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Final

CHEM 2220 Final Exam 2010Exam


Department
Chemistry
Course Code
CHEM 2220
Professor
All
Study Guide
Final

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ANSWER KEY Page 1 of 10
CHEM 2220 Organic Chemistry II: Reactivity and Synthesis
Prof. P.G. Hultin, Prof. T. Hegmann, Dr. H. Luong
FINAL EXAM – Winter Session 2010R
Wednesday April 14, 2010 1:30 pm – 4:30 pm
Frank Kennedy Gold Gym
Students are permitted to bring into the exam room ONE SHEET of 8½ x 11 paper with any
HANDWRITTEN notes they wish (both sides). Molecular model kits and calculators (no text or graphics
memory!) are permitted but no other aids may be used.
Question 1 – Reactions and Products (42 Marks)
Question 2 – Synthesis (10 Marks)
Question 3 – Mechanism (8 Marks)
Question 4 – Mechanism (10 Marks)
Question 5 – Mechanism (10 Marks)
Question 6 – Laboratory (15 Marks)
Question 7 – Spectroscopy (5 Marks)
TOTAL: (100 Marks)

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CHEM 2220 Final Exam 2010 ANSWER KEY Page 2 of 10
1. (42 MARKS) Reactions and Products. Supply the missing molecular structure or
reagent/solvent/reaction conditions to correctly complete the following reactions.
(a)
Br
Et3N
CH2Cl2, heat
(2 Marks)
(b)
OO
pTsOH
acetone
OH OH
(2 Marks)
(c)
O
OCH3
H3C
O
OH OCH3
O
Br
PBr3,Br
2
then
CH3OH
Zn
CHO
ether
aq acid workup
(4 Marks)
OH CrO3
pyridine
1.
2.
BH3,THF
NaOH (aq.)
OH
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