Question

Draw the zaitsev product formed when 2,3-dimethylpentan-3-ol undergoes an e1 dehydration.

Answer 1

Answer: ince 2,4-dimethylpentan-3-ol is symmetrical there will only be one product formed after dehydration. It is 2,4-dimethyl-2-pentene

Answer 2

Zaitsev product formed when ${\mathbf{2,3 - dimethylpentan - 3 - ol}}$ undergoes dehydration is drawn in the attached image.

Further Explanation:

In the elimination reaction, a pair of groups are eliminated from the molecule by a dehydrating agent such as ${{\text{H}}_{\text{2}}}{\text{S}}{{\text{O}}_{\text{4}}}$ or ${{\text{P}}_{\text{2}}}{{\text{O}}_{\text{5}}}$. Removal of either an alkyl halide or water molecule may occur ant it results in formation of an alkene. The formation of major and minor alkene is governed by the Hoffman rule or Zaitsev rule.

There are two kinds of elimination reactions namely E1 and E2. The unimolecular elimination reactions proceed through two steps that involve carbocation formation and rearrangement. The product is governed by the pathway that leads to more stable carbocation.

Zaitsev rule says that a formation of a more substituted alkene is more favored in an elimination reaction while the Hoffman rule predicts that a least substituted alkene is more favored if the alkene is formed from asymmetrically amines such as quaternary ammonium salt.

The usual dehydration reaction of alcohol follows the Zaitsev rule. More substituted alkene is the major product formed from the elimination of water from ${\text{2,3 - dimethylpentan - 3 - ol}}$. (Refer to the attached image).

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Answer details:

Grade: Senior School

Subject: Chemistry

Chapter: Redox reactions

Keywords: elimination reaction, Loss of water molecule, dehydration, alkene, E 1 elimination, unimolecular, Zaitsev rule, carbocation, quaternary ammonium salt, and Hoffman rule.