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Unformatted text preview: Practice Exam 7 (10/11/10)
I. Give the systematic name for the following structure. Cl (Z, 2R)-3-bromo-2-chloro-3-hexene Br II. Give the structure for the following compound. Cl (E)-1-chloro-2-ﬂuoro-1-iodo-1-pentene I F III. Predict the major product. Me OH H heat Me IV. For the following elimination reaction, predict the major product and explain why the product of your choice is formed selectively among the possible products. NaOEt Cl heat H Me Cl Me
tBu available for β-elimination H
tBu only possible one for anti-periplanarity in elimination Cl V. Draw the major product for each reaction, including stereochemistry if any. OH cat. H2SO4
mol. formula: C6H12 Br KOtBu Ph Ph H2, Pd/CaCO3
quinoline Ph Ph VI. Draw a plausible mechanism for the following reaction. OH H H heat OH2 3 ° carbocation release of ring strain H 2 ° carbocation VII. Complete the following syntheses showing isolable intermediates and conditions. VIIa.
from O Ph to Ph Ph O Ph PCl5 Cl Ph Cl NaNH2 Ph Br Na/NH3 Ph Ph Ph Ph Ph VIIb.
from to Hint: A double bond between two rings is too strained. The species just below is not a viable intermediate. Not stable HO H Br2 Br Br
base such as BuO- or NH2- ...
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This note was uploaded on 10/18/2010 for the course CHEM 13222 at USC.