Which reagant is more nucleophilic?
Nucleophilic Character of a compound is revealed by the fact when it donates a pair of electrons for the formation of chemical bond in a reaction. Nucleophiles are ions or molecules which has a pair of free electrons or a pi bond. As they donate electrons they are also known as Lewis Bases.
CH3CH2OH or CH3CH2O-
Coming to Ethanol (CH3CH2OH) and Ethoxy radical(CH3CH2O-) the more nucleophilic character is exhibited by Ethoxy Radical(CH3CH2O-). In an Ethoxy radical the destabilisation of Oxygen by the inductive effects results in the donation of electron Pair by the Oxygen.
Whereas Ethanol is a poor nucleophile because of its weak alcohol group. Also it containes electronegative Oxygen, it cannot donate a pair of electrons to perform as a nucleophile.
Ph-S- or Ph-O-
Ph-S- is more nucleophilic because of the largest Sulphur atom present. It is bigger than Oxygen. The Polarisability of electrons leads to possess more nucleophilic character in Ph-S-.
Page 2 3. I State which reagent you would expect to be more nucleophilic. (1 pt.)...
3. State which reagent you would expect to be more nucleophilic (1 pt.) ii. Explain why you would expect your choice to be more nucleophilic (2 pts.) a) CH CH.OH or CH CHO b) Ph-5 or Ph-O-
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