CHEM 109A Elimination Reactions 1.

Predict the products of the following reactions

Br
O

CLAS

H O

a.

-O

d.

Br

H O

-O

b.

Br

e.

-O

HO

c.

Cl

f.

Br

2. Which reactant in each of the following pairs will undergo an elimination reaction more rapidly? Explain your choice and show the mechanism.
OH Cl

OHBr

a.

H 2O

or

H 2O

CH3O CH 3OH

CH3O -

b.

Br

or

Br

CH 3OH

3. For each of the following, give the major elimination product; if the product can exist as stereoisomers, indicate which stereoisomer is obtained in greater yield. a. (R)-2-bromohexane + high concentration HO- b. (R)-2-bromohexane + H2O c. trans-1-chloro-2-methylcyclohexane + high concentration CH3O- d. trans-1-chloro-2-methylcyclohexane + methanol e. (R)-2-bromohexane + high concentration sodium tert-butoxide f. (2-Bromo-3-methyl-butyl)-benzene/2-bromo-3-methyl-1-phenylbutane + high concentration methoxide

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