Chem 212
Survey of Organic and Biochemistry
Summer 2006
_____________________________
Print your full name legibly in the space above.
Exam 1: Ch. 1-5
22 June 2006
Instructions:
1. If you leave the room for any reason you may not return to continue the exam.
2. No books, notes, or calculator of any kind are permitted (including cell phones.) 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. H2CO
b. N3- (linear molecule)
c. SO42-
2. State whether the structures in each pair below are the same molecule, cis-trans isomers,
constitutional isomers, or not related.
H3C
CH3
H3C
H3C
CH3
CH3
(CH 3)3CCH 2CH 2CH 2C(CH 3)2CH 2CH 2CH 3
CH3
CH3
CH3
CH3
H3C
CH3
H3C
CH3
CH3
H3C
CH3
CH3
Br
Br
CH3
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Chem 212
Survey of Organic and Biochemistry
Summer 2006
3. Answer the following questions about the structure below, which is atorvastatin, or
Lipitor ®, one of the most widely prescribed drugs today.
H3C
a
4
CH3
O
OH
f
e
b
N
NH
OH
2
1
O
c
d
OH
3
F
a. How many carbon atoms are in the structure? ___________
b. What is the degree of hydrogen deficiency (unsaturation) of the structure? __________
Hint: When using the usual calculation formula, subtract the number of fluorine atoms
just like you do with hydrogen.
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, triangular planar/bent, tetrahedral, tetrahedral/triangular
pyramidal, tetrahedral/bent, triangular bipyramidal, octahedral, octahedral/square planar)
a
____________
d
____________
b
____________
e
____________
c
____________
f
____________
g. Give approximations for the angles around each of the numbered atoms in Lipitor:
1
3
2
4
4. Draw two Newman projections, one for a staggered and one for eclipsed conformations of 2bromo-3-chloropentane looking down the C2-C3 bond:
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Chem 212
Survey of Organic and Biochemistry
5. Give the chemical name for the following molecules:
CH3
CH3
H3C
H3C
CH
CH3 3
HO
OH
H3C
CH3
O
H3C
OH
H3C
NH2
Br
H3C
OH
CH3
HS
CH3
H3C
H3C
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Summer 2006
Chem 212
Survey of Organic and Biochemistry
6. Next to each name, draw the correct line-bond structure:
2-isopropyl-5-methyl-cyclohexanol
trans-1,4-cyclohexanediol
1-chloro-2-propanol
m-bromostyrene
3-methylcyclohexene
3-cis-5-cis-2,4-dimethyl-3,5-decadiene
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Summer 2006
Chem 212
Survey of Organic and Biochemistry
Summer 2006
7. For each example, draw three different line angle structures:
a. C5H10, with an alkene (may have other functional groups as well) Draw three
different structures!
b. C8H12O2, with an acid (may have other functional groups as well) Draw three
different structures!
c. C6H14O 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 2006
8. Draw the structure of the starting materials and the organic products for each of the following
reactions. If more than one product can forms, draw only one structure for each.
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 (H2SO4) and nitric acid (HNO3)
d. o-chlorophenol treated with sodium hydroxide
e. 1-Pentanol treated with K2Cr2O7
f. trans-2-hexene treated with bromine
g. 1-pentene treated with water and sulfuric acid
h. 2-methyl-2-butanol treated with sulfuric acid and heat
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Chem 212
Survey of Organic and Biochemistry
Summer 2006
9. On each arrow, write the reagents required for each reaction.
OH
H3C
OH
H3C
O
CH2
CH3
H3C
OH
OH
CH3
CH3
CH3
10. Draw two molecules of ethanol that have a hydrogen bond between them. Use a dashed line
for the hydrogen bond
11. Draw the structure of a compound with the formula C5H10O2 that reacts with bromine and is
very soluble in water.
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