Organic Chemistry

Please write your final answers neatly on these pages.

Unclear, messy, or hard-to-find answers will be downgraded significantly.

1.) (14 pts.)

a.) Draw the two possible intermediates of the reaction shown.

b.) Draw the complete structures of all of the possible products that are formed from these intermediates.

c.) Indicate clearly what product(s) would be obtained exclusively if the reaction were run using oxymercuration-demercuration conditions.

2.) (16 pts.) Provide complete structures and names of all of the possible products of the following reaction.

Note: On this problem, each structure + name combination must be completely correct for credit, no partial credit.

3.) Three unknown compounds may react with H-Br resulting in a product mixture (spectroscopic data for the products shown). Starting materials and products all have four carbons. The remaining information can be deduced from the spectroscopic data and our current knowledge of organic chemistry…

a.) (6 pts.) Draw the complete structures of the products.

b.) (8 pts.) Label one of the product structures with 1H and 13C NMR peak assignments using the proper format (as discussed previously).

c.) (6 pts.) Draw the structures of the three possible starting materials.

H-Cl

intermediate1intermediate2

possible

products:

H

2

O

H

2

SO

4