Question

For the following dihydroxylation reaction which of the following statements is correct regarding the expected products? 1. MCPBA 2. H, H2O CH(CH3)2 H3CH2CH н-он CH2CH3 CH(CH3)2 H3CH2CtoH нонн CH2CH3 CH(CH3)2 HoCH2CH3 нонн CH2CH3 CH(CH3)2 Ho+CH2CH3 H -OH CH2CH3 O Equal amounts of I and IV produced Equal amounts of I and III produced Equal amounts of II and III produced O Equal amounts of I and II produced Equal amounts of III and IV produced

Answer 1

Solution:

Correct option is B (equal amounts of I and III )

The given reaction is completed in two steps:

1) Epoxidation

2) Acid catalysed ring opening of epoxide.

Thus, H2O attacks from highly hindered side of epoxide which result into the formation of trans-diols. Product I and III are trans diols. Therefore, they will form in equal amounts.