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ochem practice exam 2 at universityof wa
Typology: Exercises
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Key
1. Fill in the boxes with the reagents that facilitate the reaction shown ( 21 points ).
must be the cis alkene NazCrz07 ,^ MzSOy^ OR KMnOy , NaOH^ OR CrOz NaOY K MCPBA
H unj
e) Circle the compound that will undergo bromination (reaction shown in the box) most rapidly. Put a box around the compound that will undergo bromination most slowly. 3. Using Hückel’s Rule, classify the following compounds as aromatic, anti-aromatic or neither (non-aromatic). Assume all sp^2 hybridized atoms are in the same plane. Assume that all charged carbon atoms are sp^2 hybridized. Consider all significant resonance structures. If a molecule is aromatic or anti-aromatic, specify how many electrons are part of the aromatic or anti-aromatic system. ( 25 points ) O O (^) O O O O
aromatic^ anti-aromatic^ neither
Fans
4. Draw a detailed electron pushing mechanism for the formation of the product shown. Be sure to include all relevant intermediate and resonance structures. ( 12 points )
it Ho P-^ of
g in^ in
med
6. ( 14 points ) In class we learned that it is possible to convert tertiary alcohols into alkyl bromides ( reaction A ) with an excess of HBr. Using the same conditions, would the alcohol shown in reaction B be converted to bromobenzene (circle yes or no)? Yes or No Draw a reaction energy coordinate diagram for Reaction A. Include as much information about relative energies of the starting material, intermediate, transition state, and product as you can based on your knowledge of organic chemistry and the mechanism of this reaction ( Note: To simplify your diagram, do not include protonated intermediates (for example, protonated alcohols) in your reaction energy coordinate diagram ).
HBr (Excess) Br HO HBr (Excess)
Br
formed? Go
Br (^) + 1,
Draw a reaction energy coordinate diagram for Reaction B. Include as much information about relative energies of the starting material, intermediate, transition state, and product as you can based on your knowledge of organic chemistry and the mechanism of this reaction ( Note: To simplify your diagram, do not include protonated intermediates (for example, protonated alcohols) in your reaction energy coordinate diagram ). Referring to features in your reaction energy coordinate diagrams, explain why you answered yes or no to whether reaction B occurs in 15 words or less.
N
TB AGF ET+^ HBr NTB4H AGt to^ form^ the^ c
high as an (^) sp hybridized
is (^) unstable.
