Name: _________________________________
CHEM 332. Midterm 2
Spring 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 10 pages in this exam. Please check that your test has 10 pages before you
begin. The last 3 pages are blank and may be used as scratch paper.
Question
Points
1
_____ /21
2
_____ /25
3
_____ /12
4
_____ /12
5
_____ /15
6
_____ /15
Total
____
/100
1
Name: _________________________________
1. (21 points, 7 point each) For each of the following, please rank (1-3) according to
listed property and provide a brief (20 word or less) justification in the box below.
A) Acidity of OH (1 most acidic, 3 least acidic):
O
O
O
OH
OH
Me
OH
O
MeO
O
Rank:
Justification:
B) Acidity of protons alpha to carbonyl (1 most acidic, 3 least acidic):
O
Et
O
NMe 2
Et
O
Me
Me
Me
Et
OMe
Rank:
Justification:
C) Predicted C=O Bond length (1 longest, 3 shortest):
O
O
NMe 2
O
Cl
OMe
Rank:
Justification:
2
Name: _________________________________
2. (25 points, 5 points each) Please draw any significant product(s) expected for each of
the following reactions. If more than one product is expected, please indicated relative
ratio (major, minor, trace, etc). If no reaction is expected, write “No Reaction.”
O
a)
Me
1) NaOEt, then PhCH 2Br
2) HCl, H 2O, heat
O
O
Et
O
O
1)
Me
b)
O
Me
, AlCl3
2) Br 2, cat. HCl, H 2O
O
NMe 2
c)
O
LDA, -78 °C; then MeI
Me
d)
O
e)
LiAlH 4, then H 3O+
Me
m-CPBA
3
Name: _________________________________
3. (10 points) In the space below, provide a mechanism for the following transformation.
Please include any important resonance structures that are important to the reaction
progressing.
O
O
Me
NaOH, heat
Me
4
Name: _________________________________
4. (10 points) In the space below, provide a mechanism for the following transformation.
Please include any important resonance structures that are important to the reaction
progressing.
O
O
Cl
BuNH 2 (excess)
NHBu
5
Name: _________________________________
5. (15 points) Using 13C carbon dioxide (1) as your only source of isotopically enriched
starting material, please propose a synthesis of ester 2 containing a 13C label at the
indicated position.
O
O
OBu
= 13 C
O
1
2
6
Name: _________________________________
6. (15 points) Propose a synthesis of ester 4 using compound 3 as your only source of
aromatic carbons. You may use any other chemically reasonable reagents you need.
O
Me
OMe
Me
Me
3
4
7
Name: _________________________________
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8
Name: _________________________________
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9
Name: _________________________________
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10