Answer to Question #225536 in Organic Chemistry for Simal Kumar Mandi

Question

How will you prepare isopropanol and acetic acid from CH3MgBr?

Answer 1

When aldehydes​ react with water it gives hydrates(diols) as a product. And reaction is nucleophilic addition. So, in case of D2O,

• When D2O reacts with aldehydes -OD attacks on C=O bond and gives products as above.

[Note: There are no traces of such reaction in any book. So, maybe this reaction is not possible. Tell me why, if you know.]

Or else -OD ion attacks on α-hydrogens. And in the end of the reaction all α hydrogens will be replaced by deuterium.[1]

Large excess of D2O is used in deuteration of carbonyl compounds. C-D bond is stronger than C-H bond. So, it is easy to replace all α-H by α-D.