Alkane Reactions

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Description and Tags

Chemistry

Organic Chemistry

Alkane

Alkane reactions

reagents

University/Undergrad

10 Terms

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Hydrohalogenation

Markovnikov’s rule (most substituted)
Carbocation rearrangement

Reagents: H-Br or H-Cl

<ul><li><p>Markovnikov’s rule (most substituted)</p></li><li><p>Carbocation rearrangement</p></li></ul><p>Reagents:<mark data-color="yellow" style="background-color: yellow; color: inherit"> H-Br</mark> or <mark data-color="yellow" style="background-color: yellow; color: inherit">H-Cl</mark></p>

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Hydrohalogenation

over ROOR
Anti-Markovnikov (least substituted)

Reagents: H-Br/ROOR

<ul><li><p>over <mark data-color="yellow" style="background-color: yellow; color: inherit">ROOR</mark></p></li><li><p>Anti-Markovnikov (least substituted)</p></li></ul><p>Reagents: H-Br/<mark data-color="yellow" style="background-color: yellow; color: inherit">ROOR</mark></p>

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Acid-Catalyzed hydration

Markovnikov’s rule (most substituted)
Carbocation rearrangement possible

Reagent: H₃O+

<ul><li><p>Markovnikov’s rule (most substituted)</p></li><li><p>Carbocation rearrangement possible</p></li></ul><p>Reagent: <mark data-color="yellow" style="background-color: yellow; color: inherit">H<sub>3</sub>O+</mark></p>

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Oxymercuration-demercuration

anti-addition
Markovnikov’s rule (most substituted)

Reagent: Hg(OAc)₂,H₂O / NaBH₄ or Hg(OAc)₂, EtOH / NaBH₄

<ul><li><p>anti-addition</p></li><li><p>Markovnikov’s rule (most substituted)</p></li></ul><p>Reagent: <mark data-color="yellow" style="background-color: yellow; color: inherit">Hg(OAc)<sub>2</sub>,H<sub>2</sub>O / NaBH<sub>4</sub></mark> or <mark data-color="yellow" style="background-color: yellow; color: inherit">Hg(OAc)<sub>2</sub>, EtOH / NaBH<sub>4</sub></mark></p>

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Hydroboration

Anti-Markovnikov’s rule (least substituted)
Adds OH^-on the least substituted C
Syn addition (cis H⁺ & OH^- both on a wedge or both on a dash)

Reagent: BH₃(THF) / H₂O₂, NaOH

<ul><li><p>Anti-Markovnikov’s rule (least substituted)</p></li><li><p>Adds OH<sup>- </sup>on the least substituted C</p></li><li><p>Syn addition (cis H<sup>+</sup> & OH<sup>-</sup> both on a wedge or both on a dash)</p></li></ul><p>Reagent: <mark data-color="yellow" style="background-color: yellow; color: inherit">BH<sub>3</sub>(THF) / H<sub>2</sub>O<sub>2</sub>, NaOH</mark></p>

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Hydrogenation

adding a halogen across a double bond
Alkene to alkane
Syn addition

Reagents: H₂ / Pd/C

<ul><li><p>adding a halogen across a double bond</p></li><li><p>Alkene to alkane</p></li><li><p>Syn addition</p></li></ul><p>Reagents: <mark data-color="yellow" style="background-color: yellow; color: inherit">H<sub>2</sub> / Pd/C</mark></p>

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Halogenation

adding a halogen across a double bond
anti-addition
if over H₂O, add one OH instead of Br or halogen !!

Reagents: Br₂ or Br₂/H₂O

<ul><li><p>adding a halogen across a double bond</p></li><li><p>anti-addition</p></li><li><p>if over H<sub>2</sub>O, add one OH instead of Br or halogen !!</p></li></ul><p>Reagents: <mark data-color="yellow" style="background-color: yellow; color: inherit">Br<sub>2</sub></mark> or <mark data-color="yellow" style="background-color: yellow; color: inherit">Br<sub>2</sub>/H<sub>2</sub>O</mark></p>

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Ozonalysis

cleaves a C=C and gives us either C=O-H or C=O
draw a line between double bond (or CUT the double bond in half)
add substituents AFTER drawing products

Reagents: O₃/DMS or O₃/DMS

<ul><li><p>cleaves a C=C and gives us either C=O-H or C=O</p></li><li><p>draw a line between double bond (or CUT the double bond in half)</p></li><li><p>add substituents AFTER drawing products</p></li></ul><p>Reagents: <mark data-color="yellow" style="background-color: yellow; color: inherit">O<sub>3</sub>/DMS</mark> or <mark data-color="yellow" style="background-color: yellow; color: inherit">O<sub>3</sub>/DMS</mark></p>

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Anti hydroxylation

adding 2OH^-groups across a double bond
epoxide intermediate
Trans product
One OH is on a wedge and one is on a dash

Reagent: RCO₃H / H₃O⁺

<ul><li><p>adding 2OH<sup>- </sup>groups across a double bond</p></li><li><p>epoxide intermediate</p></li><li><p>Trans product</p></li><li><p>One OH is on a wedge and one is on a dash</p></li></ul><p>Reagent: <mark data-color="yellow" style="background-color: yellow; color: inherit">RCO<sub>3</sub>H / H<sub>3</sub>O<sup>+</sup></mark></p>

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Syn dihydroxylation

adding 2OH^-groups across a double bond
cis product

Reagent: OSO₄ / NaHSO₃, H₂O or KMnO₄, NaOH / cold

<ul><li><p>adding 2OH<sup>- </sup>groups across a double bond</p></li><li><p>cis product</p></li></ul><p>Reagent: <mark data-color="yellow" style="background-color: yellow; color: inherit">OSO<sub>4</sub> / NaHSO<sub>3</sub>, H<sub>2</sub>O </mark>or <mark data-color="yellow" style="background-color: yellow; color: inherit">KMnO<sub>4</sub>, NaOH / cold</mark></p>