Test 7 (Lecture 7 / Module 7): 5 points
1. Please predict the products for each of the following reactions. If a mixture of enantiomers is formed,
please draw all the enantiomers. (2 points):
Hint: For HBr and ROOR example, 4 enantiomers will be formed: RR, SR, RS, SS.
2. Draw a detailed mechanism for each of the following reactions (draw each step and intermediate clearly,
show all appropriate electron pushing a
ows). Name all the intermediates (ca
ocations) and describe each
mechanistic step. For example, proton transfer, alkyl migration, rea
angement, etc. (1 point):
Hint: Review Chapter 11.4.
(a) (0.5 point):
Mechanism:
(b) (0.5 point):
Mechanism:
3. Which reagent would you use to accomplish each of the following transformations. (1 point):
(a) (0.2 points):
(b) (0.2 points):
(c) (0.2 points):
(d) (0.2 points):
(e) (0.2 points):
4. Predict all the products for each of the following reactions (1 point):
(a XXXXXXXXXXpoints): Only one product is formed (explain why):
Name the product including the stereochemistry for each chiral center (0.25 point):
Name:
(b XXXXXXXXXXpoints): Two products are formed (explain why):
Name each product including the stereochemistry for each chiral center (0.25 point):
Name Product A:
Name Product B:
4. BONUS Questions:
1. Draw a detailed mechanism for the following reactions (draw each step and intermediate clearly, show all
appropriate electron pushing a
ows). Name all the intermediates (ca
ocations) and describe each
mechanistic step. For example, proton transfer, alkyl migration, rea
angement, etc. (0.5 points):
Mechanism:
2. Answer the questions below (0.5 points):
(a) Predict the product for the following reaction (0.05 point).
(b) Draw an appropriate chair conformation (0.15 points) and draw a chair flip if it is possible (0.05 points):
Hint: Draw two fused chair conformations with the appropriate configuration (cis or trans).
(a) Predict the product for the following reaction (0.05 points).
(b) Draw an appropriate chair conformation (0.15 points) and draw a chair flip if it is possible (0.05 points):
Hint: Draw two fused chair conformations with the appropriate configuration (cis or trans).