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Description and Tags

Biology

Anatomy

Alkyne

Reactions

Reagents

University/Undergrad

9 Terms

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S_N2 Formation

increase by 2 carbons

Reagent: NaC≡C-H / DMSO

<ul><li><p>increase by 2 carbons</p></li></ul><p>Reagent: <mark data-color="yellow" style="background-color: yellow; color: inherit">NaC</mark><span><mark data-color="yellow" style="background-color: yellow; color: inherit">≡C-H / DMSO</mark></span></p>

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Dihalide elimination

no increase in carbons

Reagents: Xs NaNH₂ / H₂O

<ul><li><p>no increase in carbons</p></li></ul><p>Reagents: <mark data-color="yellow" style="background-color: yellow; color: inherit">Xs NaNH<sub>2</sub> / H<sub>2</sub>O</mark></p>

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Halogenation/Hydrohalegenation

2 equivalents mean add 2 halogens (BREAK TRIPLE bond)
1 equivalent means add 1 halogen (KEEP DOUBLE bond)

Reagents: 2-HCL / (2 eq) or 1 (eq)

<ul><li><p>2 equivalents mean add 2 halogens (BREAK TRIPLE bond)</p></li><li><p>1 equivalent means add 1 halogen (KEEP DOUBLE bond)</p></li></ul><p>Reagents: <mark data-color="yellow" style="background-color: yellow; color: inherit">2-HCL / (2 eq)</mark> or <mark data-color="yellow" style="background-color: yellow; color: inherit">1 (eq)</mark></p>

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Oxymercuration/acid

TERMINAL triple bond: form a methyl ketone
INTERNAL triple bond: form a mixture

Reagent: HgSO₄ / H₂SO₄, H₂O

<ul><li><p><span style="color: red">TERMINAL</span> triple bond: form a methyl ketone</p></li><li><p><span style="color: red">INTERNAL</span> triple bond: form a mixture</p></li></ul><p>Reagent: <mark data-color="yellow" style="background-color: yellow; color: inherit">HgSO<sub>4</sub> / H<sub>2</sub>SO<sub>4</sub>, H<sub>2</sub>O</mark></p>

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Ozonalysis

INTERNAL triple bond: form carboxylic acids
TERMINAL triple bond: form carboxylic acid and CO₂

Reagent: O₃ / H₂O

<ul><li><p>INTERNAL triple bond: form carboxylic acids</p></li><li><p>TERMINAL triple bond: form carboxylic acid and CO<sub>2</sub></p></li></ul><p>Reagent: O<sub>3</sub> / H<sub>2</sub>O</p>

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Hydroboration

TERMINAL
forms an aldehyde (O=C-H)

Reagents: 9-BBN / H₂O₂, NaOH

<ul><li><p>TERMINAL</p></li><li><p>forms an aldehyde (O=C-H)</p></li></ul><p>Reagents: <mark data-color="yellow" style="background-color: yellow; color: inherit">9-BBN / H<sub>2</sub>O<sub>2</sub>, NaOH</mark></p>

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Alkylation

Terminal to internal
adding a methyl group

Reagent: NaNH2 / MeBr

<ul><li><p>Terminal to internal</p></li><li><p>adding a methyl group</p></li></ul><p>Reagent: <mark data-color="yellow" style="background-color: yellow; color: inherit">NaNH2 / MeBr</mark></p>

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Halogenation

form a cis alkene when reagent is: leg Br₂
add amount of halogens specified example of reagent: 2Cl₂ / CCl₄

<ul><li><p>form a <span style="color: red">cis alkene</span> when reagent is: <mark data-color="yellow" style="background-color: yellow; color: inherit">leg Br<sub>2</sub></mark></p></li><li><p>add amount of halogens specified example of reagent: <mark data-color="yellow" style="background-color: yellow; color: inherit">2Cl<sub>2</sub> / CCl<sub>4</sub></mark></p></li></ul><p></p>

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Hydrogenation

form CIS when reagent is: H₂ / Lindlar’s catalyst

form ALKANE when reagent is: H₂ / pt

form TRANS ALKENE when reagent is: Na or Li / NH₃

<p>form <span style="color: red">CIS</span> when reagent is: <mark data-color="yellow" style="background-color: yellow; color: inherit">H<sub>2</sub> / Lindlar’s catalyst</mark></p><p>form <span style="color: red">ALKANE</span> when reagent is: <mark data-color="yellow" style="background-color: yellow; color: inherit">H<sub>2</sub> / pt</mark></p><p>form <span style="color: red">TRANS ALKENE</span> when reagent is: <mark data-color="yellow" style="background-color: yellow; color: inherit">Na or Li / NH<sub>3</sub></mark></p>