10 Elementary Steps

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12 Terms

1
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SN2

nucleophile attacks electrophilic carbon & leaving group leaves

<p>nucleophile attacks electrophilic carbon &amp; leaving group leaves</p>
2
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Proton Transfer (P.T.)

  • e- rich species attacks H on e- poor species

  • bond between H & e- poor species breaks

<ul><li><p>e- rich species attacks H on e- poor species</p></li><li><p>bond between H &amp; e- poor species breaks</p></li></ul><p></p>
3
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Coordination step

nucleophile attacks carbocation (lewis base attacks lewis acid)

<p>nucleophile attacks carbocation (lewis base attacks lewis acid)</p>
4
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Heterolysis

exact opposite of a coordination step

<p>exact opposite of a coordination step</p>
5
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Nucleophilic addition

  • nucleophile attacks polarized, electrophilic carbon

  • pi bond breaks

<ul><li><p>nucleophile attacks polarized, electrophilic carbon</p></li><li><p>pi bond breaks</p></li></ul><p></p>
6
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Nucleophilic Elimination

  • electrons on negatively charged species in tetrahedral intermediate go back to carbon

  • leaving group leaves

<ul><li><p>electrons on negatively charged species in tetrahedral intermediate go back to carbon</p></li><li><p>leaving group leaves</p></li></ul><p></p>
7
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E2

  • hydrogen & leaving group have to be anti- pari planar to each other

  • base attacks hydrogen on beta carbon

    • bond between hydrogen & beta carbon breaks and goes to bond between beta & alpha carbon

  • leaving group leaves

<ul><li><p>hydrogen &amp; leaving group have to be anti- pari planar to each other</p></li><li><p>base attacks hydrogen on beta carbon</p><ul><li><p>bond between hydrogen &amp; beta carbon breaks and goes to bond between beta &amp; alpha carbon</p></li></ul></li><li><p>leaving group leaves</p></li></ul><p></p>
8
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Electrophile Elimination

  • base grabs hydrogen

  • hydro-carbon bond moves to create alkene

<ul><li><p>base grabs hydrogen</p></li><li><p>hydro-carbon bond moves to create alkene</p></li></ul><p></p>
9
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Electrophilic Addition

pi bond grabs H & L.G. leaves

<p>pi bond grabs H &amp; L.G. leaves</p>
10
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1,2 Hydride / 1,2 - Alkyl Shifts

  • take H attached t o B carbon & move it to create new carbocation

    • new carbocation has to be more stable

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Sn1

heterolysis then coordination (Sn2 but in two steps)

12
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E1

heterolysis then electrophile elimination (E2 but in two steps)