Question

In the acid-catalyzed dehydration of 2−methyl−1−propanol, what carbocation would be formed if a hydride shift accompanied cleavage of the carbon-oxygen bond in the alkyloxonium ion?

Answer 1

t-butyl cation

Step-by-step explanation:

Generally a dehydration reaction occurs when an organic compound loses water molecules to form alkenes. However, in an acid-catalyzed dehydration, the dehydration reaction occurs in the presence of an acidic compound which acts as a catalyst. Therefore, for this specific case, the hydride will migrate and a t-butyl cation will be formed. This is because it is more stable due to the presence of three electron releasing alkyl groups which can stabilize a positive charge compared with the secondary cation formed when the methyl group migrates.