Chem 25b M. Walker

Practice Quiz #1           YOUR NAME____ANSWER KEY______________

1.  Draw all possible products from the reaction shown.  Which product is the most stable?  Which product is formed the fastest?  Given that under the conditions given this reaction is kinetically controlled, which product will be the major product? [Note: AIBN is a free radical initiator, like hv or ROOR.]

A is formed from the more stable resonance form of the radical intermediate, and so we expect this to be the product formed the fastest, i.e. it will be major under conditions of kinetic control. However B is thermodynamically more stable than A, because it contains a trisubstituted double bond instead of only a disubstituted one- so B is the more stable product.

2.  Predict the product of the following reactions.  Indicate stereochemistry where appropriate, including whether the product is racemic or nonracemic.

3.  What reagent(s) might you use to effect the following transformation?