Spring 2011
Instructor: Maxi Boeckl
Your Name: ______________________
EXAM 1 – CHEM 131 (75 pts)
1. (10 pts) Determine if each of the following statements is true or false. Circle the correct answer.
a)
Bond angles on a carbon that is part of a carbon-carbon double bond
has a bond angle of 109.5°.
True
or
False
True
or
False
The delocalized pi system of an aromatic ring doesn’t allow them to
undergo addition reactions.
True
or
False
d) A carbon-carbon triple bond has one σ (sigma) and two π (pi) bonds.
True
or
False
True
or
False
b) Toluene has a molecular formula of C7H8.
c)
e)
Markovnikov’s rule states that hydrogen will add to the carbon that
has more substituents.
2. (12 pts) Draw the skeletal line structure for the following compounds:
a) 3,4-diethyl-2-fluoro-3-methylheptane
b) 1-chloro-2-ethyl-3,5-dimethylcyclohexane
c) o-ethylaniline
d) 4-ethyl-2-phenyl-1,3-pentadiene
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3. (16 pts) For each of the following reactions, give the major product that is formed. If there is no
reaction write “no reaction”.
a)
H2SO4
+ excess H2O
b)
CH3
H3C
C
C
CHCH3
+ excess Br2
c)
+ HF
d)
Ni
+ excess H2
4. (6 pts) Determine if the following pairs are identical, structural isomers, geometric isomers, or
different conformations of each other.
a)
CH3
H3C
CH3
H3C
CH
CH
CH3
b)
H3C
CH3
H3C
CH2
CH3
CH
CH3
c)
CH
CH
C
CH3
CH2
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5. (15 pts) Name these compounds using IUPAC nomenclature.
a)
Br
F
b)
F
CH2CH3
c)
H3C
d)
C
C
CHCH3
Br
(make sure to indicate the correct geometry on double bond)
NH2
e)
6. (2 pts) Write the condensed structural formula for the following compound.
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7. (6 pts) The following compounds are named incorrectly. Draw the structure and give the correct
IUPAC name.
a) 1,1,4,4-tetramethyl-2-butyne
b) 1,3-dibromo-4-cyclopentene
8. (8 pts) For each of the following reactions, identify one possible starting material that would
lead to the product indicated under the given reaction conditions. Note that the reagent is written
above the arrow. Identify each one as hydrogenation, hydration or halogenations.
Name of Reaction
a)
_______________________
HBr
Br
b)
H2O
OH
+
H2SO4
OH
_______________________
Extra Credit:
9. (2 pt) Instead of using the conventional name for benzene, what is the name using strict IUPAC
rules for the compound on the right?
10. (2 pts) Briefly explain what trans fatty acids are and during what process they are produced.