Name: ________________________
Section: _______
CHEM 331. Final Exam
Fall 2014
Prof Donald Watson
Please write your answers clearly in the boxes provided. If your answer is
illegible or outside the box, it will not be graded. You may use the back of test
pages for scratch work.
You may use molecular models.
Use of calculators, cell phones, headphones, or any other electronic device
during this exam is prohibited.
No notes or books may be used during this exam.
You may raise your hand to ask a question if you are not sure what is being
asked of you.
There are 16 pages in this exam. Please check that your test has 16 pages
before you begin. The last 4 pages are blank and may be used as scratch paper.
Question
Points
Points
1
_____ /6
7
_____ /10
2
_____ /4
8
_____ /10
3
_____ /10
9
_____ /10
4
_____ /10
10
_____ /10
5
_____ /10
11
_____ /10
6
_____ /10
Total:
Question
/100
Name: ________________________
Section: _______
1. (6 points) Provide the bond dissociation energy of the indicated bonds in each
of the following molecules:
Me
Me
Me
BDE=
H
H H
H
BDE=
H
H
BDE=
Name: ________________________
Section: _______
2. (4 points) Assign the stereocenter in the following molecules as (R) or (S).
NH
Me
OH
NHMe
HO
OH
Name: ________________________
Section: _______
3. (10 points) Predict the product or products of each of the following reactions.
Be sure to include stereochemistry if necessary.
ONa
Me
Me
Cl
Me
Me
Br 2
AIBN
H2
Pd/C
Me
O3
then Me 2S
OMe
Me
Br 2
O
Me
Name: ________________________
Section: _______
4. (10 points) Provide the reagents to perform the following transformations. If
multiple steps are necessary, list them in order.
OH
Cl
OH
Me
Et
Et
Me
OH
OH
O
Me
OH
CN
O
O
Me
Me 2N
Me
Me 2N
HO
N
Me
N
Me
Name: ________________________
Section: _______
5. (10 points) Provide all reasonable resonance structures for the following
molecules.
Me
N
Me
Me
O
OMe
Name: ________________________
Section: _______
6. (10 points) For each of the following ions, draw a molecular orbital diagram
and use it to explain the observed geometry.
allyl cation
planar
Me
Me
Me
tert-butyl anion
pyramidal
Name: ________________________
Section: _______
7. (10 points) A chemist (who hasn’t taken CHEM331) runs the following
reaction, expecting to get one product. However, after work-up they discover
that there are actually two products. Draw the two products (in the first two
boxes) and provide a mechanism for the formation of each product (in the larger
box).
OMe
mCPBA
N
O
2 products
OEt
Product 2:
Product 1:
2 points
2 points
Mechanisms:
6 points
Name: ________________________
Section: _______
8. (10 points) Provide a mechanism for the following transformation:
Me Me
HBr
Me Br
OH
O
Me
Name: ________________________
Section: _______
9. (10 points) Provide a mechanism for the following transformation:
O
OMe
Me
O
HBr
AIBN
OMe
Br
Me
Me
Me
Name: ________________________
Section: _______
10. (10 points) Propose a synthetic sequence to accomplish the given
transformatioin. You do not need to provide mechanisms.
Me
Me
steps
Me OH
OH
Name: ________________________
Section: _______
11. (10 points) Propose a synthetic sequence to accomplish the given
transformatioin. You do not need to provide mechanisms.
steps
OMe
Name: ________________________
Section: _______
This page was intentionally left blank and may be used for scratch paper.
Name: ________________________
Section: _______
This page was intentionally left blank and may be used for scratch paper.
Name: ________________________
Section: _______
This page was intentionally left blank and may be used for scratch paper.
Name: ________________________
Section: _______
This page was intentionally left blank and may be used for scratch paper.