Page Points

1 ______ (15)

2 ______ (14)

3 ______ (14)

4 ______ (24)

5 ______ (13)

6 ______ (10)

Total ______ (100)

1. Provide IUPAC names for the following molecules. Don't forget to indicate stereochemistry when applicable (i.e R or S or Z or E). (9 pts)

2. Provide structures for the following molecules. (6 pts)
meso-1,2-dibromocyclopentane (S)-E-2-hexenol

3. Plexiglass has the following general formula. What monomer is it synthesized from? (2 pts)

4.. The following alkyl halide undergoes an E2 elimination reaction with ethoxide to yield only one alkene product. (4 pts)

a. Draw the alkene formed and using stereochemical structures explain why it is the only alkene formed.

5. Using the R and S convention, assign the absolute configuration of every stereocenter (marked with an asterisk) in each of the following molecules. (8 pts)

6. Show an arrow pushing mechanism which explains the product in the following reaction. (5; pts)

7. Predict the products of the following reactions. (9 pts)

8. For each of the following pairs of structures, circle the appropriate letter to indicate whether the molecules are enantiomers (E), diastereomers (D), or identical (I). (8 pts)

9. Fill in the appropriate reagents to carry out the following reactions. (16 pts)


10. Label the following molecules as chiral or achiral. (6 pts)

a) 5-methylnonane _________________

b)
_________________

c)
__________________

11. Refer to the following alkyl halides for parts a and b.

(a) (2 pts) Which isomer would react fastest with OH- by an SN2 reaction?

(b) (2 pts) Which isomer is the best substrate for a solvolysis reaction, SN1 (i.e. would react fastest under solvolysis conditions)?

12. Predict the product for the following SN2 substitution reaction. (3 pts)

13. Predict the products of the following dehydration reaction and label the products as major or minor. (3 pts)

14. What alkyl halide and nucleophile are needed to produce the following compounds? (4 pts)
a.

b.

15. Using Fischer projections draw all the steroisomers for 2,3-dihydroxy butane. (3 pts)