CHE 232-1, Summer 2008

Dr. Harris

Name (please print)___________________________________

Student ID #­­­­­­­­­­­­­­­­­­______________________________________

Short Answer (20 pts)

1. Draw (R)-3-methyl-2-heptanone.

2. Circle the weakest conjugate base.

3. Draw isobutyl-2,2'-dimethylpropanoate.

4. Name the compound below: N-ethyl-N-isopropyl-3-methylbutanamide

5. Given the following data, circle the correct compound:

• IR peak at 1802 cm^-1

• NMR data

1. 0.95 (triplet, 3H)

2. 1.07 (multiplet, 2H)

3. 2.90 (triplet, 2H)

Predict the Product(s) - Show stereochemistry (20 pts.)

6)

7)

8)

9)

10)

Fill in the missing parts of this synthesis. (40 pts.)

11)

12)

Mechanism: (Show and label all steps) (20 pts.)

14)

(5 points)

(5 points)

(5 points)

(5 points)

Exam Score

1-5 _________ (/20)

6-10_________ (/20)

11-12 ________ (/40)

13 _________ (/20)

Total________ (/100)

171

200

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