Ch_322a_8.02 - CH 2 =CHCH 3 H Br CH 3 CHCH 3 Br propene...

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Addition of Hydrogen Halides to Alkenes Markovnikov's Rule Hydrogen halides (HCl, HBr, HI) add to alkenes: C=C + HX C C H X X = Cl, Br, I These reactions may be carried out by adding HX to a solvent such as acetic acid or dichloromethane in the presence of the alkene, or by bubbling gaseous HX into a solution of the alkene. The reactivity order of HX in these additions is HI > HBr > HCl The reactivity of HCl is very low except with highly substituted alkenes.
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Regiochemistry of the Addition Reaction Regiochemistry means the specific carbons of the alkene to which the H and X attach. In unsymmetrical alkenes, there are two possible regiochemistries:
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Unformatted text preview: CH 2 =CHCH 3 + H Br CH 3 CHCH 3 Br propene 2-bromopropane CH 3 CH 2 CH 2 Br 1-bromopropane very little formed C=CH 2 CH 3 CH 3 2-methylpropene + H Br CH 3 CCH 3 CH 3 Br 2-bromo-2-methylpropane CH 3 CHCH 2 Br CH 3 1-bromo-2-methyl-propane very little formed Markovnikov's Rule Vladimir Markovnikov (University of Kazan) in 1869: "The hydrogen of the acid attaches to the carbon that already holds the greater number of hydrogens." This prediction is called "Markovnikov's Rule." CH 2 =CH-CH 3 H Br CH 2-CH-CH 3 H Br Markovnikov addition product Addition reactions that follow this rule are called Markovnikov Additions ....
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This note was uploaded on 07/22/2009 for the course CHEM 322AL taught by Professor Jung during the Summer '07 term at USC.

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Ch_322a_8.02 - CH 2 =CHCH 3 H Br CH 3 CHCH 3 Br propene...

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