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JEE Advanced2023Paper 1CHEM-IV
Q.

Match the reactions in List-I with the features of their products in List-II and choose the correct option.

  1. A

    P 1; Q 2; R 5; S 3

  2. B

    P 2; Q 1; R 3; S 5

  3. C

    P 1; Q 2; R 5; S 4

  4. D

    P 2; Q 4; R 3; S 5

Solution

(P) 1-Bromo-2-ethylpentane via S2. The leaving group is on a primary carbon; the stereocentre at C-2 is not the site of substitution. Hence its configuration is preserved: retention of configuration at the existing stereocentre. Match (2).

(Q) 2-Bromopentane via S2. Substitution occurs at the stereocentre; bimolecular back-side attack causes Walden inversion. Inversion of configuration. Match (1).

(R) 3-Bromo-3-methylhexane via S1. Ionisation generates a planar tertiary carbocation at the stereocentre. Hydroxide attacks both faces equally, giving a racemic mixture: mixture of enantiomers. Match (3).

(S) S1 on a substrate with two stereocentres. Ionisation at one stereocentre yields a planar carbocation; hydroxide attacks either face. Because the second (unchanged) stereocentre remains intact, the two product alcohols differ at only one stereocentre, giving a pair of diastereomers. Match (5).

Mapping: P 2, Q 1, R 3, S 5. Answer: (B).

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