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Rules of the Day 10 - Rules of the Day 1 Aldehydes and...

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Rules of the Day 2-11-09 1. Aldehydes and Ketones connect to your 310M and roadmaps through alkenes (ozonolysis breaks C=C bond!) and oxidation of primary (PCC gives aldehydes) and secondary (PCC or H 2 CrO 4 gives ketones) alcohols. 2. The anions of terminal alkynes add to aldehydes and ketones to give tetrahedral alkoxide intermediates (can be isolated). These alkoxides are protonated when the chemist opens the flask and adds acid to give alkyne alcohols. Mechanism A . Carbon-carbon bond forming! 3. HCN is in equilibrium with H+ and CN-. CN- reacts with aldehydes and ketones to give a tetrahedral alkoxide intermediate that cannot be isolated becuase it is immediately protonated to give a cyanohydrin product . Mechanism A . Carbon-carbon bond forming! Time Capsule: Cyanohydrins are hydrolyzed in strong H 3 O+ to give α -hydroxy carboxylic acids. 4. Wittig reactions form C=C bonds from C=O bonds through reaction of the nucleophilic ylide via the famous four-membered ring intermediate (See Pictures of the Day). This is a useful reaction because carbonyl compounds are easily made, and the ylides are made from alkyl
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