Aldehydes, Ketones, and Hydride Reductions

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16 Terms

1
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addition of water (hydrate formation)

  • reagents: H2O (forward), H3O+ or OH- (reverse)

  • formation of a double hydroxyl group attachment to a carbon

  • anti-addition

<ul><li><p>reagents: H<sub>2</sub>O (forward), H<sub>3</sub>O<sup>+</sup> or OH<sup>-</sup> (reverse)</p></li><li><p>formation of a double hydroxyl group attachment to a carbon</p></li><li><p>anti-addition</p><p></p></li></ul><p></p>
2
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base-catalyzed addition of alcohol (hemiacetal formation)

  • reagents: RO- (forward), ROH (reverse)

  • anti-addition

  • formation of a hemiacetal

<ul><li><p>reagents: RO<sup>-</sup> (forward), ROH (reverse) </p></li><li><p>anti-addition</p></li><li><p>formation of a hemiacetal </p><p></p></li></ul><p></p>
3
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acid-catalyzed addition of alcohol (acetal formation); reversible with H3O+

  • reagents: ROH (forward), H3O+ (reverse)

  • anti-addition

  • formation of an acetal

4
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acid-catalyzed addition of primary amine (imine formation); reversible with H3O+

  • reagents: NRH2 (forward), H3O+ (reverse)

  • formation of imine

<ul><li><p>reagents: NRH<sub>2</sub> (forward), H<sub>3</sub>O<sup>+</sup> (reverse)</p></li><li><p>formation of imine </p><p></p></li></ul><p></p>
5
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acid-catalyzed addition of secondary amine (enamine formation); reversible with H3O+

  • reagents: NR2H (forward), H3O+ (reverse)

  • formation of enamine

<ul><li><p>reagents: NR<sub>2</sub>H (forward), H<sub>3</sub>O<sup>+</sup> (reverse)</p></li><li><p>formation of enamine </p><p></p></li></ul><p></p>
6
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wittig reaction

  • reagents: PPh3=- (phsphorus ylide)

  • formation of alkene

<ul><li><p>reagents: PPh<sub>3</sub>=- (phsphorus ylide)</p></li><li><p>formation of alkene</p><p></p></li></ul><p></p>
7
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reduction of ester to primary alcohol

  • reagents: 1. LiAlH4 2. H3O+

<ul><li><p>reagents: 1. LiAlH<sub>4</sub> 2. H<sub>3</sub>O<sup>+</sup></p><p></p></li></ul><p></p>
8
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reduction of acyl chloride to primary alcohol

  • reagents: 1. LiAlH4 2. H3O+

<ul><li><p>reagents: 1. LiAlH<sub>4</sub> 2. H<sub>3</sub>O<sup>+</sup></p></li></ul><p></p>
9
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reduction of carboxylic acid to primary alcohol

  • reagents: 1. LiAlH4 2. H3O+

<ul><li><p>reagents: 1. LiAlH<sub>4</sub> 2. H<sub>3</sub>O<sup>+</sup></p></li></ul><p></p>
10
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reduction of aldehyde to primary alcohol

  • reagents: 1. LiAlH4 2. H3O+ or 1. NaBH4 2. H3O+

<ul><li><p>reagents: 1. LiAlH<sub>4</sub> 2. H<sub>3</sub>O<sup>+</sup> or 1. NaBH<sub>4</sub> 2. H<sub>3</sub>O<sup>+</sup></p><p></p></li></ul><p></p>
11
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reduction of ketone to secondary alcohol

  • reagents: 1. LiAlH4 2. H3O+ or 1. NaBH4 2. H3O+

<ul><li><p>reagents: 1. LiAlH<sub>4</sub> 2. H<sub>3</sub>O<sup>+</sup> or 1. NaBH<sub>4</sub> 2. H<sub>3</sub>O<sup>+</sup></p><p></p></li></ul><p></p>
12
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reduction of ester to an aldehyde

  • reagents: 1. DIBAL-H, -70oC 2. H2O

<ul><li><p>reagents: 1. DIBAL-H, -70<sup>o</sup>C 2. H<sub>2</sub>O</p></li></ul><p></p>
13
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reduction of acyl chloride to aldehyde

  • reagents: LiAlH[O(CH3)3]3 or LTBA

<ul><li><p>reagents: LiAlH[O(CH<sub>3</sub>)<sub>3</sub>]<sub>3</sub> or LTBA </p><p></p></li></ul><p></p>
14
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reduction of amide to amine

  • reagents: 1. LiAlH4 2. H2O

<ul><li><p>reagents: 1. LiAlH<sub>4</sub> 2. H<sub>2</sub>O</p></li></ul><p></p>
15
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reduction of nitrile to amine

  • reagents: 1. LiAlH4 2. H3O+

<ul><li><p>reagents: 1. LiAlH<sub>4</sub> 2. H<sub>3</sub>O<sup>+</sup></p></li></ul><p></p>
16
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hofmann rearrangement

  • reagents: 1. Br2 2. NaOH

  • formation of primary amine from amide (with ethyl group)

<ul><li><p>reagents: 1. Br<sub>2</sub> 2. NaOH</p></li></ul><ul><li><p>formation of primary amine from amide (with ethyl group)</p></li></ul><p></p>