How many products (including stereoisomers) are expected from monochlorination of the following compound? [figure]
- 5
- 6
- 2
- 3
Answer
(2) 6
Solution
2-Methylbutane, (CH3)2CH-CH2-CH3, has four types of H atoms. Monochlorination gives:
(i) ClCH2-CH(CH3)-CH2-CH3 (1-chloro-2-methylbutane): C-2 is chiral → 2 enantiomers
(ii) (CH3)2CCl-CH2-CH3 (2-chloro-2-methylbutane): achiral → 1
(iii) (CH3)2CH-CHCl-CH3 (2-chloro-3-methylbutane): C-2 is chiral → 2 enantiomers
(iv) (CH3)2CH-CH2-CH2Cl (1-chloro-3-methylbutane): achiral → 1
Total products = 2 + 1 + 2 + 1 = 6
Answer: (2)