Answer Happy

5-A well-written problem meeting all guidelines, accompanied with the correct answer 4-A well-written problem meeting all guidelines, but minor errors in the answer 3-An acceptable problem meeting all guidelines, but deficiencies in the answer 2 or 1-not assigned (I might change my mind about this!!) 0-One or more guidelines not met OR a meaningless problem OR an incomplete/nonsensical answer Problem 1: A curved-arrow mechanism • Based on any one of the following transformations (Klein sections 7.12, 12.9, 13.6) o Alcohol to an alkyl halide o Alcohol to an alkene o An alcohol to another alcohol with skeletal rearrangement o An ether to an alcohol • The transformation you choose MUST involve a carbocation rearrangement. Be explicit about the reagent(s) required for the transformation you choose. • Problem 2: A multi-step synthesis problem with an aromatic alcohol, ether, aldehyde, ketone or a carboxylic acid as the target (Klein sections 12.4 & 12.6, 12.10) A vicinal diol to a ketone o Alkylation of benzene with an electrophile generated from a secondary alcohol • At least 4 synthetic steps • Must involve either a reduction (section 12.4) or an oxidation (section 12.10) or both Must involve at least one C-C bond formation reaction (reactions with organomagnesium or organolithium compounds, Friedel-Crafts acylation or alkylation) Building blocks - Any aliphatic building blocks up to 4 carbons are acceptable. You may also utilize benzene or phenol as a starting material. You may include additional stipulations/restrictions about the building blocks if it makes your problem more interesting. • • . Your answer must include all reagents clearly. Include aqueous work-up where required (enumerate on one arrow), but not as a separate synthetic step.