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Exam 2 -- Fall 2003 -- Blank

Exam 2 -- Fall 2003 -- Blank - Name_KEY Page 1 I(20 points...

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Name_________ KEY ___________ Page 1 I. (20 points) When Compound A is treated with one equivalent of lithium diisopropylamide (LDA) followed by addition of cyclohexanone at -78 o C, Compound B is the major product. If the reaction is carried out at 0 o C, then the major product is Compound C . Compound B can be converted into Compound C by treatment with LDA at 0 o C . CH CH C OCH 2 CH 2 OCH 2 CH 3 N Compound A 1. LiN[CH(CH 3 ) 2 ] 2 (LDA) 2. O O CH 2 CH C C OCH 2 CH 2 OCH 2 CH 3 N Li Compound B O Li Compound C CH 2 CH C C CH 3 CH 2 OCH 2 CH 2 O N CH 2 + (cyclohexanone) (a) Draw the structure (include the three most significant resonance forms) of the conjugate base formed when Compound A is treated with one equivalent of LDA. 6 (b) Using the information provided, complete the following energy diagram for the formation of Compounds B and C from the conjugate base of Compound A and cyclohexanone. For full credit clearly show the relative energies and label the points in the energy diagram corresponding to the respective transition states ( TS-B and TS-C ) and products ( B and C ). G conjugate base of Compound A + O 6 The kinetic product is: The thermodynamic product is: 2 2 reaction coordinate (3 pts B higher than C) (c) Specifically what has happened upon changing the temperature from -78 o C to 0 o C that caused the change in the major product?
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