nd. (c) Under acidic we a one position (eft position will (a be weak and the is
ID: 479820 • Letter: N
Question
nd. (c) Under acidic we a one position (eft position will (a be weak and the is is tertiary, is protonated, When a electrophile Me is the powerful secondary. epoxide which (EtOH) very Ethanol decide (right) must case, conditions, position epoxide) and this other generating In thereby protonated nucleophile, attacked. the competition is between a secondary position and a and tertiary position, electronic factors dominate and the tertiary position is attacked. Back-side attack causes inversion of configuration at the chirality center being attacked. Finally, a proton is removed (the most likely base is the solvent, ethanol). Et [H2SO4] EtOH Et Eto Me nated, EtOH le (a Et H de is Et OH s case either Et Me EtoH Et Me (d) Under acidic conditions, the epoxide is protonated, thereby generating a very powerful electrophile (a protonated epoxide). Water (H2O) is a weak nucleophile, and we must decide which position will be attacked. In this case, one position (left) is tertiary, and the other position (right) is secondary. When theExplanation / Answer
ANSWER
In inversion R isomer gets converted to S and S to R. In this case inversion has taken place indeed. In the reactant the Configuration at tertiary carbon is S and in product the cofiguration is R. In
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