Problem Set

Chem 31
Due on 1 April 2016
A. Use the curved arrow formalism to trace formation of intermediates and products in the
following reactions:

B. Predict the products of the following reactions:

C. Some exercises on stereochemistry.

How many asymmetric/chiral centers are found Butaclamol? This drug is a potent
antipsychotic and has been used in the treatment of schizophrenia.

Does this molecule possess an R or S configuration?

D. On substitution and elimination (please attempt to draw the structures)
a. Which will react more rapidly via SN1? 1-bromo-2,2-dimethylpropane or
1-bromo-1,1-dimethylpropane? Explain.
b. Which will react faster via SN2? 1-chlorocyclohexane or 1-chloro-1-methylcyclohexane?
Explain.
c. In the reaction between 1-methylcyclohexanol with hydrogen bromide to form
1-bromo-1-methylcyclohexane and water,
a) How would the rate be affected if the concentration of alcohol is doubled?
b) How would the rate be affected if the concentration of HBr is doubled?