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Chemistry2210
Fall2013
PracticeExam#3
(90minutes)
***Similarinformat,butnotthesamequestions!!!!!
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1. Select non-polar, polar aprotic, or polar protic to describe each of the following solvents:
a) ammonia
polar protic
b) benzene
non-polar
O
c) dimethylformamide
CH3
H
polar aprotic
CH 3
___Z______E___
__N/A______E_____N/A__
3. Applying the correct rules for IUPAC nomenclature, provide names for the following compounds. Make sure to include
correct stereochemistry when appropriate for full points.
a.
b.
(R,Z)4,5dimethylhex3en2ol
(S,Z)5bromo3ethyl2methylhex3ene
c.
d.
e.
(1S,4S)4phenylcyclohex2enol
2fluorocyclohexa1,3diene
(R,E)3fluoro5propyloct2en7yn2ol
4. Classify the description for each item below as SN1, SN2, E1, or E2. You may use options more than once.
a) _ E2__ The result of a strong bulky base on a haloalkane
b) _ SN2__Inversion of configuration
c) _ E1__Yields alkene in two (or more) steps
d) _ E1__ALWAYS gives the lower energy E-alkene
6. A saturated compound has the formula C10HnCl4F2N3O2. How many H does that mean that it has in the
formula?
C2n+2 = 2x10+2=22H 4H from Cl=H 2H from F=H + 3H from N
C10H19Cl4F2N3O2
7. Demonstrate knowledge of the hydroboration reaction by providing the full arrow pushing mechanism, an
unambiguous structural formula for the transition state intermediate, and the product that results from this step
of the reaction.
8. One of the stereoisomers below undergoes E2 reactions in the presence of a strong base MUCH faster than
the other. (Selecting the correct isomer is not enough to earn points on this question! Your explanation should
be sufficiently clear and complete that the reader/grader is left with no doubt that you understand.)
a) Construct both the chair and its flipped conformer for the two stereoisomers below.
b) Determine which stereoisomer will have the faster rate of reaction:
a)
or
b)
c) Explain this observation mechanistically using full sentences making sure to answer the question of WHY
one will undergo an E2 reaction faster than the other. The conformations with the bulky tert-butyl group in
the equatorial position are considerably lower in potential energy than if the tert-butyl group was
creating 1,3-diaxial torsional strain and are the favored conformers . Since reactions require both proper
orientation as well as productive collisions of the base, structure A has the correct anti-coplanar
orientation for E2 elimination more than ninety-nine percent of the time and will eliminate much faster.
Structure Bs favored conformer doesnt allow for the proper anti-coplanar orientation and must
undergo the conformational ring flip to react. Since it spends so little of its time in the proper orientation,
it will be very slow to react.
Br
Br
a)
b)
Proposed E2 regioselective mechanism for isomer identified above and product it forms:
CH3
Base
H
Base
CH3
H
Br
Br
9. Give all possible product/products and designate stereoselectivity &/or regioselectivity by using wedges and
dashes.
a)
b)
c)
d)
e)
f)
g)
h)
/25.5
i)
j)
k)
l)
10. Provide the product(s) from the following two step reactions.
O
a)
b)
c)
? NaOtBu
HOtBu, heat
Br
d)
? 1. BH3 - THF
2. HOOH, NaOH
OH
12. Compare the following reactions and decide which would occur faster. Write you answer as a complete
sentence and defend your choice. Since bromide is a better leaving group than fluoride, the SN2 reaction B
would proceed faster.
a.
b.
13. Create the full arrow pushing mechanism which shows all intermediates and the products that result from
these reactions.
H2SO4 (cat.)
H2O, 25oC
H
H
O
H
H O
H
H
H
H2O
a.
H
H
H
H
H
H
H2O
H
H O
H
H
H
H
b.