OCHEM Ch. 5 Alkene Addition Reactions

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Last updated 4:42 AM on 5/23/26
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20 Terms

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alkenes

act as nucleophiles

  • two groups add across a C=C double bond

<p>act as nucleophiles</p><ul><li><p>two groups add across a C=C double bond</p></li></ul><p></p>
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Regiochemistry

the study of regioselectivity in chemical reactions, which identifies the preferred direction of bond formation when multiple, non-equivalent, positions are possible

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regiochemistry: Markovnikov

nucleophile adds to more substituted carbon

<p>nucleophile adds to more substituted carbon</p>
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regiochemistry: Anti-Markovnikov

nucleophile adds to less substituted carbon

<p>nucleophile adds to less substituted carbon</p>
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stereochemistry: Syn Addition

both groups add to the same face

<p>both groups add to the same face</p>
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stereochemistry: Anti Addition

groups add to oppostite faces

<p>groups add to oppostite faces</p>
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radical addition (w/ ROOR)

  • regiochemistry: Anti-Markovnikov

  • limitations: only HBr + ROOR (peroxide)

    • radical mechanism (no carbocation)

<ul><li><p>regiochemistry: Anti-Markovnikov</p></li></ul><ul><li><p>limitations: only HBr + ROOR (peroxide)</p><ul><li><p>radical mechanism (no carbocation)</p></li></ul></li></ul><p></p>
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oxidation reactions: ozonolysis reductive workup

  • converts alkene → aldehydes/ketones

  • reagents: 1. O3 2. DMS or Zn, HOAc

<ul><li><p>converts alkene → aldehydes/ketones</p></li></ul><ul><li><p>reagents: 1. O<sub>3</sub> 2. DMS or Zn, HOAc</p></li></ul><p></p>
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oxidation reactions: ozonolysis oxidative workup

  • converts alkene → carboxylic acids/ketones

  • reagents 1. O3 2. H2O2 or 1. KMnO4 2. H3O+

<ul><li><p>converts alkene → carboxylic acids/ketones</p></li><li><p>reagents 1. O<sub>3</sub> 2. H<sub>2</sub>O<sub>2</sub> or 1. KMnO<sub>4</sub> 2. H<sub>3</sub>O<sup>+</sup></p></li></ul><p></p>
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syn dihydroxylation (OH-OH)

  • stereochemistry: (OH) Syn addition

  • reagents: 1. cold KMnO4 2. NaOH or 1. OsO4 2. H2O2 or NaHSO3

<ul><li><p>stereochemistry: (OH) Syn addition</p></li><li><p>reagents: 1. cold KMnO<sub>4</sub> 2. NaOH or 1. OsO<sub>4</sub> 2. H<sub>2</sub>O<sub>2 </sub>or NaHSO<sub>3</sub></p></li></ul><p></p>
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Anti Dihydroxylation (OH-OH)

  • stereochemistry: Anti addition

  • reagents: 1. RCO3H 2. H3O

  • steps:

    • forms epoxide with mCPBA

    • reacts with H3O+ or NaOH

<ul><li><p>stereochemistry: Anti addition</p></li><li><p>reagents: 1. RCO<sub>3</sub>H 2. H<sub>3</sub>O</p></li><li><p>steps:</p><ul><li><p>forms epoxide with mCPBA </p></li><li><p>reacts with H<sub>3</sub>O<sup>+</sup> or NaOH</p></li></ul></li></ul><p></p>
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expoxidation

forms epoxide (3-membered ring with O)

  • both enantiomers formed

if chiral center created

reagent: RCO3H (ex: mCPBA)

<p>forms epoxide (3-membered ring with O)</p><ul><li><p>both enantiomers formed</p></li></ul><p>if chiral center created</p><p>reagent: RCO<sub>3</sub>H (ex: mCPBA)</p><p></p>
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acid-catalyzed hydration

  • regiochemistry: Markovnikov

  • intermediate: carbocation, rearrangements possible

  • reagents: H3O+ / H2SO4 + H2O

<ul><li><p>regiochemistry: Markovnikov</p></li><li><p>intermediate: carbocation, rearrangements possible</p></li><li><p>reagents: H<sub>3</sub>O<sup>+</sup> / H<sub>2</sub>SO<sub>4</sub> + H<sub>2</sub>O</p></li></ul><p></p>
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oxymercuration-demercuration

  • regiochemistry: Markovinikov

    • no rearrangements

  • steroselectivity: 2 or 4 stereoisomers possible

  • reagents: 1. Hg(OAc)2, H2O, THF 2. NaBH4

Markovnikov addition of a single OH group that is anti to the H atom added with no rearrangements

<ul><li><p>regiochemistry: Markovinikov</p><ul><li><p>no rearrangements</p></li></ul></li><li><p>steroselectivity: 2 or 4 stereoisomers possible</p></li><li><p>reagents: 1. Hg(OAc)<sub>2</sub>, H<sub>2</sub>O, THF 2. NaBH<sub>4</sub></p></li></ul><p><span>Markovnikov addition of a single OH group that is anti to the H atom added with no rearrangements</span></p>
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hydroboration-oxidation

  • regiochemistry: Anti-Markovnikov

    • no rearrangements

  • stereochemistry: Syn addition

  • reagents: 1. BH3, THF; 2. H2O2, NaOH

<ul><li><p>regiochemistry: Anti-Markovnikov</p><ul><li><p>no rearrangements</p></li></ul></li><li><p>stereochemistry: Syn addition</p></li><li><p>reagents: 1. BH<sub>3</sub>, THF; 2. H<sub>2</sub>O<sub>2</sub>, NaOH</p></li></ul><p></p>
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dihalogenation (X-X)

  • sterochemistry: Anti addition

  • reagents: Br2 or Cl2 in CCl4

<ul><li><p>sterochemistry: Anti addition</p></li><li><p>reagents: Br<sub>2</sub> or Cl<sub>2</sub> in CCl<sub>4</sub></p></li></ul><p></p>
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halohydrin formation (X-OH)

  • stereochemistry: Anti addition

  • regiochemistry: OH adds to more substituted C (Mark.)

  • reagents: Br2 or Cl2 in H2O

<ul><li><p>stereochemistry: Anti addition</p></li><li><p>regiochemistry: OH adds to more substituted C (Mark.)</p></li><li><p>reagents: Br<sub>2</sub> or Cl<sub>2</sub> in H<sub>2</sub>O</p></li></ul><p></p>
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catalytic hydrogenation (H-H)

  • sterochemistry: Syn addition

    • converts alkene → alkane

    • both enantiomers form if chiral center is present

  • reagents: H2 + metal catalyst (Pd, Pd/C, Pt)

<ul><li><p>sterochemistry: Syn addition</p><ul><li><p>converts alkene → alkane</p></li><li><p>both enantiomers form if chiral center is present</p></li></ul></li><li><p>reagents: H<sub>2</sub> + metal catalyst (Pd, Pd/C, Pt)</p></li></ul><p></p>
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hydrohalogenation (H-X)

  • regiochemistry: Markovnikov

  • intermediate: Carbocation, rearrangements possible

  • stereoselectivity: None, racemic if chiral center forms

  • reagents: HX (HCl, HBr, HI)

  • add H to the alkene C that produces the most stable carbocation (least substitutions)

<ul><li><p>regiochemistry: Markovnikov</p></li><li><p>intermediate: Carbocation, rearrangements possible</p></li><li><p>stereoselectivity: None, racemic if chiral center forms</p></li><li><p>reagents: HX (HCl, HBr, HI)</p></li><li><p>add H to the alkene C that produces the most stable carbocation (least substitutions) </p></li></ul><p></p>
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Reacting an alkene with HOT _______ will result in oxidative cleavage (oxidizing conditions). The conditions at which KMnO4 is reacted with alkenes are very important for the type of reaction it will perform. 

KMnO4