mcI07e1 - 1 MEDICINAL CHEMISTRY I EXAM#1 Name SECTION A...

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MEDICINAL CHEMISTRY I
EXAM #1
September 28, 2007
Name
SECTION A. Answer each question in this section by writing the letter corresponding to the
best answer on the line provided (2 points each; 50 points total)
1. The compound shown below:
H
N
O O
I Is a cyclic urea
II Is piperidine-2,5-dione
III Is a cyclic imide
a) I only
b) III only
c) I and II only
d) II and III only
e) I, II, and III Answer
2. The compound illustrated below:
CH
3
CH
3
H
3
C
H
H
H
I Has cis -1,4-dimethyl groups
II Has trans -1,2-dimethyl groups
III Is drawn in its lowest energy conformation
3. For the structures illustrated below:
OH H
3
C OH NC
A B
I Compound A has a larger pK
a
than
compound B
II Compound A has a higher log P than
compound B
III The K
a
for Compound B is larger than the
K
a
for Compound A

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4. The compound illustrated below:
N
O
I Is 1-Benzyl-4-benzoylisoquinoline
II Is 1-Benzoyl-4-benzylisoquinoline
III Is 4-Benzoylbenzo[a]isoquinoline
5. The compound illustrated below:
N
O
I Is aromatic
II Has the lone pair of electrons (on the
nitrogen), in the plane of the ring
III Is non-aromatic
a) I only
b) III only
c) I and II only
d) II and III only
e) I, II, and III Answer
6. T he compound shown below:
O
H
3
C
CH
3
I Is 2H-2,7-dimethyl-5,6,7,10-
tetrahydrooxecine
II Has two alkenes that have (E)-
stereochemistry
III Is antiaromatic

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7. For the compounds illustrated below:
CH
3
H
3
C CH
3
OH
H
CH
3
H
3
C CH
3
H
HO
A B
I Compound A has four chiral centers
II Compound A is a diastereomer of
Compound B
III Compound B is the enantiomer of
Compound A
8. The compound illustrated below:
S
N
CH
3
I Is 10-methylphenothiazine
II Has a conjugate acid with a pK
a
of 2
III Is 5-methylphenothiazine