Test 10 (Lecture 10 / Module 10): 5 points
1. Please predict the products for each of the following reactions. Make sure to clearly indicate the co
ect
stereochemistry for each compound (2 points):
2. Propose best Williamson ether syntheses for the following compounds. In each case draw the structure of
the starting alcohol, and show the reagents necessary to convert the alcohol into the desired product. Some
compounds cannot be made using Williamson synthesis reaction, please clearly indicate it. (1 point):
(a) (0.2 points)
(b XXXXXXXXXXpoints)
(c XXXXXXXXXXpoints)
(d XXXXXXXXXXpoints)
(e) (0.2 points)
3. Predict the expected product for each reaction and draw the co
ect starting material to yield the desired
epoxide (2 points):
(a) (0.2 points):
(b) (0.2 points):
(c) (0.2 points):
(d) (0.2 points):
(e) (0.2 points):
FINAL (Lecture 1-10 / Module 1-10): 25 points
1. Draw the most stable and least stable conformations for each of the following compounds. In each case
fill in the group on the Newman projections below (5 points):
(a) (1 point):
(b) (1 point):
(c) (1 point):
(d) (1 point):
(e) (1 point):
2. Draw the structures of the following compounds. Make sure to clearly indicate the stereochemistry where
applicable (5 points):
(a) (R)-2-isopropyl-2,3,3-trimethylbutan-1-ol (1 point):
(b) (2E, 4Z, 6Z, 8E)-deca-2,4,6,8-tetraene (1 point):
(c) (S)-3-methylpent-1-ene (1 point):
(d) (E)-3,7-dimethyl-2,6-octadien-1-ol (geraniol) (1 point):
(e) (R)-4-methyl-4-phenylcyclohex-2-en-1-one (1 point):
3. Draw the expected products for each of the following reactions. (5 points):
4. Draw a detailed mechanism for the following reactions (draw each step and intermediate clearly, show all
appropriate electron pushing a
ows). Describe each mechanistic step. For example, proton transfer, alkyl
migration, rea
angement, etc. (5 points):
(a) (2.5 points):
Mechanism:
(b) (2.5 points):
Mechanism:
3. Draw the expected products for each of the following reactions. (5 points):
1. BONUS: (A) Show what reagent you would use to make the alkene. (B) Draw the products that are
expected when the alkene is treated with a peroxy acid (0.5 points):
2. BONUS: Draw the appropriate Newman projection which leads to the minor and major E2 ELIMINATION
product. Hint: D is a deuterium atom (D is an isotope of H atom and has very similar chemical properties). You
have to decide if beta-H or beta-D atom will be eliminated to form the minor and major product. You will have
to draw two Newman projections and decide which one is the most stable (energetically) (1 point):
3. BONUS: Draw the enantiomer and at least one diastereomer for the following compound (0.5 points):