Question

Acid-catalyzed dehydration of 3,3-dimethyl-2-butanol gives three alkenes: 2,3-dimethyl-2-butene, 3,3-dimethyl-1-butene, and 2,3-dimethyl-1-butene. Draw the structure of the carbocation intermediate leading to the formation of 2,3-dimethyl-2-butene.

Answer 1

1,1-hexene > 2,3,3-dimethyl-2-butene > 3-methyl-3-hexene > cis-3-hexene

The Saytzeff rule states that an alkene becomes more stable the more highly substituted it is. Since 2,3-dimethyl-2-butene is the most substituted alkene among the ones listed, it will thus be the most stable.

Ozone treatment of 2,3-dimethyl but-2-ene results in ozoinde, which with further reduction yields propanone and water. Trans-2-butene undergoes ozonolysis, producing the main ozonide. Acetaldehyde, syn- and anti-acetaldehyde oxide, and this main ozonide are the products of its breakdown.

Let's not forget that the alkenes' pi bonds are least stabilized by alkyl groups, making terminal alkenes the least stable of the group. This means that among the alkenes listed, 1-hexene is the least stable.

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