CHEM_351_SP09_e3_FR_key

CHEM_351_SP09_e3_FR_key - 3 pts The more stable, more...

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Part II – Answer the following questions in the space provided and then tear off this page and turn it in with your scantron answer sheet for Part I. N a m e : ( Please print first and last name neatly ) 1. (30 points) Draw the MAJOR product(s) for each of the following reactions. Be sure to indicate stereochemistry where appropriate. If no reaction will occur, write “no reaction”. Indicate whether the reaction conditions are first (1 st ) or second (2 nd ) order by writing a 1 or a 2 in the box provided under the reaction arrow. 6 pts each a) Br CH 3 OH OCH 3 OCH 3 ++ 1 b) Cl I NO REACTION 2 I c) I tBuO 2 d) I 1 H 2 H CH 3 O OCH 3 1 H 2 H 2 e) Ph Ph Br H 3 C H H 3 C CH 3 CH 2 O Ph H 3 C Ph
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2. (15 points) Dehydration of 2-methylcyclopentanol yields three isomeric alkenes. CH 3 OH H 2 SO 4 CH 3 CH 2 CH 3 * a) Draw the 3 products and put an asterisk under the major product. You will lose points for any products that are incorrectly identified with an asterisk. 12 pts b) Provide a brief (1-2 sentence) explanation for your choice.
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Unformatted text preview: 3 pts The more stable, more substituted alkene (Saytzeff) is formed from the more stable, more substituted (3 o from rearrangement) carbocation. 3. (15 points) Consider the following S N 2 reaction. HO + + CH 3 Br Br CH 3 OH a) Draw in the curved arrows that show the electron flow from reactants to products above. 6 pts b) Given that the reaction is exothermic, sketch a reaction vs energy diagram. Label the reactants and products. Draw the structure of the rate limiting transition state at the appropriate location on your diagram . Be careful to illustrate clearly the geometry around the carbon atom. For full credit, be sure to show whether or not the transition state is reactant-like or product-like, by indicating which of the two partial bonds is longer. 9 pts CH 3 Br + OH-CH 3 OH + Br-Energy Reaction C H H H HO Br...
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CHEM_351_SP09_e3_FR_key - 3 pts The more stable, more...

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