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dehydration of an alcohol (3-methyl-1-phenylbutan-2-ol)
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Posted by
Oleg Savkin
dehydration of an alcohol (3-methyl-1-phenylbutan-2-ol)
Zaitsev's rules are nothing but a set of rules that were used to explain experimental results that were observed. It was not the other way around.
The real rule you have to use here is the Hammond's Postulate. This states:
The transition state of a reaction resembles either the reactants or the products, to whichever it is closer in energy.
So, in this case, the transition state is closer to the final product and so resembles the product which is a double bond. Therefore, the more thermodynamically stable product is preferred.
In essence, even Zaitsev's rule is used to explain the same thing, the reason for a more substituted alkene being favored is because of the higher number of hyperconjugative structures that are made possible due to more groups attached.
Therefore in this case, the product formed will be 3-methyl-1-phenylbut-1-ene(E) or (Z), since the stereochemistry is unknown.
Zaitsev's rules are nothing but a set of rules that were used to explain experimental results that were observed. It was not the other way around.
The real rule you have to use here is the Hammond's Postulate. This states:
The transition state of a reaction resembles either the reactants or the products, to whichever it is closer in energy.
So, in this case, the transition state is closer to the final product and so resembles the product which is a double bond. Therefore, the more thermodynamically stable product is preferred.
In essence, even Zaitsev's rule is used to explain the same thing, the reason for a more substituted alkene being favored is because of the higher number of hyperconjugative structures that are made possible due to more groups attached.
Therefore in this case, the product formed will be 3-methyl-1-phenylbut-1-ene(E) or (Z), since the stereochemistry is unknown.
Zaitsev's rules are nothing but a set of rules that were used to explain experimental results that were observed. It was not the other way around.
The real rule you have to use here is the Hammond's Postulate. This states:
So, in this case, the transition state is closer to the final product and so resembles the product which is a double bond. Therefore, the more thermodynamically stable product is preferred.
In essence, even Zaitsev's rule is used to explain the same thing, the reason for a more substituted alkene being favored is because of the higher number of hyperconjugative structures that are made possible due to more groups attached.
Therefore in this case, the product formed will be 3-methyl-1-phenylbut-1-ene (E) or (Z), since the stereochemistry is unknown.
Zaitsev's rules are nothing but a set of rules that were used to explain experimental results that were observed. It was not the other way around.
The real rule you have to use here is the Hammond's Postulate. This states:
So, in this case, the transition state is closer to the final product and so resembles the product which is a double bond. Therefore, the more thermodynamically stable product is preferred.
In essence, even Zaitsev's rule is used to explain the same thing, the reason for a more substituted alkene being favored is because of the higher number of hyperconjugative structures that are made possible due to more groups attached.
Therefore in this case, the product formed will be 3-methyl-1-phenylbut-1-ene(E) or (Z), since the stereochemistry is unknown.
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