AldKetones_notes

AldKetones_notes - s i s o f n i t r i l e g r o u p f o l...

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Relative reactivities of carbonyl compounds towards nucleophiles: An aldehyde has a greater partial positive charge on its carbonyl carbon than does a ketone • Steric factors contribute to the reactivity of an aldehyde • The carbonyl carbon of an aldehyde is more accessible to the nucleophile • Ketones have greater steric crowding in their transition states and in the final products, so they are less reactive General trend in reactivities of carbonyl compounds: acyl halide > acid anhydride > aldehyde > ketone > > ester ~ carboxylic acid > amide > carboxylate anion
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Cyanohydrins Formed by Addition of Hydrogen Cyanide CO R' R HC N + C R' R OH C N CN R, R' = H, alkyl, aryl a cyanohydrin Practically, HCN is generated in situ by mixing HCl with e x c e s s NaCN (sodium cyanide) Mechanism: CO R' R CN C R' R O C N HC N C R' R OH C N Applications in synthesis R e d u c t i o n o f n i t r i l e g r o u p : O C HO N HO NH 2 1) LiAlH 4 2) H 2 O H y d r o l y
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Unformatted text preview: s i s o f n i t r i l e g r o u p f o l l o w e d b y e l i m i n a t i o n : C HO N H + , H 2 O heat HO OH O conc. H 2 SO 4 heat H O OH H O OH + , -unsaturated carboxylic acid (mixture of E and Z isomers) What are the factors influencing the equilibrium position in the hydration reaction? The equilibrium constant for the reaction depends on the relative stabilities of the reactants and products Protecting an OH group: silyl protecting groups O OH TBDMS-Cl imidazole O OTBDMS OTBDMS 1) CH 3 MgBr 2) aqueous NH 4 Cl HO CH 3 (e.g. Bu 4 N + F-) F OH HO CH 3 H 2 O Si CH 3 tert-Bu CH 3 t ert-B utyl d i m ethyl s ilyl (TBDMS) protecting group R-OH Si CH 3 tert-Bu CH 3 Cl-Cl Si CH 3 tert-Bu CH 3 OR H N N H Si CH 3 tert-Bu CH 3 OR highly stable in basic conditions...
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This note was uploaded on 09/25/2011 for the course CHEM 2262 taught by Professor Smith during the Spring '08 term at LSU.

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AldKetones_notes - s i s o f n i t r i l e g r o u p f o l...

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