Chem210-1-2007-Exam2

Chem210-1-2007-Exam2 - Chem 210-1, November 5, 2007,...

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1 Chem 210-1, November 5, 2007, Mid-Term Exam 2 NAME:___________________________________ This exam has 100 total points with the point breakdown for each problem given below. 1. (20 points) Give the major product of the following reactions. Indicate which of the following mechanisms is in operation: S N 1, S N 2, E1, E2. If no reaction takes place, write “no reaction”. (2 points each for product, 2 points each for identifying the mechanism) A) I EtOH Δ B) CH 2 Cl H K +- OtBu t-BuOH C) F KBr DMF D) NaOEt EtOH Br E) Br EtOH Δ
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2 2. (10 points) The reaction shown below is called the pinacol rearrangement. It involves 1) formation of a carbocation intermediate, 2) a methyl shift to generate a resonance stabilized carbocation, and 3) proton loss. Show the stepwise mechanism of this reaction. OH HO O H 2 SO 4 ,hea t
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3 3. (20 points) Give the major product of each reaction. (2 points each) Also label the chiral centers and give the (R,S) configurations of both the starting materials and the products (2 points). Careful! some have two chiral centers. If the product is optically
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Chem210-1-2007-Exam2 - Chem 210-1, November 5, 2007,...

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