Alcohols, Ethers, Epoxide, Nitrile Reactions

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16 Terms

1
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williamson ether synthesis (SN2 reaction)

  • reagent:

    Step 1: NaH

    Step 2: alkyl halide

  • conversion of an alcohol to an ether

<ul><li><p>reagent: </p><p>Step 1: NaH</p><p>Step 2: alkyl halide </p></li><li><p>conversion of an alcohol to an ether </p><p></p></li></ul><p></p>
2
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base catalyzed opening of epoxide (nucleophile attacks less substituted side)

  • reagents: -OCH3 (above) and HOCH3 (below)

  • opening of epoxide to form a 2o alcohol with an ether

<ul><li><p>reagents: <sup>-</sup>OCH<sub>3</sub> (above) and HOCH<sub>3</sub> (below)</p></li><li><p>opening of epoxide to form a 2<sup>o</sup> alcohol with an ether </p></li></ul><p></p>
3
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acid-catalyzed opening of epoxide (nucleophile attacks more substituted side)

  • reagents: H3O+ or HBr

  • opening of an epoxide to form a dialcohol olecule or a 2o carbon with a bromine group and a primary alcohol

<ul><li><p>reagents: H<sub>3</sub>O<sup>+</sup> or HBr </p></li><li><p>opening of an epoxide to form a dialcohol olecule or a 2<sup>o</sup> carbon with a bromine group and a primary alcohol </p><p></p></li></ul><p></p>
4
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acid-catalyzed alcohol dehydration (E1 reaction)

  • reagents: H3O+ (above), delta (below)

  • conversion of a 2o alcohol to a trans alkene

<ul><li><p>reagents: H<sub>3</sub>O<sup>+ </sup>(above), delta (below)</p></li><li><p>conversion of a 2<sup>o</sup> alcohol to a trans alkene </p></li></ul><p></p>
5
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oxidation of 1o alcohol to aldehyde

  • reagent: PCC

<ul><li><p>reagent: PCC</p><p></p></li></ul><p></p>
6
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oxidation of 1o alcohol to carboxylic acid

  • reagents: KMnO4 or CrO3/H2SO4

<ul><li><p>reagents: KMnO<sub>4</sub> or CrO<sub>3</sub>/H<sub>2</sub>SO<sub>4</sub></p></li></ul><p></p>
7
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oxidation of 2o alcohol to ketone

  • reagents: KMnO4 or CrO3/H2SO4 or PCC

<ul><li><p>reagents: KMnO<sub>4</sub> or CrO<sub>3</sub>/H<sub>2</sub>SO<sub>4 </sub>or PCC</p><p></p></li></ul><p></p>
8
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converting 2o/3o alcohols to alkyl halides (SN1) reaction

  • reagents: HX

<ul><li><p>reagents: HX </p><p></p></li></ul><p></p>
9
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converting 1o/2o alcohols to alkyl bromides (SN2 reaction)

  • reagent: PBr3

  • for stereochemistry: causes an inversion of stereochemistry

<ul><li><p>reagent: PBr<sub>3</sub></p></li><li><p>for stereochemistry: causes an inversion of stereochemistry</p><p></p></li></ul><p></p>
10
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converting 1o/2o alcohols to alkyl chlorides

  • reagent: SOCl2 (above), pyridine (below)

  • for stereochemistry: causes an inversion of stereochemistry

<ul><li><p>reagent: SOCl<sub>2</sub> (above), pyridine (below) </p></li><li><p>for stereochemistry: causes an inversion of stereochemistry</p></li></ul><p></p>
11
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tosylate ester formation

  • reagents: TsCl

  • for stereochemistry: retention of stereochemistry

<ul><li><p>reagents: TsCl </p></li><li><p>for stereochemistry: retention of stereochemistry</p></li></ul><p></p>
12
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oxidative cleavage of 1,2 diol

  • reagents: HIO4

  • conversion of 1,2 diol to a ketone and aldehyde

<ul><li><p>reagents: HIO<sub>4</sub></p></li><li><p>conversion of 1,2 diol to a ketone and aldehyde </p><p></p></li></ul><p></p>
13
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swern oxidation

  • reagents: 1. DMSO, COCl2 2. Et3N

  • conversion of a primary alcohol into an aldehyde or secondary alcohol into a ketone

14
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SN2 formation of nitrile with cyanide and alkyl halide

  • reagent: NaCN

  • conversion of alkyl halide to nitrile with cyanide

<ul><li><p>reagent: NaCN </p></li><li><p>conversion of alkyl halide to nitrile with cyanide </p></li></ul><p></p>
15
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acid-catalyzed hydrolysis of nitriles

  • reagents: H3O+ , heat

  • conversion of nitrile to carboxylic acid

<ul><li><p>reagents: H<sub>3</sub>O<sup>+ </sup>, heat</p></li><li><p>conversion of nitrile to carboxylic acid</p><p></p></li></ul><p></p>
16
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cyanohydrin formation using aldehydes/ketones and cyanide

  • reagent: NaCN

  • formation of a cyanohydrin from an aldehyde or ketone

<ul><li><p>reagent: NaCN</p></li><li><p>formation of a cyanohydrin from an aldehyde or ketone </p><p></p></li></ul><p></p>

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