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March 1, 2013

Organic chemistry teaching

Dear Reader,

Like many things in life carbonyl chemistry keeps on going, it is the gift which keeps on giving ! One bit of carbonyl chemistry I want to share with you is the chemistry of sodium hydrogen sulfite, this is a reagent which is very much maligned and misunderstood. If this reagent was a person I would say that he/she is something of a genius.

Now here is the reagent it is a simple anion made up of sulfur, oxygen and hydrogen atoms.

Now we have two places on the ion where it could act as a nucleophile, we have the oxygen atoms and the sulfur atom. For a set of electronic reasons (summed up in the HSAB theory) it tends to react using the lone pair on the sulfur. A classic use of this reagent is the purification of ketones and aldehydes, the hydrogen sulfite anion can react with ketones and…

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