Test 3
Dr. Bachrach
CHEM 2319-2
4/2/2008

1) (12 points) Provide the IUPAC name for the following compounds.

2) (15 points) Provide the MAJOR product the following reactions.

a)

Bromination preferentially at 3° positions

b)

E2 with Zaitsev rule

c) Note that this reaction proceeds with stereoinversion

3) (12 points) For the following reaction below, will the reaction proceed faster in ethanol (CH₃CH₂OH) or diethyl ether (CH₃CH₂OCH₂CH₃)? Explain your choice.

4) (12 points) For each pair of reactants, circle which one will react faster and identify the reaction mechanism.

a)

b)

c)

5) (25 points) Predict the product(s) of the following reactions. Indicate the major product if there is more than one product obtained.

a)

S_N2 – good leaving group, strong nucleophile – goes with inversion

b)

3° alkyl bromide – form cation – in this case allyl cation!

c)

3° alkyl bromide – form cation – since Cl^- is very poor base, get substitution (racemic)!

d)

e)

6) (12 points) Predict the major product and draw the reaction mechanism for the following reaction.

7) (12 points) Using any alkane or alkylhalide having four or fewer carbon atoms you desire and any inorganic reagents, prepare 3,4-dibromohexane.