Round 2 of Chem 239 studying

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Last updated 4:54 AM on 4/23/26
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When doing nucleophilic acyl substitutions, why do you need to add a base? And when?

Because the byproduct will be, for example, H+ and Cl-, which combine to form a strong acid HCl. This strong acid will protonate the rest of the uncreated nucleophiles, making them unreactive.

Unless the nucleophile is an anion, then no H+ is produced so there is no need to quench with a base.

You also have to think about the strength of the base. Alcohol is a very weak base, while NH3 is a strong base

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How to revert a ketal back into the original ketone

React it in H3O+

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