Chem 212 Survey of Organic and Biochemistry Summer 2004
_____________________________
Print your full name legibly in the space above.
Exam 2: Ch. 5-9
12 July 2004
Instructions:
1. If you leave the room for any reason you may not return to continue the exam.
2. No books or notes of any kind are permitted. You may borrow a model kit.
3. Put all your answers on this exam paper. If you want something graded which is
written on scratch paper, you must indicate so in the regular space for the answer.
Good Luck!
1.
Draw the structures of the major organic product(s) of the following reactions.
(Do not repeat a structure in your answer):
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Chem 212 Survey of Organic and Biochemistry Summer 2004
2.
Rank the following six compounds in order of solubility in water (1=most soluble).
SH
OH
OH
H
3
C CH
3
H
3
C CH
3
H
3
C
CH
3
H O
OH
H
3
C O H
3
C
CH
3
H
3
C
CH
3
3.
Explain how you derived your ranking of the solubilities for question #2
CH
3
4.
Indicate with an asterisk those carbons that are stereocenters
5.
Assign the priorities in each of the following sets of groups a.
–CH=CH
2
–CH
2
CH
2
CH
2
CH
3
–CH
3
OH b.
–CH
3
–CH
2
SH –NH
2 c.
–OH –CH
2
OH -CH
3
–C(CH
3
–COOH
)
3
–CH(OCH
3
)
2
6.
For each of the following tetrahedral centers with priorities shown, assign the chirality designation as either R or S:
4
2
1
4
4 1
3 2
1
3
3
2
3 2 4
1
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Chem 212 Survey of Organic and Biochemistry Summer 2004
7.
Assign the chirality (R or S) for each of the chiral centers in the following molecules.
8.
List the properties that are the same for each enantiomer of a chiral molecule.
9.
List the properties that are different for each enantiomer of a chiral molecule.
10.
List the properties that are the same for each diastereomer of a chiral molecule.
11.
Predict the products for the following reactions, and (using the table provided) predict the side (products or reactants) favored at equilibrium
12.
Which is the stronger acid in each pair?
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Chem 212 Survey of Organic and Biochemistry Summer 2004
13.
Classify the following amines with all of the appropriate descriptors from among the following list: primary, secondary, tertiary, quaternary, aliphatic, aromatic, heterocyclic.
14.
Give the IUPAC name for each of the following:
15.
Draw the structure for each of the following named compounds a.
N,N-diethyloctanamine b.
2-methylcyclohexanol c.
2-propanethiol d.
triethylamine e.
2-methylcyclopentanone f.
decanal
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Chem 212 Survey of Organic and Biochemistry Summer 2004
16.
The following structure represents a possible new drug candidate. However, this molecule is not soluble in water, and the preferred drug delivery method requires a water-soluble drug. Furthermore, this molecule decomposes in air. Draw the structure of a related molecule that solves these problems.
H
N
CH
3
OH
17.
The following structure represents another possible new drug. Biochemical research suggests that the OH group is required for activity, and suggests that if this OH group were made more acidic, the activity of the drug would be improved. Suggest a related structure that would be expected to have greater acidity at this position.
Br CH
3
N
CH
3
CH
3
H O
18.
The following structure represents a third possible new drug. Research suggests that it would be longer acting if it were less water soluble and more soluble in fat. Suggest a related structure that would be expected to have greater fat solubility, without removing any of the functional groups already present.
H O
CH
3
HOOC
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