Addition, Reduction, & Oxidation Reactions

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38 Terms

1
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Mechanism I

1) Proton (H+) adds to alkene to form C+

2) Nucleophile adds to C+

  • stereoselectivity: syn + anti products

  • regioselectivity: Markovnikov (more stable C+)

<p>1) Proton (H+) adds to alkene to form C+</p><p>2) Nucleophile adds to C+ </p><ul><li><p>stereoselectivity: syn + anti products</p></li><li><p>regioselectivity: Markovnikov (more stable C+) </p></li></ul><p></p>
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Mechanism I stereoselectivity

syn + anti products

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Mechanism I regioselectivity

Markovnik (more stable C+)

4
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Mechanism II

1) Electrophile (E+) adds to form 3-membered cyclic intermediate

2) Nucleophile attacks the cyclic intermediate to open it and form the final product

  • stereoselectivity: anti

  • regioselectivity: X- adds to side that best stabilizes to partial (+)

<p>1) Electrophile (E+) adds to form 3-membered cyclic intermediate</p><p>2) Nucleophile attacks the cyclic intermediate to open it and form the final product</p><ul><li><p>stereoselectivity: anti</p></li><li><p>regioselectivity: X- adds to side that best stabilizes to partial (+)</p></li></ul><p></p>
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Mechanism II stereoselectivity

anti products

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Mechanism II stereoselectivity

X- adds to side that best stabilizes partial (+)

7
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Mechanism III

two groups that are connected to each other add simultaneously to alkene

  • stereoselectivity: syn

  • regioselectivity: matching partial (+) or (-) or based on size

<p>two groups that are connected to each other add simultaneously to alkene</p><ul><li><p>stereoselectivity: syn</p></li><li><p>regioselectivity: matching partial (+) or (-) or based on size</p></li></ul><p></p>
8
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Mechanism III stereoselectivity

syn products

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Mechanism III regioselectivity

matching partial (+) or (-) or based on size

10
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hydrohalogenation electrophile

H-X

(HCl, HBr, HI)

<p>H-X</p><p>(HCl, HBr, HI)</p>
11
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<p>hydrohalogenation intermediate + reagent in second step</p>

hydrohalogenation intermediate + reagent in second step

X-

<p>X-</p>
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<p>hydrohalogenation product(s)</p>

hydrohalogenation product(s)

  • Mechanism I

  • syn + anti

  • Markovnikov

<ul><li><p>Mechanism I</p></li><li><p>syn + anti</p></li><li><p>Markovnikov</p></li></ul><p></p>
13
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hydration electrophile

  • H2O + catalytic acid

  • ROH + catalytic acid

<ul><li><p>H2O + catalytic acid</p></li></ul><ul><li><p>ROH + catalytic acid</p></li></ul><p></p>
14
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<p>hydration intermediate + reagent in 2nd step</p>

hydration intermediate + reagent in 2nd step

  • H2O

  • ROH

<ul><li><p>H2O</p></li><li><p>ROH</p></li></ul><p></p>
15
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<p>hydration product(s)</p>

hydration product(s)

  • Mechanism I

  • syn + anti

  • Markovnikov

<ul><li><p>Mechanism I</p></li><li><p>syn + anti</p></li><li><p>Markovnikov</p></li></ul><p></p>
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halogenation electrophile

X2

(Br2, Cl2)

<p>X2</p><p>(Br2, Cl2)</p>
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<p>halogenation intermediate + reagent in 2nd step</p>

halogenation intermediate + reagent in 2nd step

X-

<p>X-</p>
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<p>halogenation product(s)</p>

halogenation product(s)

  • Mechanism

  • anti addition

<ul><li><p>Mechanism</p></li><li><p>anti addition</p></li></ul><p></p>
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halohydrin electrophile

  • X2, H2O or HOX

  • X2, ROH or ROX

<ul><li><p>X2, H2O or HOX</p></li><li><p>X2, ROH or ROX</p></li></ul><p></p>
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<p>halohydrin intermediate + reagent in 2nd step</p>

halohydrin intermediate + reagent in 2nd step

  • H2O

  • ROH

<ul><li><p>H2O </p></li><li><p>ROH</p></li></ul><p></p>
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<p>halohydrin product(s)</p>

halohydrin product(s)

  • Mechanism II

  • anti addition

  • addition of “OH”/”OR” to more substituted C

<ul><li><p>Mechanism II</p></li><li><p>anti addition</p></li><li><p>addition of “OH”/”OR” to more substituted C</p></li></ul><p></p>
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hydroboration electrophile

1) BH3 or B2H6

2) H2O2, NaOH

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<p>hydroboration intermediate + reagent in 2nd step</p>

hydroboration intermediate + reagent in 2nd step

  • H2O2

  • NaOH

<ul><li><p>H2O2</p></li><li><p>NaOH</p></li></ul><p></p>
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<p>hydroboration product(s)</p>

hydroboration product(s)

  • Mechanism III

  • syn additions

  • anti Markovnikov

<ul><li><p>Mechanism III</p></li></ul><ul><li><p>syn additions</p></li><li><p>anti Markovnikov</p></li></ul><p></p>
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dihydroxylation reagents

  • OsO4

  • KMnO4

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OsO4 (dihydroxylation) intermediate + reagents in 2nd step

  • Na2SO3

  • H2O

<ul><li><p>Na2SO3</p></li><li><p>H2O</p></li></ul><p></p>
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OsO4 (dihydroxylation) products

  • Mechanism III

  • syn addition

<ul><li><p>Mechanism III</p></li><li><p>syn addition</p></li></ul><p></p>
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KMnO4 (dihydroxylation) intermediate + reagents in 2nd step

  • NaOH

  • H2O

<ul><li><p>NaOH</p></li><li><p>H2O</p></li></ul><p></p>
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KMnO4 (dihydroxylation) products

  • Mechanism III

  • syn addition

<ul><li><p>Mechanism III</p></li><li><p>syn addition</p></li></ul><p></p>
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ozonolysis reagent

O3

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ozonolysis intermediate + reagents in 2nd step

  • reductive workup: Zn, H2O OR (H3C)2S

  • oxidative workup: H2O2

<ul><li><p>reductive workup: Zn, H2O OR (H3C)2S</p></li><li><p>oxidative workup: H2O2</p></li></ul><p></p>
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ozonolysis product(s)

reductive (top) & oxidative (bottom)

  • Mechanism III

  • no stereoselectivity

<p>reductive (top) &amp; oxidative (bottom)</p><ul><li><p>Mechanism III</p></li><li><p>no stereoselectivity</p></li></ul><p></p>
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epoxidation

  • mCPBA

  • no second step!

<ul><li><p>mCPBA</p></li><li><p>no second step!</p></li></ul><p></p>
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<p>epoxidation (mCPBA) product(s)</p>

epoxidation (mCPBA) product(s)

  • Mechanism III

  • syn addition

<ul><li><p>Mechanism III</p></li><li><p>syn addition</p></li></ul><p></p>
35
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<p>reduction reagents to create syn addition</p>

reduction reagents to create syn addition

  • H2

  • Pd, Pd/C, PtO2, or Ni

<ul><li><p>H2</p></li><li><p>Pd, Pd/C, PtO2, or Ni</p></li></ul><p></p>
36
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<p>reduction reagents to create syn addition</p>

reduction reagents to create syn addition

  • H2

  • Pd, Pd/C, PtO2, or Ni

  • Mechanism III

<ul><li><p>H2</p></li><li><p>Pd, Pd/C, PtO2, or Ni</p></li><li><p>Mechanism III</p></li></ul><p></p>
37
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<p>reduction reagents to create syn addition (with poisoned catalyst)</p>

reduction reagents to create syn addition (with poisoned catalyst)

  • H2

  • Pd-CaCO3, OR Pd-BaSO4

  • quinoline OR PbO

  • Mechanism III

<ul><li><p>H2</p></li><li><p>Pd-CaCO3, OR Pd-BaSO4</p></li><li><p>quinoline OR PbO</p></li><li><p>Mechanism III</p></li></ul><p></p>
38
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<p>reduction reagents to create anti addition </p>

reduction reagents to create anti addition

  • Na OR Li

  • in NH3

<ul><li><p>Na OR Li</p></li><li><p>in NH3</p></li></ul><p></p>