1. Rank the following compounds from least to most stable.

a, b, c c, b, a b, a, c b, c, a c, a, b 2. Predict the product(s) in the reaction below.

B C B and C A and B A 3. Determine the product(s) in the reaction below.

E B D A C

4.Markovnikov addition of HBr to CH3CH formation of a primary carbocation. initial attack by Br . initial attack by Br. isomerization of CH3CH2CH2Br. formation of a secondary carbocation.

CH2 involves:

5.Consider the dicarbonyl compound A drawn below. Which of the following compounds can be an enol tautomer of A?

c only a only a and c b only a and b 6.Determine the product(s) in the reaction below.

B D C A E

7.Predict the major product of the following reaction.

B A D C 8.Select the correct product(s) of the following reaction.

A B D C 9.Which of the following alcohols is most likely to yield a carbocation that is susceptible to rearrangements?

D C E B A

10.Determine the product of the following reaction.

D A E C B 11.What is the product in the reaction below?

A C D B 12.Determine the product of the following reaction.

B A C

13.Determine the product of the following reaction.

D C E A B 14.Select the correct product(s) and (or) stereochemistry.

C B A D 15.Which of the following alcohols undergoes dehydration most readily?

E A C B D

16.For which of the following alkenes is E-Z isomerism possible? A. CH3CH2CH=CHCH2CH3 B. CH3CH2CH=CHBr C. (CH3)2C=CHCH3 D. H2C=CHCH2CH(CH3)2 A and C B and D A, B, C, and D A, B, C A and B 17. Which of the following alkenes will react fastest with water in the presence of a small amount of H2SO4?

D E A C B 18.What is (are) the missing reagent(s) in the reaction below?

NBS [1]Br2, [2] H2O 9-BBN [1] BH3, [2] H2O2/OH Br2/CCl4 19.What is the relationship between the keto and enol forms of acetone, CH3COCH3? Conformational isomers Same compounds Diastereoisomers Resonance structures Constitutional isomers

20.Predict the product(s) of the following reaction.

A, B, C and D B and C B A A and D