(i) How many monochloro products would you expect when 2-methylbutane is chlorinated? Write their structures and IUPAC names. One of them may have stereoisomer. Indicate it.

Explanation

Chlorination of 2-methylbutane gives a mixture of isomeric products given below:

2-Chloro-3-methylbutane may have stereoisomers because C-2 is a chiral centre, i.e., attached to four different groups.
(ii) 2-chloro-2-methylbutane on dehydrohalogenation gives two products :

2-Chloro-3-methylbutane also gives two products on dehydrohalogenation.