week2 (2) - both have alpha hydrogens) i. Best performed...

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Chem 35 Sections 9 and 12 Oct 8 2008 I. Exchanges (Acidic Protons) a. Acidic protons can exchange with deuterated solvents (e.g D 2 O, CD 3 OD). Most acidic protons will exchange first, followed by lesser acidic protons. Non acidic protons will not exchange O O D 2 O D D D D II. Halogenation of alpha carbon a. Acid catalysis – activates carbonyl, reduces basicity of carbonyl post reaction, only see 1 addition O X 2 , H 3 O + O X b. Base catalysis – activates nucleophile, results in reaction multiple times to replace all alpha carbons in the molecule O X 2 , NaOH O X X X X X X III. Aldol Reactions a. Forming a carbon-carbon bond b. Reaction of enol or enolate with carbonyl c. Non specific reaction: if start with 2 aldehydes or ketones, then form 4 possible products (if
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Unformatted text preview: both have alpha hydrogens) i. Best performed with one carbonyl lacking any alpha hydrogens (eg benzaldehyde) and other carbonyl having limited alpha hydrogens ii. Always results in beta-hydroxycarbonyl iii. Use of LDA to create only one product via stoichiometric equivalents (1 carbonyl(A) : 1 equiv LDA enolate, add 1 equiv carbonyl(B) product O H O OH O Bond Formed IV. Alkylation a. Use of LDA to control reactivity (K eq = 10 17 for enolate formation) b. Can also before with alpha, beta diketones O N Li O R-X O R Bond Formed O O NaOH (cat) R-X O O R Bond Formed...
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week2 (2) - both have alpha hydrogens) i. Best performed...

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