1. (a) Consider the El reaction of the alcohol below (as the single enantiomer shown) with acid and heat. Draw the complete mechanism of the formation of the major product (there may be several products which you expect to be equivalently "major" - you may pick any one for your mechanism), and the structures only (no mechanisms required) for all other possible products. Be careful with both stereochemistry and deuterium. Some of the products may only form as a single stereoisomer, where others may be mixtures of stereoisomers - be careful to distinguish those outcomes. Also, some products might only be formed with or without) the deuterium, while other products may be formed in a way that the deuterium may or may not remain, forming a mixture of deuterated and undeuterated product. Remember, deuterium reacts chemically identically to hydrogen. (10 points) OH H2SO4 heat HC D (b) For your answer above, assume any products formed via a rearrangement are formed by a stepwise mechanism. If the rearrangement were concerted instead of stepwise, how would that affect the products formed? Which products would be affected, and why? (2 points) (c) Draw the mechanism of the concerted rearrangement step. Be careful with stereochemistry, and be certain to use the conformation of the reactant which actually undergoes the concerted rearrangement. (3 points)