13. Alcohols and Carbonyl Compounds

Show how you would accomplish the following synthetic conversions.

(c)

Suggest a synthesis of the following molecule starting with the reagents shown, using cuprate cross-coupling as the key step.

What are the products of the following reactions? Show all stereoisomers that are formed.

a.

b.

Muscalure is the sex attractant of the common housefly. Flies are lured to traps filled with bait that contain muscalure and an insecticide. Eating the bait is fatal. How could you synthesize muscalure using 1-bromopentane as one of the starting materials?

Predict the product that would result from the reaction of an organolithium reagent with a ketone when a hydroxyl group is present in the ketone substrate.

Predict the major products of the following reactions, and give the structures of any intermediates. Include stereochemistry where appropriate.

(o)

Predict the product of the following aldehyde and ketone addition reactions.

(c)

For each of the following carbonyl addition reactions, would you expect a racemic mixture or a mixture enriched in one stereoisomer? In each case, draw both possible stereoisomeric products.

(a)