JEE Main · 2020 · 07 Jan 2020 · Shift 2 · General Organic Chemistry

The correct order of stability for the following alkoxides is

(A)(B) $>$ (C) $> A$
(B)(C) $>$ (A) $>$ (B)
(C)(C) $>$ (B) $>$ (A)✓ Correct
(D)(B) $>$ (A) $>$ (C)

Answer: (C)

Solution

An alkoxide is more stable the better its negative charge can be spread out. In structure C the nitro group is placed so that it conjugates directly with the oxygen's charge, giving the strongest resonance stabilisation; in B the nitro group helps less from its meta-type position; and in A, where the nitro group sits isolated on a saturated carbon, there is almost no delocalisation. The stability order is therefore C greater than B greater than A.

JEE Main · 2020 · 07 Jan 2020 · Shift 2 · Single correct option

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