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.

compound w, c8h17br, and x, c8h17cl, are products of the radical bromination (w), and chlorination (x), of 2,4-dimethylhexane. w and x are each chiral. w reacts readily in water to form a chiral substitution product y, c8h17oh. reaction of a single enantiomer of w produces a single enantiomer of y as the only substitution product. x likewise reacts readily in water though at a slower rate than w; a chiral substitution product z, c8h17oh, is again formed. unlike w, however, reaction of a single enantiomer of x produces z that is nearly racemic. propose structures for w and x.

compound a has the formula c9h19cl. b is a c9h19br compound. a and b undergo base-promoted e2 elimination to give the same alkene c as the major product as well as different minor products. c reacts with one molar equivalent of hydrogen in the presence of a palladium catalyst to form 2,6-dimethylheptane. addition of hcl to c yields a as the major product. propose structures for a and b.