How many chiral compounds are possible on monochlorination of $2-$methyl butane ?

How many chiral compounds are possible on monochlorination of $2-$methyl butane ?
  1. $8$
  2. $2$
  3. $4$
  4. $6$

Solution

$\mathrm{H}_3 \mathrm{C}-\mathrm{CH}_2-\mathrm{CH}\left(\mathrm{CH}_3\right)-\mathrm{CH}_3$ on monochlorination gives $\mathrm{H}_2 \mathrm{C}(\mathrm{Cl})-\mathrm{CH}_2-\mathrm{CH}\left(\mathrm{CH}_3\right)-\mathrm{CH}_3$ (I) Achiral $\mathrm{H}_3 \mathrm{C}-\mathrm{CH}(\mathrm{Cl})-\mathrm{CH}\left(\mathrm{CH}_3\right)-\mathrm{CH}_3$ (II) Chiral
(III) Achiral
(IV) chiral

Asked in: JEE Main 2012 (Offline)

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