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CHEM 301 EXAM 3A NAME ____________________________

1 December 2011

Dr. Suzanne Ruder Student ID: _________________________

Group #

On my honor, I have neither given nor received aid on this exam______________________


INSTRUCTIONS: There are six pages to this exam. Read all questions carefully. If you have a question, raise your hand and someone will assist you. Paper other than the exam paper and molecular models are not permitted. Do your own work, and cover your answers.

Part 1: Multiple Choice (4 pts each). Use the form provided to scratch off your answer. If your answer is correct there will be a star; if your answer is not correct, scratch off your second choice to receive partial credit for your answer. Scratch off questions 1-12 on your form.

1. What is the product of the following reaction?


A) B) C) D)

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2. What reagents will accomplish the following transformation?


A) 1. NaNH2 2. CH3CH2CHO 3. H2, Pd

B) 1. NaNH2 2. CH3CH2CH2Br 3. Sia2BH; H2O2, NaOH

C) 1. NaNH2 2. CH3SH2CH2Br 3. H2O, H2SO4, HgSO4

D) 1. NaNH2 2. CH3CH2CHO 3. KMnO4, heat

3. What major elimination product would form on reaction of the following compound with NaOCH3?


A) (E) 3-phenyl-hex-2-ene

B) 2-methyl-1-phenylpent-1-ene

C) (2S, 3R) 2-methoxy-3-phenylhexane

D) (Z) 3-phenyl-hex-2-ene

4. What reagent would give anti-Markovnikov addition to an alkene?

A) Br2


C) HBr

D) both A and B

5. The following compound is reacted with concentrated hot KMnO4. What main product is formed?


A) B) C) D)

[pic] [pic] [pic] [pic]

6. Provide the reagents necessary to complete the following transformation.


A) KMnO4, Heat

B) O3, Me2S

C) OsO4, H2O2

D) 1. CH3CO3H 2. H3O+

7. Which of the following...