Final Exam -- Fall 2005 -- Blank copy

Final Exam -- Fall 2005 -- Blank copy - I. (36 points) Name...

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Name _______________________ Page 1 F.05.210FEP1 I. (36 points) A. The following electrophilic addition reaction was reported ( OL 2005 7 5163). Provide a complete, step-wise mechanism for this transformation. Include stereochemical considerations in your drawings, showing the formation of the enantiomer shown; you do not need to show the formation of the other enantiomer. I-Cl,CH 3 O Na CH 3 OH + enantiomer N O O C(CH 3 ) 3 H H N O O C(CH 3 ) 3 H H I OCH 3 B. In the subsequent step of the reaction, the product from the reaction show above was heated with trifluoroacetic acid at 140°C, resulting in the subsequent transformation (shown below). N O O C(CH 3 ) 3 H H I OCH 3 N O O C(CH 3 ) 3 H I O C O CF 3 140°C (a) What is the most likely reaction mechanism (check one)? S N 2 S N 1 E2 E1 electrophilic addition electrophilic substitution (b) Provide the complete, step-wise mechanism (use the specific acid shown, and its conjugate base, in your mechanism, rather than any generic symbols): + CH 3 OH N O O C(CH 3 ) 3 H H I OCH 3 N O O C(CH 3 ) 3 H I H O C O CF 3 H 12 4 20 + enantiomer N O O C(CH 3 ) 3 H H N O O C(CH 3 ) 3 H H I OCH 3
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Name _______________________ Page 2 F.04.210FEP2 II. (47 points) A. Para -hydroxyacetophenone is a component of the pheromone of the smaller European elm bark beetle. C O CH 3 O para -hydroxyacetophenone pKa 4.2 O phenol pKa 10 (a) Note that the pKa of para -hydroxyacetophenone is significantly lower than that of phenol. Provide the single resonance form for the conjugate base of para -hydroxyacetophenone that illustrates the significance of the C=O functional group. Include any charges and non- bonding electron pairs.
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Final Exam -- Fall 2005 -- Blank copy - I. (36 points) Name...

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