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JEE Advanced2025Paper 2CHEM-I
Q.

Monocyclic compounds P, Q, R and S are the major products formed in the reaction sequences given below.

The product having the highest number of unsaturated carbon atom(s) is-

  1. A

    P

  2. B

    Q

  3. C

    R

  4. D

    S

Solution

Identify each major product and count its sp/sp carbons.

P (Hell-Volhard-Zelinsky on PhCHCOOH): -bromination gives Ph-CH-CHBr-COOH. Unsaturated carbons = 6 (the benzene ring).

Q (crossed aldol of PhCHO with CHCHO at 293 K): dehydration gives cinnamaldehyde, Ph-CH=CH-CHO. Unsaturated carbons = 6 (ring) + 2 (C=C) + 1 (C=O) = 9.

R (phenylacetylene + allyl bromide via NaNH, then Hg/HO): alkylation gives Ph-CC-CH-CH=CH; Markovnikov hydration places the carbonyl next to the phenyl: Ph-CO-CH-CH-CH=CH. Unsaturated carbons = 6 (ring) + 1 (C=O) + 2 (C=C) = 9.

S (2-methylindene reaction sequence): ozonolysis of the cyclopentene C=C in the indene ring breaks it to give an ortho-disubstituted benzene bearing CHO and COCH side chains (a 1,2-disubstituted benzene-acetaldehyde and methyl ketone). Two equivalents of CHMgBr add to both carbonyls; subsequent H/heat dehydrates both alcohols to alkenes. The final product is an ortho-disubstituted benzene with two alkene side chains (one vinyl and one 2-methylprop-1-enyl, i.e. CH=CH and CH=C(CH) or analogous). Unsaturated carbons = 6 (ring) + 2 (C=C in first side chain) + 2 (C=C in second side chain) = 10.

S has the most unsaturated carbons. Option (D).

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