Question

11. Provide the expected major product for reaction shown 1. SOCl, Br, 2. CH2OH 3. NH3 OH 12. The expected major product of the following reaction is 1. (CH)Culi, (excess) f. no reaction

Answer 1

11. The reaction with SOCl₂ yields an acyl chloride, which then reacts with methanol to form an ester and, finally, the reaction with ammonia yields an amide, which will be the major product:

12. Gilman reagents (alkyl-CuLi salts) will react with beta insaturated carbonyl groups to yield 1,4-additions and also with acyl chlorides to yield ketones. Both of this are possible with the given compound, since there is an excess of Gilman reagent. The product is b: The methyl group in the carbon next to the cycle is from the 1,4 addition and the methyl group bonded to the carbonyl carbon is from the reaction with the acyl chloride functional group.