CHEM261 Chapter 8 Alkene Reactions

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11 Terms

1
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Halogenation (Give intermediate + Major Product)

  • Br2, Cl2

  • Anti/Trans

<ul><li><p>Br<sub>2</sub>, Cl<sub>2</sub></p></li><li><p>Anti/Trans</p></li></ul><p></p>
2
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Halohydrin from Alkene

  • Br2 / H2O

  • Products: Br + OH

  • Anti/Trans

  • Follows Mark’s Rule

<ul><li><p>Br<sub>2</sub> / H<sub>2</sub>O</p></li><li><p>Products: Br + OH</p></li><li><p>Anti/Trans</p></li><li><p>Follows Mark’s Rule</p></li></ul><p></p>
3
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Halohydrin (NBS)

NBS / H2O DMSO

Products: Br + OH

  • OH goes to more substituted Carbon

  • Anti/Trans

<p>NBS / H<sub>2</sub>O DMSO</p><p>Products: Br + OH</p><ul><li><p>OH goes to more substituted Carbon</p></li><li><p>Anti/Trans</p></li></ul><p></p>
4
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Hydration

H2O/H2PO4 / 250oC

Creating an Alcohol by addiing OH to more substituted Carbon

<p>H<sub>2</sub>O/H<sub>2</sub>PO<sub>4</sub>&nbsp;/ 250<sup>o</sup>C</p><p>Creating an Alcohol by addiing OH to more substituted Carbon</p><p></p>
5
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Hydroboration

BH3/THF / H2O2

Products: H + OH

Syn/Cis

AntiMark’s Rule

<p>BH<sub>3</sub>/THF / H<sub>2</sub>O<sub>2</sub>  </p><p>Products: H + OH</p><p>Syn/Cis</p><p>AntiMark’s Rule</p>
6
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Hydrogenation

H2/ Pd/C in ethanol

Products H + H

Syn/CIs

Remove double bond

<p>H<sub>2</sub>/ Pd/C in ethanol</p><p>Products H + H</p><p>Syn/CIs</p><p>Remove double bond</p>
7
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Expoxidation

X2 / H2

Step 1: Halohydrin Formation

Products: OH + X

Anti/Trans

Step 2 Epoxide

Base/ NaOH

Product: O

Syn/Cis

<p>X<sub>2</sub>&nbsp;/ H<sub>2</sub>O&nbsp;</p><p>Step 1: Halohydrin Formation</p><p>Products: OH + X</p><p>Anti/Trans</p><p></p><p>Step 2 Epoxide</p><p>Base/ NaOH</p><p>Product: O</p><p>Syn/Cis</p>
8
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Epoxidization (Peroxy Acids)

RCO3H

Product: O

Syn/Cys

<p>RCO<sub>3</sub>H </p><p>Product: O</p><p>Syn/Cys</p>
9
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Hydroxylation of Epoxides

H3O+/H2O

Products: OH+ OH

Anti/Trans

<p>H<sub>3</sub>O<sup>+</sup>/H<sub>2</sub>O </p><p>Products: OH+ OH</p><p>Anti/Trans</p>
10
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Ozonolysis

O3, -78oC / Either Zn, Acetic Acid

Everywhere a double bond is/ make it an O

<p>O<sub>3</sub>, -78<sup>o</sup>C / Either Zn, Acetic Acid</p><p>Everywhere a double bond is/ make it an O</p>
11
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Oxidization

KMnO3 / H3O+

Similar to ozonylsis, but OH is added to the central carbon to create carboxylic acid

<p>KMnO<sub>3</sub> / H<sub>3</sub>O<sup>+</sup></p><p>Similar to ozonylsis, but OH is added to the central carbon to create carboxylic acid</p>

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