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Chemistry 303
fall, 2005
THIRD EXAMINATION
7:00 pm December 6th
Duration: 2 hr
Name________________________KEY

Revised Question II-C_________________________

Lab TA__________________________________________________________
(if you do not know his/her name, give day of lab section. NOT Brow or Clay)
This is an "open book" examination; you may use anything which is not alive.
Note: if you do not know the complete or specific answer, give a partial or general answer-WRITE SOMETHING
Write only in the space provided for each question.
Score:
p2______/14

p6______/12

p3_______/13

p7_____/10

p4_______/08

p8____/11

p5_______/11

p9_____/06

p10_____/07

p11_____/10

Total: _________/102
There are 12 pages in this exam. Please check now to be sure you have a complete set.
If you are using a resonance argument in your answer, draw the relevant resonance structures.
If you are asked to analyze a structure and you have no idea what it is, do a general analysis of the data and
propose partial structures.
Please be aware that a small number of students will be taking the exam at different times up until late morning
on Wednesday. It would be well not to discuss the exam until after that time.
NOTE: You will be asked to write mechanisms; that requires you always use the arrow formalism.
Please use it precisely, carefully, and correctly. Show charges carefully. Distinguish between an
intermediate and a transition state. When you draw cyclohexanes in the chair form, be sure to indicate
the angle of the axial and equatorial substituents accurately.`

PLEDGE:________________________________________________________________

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C. (8 pts). For the slightly more complicated case, B is converted to C by a multi-step process.
Draw the mechanism carefully making clear the configuration of each carbon at each step.
Name each step [SN1, SN2, E1, E2]. HINT: Note carefully the location of the Me and Et groups.
This is tough to visualize and the product is deliberately drawn to not correlate directly with B.
Do some visual gymnastics.
Indicate the configuration of all stereogenic carbons in the product using the R,S nomenclature.
R-configuration
O
H
Et

MeS

H
Cl

MeSNa

H
Et

THF solvent

Me H
B

Me H
SN2
H
Et

O H
Cl

MeS Me H

Et
H

SMe
MeS
H
Et
MeS

O H

SN2
H
Me

Cl

R-configuration

H
O
Me
H

R-configuration