Chem 212 Survey of Organic and Biochemistry Summer 2005
_____________________________
Print your full name legibly in the space above.
Exam 1: Ch. 1-5
30 June 2005
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 a reasonable Lewis structure for each of the following, showing all lone pairs and formal charges where relevant: a.
CH
3
BH
2 b.
HCN c.
HNO
3
nitric acid (hint: 3 O’s attached to N, H attached to one O)
2.
State whether the structures in each pair below are the same molecule, cis-trans isomers, constitutional isomers, or not related.
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Chem 212 Survey of Organic and Biochemistry
H
3
C
H
3
C
CH
3
CH
3
CH
3
H
3
C
CH
3
CH
3
(CH
3
)
3
CCH
2
CH
2
CH
2
C(CH
3
)
2
CH
2
CH
2
CH
3
CH
3
Summer 2005
H
3
C
CH
3
H
3
C CH
3
Br
CH
3
H
3
C
CH
3
CH
3
CH
3
Br
CH
3
3.
Answer the following questions about the structure below, which is RU-486, also known as Mifeprex or “the abortion pill”.
CH
3
N
H
3
C
CH
3
OH
CH
3
O a.
How many carbon atoms are in the structure? ___________ b.
What is the degree of hydrogen deficiency of the structure? ________ c.
How many hydrogen atoms are in the structure? __________ d.
On the structure above, indicate with an arrow one bond that can freely rotate around 360°. Do not point to an atom!!!!!! e.
Circle and name three functional groups in the structure above. f.
Use the VSEPR method to predict the geometry around each of the following atoms (linear, triangular planar, tetrahedral, triangular bipyramidal, octahedral) a d b e c f g.
Give approximations for the following bond angles:
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Chem 212 Survey of Organic and Biochemistry Summer 2005 h.
Label the following atoms as primary (1°), secondary (2°), tertiary (3°), or quaternary (4°):
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Chem 212 Survey of Organic and Biochemistry Summer 2005
4. Using the following template, draw a Newman projection for 2-phenyl-3chloropentane looking down the C
2
-C
3
bond:
5. Give the chemical name for the following molecules:
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Chem 212 Survey of Organic and Biochemistry
CH
3
CH
3
H
3
C
H
3
C
CH
3
CH
3
H O
H
3
C
CH
3
H
3
C
H
3
C
H
3
C
CH
3
O
OH
NH
2
Br
OH
CH
3
H S
OH
H
3
C
H
3
C
6. Next to each name, draw the correct line-bond structure:
2-isopropyl-5-methyl-cyclohexanol
trans-1,4-cyclohexanediol
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Summer 2005

Chem 212 Survey of Organic and Biochemistry Summer 2005
1-chloro-2-propanol m-bromostyrene
3-methylcyclohexene
3-cis-5-cis-2,4-dimethyl-3,5-decadiene
7. For each example, draw three different line angle structures: a.
C
5
H
10
, with an alkene (may have other functional groups as well) Draw three different structures!
b.
C
8
H
12
O
2
, with an acid (may have other functional groups as well) Draw three different structures!
c.
C
6
H
14
O with a tertiary alcohol (may have other functional groups as well) Draw three different structures!
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Chem 212 Survey of Organic and Biochemistry Summer 2005
8. Draw the structure of the starting materials and the organic products for each of the following reactions. If more than one product forms, circle the major product a.
1-Methylcyclopentene treated with hydrogen and a metal catalyst b.
cyclopentane treated with bromine and light c.
1,4-Dichlorobenzene treated with sulfuric acid (H
2
SO
4
) and nitric acid (HNO
3
) d.
o-chlorophenol treated with sodium hydroxide e.
1-Pentanol treated with K
2
Cr
2
O
7 f.
trans -2-hexene treated with bromine g.
1-pentene treated with water and sulfuric acid
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Chem 212 Survey of Organic and Biochemistry Summer 2005 h.
2-methyl-2-butanol treated with sulfuric acid and heat
9. Show how each of the following multi-step transformations can be accomplished. Be sure to draw the structure of the intermediates and all reagents in each case.
O
H
3
C
OH
H
3
C
O
CH
3
OH
CH
3
CH
3
10. Draw the structure of three compounds with the formula C
6
H
14
O
2
that you would expect to have very different solubility in water, and rank them as “very soluble”, “less soluble” and “least soluble”
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Chem 212 Survey of Organic and Biochemistry Summer 2005
11. Draw the structure of a compound with the formula C
5
H
10
O
2
that does not react with bromine and is soluble in water.
12. Draw the structure of two molecules of ethanol hydrogen bonding to each other.
13. Why does the chromic acid test for the presence of alcohol (ethanol) in breath not work for the presence of tertiary butanol?
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