CHEM 3410 1st Edition Lecture 14Outline of CurrentI. Preparation of Alcohols from carbonyls reacted with Grignard ReagentsII. Alcohol ReactionsA. Alcohols to alkyl halidesB. Alcohols to TosylatesC. DehydrationD. Manipulating stereochemistry (R,S)III. Outline of Last LectureIV. Alcohol Reactivity: Alkoxide FormationV. Preparation of AlcoholsVI. Reduction of Aldehydes/ KetonesVII. Reductive of EstersVIII. Selective ReductionIX. Preparation of Alcohols from carbonyls reacted with Grignard ReagentsCurrent LectureI. Preparation of Alcohols from Carbonyls Reacted with Grignard ReagentsAldehyde: These notes represent a detailed interpretation of the professor’s lecture. These notesare best used as a supplement to your own notes, not as a substitute.Ketone:Esters:Limitations:-Water destroys Grignard reagents.- Grignard reagents are reactive with-H2O, R-OH, R-SH, R-NH2, R-COOH-You also cannot make Grignard with those functionalities:Major Point: Aldehydes -> primary alcohols. Ketones -> Secondary alcohols. Esters-> Tertiary alcoholsII. Reactions of AlcoholsAlcohols -> Alkyl Halides You must use very different conditions in order to convert secondary or primary alcohols to alkyl halides.Alcohols ->TosylatesAlcohols ->DehydrationThis dehydration does not work at all on primary alcohols. It does not work well on secondaryalcohols, and gives a yield that is garbage. Dehydration with sulfuric acid only really works well with tertiary alcohols. This is how to dehydrate primary and secondary alcohols:Mechanisms: Secondary:Tertiary:(E1)Controlling Stereochemistry: MECHANISM WILL BE ON EXAM
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