Lecture25outline - I Review Acid chlorides react with two...

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I. Review • Acid chlorides react with two equivalents of alkyllithium and Grignard reagents to give tertiary alcohols • Cuprates react with acid chlorides to give ketones • A more common method for converting acid chlorides to ketones proceeds through the addition of alkylzinc reagents in the presence of a Pd catalyst • This reaction is successful because alkylzinc reagents are unreactive toward acid chlorides or ketones but can react with the acylpalladium chloride intermediate, and because ketones are inert toward Pd catalysts • Esters are less reactive than acid chlorides, anhydrides, aldehydes and ketones • The key 1 H NMR feature of esters is that the downfield shift of the hydrogens on the carbon that is bonded to oxygen (relative to ethers or alcohols) that results from the electron withdrawing nature of the carbonyl group • Esters react with water or other alcohols under acidic conditions to give acids or other esters
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