Question

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


The observed pattern of electrophilic substitution can be explain by:

• A. The steric effect on the halogen
• B. The steric effect of the tert-butyl group
• C. The electronic effect of the phenolic group
• D. The electronic effect of the tert-butyl group

Answer 1

Answer: (A), (B), (C)

The electronic effect of the phenolic group

Steric effect of halogens are as follows $C{l}_2<B{r}_2<I_2$. 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:



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.