Question

Compound w , c6h13cl, undergoes base-promoted e2 elimination to give a single c6h12 alkene, y. compound x, c6h13br, undergoes a similar reaction to form y and an isomeric alkene z. w is chiral; x is not. catalytic hydrogenation of y and z produces 2-methylpentane. propose structures for w and x.

Answer 1

Answer: W must be 5-chloro-2-methylpentane. It can give only 4-methy-1-pentene (Y) upon dehydrohalogenation: X must be 4-chloro-2-methylpentane. Dehydrohalogenation yields both Y and 4-methyl-2-pentene. (Z)