Chem210-1 F08 Ex1 p04a

Chem210-1 F08 Ex1 p04a - between those extremes If'A...

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5. Imagine a situation in which a researcher left a sample of diacetylperoxide (compound 'A' below) dissolved in the solvent tetrahydrofuran (designated as 'THF' below): 'A' = H 3 C C O O O C O CH 3 THF = O After a period of time, the solution detonated in a violent explosion. It is likely that 'A' acted as a radical initiator, leading to the formation of unstable hydroperoxide derivatives by the reaction of THF with oxygen in the air, according to the general scheme below: R H + O O R O O H (note : O 2 reacts as a diradical) (equation 1) a) The C-H bonds in compound 'A' have a bond dissociation energy of about 90 k-cal/mole; the O-O bond in 'A' has a BDE of about 30 k-cal /mole, and the C-C bonds are likely
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Unformatted text preview: between those extremes. If 'A' undergoes a homolytic cleavage to form a radical initiator, propose a structure for the iniator radical, given the BDE information (4 pts) b) Using the abbreviation "In " to represent the initiator in this reaction, propose steps for a radical chain process which would account for the hydroperoxide product shown below (8 pts) O (initiator 'A') O 2 O O O H (continued on the next page) H 3 C C O O O H H + In O H + In-H O H + O O O O O O O O + O H H O O O H O H + (then the last two steps cycle as a chain)...
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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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