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.