Reduction Reactions of Carbonyl Compounds

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9 Terms

1
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Hydrogen gas with a metal catalyst (H2, Pt or Pd)

  • ketones and aldehydes to alcohols, but used rarely

  • not chemoselective

  • it’s not that it doesn’t happen, it’s just very slow, so it’s unlikely

<ul><li><p>ketones and aldehydes to alcohols, but used rarely</p></li><li><p>not chemoselective</p></li><li><p>it’s not that it doesn’t happen, it’s just very slow, so it’s unlikely</p></li></ul><p></p>
2
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Sodium Borohydride (NaBH4)

  • ketones and aldehydes to alcohols w/ chemoselectivity

  • selectively reacts w/ one functional group over others

<ul><li><p>ketones and aldehydes to alcohols w/ chemoselectivity</p></li><li><p>selectively reacts w/ one functional group over others</p></li></ul><p></p>
3
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Lithium aluminum hydride (LiAlH4)

extremely reactive, most carbonyl compounds are reduced to alcohols

<p>extremely reactive, most carbonyl compounds are reduced to alcohols</p>
4
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Diisobutylaluminum hydride (DIBAL-H, (i-Bu)2AlH

esters, amides, and nitriles are selectively reduced to aldehydes at low temperature

<p>esters, amides, and nitriles are selectively reduced to aldehydes at low temperature</p>
5
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Aqueous chromic acid (Na2Cr2O7,H2SO4(aq) or CrO3,H2SO4(aq))

  • Oxidizes primary alcohols to carboxylic acids, and secondary alcohols to ketones

  • called the Jones Oxidation

6
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Anhydrous Pyridium chlorochromate (PCC)

oxidizes primary alcohols to aldehydes OR secondary alcohols to ketones

7
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Swern Conditions (1. DMSO, (COCl)2; 2. Net3)

oxidizes primary alcohols to aldehydes OR secondary alcohols to ketones

8
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Dess-Martin periodinane (DMP)

oxidizes primary alcohols to aldehydes OR secondary alcohols to ketones

9
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NAD(P)+, H+

biochemical oxidizing agents capable of a wide variety of enzymatic oxidation reactions (*** but don’t use in synthesis)