How are Regiochemistry & Stereochemistry involved?
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3-8-2019
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How are Regiochemistry & Stereochemistry involved?
In terms of regiochemistry, Zaitsev's rule states that although more than one product can be formed during alkene synthesis, the more substituted alkene is the major product. This infers that the hydrogen on the most substituted carbon is the most probable to be deprotonated, thus allowing for the most substituted alkene to be formed.
Unlike E2 reactions, E1 is not stereospecific. Thus, a hydrogen is not required to be anti-periplanar to the leaving group.
In this mechanism, we can see two possible pathways for the reaction. One in which the methyl on the right is deprotonated, and another in which the CH2 on the left is deprotonated. Either one leads to a plausible resultant product, however, only one forms a major product. As stated by Zaitsev's rule, deprotonation of the most substituted carbon results in the most substituted alkene. This then becomes the most stable product due to hyperconjugation, and is also more common than the minor product.
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