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NEET2025Chemistry
Q.

How many products (including stereoisomers) are expected from monochlorination of the following compound?

  1. A

    2

  2. B

    3

  3. C

    5

  4. D

    6

Solution

The substrate 2-methylpentane (CH)CHCHCHCH has the following non-equivalent hydrogens, and monochlorination at each gives a distinct constitutional isomer:

(a) terminal CH groups at C-1 (equivalent pair) → 1-chloro product (1 isomer).

(b) CH at C-2 (the branched carbon) → 2-chloro product (this carbon is a stereocenter after Cl substitution, but only one structural isomer; counted as 2 stereoisomers — R and S).

(c) CH at C-3 → 3-chloro product (introduces a stereocenter at C-3 too → 2 stereoisomers).

(d) CH at C-4 → 4-chloro product (1 isomer; not chiral).

(e) CH at C-5 → 5-chloro product (1 isomer).

Counting constitutional isomers plus the stereoisomeric pairs where applicable gives a total of products including stereoisomers.

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