CHE 232-1, Spring 2008

Dr. Harris

Name (please print)___________________________________

Student ID #­­­­­­­­­­­­­­­­­­______________________________________

Short Answer (30 pts)

1. (5 pts) Draw (R)-2-chloropropanoic acid.

2. (5 pts) Circle the most acidic compound.

3. ( 5 pts ) Of the three compounds in question 2, draw the one with the strongest conjugate base.

4. ( 2.5 pts each) You are given a mixture of the following two compounds, and use a mixture of diethyl ether and water to extract them. In which layer is each compound?

They are both in the diethyl ether layer.

5. (5 pts ) If you replace water with a 20% NaOH solution, which layer would contain compound A.

diethyl ether layer

6. ( 5 pts )How would you distinguish between formaldehyde and acetaldehyde using proton NMR (Give the ppm range for this peak)?

The proton NMR of acetaldehyde would have a peak (2-2.5ppm) representing the protons on the alpha carbon.

Predict the Products.-Show stereochemistry (25 pts.)

7) (5 pts each)

8) (2.5 pts each)

9) (5 pts)

NO REACTION

10) (2.5 pts each)

11) (5 pts)

Fill in the missing parts of this synthesis. (30 pts.)

12) (16 pts)

13) (14 pts)

Mechanism: (Show and label all steps) (15 pts.)

14) (5 pts for carbocation, 5 pts for hemiacetal, 5 pts for acetal)

Exam Score

1-6 _________ (/30)

6-11_________ (/25)

12-13 ________ (/30)

14 _________ (/15)

Total________ (/100)

171

200

---