Exam 2a Name___________________________________ MULTIPLE CHOICE. Choose the one alternative that best completes the statement or answers the question. 1) Which of the following compounds has an R configuration? A)

B)

C)

D)

E)

2) What configurations are found in the product(s) of the reaction below?

A) 1R,2S only B) 1S,2S only C) 1R,2R only D) an equal mixture of 1R,2R and 1S,2S E) an equal mixture of 1R,2R and 1R,2S

3) Provide the major organic product in the reaction below.

A)

B)

C)

D)

E)

4) Identify all meso compounds.

A) B and D, A and C B) A and B, A and D, B and C, C and D C) B and D D) A and C E) B and D, A and B, A and D, B and C, C and D

5) How many asymmetric centers are present in the compound shown below?

A) 1 B) 2 C) 3 D) 4 E) 5 WRITTEN ANSWER. 6) Propose a mechanism for the following reaction: Make sure to include all possible stereochemical outcomes. 10 PTS

MULTIPLE CHOICE. Choose the one alternative that best completes the statement or answers the question. 7) Name the structure.

A) 2-methyl-2,4-pentadiene B) 2-methyl-1,4-pentadiene C) 4-methylene-2-pentene D) 4-methyl-1,4-pentadiene E) 2-methylene-4-pentene

8) Which of the following is an allylic alcohol? A) CH2=CHCH2CH3 B) CH3CH=CHCH2OH C) CH2=CHCH2OCH3 D) CH2=CHCH2CH2OH E) HOCH=CHCH2CH3 9) Which of the following is not a nucleophile? A) NH3 B) CH3OCH3 C) Br-

D) FeBr3

E)

10) Which of the following compounds is chiral? A)

B)

C)

D)

E)

11) Which of the following is capable of exhibiting cis-trans isomerism? A) 2-butene B) cyclohexene C) 1-pentene D) ethene E) 1-butene

12) Which of the following best describes the geometry about the carbon-carbon double bond in the alkene below?

A) E B) Z C) neither E nor Z WRITTEN ANSWER. 13) Provide the major organic product(s) in the reaction below. 10 PTS

MULTIPLE CHOICE. Choose the one alternative that best completes the statement or answers the question. 14) Name the structure.

A) cis-3-ethyl-4-hydroxymethyl-hex-3-en-1-yne B) trans-3,4-diethylpent-3-en-1-yn-5-ol C) trans-2,3-diethylpent-2-en-4-yn-1-ol D) cis-3,4-diethylpent-3-en-1-yn-5-ol E) cis-2,3-diethylpent-2-en-4-yn-1-ol

15) Identify all pairs of enantiomers.

A) B and D B) B and D, A and B, A and D, B and C, C and D C) A and C D) B and D, A and C E) A and B, A and D, B and C, C and D 16) Identify all pairs of diastereomers.

A) A and C B) B and D C) B and D, A and B, A and D, B and C, C and D D) A and B, A and D, B and C, C and D E) B and D, A and C WRITTEN ANSWER. 17) Provide the major organic product in the reaction below. Draw out the mechanism in detail. Make sure to include all possible stereochemical outcomes. 5 PTS

CH3CO3H

18) Provide a detailed, step-by-step mechanism for the reaction shown below. Make sure to include all possible stereochemical outcomes of the reaction. 10 PTS

19) Draw the major organic product generated in the reaction below. Make sure to include the stereochemical outcomes (if any) by using dashed wedges and solid wedges. Include the mechanism of the reaction. 10 PTS

MULTIPLE CHOICE. Choose the one alternative that best completes the statement or answers the question. 20) Which of the following is not an electrophile? A) H+

B) +NO2 C) BF3 D) CH2CH2 E) Fe+3

1) A 2) D 3) C 4) D 5) C 7) B 8) B 9) D 10) C 11) A 12) C 14) C 15) A 16) D 20) D