l15 - Hydrate or gem-diol N H Imine N H H H2O O OH H OH O R...

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OH Hydrate or gem -diol N H OH Hemiacetal H N H Imine H 2 O OH H OH O H + H H O OH H + H + Enamine OH O H + N N H H O Aceta H Know these reactions and be able to draw curved arrow mechanisms Acetal O HCN H + + CN - OH R R R R C N Cyanohydrin Cyanohydrin CH 2 NH 2 β -amino alcoho H H C R O N H LiAlH 4 R O H alcohol HCl H O hea H 2 O heat C O OH α -hydroxy conc H 2 SO 4 R O H acid C O OH heat In the book α - β unsaturated acid R More in Ch. 18 O HCN 1. LiAlH 4 1. CH 3 Li PCC H 2. H 2 O 2. H 2 O Predict the product . CH 3 Li O H + OH PCC O OH HCN H CH 3 CH 3 CH 3 CH 3 C N LiAlH 4 OH OH NH 2 NH 2 NH 2 OH NH 2 OH A B C D plus enantiomers Great Synthetic Reaction Number 1 Diels Alder Reaction Great Synthetic Reaction Number 2 Wittig Reaction O R 1 + (C 6 H 5 ) 3 P R 3 R 1 R 3 (C 6 H 5 ) 3 PO + R 2 R 4 R 2 R 4 Aldehyde or ketone Alkene Phosphine oxide (C 6 H 5 ) 3 P R 3 R 4 Phosphorous Ylide P Br (C 6 H 5 ) 3 P Li H H Triphenylphosphine (C 6 H 5 ) 3 P H (C 6 H 5 ) 3 P H O R 1 + (C 6 H 5 ) 3 P R 3 R 1 R 3 (C 6 H 5 ) 3 + R 2 R 4 R 2 R 4 Aldehyde or
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This note was uploaded on 01/09/2011 for the course CHE 322 taught by Professor Staff during the Spring '08 term at SUNY Stony Brook.

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l15 - Hydrate or gem-diol N H Imine N H H H2O O OH H OH O R...

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