assuming that the reaction was SN2, which atom appears to be more nucleophilic:
ID: 900026 • Letter: A
Question
assuming that the reaction was SN2, which atom appears to be more nucleophilic: N or O?
Describe and explain the possible effect on your results of the following experimental errors or variations.
a. The regent bottle labeled “sodium saccharin” contained saccharin instead.
b. You used water as the reaction solvent rather than DMF.
c. You heated the reaction mixture for 3 hours under reflux.
What is another solvent besides DMF that would have been suitable for this reaction?
Explanation / Answer
Nitrogen atom appears to be more nucleophilic than O because N has less electronegativity than O.
a. If the bottle contains saccharin instead of sodium saccharin rate of the reaction decreases because saccharin has less nucleophilicity than sodium saccharin.
b. If we use water as a solvent rather than DMF rate of the reaction decreases, because it is SN2 reaction which is more faster in polar aprotic solvent such as DMF. water is polar protic solvent hence it decreases the rate of reaction.
c. If we heat the reaction mixture for 3 hours under reflux, there is a chance to elimination which results alkene instaed of substitution product.
For the SN2 reaction DMSO is a suitable solvent besides DMF. Because DMSO is very good polar aprotic solvent.
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