Alkyne Reaction and Free Radical Halogenation Reactions

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18 Terms

1

Catalytic Hydrogenation (Catalytic Reduction)

What’s added: 4 H atoms

Stereoselectivity: Anti

Rearrangement: Not possible

Note: You may see Pt used as well. This is just the catalyst and does not change the outcome of the products.

<p>What’s added: 4 H atoms</p><p> Stereoselectivity: Anti </p><p>Rearrangement: Not possible </p><p>Note: You may see Pt used as well. This is just the catalyst and does not change the outcome of the products.</p>
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2

Reduction to Cis-Alkene

What’s added: 2 H atoms

Stereoselectivity: Syn

Rearrangement: Not possible

<p>What’s added: 2 H atoms </p><p>Stereoselectivity: Syn </p><p>Rearrangement: Not possible</p>
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3

Reduction to Trans-Alkene

What’s added: 2 H atoms

Stereoselectivity: Anti

Rearrangement: Not possible

<p>What’s added: 2 H atoms </p><p>Stereoselectivity: Anti </p><p>Rearrangement: Not possible</p>
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4

Hydrohalogenation with HBr (Terminal Alkyne)

What’s added: 1 H atom and 1 halogen atom (can be F, Br, I, or Cl) per equivalent of HX

Regioselectivity: Markovnikov

Intermediate: Carbocation

Rearrangement: Not possible

<p>What’s added: 1 H atom and 1 halogen atom (can be F, Br, I, or Cl) per equivalent of HX </p><p>Regioselectivity: Markovnikov </p><p>Intermediate: Carbocation </p><p>Rearrangement: Not possible</p>
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5

Hydrohalogenation with HBr (Internal Alkyne)

What’s added: 1 H atom and 1 halogen atom (can be Cl or Br) per equivalent of HX

Regioselectivity: Markovnikov

Intermediate: Carbocation

Rearrangement: Not possible

<p>What’s added: 1 H atom and 1 halogen atom (can be Cl or Br) per equivalent of HX </p><p>Regioselectivity: Markovnikov </p><p>Intermediate: Carbocation </p><p>Rearrangement: Not possible</p>
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6

Halogenation with Br2

What’s added: 2 halogen atoms (can be F, Br, I, or Cl) per equivalent of X2

Stereoselectivity: Anti

Intermediate: Bromonium ion

Rearrangement: Not possible

<p>What’s added: 2 halogen atoms (can be F, Br, I, or Cl) per equivalent of X2 </p><p>Stereoselectivity: Anti </p><p>Intermediate: Bromonium ion </p><p>Rearrangement: Not possible</p>
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7

Hydration of an Internal Alkyne

What’s added: 1 O atom

Rearrangement: Not possible

Do know that this reaction produces enols, which then tautomerize to form ketones.

<p>What’s added: 1 O atom </p><p>Rearrangement: Not possible </p><p>Do know that this reaction produces enols, which then tautomerize to form ketones.</p>
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8

Hydration of a Terminal Alkyne (Markovnikov)

What’s added: 1 O atom

Regioselectivity: Markovnikov

Rearrangement: Not possible

<p>What’s added: 1 O atom </p><p>Regioselectivity: Markovnikov </p><p>Rearrangement: Not possible</p>
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9

Hydration of a Terminal Alkyne (Anti-Markovnikov)

What’s added: 1 O atom

Regioselectivity: Anti-Markovnikov

Rearrangement: Not possible

<p>What’s added: 1 O atom </p><p>Regioselectivity: Anti-Markovnikov </p><p>Rearrangement: Not possible</p>
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10

SN2 Addition of an Acetylide Ion to an Alkyl Halide

What’s added: additional C atoms (-R of alkyl halide)

Intermediate: Acetylide Ion

Rearrangement: Not possible

<p>What’s added: additional C atoms (-R of alkyl halide) </p><p>Intermediate: Acetylide Ion </p><p>Rearrangement: Not possible</p>
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11

SN2 Addition of an Acetylide Ion to a Ketone

What’s added: 1 alkyl group

Intermediate: Acetylide Ion

Rearrangement: Not possible

<p>What’s added: 1 alkyl group </p><p>Intermediate: Acetylide Ion </p><p>Rearrangement: Not possible</p>
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12

SN2 Addition of an Acetylide Ion to an Epoxide

What’s added: 2-hydroxylpropane (from epoxide)

Intermediate: Acetylide Ion

Rearrangement: Not possible

<p>What’s added: 2-hydroxylpropane (from epoxide) </p><p>Intermediate: Acetylide Ion </p><p>Rearrangement: Not possible</p>
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13

Ozonolysis/Oxidative Cleavage on an Internal Alkyne

What’s added: 4 O atoms and 2 H atoms

Know that the reaction cuts the triple bond in half. An O replaces two of the bonds as C=O and the third lone bond becomes a bond to -OH.

<p>What’s added: 4 O atoms and 2 H atoms </p><p>Know that the reaction cuts the triple bond in half. An O replaces two of the bonds as C=O and the third lone bond becomes a bond to -OH.</p>
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14

Ozonolysis/Oxidative Cleavage on a Terminal Alkyne

What’s added: 4 O atoms and 1 H atom

Know that the reaction cuts the triple bond in half. On the internal side, an O replaces two of the bonds as C=O and the third lone bond becomes a bond to -OH. On the terminal side, two oxygens O replace all the bonds on carbon, forming the most oxidized form of carbon: CO2.

<p>What’s added: 4 O atoms and 1 H atom </p><p>Know that the reaction cuts the triple bond in half. On the internal side, an O replaces two of the bonds as C=O and the third lone bond becomes a bond to -OH. On the terminal side, two oxygens O replace all the bonds on carbon, forming the most oxidized form of carbon: CO2.</p>
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15

Alkyne Formation from Double Elimination of a Vicinal Dihalide

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16

Free Radical Halogenation using Bromine (more selective)

What’s added: 1 Br atom

Regioselectivity: Most Substituted Product

Intermediate: Radical Intermediate

Rearrangement: Not possible

<p>What’s added: 1 Br atom </p><p>Regioselectivity: Most Substituted Product </p><p>Intermediate: Radical Intermediate </p><p>Rearrangement: Not possible</p>
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17

Free Radical Halogenation using Chlorine (less selective)

What’s added: 1 Cl atom

Intermediate: Radical Intermediate

Rearrangement: Not possible

<p>What’s added: 1 Cl atom </p><p>Intermediate: Radical Intermediate </p><p>Rearrangement: Not possible</p>
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18

Allylic/Benzylic Bromination

What’s added: 1 Br atom

Intermediate: Allylic Radical Intermediate

Rearrangement: Not possible

Note: this reaction results in the formation of allylic radical intermediates which resonate and thus allow for the formation of multiple products.

<p>What’s added: 1 Br atom </p><p>Intermediate: Allylic Radical Intermediate </p><p>Rearrangement: Not possible </p><p>Note: this reaction results in the formation of allylic radical intermediates which resonate and thus allow for the formation of multiple products.</p>
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