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Chemoselectivity in functional group transformation is a coveted outcome in organic synthesis. This is commonly achieved by exploiting unique characteristics inherent in closely related
Chemoselectivity in functional group transformation is a coveted outcome in organic synthesis. This is commonly achieved by exploiting unique characteristics inherent in closely related reagents. Refer to the observations noted below and advance reasons behind the observed outcomes: (You may use appropriate illustrations or mechanisms, but in either case, be brief) (2 Marks Each) (a) Resorcinol (benzene-1,3-diol) readily undergoes hydrogenation to cyclohexane- 1,3-dione in the presence of H/Ni, but benzene does not. (b) PCC oxidizes 1-methylcyclopent-2-enol, but not 1-methylcyclopent-3-enol. (c) Although imines are less reactive than aldehydes, they are reduced by the deactivated reducing agent NaBH3CN, yet aldehydes are not. (d) MCPBA epoxidizes electron-rich alkenes, while HO/NaOH epoxidizes electron-deficient alkenes. (e) Unstabilized phosphorus ylides react with aldehydes to provide Z-alkenes, yet stabilized phosphorus ylides react to provide E-alkenes.
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