Published on 15 Feb 2019
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ORGANIC CHEMISTRY I (CHEM 115/CNED 013)
EXAM #2A
October 21, 2002
Name:_____________________________________
Please read each question carefully before you begin. Your exam should have a total of 6 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
may be used. Show your work clearly, and you may receive partial credit for partially correct
answers. Good luck!
1. (30 pts) For each of the following pairs, specify whether the two molecules are enantiomers,
diastereomers, structural isomers, geometric isomers, identical molecules.
CO2H
NH2
H3C
HCH
3
H3CH
CH3
CO2H
CH3
H2N
H3CH
H3CH
CH3
__________________
CH3
B
r
CH3
B
r
Br
Br
__________________
CH2OH
H
H
CH3
CH2OH
CH3
__________________
CH3
CH3
__________________
CCC
CH3
B
r
H
H3C
CCC
CH3
HB
r
H3C
__________________
CH3
CH3
__________________
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2. (5 pts each, 15 total) Provide a name for each of the following molecules. You may use either
IUPAC names or common names, where appropriate.
(a)
(b)
(c)
CH3
3. (5 pts each, 15 total) Draw a structure for each compound.
(a) meso-3,5-dimethylheptane
(b) 5S-iodo-(2E,7E) decadiene
(c) bicyclo[3.3.2]dec-1-ene
(1 bonus point): Is this a Bredt or an anti Bredt compound? Explain.