Question

question 6 of 13
the transformation shown utilizes hydroboration - oxidation conditions.
inspect the final product and select all the reasons why hydroboration - oxidation was chosen to effect the transformation instead of the other reagents.
select the correct reasons.
oxvmercuration - demercuration reagents give the markovnikov product.
addition with acid and water as reagents avoids sigmatropic rearrangements.
addition with acid and water as reagents gives the markovnikov product.
hydroboration - oxidation reagents yield the markovnikov product of addition.
hydroboration - oxidation reagents yield the anti - markovnikov product of addition.
the reaction requires the markovnikov product without sigmatropic rearrangement.
the reaction requires anti - markovnikov product without sigmatropic rearrangement.
the reaction requires sigmatropic rearrangement.

Explanation:

• Oxymercuration - demercuration:
• Oxymercuration - demercuration gives the Markovnikov product (where the hydroxyl group adds to the more substituted carbon of the double bond). This is a key property that differentiates it from hydroboration - oxidation.
• Acid - catalyzed addition (acid and water):
• Acid - catalyzed addition of water to an alkene gives the Markovnikov product. Also, in acid - catalyzed reactions, carbocation intermediates are formed, which can undergo sigmatropic (carbocation) rearrangements (e.g., methyl or hydride shifts) to form more stable carbocations.
• Hydroboration - oxidation:
• Hydroboration - oxidation yields the anti - Markovnikov product (the hydroxyl group adds to the less substituted carbon of the double bond). It proceeds through a four - centered transition state in the hydroboration step, so there is no carbocation intermediate, and thus no sigmatropic (carbocation) rearrangements occur.

Answer:

Oxymercuration - demercuration reagents give the Markovnikov product.
Addition with acid and water as reagents gives the Markovnikov product.
Hydroboration - oxidation reagents yield the anti - Markovnikov product of addition.
The reaction requires anti - Markovnikov product without sigmatropic rearrangement.