Question 15

MATRIX MATCHHARD

The List-II contains products obtained from the reaction of compounds in List-I with $O_3/Zn-H_2O$ followed by cyclization (via more stable enolate) in the presence of aqueous $NaOH$ . Match each entry in List-I with appropriate entry in List-II and choose the correct option.

List - I

P

Row

Q

Row

R

Row

S

Row

List-II

1

List II Item 1

2

List II Item 2

3

List II Item 3

4

List II Item 4

5

List II Item 5

(A)

P-2, Q-4, R-1, S-3

(B)

P-3, Q-4, R-5, S-2

(C)

P-2, Q-1, R-5, S-3

(D)

P-3, Q-5, R-4, S-2

Detailed Solution

The reaction sequence involves:

Ozonolysis of the tetrasubstituted double bond to yield a dicarbonyl (diketone).
Intramolecular Aldol condensation of the resulting diketone under basic conditions ( $NaOH$ ).
Cyclization follows the formation of the more stable enolate and results in the most stable ring system (usually 5 or 6 membered rings).

(P) is a 6-6 fused system ( $C_{12}H_{18}$ ). Ozonolysis gives a 10-membered ring diketone. Intramolecular aldol cyclization leads to a 6-6 fused hydroxy-ketone, which is product (2).
(Q) is a 6-7 fused system ( $C_{13}H_{20}$ ). Ozonolysis gives an 11-membered ring diketone. Cyclization leads to a 6-7 fused hydroxy-ketone, which is product (1).
(R) is a 7-5 fused system ( $C_{12}H_{18}$ ). Ozonolysis gives a 10-membered ring diketone. Cyclization leads to a stable 6-6 fused hydroxy-ketone system, which is product (5).
(S) is a 6-5 fused system ( $C_{11}H_{16}$ ). Ozonolysis gives a 9-membered ring diketone. Cyclization leads to a 6-5 fused hydroxy-ketone, which is product (3).

Therefore, the correct matching is P-2, Q-1, R-5, S-3. Correct Option: C

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