CHEM 115 Georgetown Exam3(2002)

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Published on 15 Feb 2019
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ORGANIC CHEMISTRY I (CHEM 115/CNED 013)
EXAM #3
November 18, 2002
Name:_____________________________________
Please read each question carefully before you begin. Your exam should have a total of 9 pages.
You will have two hours in which to complete this exam; be sure to save time to check your
answers after you’re finished. The backs of the pages may be used for rough work, but your
answers should be written clearly on the front of the page in the spaces provided. Molecular models
and non-programmable calculators may be used. Show your work clearly, and you may receive
partial credit for partially correct answers. Good luck!
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1. (10 pts total, 5 each) Provide an IUPAC name or structure for the following.
C
CC
C
CH3
CH3
H
CCH
__________________________________
__________________________________
2. (20 pts total) Hydrobromination of 1-methylcyclohexene with HBr yields different products
with the molecular formula C7H13Br depending on the reaction conditions. Provide the structures of
all product(s) under each set of reaction conditions, paying careful attention to both regiochemistry
and stereochemistry.
HBr
HBr
(ROOR + heat)
(dark)
C7H13Br C7H13Br
Briefly explain the modern-day rationale behind Markovnikov's rule.
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3. (20 pts) Draw step-by-step mechanisms to explain the two following reactions. Make sure that
you use arrows to denote all bond breaking and bond forming steps, and show the structure for each
intermediate.
HO
H+, H2O
HO
OH-, H2O
OH O
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