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Chem 341 Practice Final Examination M. Walker
YOUR NAME ________________________________________________
3 hours duration, 360 points total. [NOTE: YOUR FINAL WILL ONLY BE TWO HOURS LONG, AND SO IT WILL BE SHORTER THAN THIS ONE].
- Give a systematic name for each of the following compounds, including stereochemistry:
Cl
Cl H
- Which is the most stable from each set of three related structures?
CH (^3)
CH 3 CH^3
- Draw a meso form and two enantiomers of 3,4-dimethylhexane:
- Predict the major product(s) of the following reactions (indicate stereochemistry):
Ph
Br 2 , H 2 O
(i) O (^3)
(ii) (CH 3 ) 2 S
CH 3 C CH
Cl (^2)
Br
HCl
(a)
(b)
(c)
(d)
(e)
hv
(f) heat
NBS
heat
(g)
(h) (i) H 2 O, Hg(OAc) (^2)
KO tBu
(ii) NaBH 4
(i) NaNH 2
(ii) CH 3 I
- Show how you might perform either one of the syntheses shown below. You must use the starting material given as your sole source for all carbons in the product (you need not synthesize reagents which are not incorporated, however)
EITHER (a) CH 3 CH 3 Cl (^) (Racemic,but only the pure cis isomer with no trans)
OR
(b)
Ph C CH
CH (^2) Ph CH^2 C^ C^ Ph
2
- 1-Chlorohexane reacts with - OCH 3 ion as shown:
(a) Draw an energy curve for the reaction, and indicate which points on the curve correspond to any intermediates or transition states.
(b) Write a rate equation for the reaction.
(c) Which would you expect to be more reactive as a substrate in this reaction, 1-chlorohexane or 1-bromohexane?
(d) What functional group has been formed in this reaction?
