STUDENT NAME: _______________ STUDENT NUMBER: ______________

FACULTY OF ARTS AND SCIENCE

Term Test

February 27, 2006

6:05 – 7:20 pm

CHEMISTRY 222/4 Section 51

Organic Chemistry II

WRITE YOUR LAST NAME AND STUDENT NUMBER ON THIS

SHEET. YOU HAVE 75 MINUTES TO COMPLETE THIS EXAM.

MAKE SURE THIS EXAMINATION CONTAINS 5 QUESTIONS.

USE OF MOLECULAR MODELS, CALCULATOR AND RULER IS

PERMITTED.

ANSWER ALL THE QUESTIONS IN THIS EXAM. HAND IN ALL

MATERIALS AT THE END OF THE EXAM.

Good luck!
MARKING SCHEME

Q1: / 15 Q2: / 15
Q3: / 15 Q4: / 15
Q5: /9

TOTAL: / 69

CHEM 222/4 SECTION 51 TERM TEST PAGE 1

QUESTION 1 (15 POINTS): Using the MS, IR, 13C NMR and 1H NMR spectra
provided below identify the structure of the compound.

CHEM 222/4 SECTION 51 TERM TEST PAGE 2

QUESTION 2 (15 POINTS): Using the MS, IR, 13C NMR and 1H NMR spectra
provided below identify the structure of the compound.

CHEM 222/4 SECTION 51 TERM TEST PAGE 3

QUESTION 3 (15 POINTS): Using the MS, IR, 13C NMR and 1H NMR spectra
provided below identify the structure of the compound.

CHEM 222/4 SECTION 51 TERM TEST PAGE 4

QUESTION 4 (15 POINTS): What would be the two major products formed
by the reaction between one equivalent of HBr and 2,3-dimethyl-1,3-
butadiene (shown below)? Show the complete mechanism for the
formation of each product including arrow pushing and all intermediates.
Indicate which is the kinetic product and thermodynamic product. Use an
energy diagram to explain your choice.

HBr

QUESTION 5: (9 POINTS): What diene and dienophile would react together

to form the following products?

(a) (b) H (c)

CO2CH3
H H
H
CN H
H CO2CH3

CHEM 222/4 SECTION 51 TERM TEST PAGE 5