JEE Main · 2019 · 11 Jan 2019 · Shift 1 · General Organic Chemistry

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Which compounds out of the following is/are not aromatic?
(a) (see structure)
(b) (see structure)
(c) (see structure)
(d) (see structure)

(A)b, c and d
(B)c and d✓ Correct
(C)b
(D)a and c

Answer: (B)

Solution

Aromaticity demands a cyclic, planar, fully conjugated ring carrying

(4 n + 2)

π

electrons. Testing the four structures against that rule, two of them fail: one has its ring conjugation broken by an

s p^{3}

centre, and the other does not satisfy the Huckel electron count for a planar conjugated ring. The two that fail the test are the compounds labelled (c) and (d), so these are the ones that are not aromatic.

JEE Main · 2019 · 11 Jan 2019 · Shift 1 · Single correct option

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