Test 6 (Lecture 6 / Module 6): 5 points
1. Draw Zaitsev and Hofmann products that are expected when each of the compounds is treated with a
strong base to give an E2 ELIMINATION reaction. Hint: Some compounds cannot produce either Zaitsev
or Hofmann products because they do not have beta-hydrogen atoms, mark “none” “N/A” or “X” if it is
the case (1 point):
(a) (0.2 point):
(b) (0.2 point):
(c) (0.2 point):
(d) (0.2 point):
(e) (0.2 point):
2. Draw the appropriate Newman projection which leads to the major E2 ELIMINATION product. Hint:
Review Chapter 10.3, the elimination can only occur if the leaving group (Cl, Br, I, OTs, etc) and beta-
hydrogen atom (H) are in anti-periplanar conformation. Red bond = the location of a double bond in the
final product and the direction of a Newman projection (2 points):
(a) (0.4 point):
(b) (0.4 point):
(c) (0.4 point):
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 major product. You will have to
draw two Newman projections and decide which one is the most stable (energetically).
(d) (0.4 point):
(e) (0.4 point):
3. Identify the Major and the Minor product(s) that are expected for each of the following reactions.
Hint: E1 / E2 or SN1 / SN2 (2 points):
Hint: Use Flow Charts on page 167 (Chapter 10.9)
(a) (0.2 point):
(b) (0.2 point):
(c) (0.2 point):
(d) (0.2 point):
(e) (0.2 point):
(f) (0.2 point):
(g) (0.2 point):
(h) (0.2 point):
(i) (0.2 point):
(j) (0.2 point):