1.

Which of the following statements is/are correct ?

Answer»

The compound (B) is (I).
The compound (B) is (II).
The compound (C ) is (I).
The compound (D) is II.

Solution :The REASONANCE STRUCTURE of 2-napthoxide ion (A) is:

(A) is an AMBIDENT nucleophile and a better nucleophile than `(A_(1))` because negative charge is on more EN oxygen atom. In the presence of polar non-PROTIC solvent (DMF, dimethyl formamide), O-alkylation is favoured to give product II (C ). In the pressence of protic solvent, hydrogen bonding with the O atom occurs, THUS reducing the nuclehilicity of oxygen. Therefore, C-alkylation is favoured to give product I (B).


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