orgo 1 exam 2 - I. (18 points) Name_ Page 1 F.09.210E There...

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Name_______________________________ I. (18 points) Page 1 F.09.210E H 3 C Br H 3 C I H 3 C Path A H 3 C I Path B P a t h A , s t e p 1 ! G˚ = –5 kcal/mol E a = +15 kcal/mol P a t h B , s t e p 1 ! G˚ = +10 kcal/mol E a = +20 kcal/mol P a t h B , s t e p 2 ! G˚ = –15 kcal/mol E a = +5 kcal/mol D. Comparing Path A with Path B, is Path A : ( circle one ) E. The rate determining step in path B is: ( circle one ) ( Z ) Kinetically Favored Thermodynamically Favored Neither Both Step 1 Step 2 Neither Both 5 kcal/mol Starting materials ( Z + NaI) 5 kcal/mol ( Y ) ( Y ) C. Draw the structure of the transition state associated with step 1 of path B . Be sure to include partial charges (to indicate a build up of positive or negative charge) and dotted bonds (to indicate where bonds are breaking or forming) where appropriate. Transition state for path B , step 1 + Br + Br H H H H H 3 C Br " + " 5 5 4 2 2 Starting materials ( Z + NaI) TS TS TS I P P R R Na I Na I -3 wrong scale -2 labels wrong/missing -2 connectivity wrong -2 charges wrong (H is optional) H E n e r g y There are two possible paths from molecule Z to molecule Y - path A and path B (shown below). E a is the activation energy for each step of the reaction, sometimes abbreviated as ! G A. Draw an energy diagram for path A to scale. The reactants are already labeled as " Z" . Label the any transition states as " TS ", any intermediates as " I ", and products " Y ". B. Draw an energy diagram for path B to scale. The reactants are already labeled as " Z" . Label the any transition states as " TS ", any intermediates as " I ", and products " Y ". + Br reaction progress reaction progress
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Name_____________________________ II. (27 points) Page 2 F.09.210E2 OCH 3 CH 3 OH catalytic H 2 SO 4 ( I, observed product, optically inactive ) ( II , observed product, optically active ) ( III, not observed product, optically active ) ( IV , not observed product, optically active ) C. Molecules I and II are: ( circle all that apply ) Stereoisomers Enantiomers Diastereomers Constitutional Isomers D. The related reaction of molecule A does not form any regioisomers. Ignoring stereochemistry , draw an arrow pushing mechanism for the reaction of A to form B . Note that hydrochloric acid molecules are not themselves the proton source in the addition reaction. Be sure to include in your answer the mechanism of
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This note was uploaded on 05/29/2010 for the course 210 chem 210 taught by Professor Sanford during the Fall '10 term at University of Michigan.

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orgo 1 exam 2 - I. (18 points) Name_ Page 1 F.09.210E There...

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