Question

Acid-catalyzed dehydration of secondary and tertiary alcohols proceeds through an E1 mechanism. The first step is the protonation of alcohol and oxygen to form an oxonium ion.

Dehydration of 3-methyl-2-butanol forms one major and two minor organic products. Draw the structures, including hydrogen atoms, of the three organic products of this reaction.

Answer 1

Most substituted alkene is produced as a major product

Step-by-step explanation:

• Dehydration of 3-methyl-2-butanol proceeds through E1 mechanism to form alkenes.
• Most substituted alkene is produced as major product because of presence of highest number of hyperconjugative hydrogen atoms corresponding to the produced double bond (Saytzeff product).
• Here, a H-shift also occurs in one of the intermediate step during dehydration to produce more stable tertiary carbocation.
• Reaction mechanism has been shown below.