Question

Acid‑catalyzed dehydration of secondary and tertiary alcohols proceeds through an E1 mechanism. The first step is the protonation of the alcohol 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

Compound with most substituted double bond appears as major product.

Step-by-step explanation:

• In acid-catalyzed dehydration of secondary and tertiary alcohols, a carbocation is produced as an intermediate after removal of a water molecule.
• Then deprotonation from adjacent carbon atom attached to positive charge bearing carbon atom takes place to produce a double bond.
• Here compound containing more substituted double bond appears as major product in accordance with saytzeff rule.
• Remember that the carbocation intermediate can undergo rearrangement to produce more stable carbocation.
• Structures of major and minor products are shown below.