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NEET CHEMISTRYMedium

When hydrolyzed with aqueous KOH, compounds that undergo racemization are: (i) [Image Missing] (ii) CH3CH2CH2Cl\text{CH}_3\text{CH}_2\text{CH}_2\text{Cl} (iii) [Image Missing] (iv) [Image Missing]

A

(i) and (ii)

B

(ii) and (iv)

C

(iv) only

D

(i) and (iv)

Step-by-Step Solution

Racemization during hydrolysis with aqueous KOH indicates that the reaction proceeds via an SN1S_N1 mechanism, which involves the formation of a planar carbocation intermediate. For a compound to undergo racemization, it must be chiral (optically active) and form a relatively stable carbocation (such as secondary, tertiary, benzylic, or allylic).

Compound (ii), 1-chloropropane (CH3CH2CH2Cl\text{CH}_3\text{CH}_2\text{CH}_2\text{Cl}), is an achiral primary alkyl halide. It typically undergoes SN2S_N2 substitution and cannot exhibit racemization.

Since the structural formulas for compounds (i), (iii), and (iv) are missing from the provided text, their chirality and carbocation stability cannot be independently evaluated. Therefore, the exact correct option cannot be definitively verified.

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