CHEM 33332 1st Edition Lecture 19 Outline of Last Lecture VI Aldehyde and Keytone Synthesis A Oxidation of Alcohols B Cleavage of Alekens by Onzolysis C Friedel Crafts Acylation D Hydrogenation of Alkynes E 1 3 Dithiane Synthesis of Aldehydes and Ketones A multi step synthesis Example F Ketones from Carboxylic Acids 1 2 3 Ex G Ketones from Nitriles Ex H Aldehydes and Keytones from Acid Chlorides 1 Reduction to aldehydes Mechanism a A milder reagent lithium aluminum tri t butoxy hydride b The rosenmunf Reduction These notes represent a detailed interpretation of the professor s lecture GradeBuddy is best used as a supplement to your own notes not as a substitute Ex 2 Conversion to ketones with litium dialkylcuprates Gilman reagent Ex A reminder use grilman reagent in the corey House reaction VII Reactions of Aldehydes and Keytones A Alpha Carbon reactions covered in Ch 22 B Nucleophilic Addition Reactions 1 Grignard Reaction 2 Addition of Acetylide 3 Addition of Hydride 4 Catalytic hydrogenation similar to hydrogenation of alkenes but aldehydes and keytones are less reactive Outline of Current Lecture deoxygenation of carbonyls Wolf Kischner Mechanism Ex Addition of 2 degree amines to aldehydes and ketones Mechanism of Enamine Formation Ex Addition of Alcohols Acetal Formation Ex Mechanism Acetals are protected carbonyls Ex Mechanism of seprotection is the reverse of acetal formation Selective Acetal Formation alcohols are weak nucleophiles therefore selective nucleophiles aldehydes are more reactive than ketones therefore alcohols selectively react with aldehydes to form acetals in the presence of ketones Ex Oxidation of Aldehydes to Carboxylic Acids Silver reagents Ex Addition of Phosphorous ylides the wittig reaction The Wittig Reaction Current Lecture
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