Chem210-1 F07 Ex2 p04a

Chem210-1 F07 Ex2 p04a - b) Provide structures for...

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4. If compound "B" is mixed with tert-butyl hypochlorite (compound "C" below) at low temperature, nothing much happens. But if the mixture is raised to a high enough temperature, a reaction begins which sustains itself over a period of time: CH 2 CH 2 CH 3 (CH 3 ) 3 C-O-Cl (CH 3 ) 3 C-O-H "B" "C" "D" + "E" + "F" + "G" Compound "D" (tert-butyl alcohol) is formed in high yield; "E", "F", and "G" are all isomers - they are formed in yields of 65%, 25%, and 10%, respectively. The structure of "G" is Ph-CH 2 -CH 2 -CH 2 -Cl. a) Propose a mechanism (include all steps) for the formation of "G" (8 points)
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Unformatted text preview: b) Provide structures for "E" and "F". (4 points) (CH 3 ) 3 C-O-Cl ( 3 29 3 - + - 2- 2- 2- + ( 3 29 3 - - 2- 2- 2 + ( 3 29 3 -- - 2- 2- 2 + ( 3 29 3 -- - 2- 2- 2- + ( 3 29 3 - ( - 29 2 3 22002200 2 3 22002200 ( 29 ( 29...
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This note was uploaded on 02/28/2012 for the course CHEM 210-1 taught by Professor Trzupek during the Fall '08 term at Northwestern.

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