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Question 35

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

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

An “unsaturated” carbon is any carbon that is part of a multiple bond (C=C or C≡C).
Therefore, to compare P, Q, R and S we must first identify the ring produced in each sequence and then count the sp2/sp hybridised carbons present in that ring.

Case 1 : Formation of P
The dihydric alcohol supplied in sequence (1) undergoes intramolecular dehydration with conc. $$H_2SO_4$$ to give a saturated cyclic ether (tetrahydrofuran type).
All ring carbons remain $$sp^3$$-hybridised, so

Number of unsaturated carbons in P = 0

Case 2 : Formation of Q
In sequence (2) the diol first forms a leaving-group derivative, followed by a single E2 elimination, producing a cyclohexene ring with one C=C bond.
Only the two carbons of that double bond are $$sp^2$$; hence

Number of unsaturated carbons in Q = 2

Case 3 : Formation of R
Sequence (3) involves two eliminations that furnish a conjugated diene ring, cyclohexa-1,3-diene. Two C=C bonds ⟹ four $$sp^2$$ carbons, so

Number of unsaturated carbons in R = 4

Case 4 : Formation of S
The reagents in sequence (4) carry out stepwise dehydrogenation until an aromatic ring is obtained. The monocyclic product is benzene (or a benzene derivative), which contains six $$sp^2$$ carbons.
Therefore,

Number of unsaturated carbons in S = 6

Comparing: $$P:0 \lt Q:2 \lt R:4 \lt S:6$$

Hence, the product possessing the largest number of unsaturated carbon atoms is S.

Option D which is: S

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