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Midterm

Exam 3 Solutions Spring 2013Exam


Department
AS.030
Course Code
AS.030.206
Professor
All
Study Guide
Midterm

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1
Exam III Chem 206 April 11, 2013 KEY
Name_______________________________
JHED ID_____________________________
I agree to complete this exam without
unauthorized assistance from any person,
materials, or device.
____________________________________
Signature and Date
1 28
2 6
3 8
4 24
5 6
6 4
7 8
8 10
9 6
total 100
Exam policy
1) No electronic devices of any kind, such as calculators, cell phones, or advanced digital
watches are allowed. Possession of such devices during the exam is grounds for awarding a
zero on the exam.
2) Molecular models are allowed, but no instruction pages are permitted.
3) Relevant tables, including the periodic table, are attached at the end of this exam.
4) Numerical values given in one question apply only to that question, and should not be used
in other questions, unless there is a specific instruction to do so. If necessary, the values
from the provided tables should be used, even if they differ from values that you may
remember from different sources.
5) When listing reagents, a backslash (/) is used between reagents that are employed
simultaneously and a semicolon (;) is used between reagents that are employed in a
stepwise fashion.
6) Use the boxes provided for your answer if they are present. Answers that are not
written in the boxes will not be considered for grading.
7) Be neat and clear. Make sure we know which answer is to be graded.
8) Some questions will have points deducted for incorrect responses. Longer synthetic routes
receive fewer points than shorter, more direct answers.
9) Keep your answers brief.
Notes: I. The stereochemistry in structural drawings and reaction schemes is not shown unless explicitly indicated
with wedge-bond designations. For example:
Br
Cl
Br
Cl
Stereochemistry not shown Stereochemistry shown
II. Abbreviations used: Me = methyl, Et = ethyl, Pr = propyl, Bu = butyl, Pe = pentyl, Ph = phenyl, (i.e., benzene
as a substituent), AcO = acetate (H3CCOO).
III. When listing reagents, a slash (/) is used between reagents that are employed simultaneously, and a semicolon
(;) is used between reagents that are employed in a stepwise fashion.

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2
1. (28 pts) Provide the missing starting material, major organic product(s),
conditions, or reagent(s) for the following transformations.
N
O
O
OO
CH2OH
OHH
OHH
HOH
O
HO
O
O
O
2OEt
O
O
OMe
O
+Cl
O
NH
OH
O
+
N
HO
NH
A.
B.
C.
D.
E.
F.
MeO
O
Me
NaOH
1.
2. OEt
OO
NaOMe
OMe
O
MeO
O
+
NaOEt
H3O+
CH2OH
OHH
OHH
HOH
O
H
Br2
H2O
Cl
O
3/4 pts
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