I. Propose a mechanism for the following reactions: 1.

spontaneous
H2N S O N H O HS

8.
H CH3 CH3 H CH3 CH3

NaOH
H O

H O

2.

9.

3.
CH3 O CH3 CH3

10.
KOH H2O
O
O

KOH
O

4.
O O

+
O O

[H+] H2O
O

HO

11.
HO

5.

OH

H2SO4

CH3

CH3 H3C CH3

H3C

CH3

12. 6.
O O Mg Br Mg Br

1. THF 2. H3O+
HO OH

13. 7.
O

+
H2C O

NaOEt EtOH
O

14. 22.

15. 23.
CH3 OH

H+
CH3 CH3

CH3 H3C CH3

2 possible products formed

16. 24.
O Br

LDA

17. 25.

18.

26. 19.

27.

20.

28.

21. 29.

II. Predict the products of the following reactions: 1.

10.

11. 2. 12.

3. 13.

4.

14. 5.

6. 15. 7.

8.

16.

17. 9.

18.

23. Identify the products in each step:

19. Identify the products in each step:

24. Identify the products in each step:

20. Identify the products in each step: III. Specify the reagents needed achieve the following products from the given starting material. Multiple steps may be required. 1.

2. 21. Deduce the structures A-D: 3.

4.

22. Identify the products in each step:

5.

6. 14.

7.

15.

16.

8. 17.

9.

18. 10.

11. 19.

12.

13.

IV. Misc. Problems What is the structure of the compound that yields the following products upon ozonolysis followed by treatment with DMS or H2O2? a.

b.

c.

d.