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Organic Chemistry Exam - CHEM 231A, Test #4, Exams of Organic Chemistry

A past organic chemistry exam from chem 231a, focusing on topics such as leaving groups in substitution and elimination reactions, solvent effects, stereochemical considerations in the sn2 reaction, and product distribution in 1st order reactions. It includes questions asking for answers, prediction of products, and explanations of mechanisms.

Typology: Exams

Pre 2010

Uploaded on 08/16/2009

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Name:
Organic Chemistry - CHEM 231A
Test #4
November 5, 2001
1. Provide answers to the following questions: (32 points)
1a. What is the importance of a leaving group in substitution and/or elimination reactions (8 points)
1b. What role does solvent play in the Sn2 reaction. Explain. (8 points)
1c. What determines product distribution in 1st order reactions. Explain. (8 points)
1d. What are the stereochemical considerations in the Sn2 Reaction. Describe each and explain their
origin and effect on the reaction. (8 points)
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Name:

Organic Chemistry - CHEM 231A

Test # November 5, 2001

  1. Provide answers to the following questions: (32 points)

1a. What is the importance of a leaving group in substitution and/or elimination reactions (8 points)

1b. What role does solvent play in the Sn2 reaction. Explain. (8 points)

1c. What determines product distribution in 1st^ order reactions. Explain. (8 points)

1d. What are the stereochemical considerations in the Sn2 Reaction. Describe each and explain their

origin and effect on the reaction. (8 points)

  1. Predict products for the following reactions and briefly explain your answer. (5 @ 8 pts = 40 points)

2a.

Cl

NaCN / Acetone

2b.

O S

O

O

NaCl (1 eq) / H 2 O

2c.

Cl

MeOH Reflux

2d. Br

O

DMF

K

2e. Br

H 2 O

  1. Consider the following problem: (26 points)

O

S

O

O

H 3 C

Make this from this

4a. Conduct a retrosynthetic analysis for the above problem. It will be beneficial to think about more than one method to make the desired molecule; the various methods do not have to be completely correct, but rather should show that you have thought of alternative routes.. ( points)

4b. Using the best approach from problem 4a, synthesize the desired molecule. Mechanism are not required, but reagents and conditions are required. (13 points)