CHEM 33332 1st Edition Lecture 20Outline of Last Lecture VI Aldehyde and Keytone SynthesisA. Oxidation of AlcoholsB. Cleavage of Alekens by OnzolysisC. Friedel-Crafts AcylationD. Hydrogenation of AlkynesE. 1,3-Dithiane Synthesis of Aldehydes and KetonesA multi-step synthesis:Example: F. Ketones from Carboxylic Acids1.2.3.Ex:G. Ketones from NitrilesEx:H. Aldehydes and Keytones from Acid Chlorides1. Reduction to aldehydesMechanisma) A milder reagent: lithium aluminum tri(t-butoxy)hydrideb) The rosenmunf ReductionEx: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 KeytonesA. Alpha-Carbon reactions – covered in Ch 22B. Nucleophilic Addition Reactions1. Grignard Reaction:2. Addition of Acetylide3. Addition of Hydride4. Catalytic hydrogenation:similar to hydrogenation of alkenes, but aldehydes and keytones are less reactiveOutline of Current Lecture Chapter 20: Carboxylic Acids (RCOOH, RCo2H)Aliphatic acids-Aromatic acids-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.Fatty AcidsStructure:Physical Properties:II. Boiling PointIII. Melting PointIV. Solubility in H20-greater solubility than alcohols-More than 6 carbons – only slightly soluble in water-The salts of most carboxylic acids are water solubleCarboxylic Acid NomenclatureI. Open chain (acyclic) drop “e” from alkane/alkene/alkyne name, add “oic” acid-COOH carbon is always #1-priority over all functional groups studiedII. Cyclic: add “carboxylic acid: to the cycloalkane ot cycloalkane nameIII. Dicarbocylic acids add “dioc acid” (acyclic) or “dicarboxylic acid” (cyclic)Acidity of Carboxylic AcidsI. Strength: weak acids:II. Factors that affect acidity:A. ResonanceB. Electron withdrawing groups C. Electron donating groups Synthesis of carboxylic Acids (review)Current
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