions are as follows

JEE Advanced 2014 Paper 1 Offline Chemistry - Alcohols, Phenols and Ethers Question 19 English Explanation
Hence, orientation in electrophilic substitution reaction is decided by

(a) The steric effect of the halogen

(b) The steric effect of the tert-butyl group

(c) The electronic effect of the phenolic group

So, (a), (b) and (c) are correct choices.

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