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What is the peroxide effect? What does it mean when there is a reversal of orientation? Detailed answers are appreciated

What is the peroxide effect? What does it mean when there is a reversal of orientation? Detailed answers are appreciated

Chemistry
Chemistry
10th Edition
ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Chapter1: Chemical Foundations
Section: Chapter Questions
Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...
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What is the peroxide effect? What does it mean when there is a reversal of orientation? Detailed answers are appreciated. Thanks in advance!

Free Radical Addition w/ Peroxides/Alkoxyl Radicals These additions synthesize anti-Markovnikov products. This is because the formation of a more substituted radical is preferred, meaning the halogen will add on the less substituted side. A small amount of peroxide will yield a minimal amount of the Markovnikov product. An appreciable amount of peroxide will lead to only the anti-Markovnikov product being created. Peroxide effect = reversal of orientation (specifically with bromine). This does not occur with chlorine. Chlorine will still add on the more substituted side/Markovnikov. Initiation: Radicals are formed. R R-O: + Propagation: A radical reacts to generate another radical. Step 1: A bromine radical adds to the double bond to generate an alkyl radical on the secondary carbon atom. Br H H₂C Br H A C-C H H H3C H -R -Br + Br -H + heat R-O + ·O-R R-0-H + Br. H-Br H Step 2: The alkyl radical abstracts a hydrogen atom from HBr to generate the product and a bromine radical. H3C C-H H Br T H-C-C-H + Br. CH3 H The bromine radical generated in Step 2 goes on to react with another molecule of the alkene in another Step 1, continuing the chain. H on the 2° carbon
Transcribed Image Text:Free Radical Addition w/ Peroxides/Alkoxyl Radicals These additions synthesize anti-Markovnikov products. This is because the formation of a more substituted radical is preferred, meaning the halogen will add on the less substituted side. A small amount of peroxide will yield a minimal amount of the Markovnikov product. An appreciable amount of peroxide will lead to only the anti-Markovnikov product being created. Peroxide effect = reversal of orientation (specifically with bromine). This does not occur with chlorine. Chlorine will still add on the more substituted side/Markovnikov. Initiation: Radicals are formed. R R-O: + Propagation: A radical reacts to generate another radical. Step 1: A bromine radical adds to the double bond to generate an alkyl radical on the secondary carbon atom. Br H H₂C Br H A C-C H H H3C H -R -Br + Br -H + heat R-O + ·O-R R-0-H + Br. H-Br H Step 2: The alkyl radical abstracts a hydrogen atom from HBr to generate the product and a bromine radical. H3C C-H H Br T H-C-C-H + Br. CH3 H The bromine radical generated in Step 2 goes on to react with another molecule of the alkene in another Step 1, continuing the chain. H on the 2° carbon
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