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Hydride Reductions - Reduction of Carbonyl Reduction of...

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1 Reduction of Carbonyl Reduction of aldehyde yields 1º alcohol. Reduction of ketone yields 2º alcohol. Reagents: Sodium borohydride, NaBH 4 Lithium aluminum hydride, LiAlH 4 Raney nickel =>
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2
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3 Raney Ni O H 2 H OH H H Raney Ni Reduces both carbonyl group and alkenes
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4 Catalytic Hydrogenation Add H 2 with Raney nickel catalyst. Also reduces any C=C bonds. O H 2 , Raney Ni OH =>
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5 New Reducing Reagents H 2 = H - + H + H - = Hydride anion NaH [sodium hydride] is too reactive [explosive]
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6 Hydride Reagents H B H H H + Hydride ion Very reactive H B H H H Hydride donor Less reactive H Li H H H + Hydride ion Very reactive H Li H H H Hydride donor Less reactive
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7 Hydride Reagents H B H H H + Hydride ion Very reactive H B H H H Hydride donor Less reactive Hydride reagents may one day serve as the source of hydrogen in fuel cells for automobiles. H B H H H H O H H B H H H H H O + + + (Fuel)
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8 Hydrogen equivalent “Reduction” of hydroxylic solvent LiAlH 4 in methanol generates hydrogen violently, which can lead to fires. NaBH
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