Test 3
Dr. Bachrach
CHEM 2319-2
4/6/2011

1) Provide the IUPAC name for the following compounds.

2) Provide only the MAJOR product of the following reactions.

a)

b)

c)

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

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

a)

This is S_N2 – not the primary alkyl halide and the very weak base I^-. OTs^- is a better leaving group than Cl^-, so the second reaction is faster.

b)

This is E₂ – tertiary halkyl halide and strong base, but the second reaction has the stronger base.

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

a)

This goes S_N2 – good nucleophile and good leaving group on a secondary carbon

b)

S_N1 to form the allyl cation – and then consider two resonance structures, expect both products near 50:50

c)

S_N1 – tertiary alkyl halide and very very poor base, expect both products near 50:50

d)

Strong base would like to go elimination, but neighboring carbon to the one that has the bromine does NOT HAVE A HYDROGEN to eliminate! So only substitution.

e)

6) The following reaction gives two products. Predict the major and minor product. Draw the mechanism that leads to the major product.

7) Draw the Lewis dot structure for the intermediate radical formed for the reaction of 1-methyl-1,4-cyclohexadiene with NBS.