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2013 5C

Posted: Thu Mar 10, 2016 11:26 pm
by AvaM1c
Why do you not use the double bond on (Z)-2-iodobut-2-enol as a nucleophile and use the NH as a nucleophile instead? Basically why does the negative atom get a higher priority of being a nucleophile?

also for the second part when it asks what type of reaction this is, how do you know it is SN2?

Re: 2013 5C

Posted: Fri Mar 11, 2016 2:47 pm
by annchen0628
NH has a fully negative charge and OH is only partially negative. It's electronegative. NH therefore is more nucleophilic. It's SN2 because it's bimolecular. Two reactants are involved in the reaction. It's substitution because it's not "added" on to a double bond.