Consider the following three pathways for the hydration of 3,3-dimethylbut-1-ene: Pathway I: Treatment with dilute H ₂ SO ₄ Pathway II: Treatment with Hg(OAc) ₂/ H ₂ O followed by NaBH ₄ Pathway III: Treatment with B ₂ H ₆/ THF followed by H ₂ O ₂/ OH ^- The major product(s) of which pathway(s) will give a positive iodoform test upon treatment with I ₂ and NaOH ?

Step-by-step solution

Pathway I involves acid-catalyzed hydration, which proceeds via a carbocation intermediate. The initially formed secondary carbocation undergoes a 1,2-methyl shift to form a more stable tertiary carbocation, yielding 2,3-dimethylbutan-2-ol as the major product. This alcohol does not contain the required CH ₃- CH(OH) - group for a positive iodoform test. Pathway II is oxymercuration-demercuration, which gives the Markovnikov addition product without rearrangement. The major product is 3,3-dimethylbutan-2-ol. This mo