chap8 - Chap 8 Reactions with Alkenes 1. Electrophilic...

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1 Chap 8 Reactions with Alkenes 1. Electrophilic addition to alkenes. A) Markovnikov's rule- (1869) addition of a proton to an alkene results in the proton bonded to the carbon that has the most hydrogens (more substituted carbon gets the addition) more stable intermediate. major B) Anti-markonikov addition. R-O-O-R 2 R-O . C C + E + C E + :Nuc C E Nuc C C H H H H + H-Br C H H H H H + C H H H H Br H Br - C C CH 3 H H 3 C H 3 C + H-Br C H 3 C H H CH 3 H 3 C + C H 3 C H CH 3 CH 3 Br H 3 C Br - + HBr Br + HBr Br
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2 Ex. Only HBr works for the radical rxn. Very endothermic for HI, HCl. Br . + Br + H Br H Br Br . + R-O . + H-Br R-O-H + Br . CH 3 H H 3 C H 3 C Br . + CH 3 H H 3 C H 3 C Br CH 3 H Br H 3 C H 3 C Two possible H Br CH 3 H H 3 C H 3 C Br H + H-Br R-O-O-R R O H Br + R O H Br + Br + H-Br Br + Br
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3 Anti-mark addition of ethers. R-O-R c) Hydroboration of Alkenes. opposite of dehydration Mark addition d) Addition of sulfuric acid. H
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This note was uploaded on 09/02/2011 for the course CHEM 12a taught by Professor Harrison during the Spring '11 term at West Valley.

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chap8 - Chap 8 Reactions with Alkenes 1. Electrophilic...

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