OChem I Reactions

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Last updated 7:32 PM on 7/20/26
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19 Terms

1
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Sn2

occurs when: strong; small nuc/base (– charge); LG attached to 2˚ or 3˚ C; polar, aprotic solvents

sterechemistry: inversion

<p>occurs when: strong; small nuc/base (– charge); LG attached to 2˚ or 3˚ C; polar, aprotic solvents</p><p>sterechemistry: inversion</p>
2
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E2

occurs when: small or bulky strong base/nuc; LG attached to 2˚ or 3˚ C; H on adjacent C that is antiperiplanar to LG; polar, aprotic solvent; alkenes

stereochemistry: flatten

<p>occurs when: small or bulky strong base/nuc; LG attached to 2˚ or 3˚ C; H on adjacent C that is antiperiplanar to LG; polar, aprotic solvent; alkenes</p><p>stereochemistry: flatten</p>
3
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Sn1

occurs when: stable carbocation (resonance, 3˚ or 2˚ C); weak nuc/base

stereochemistry: none

<p>occurs when: stable carbocation (resonance, 3˚ or 2˚ C); weak nuc/base</p><p>stereochemistry: none</p>
4
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E1

occurs when: stable carbocation (resonance, 3˚ or 2˚ C); weak nuc/base; if base isn’t bulky, more substituted alkene forms

stereochemistry: none

<p>occurs when: stable carbocation (resonance, 3˚ or 2˚ C); weak nuc/base; if base isn’t bulky, more substituted alkene forms</p><p>stereochemistry: none</p>
5
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Hydrohalogenation

addition of H and X

occurs when: strong acid (H–X); alkene or alkyne

stereochemistry: none

regiochemistry: Markovnikov

<p>addition of H and X</p><p>occurs when: strong acid (H–X); alkene or alkyne</p><p>stereochemistry: none</p><p>regiochemistry: Markovnikov</p>
6
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Hydration

addition of H and OH

occurs when: strong acid (H3O+, H2SO4, H3PO4); alkene or alkyne

stereochemistry: none

regiochemistry: Markovnikov

<p>addition of H and OH</p><p>occurs when: strong acid (H3O+, H2SO4, H3PO4); alkene or alkyne</p><p>stereochemistry: none</p><p>regiochemistry: Markovnikov</p>
7
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Halogenation

addition of X and X

occurs when: diatomic halogen; alkene or alkyne

stereochemistry: anti-addition

<p>addition of X and X</p><p>occurs when: diatomic halogen; alkene or alkyne</p><p>stereochemistry: anti-addition</p>
8
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Halohydration

addition of X and OH/OR

occurs when: diatomic halogen; alcohol group; alkene or alkyne

stereochemistry: anti-addition

regiochemistry: “Markovnikov” (X to less substituted, OH to more substituted)

<p>addition of X and OH/OR</p><p>occurs when: diatomic halogen; alcohol group; alkene or alkyne</p><p>stereochemistry: anti-addition</p><p>regiochemistry: “Markovnikov” (X to less substituted, OH to more substituted)</p>
9
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Oxymercuration-reduction

addition of H and OH/OR

occurs when: Hg(OAc)2; NaBH4; H2O; polar solvent; alkene or alkyne

stereochemistry: anti-addition

regiochemistry: “Markovnikov” (H/Hg to less substituted, OH/OR to more substituted)

<p>addition of H and OH/OR</p><p>occurs when: Hg(OAc)2; NaBH4; H2O; polar solvent; alkene or alkyne</p><p>stereochemistry: anti-addition</p><p>regiochemistry: “Markovnikov” (H/Hg to less substituted, OH/OR to more substituted)</p>
10
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Tautomerization

rearrangement of enol to ketone

11
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Hydroboration-oxidation

addition of H and OH/OR

occurs when: BH3 or BCy2 (for alkynes); H2O2; another molecule with an alcohol group; alkene or alkyne

stereochemistry: syn addition

regiochemistry: Markovnikov addition

<p>addition of H and OH/OR</p><p>occurs when: BH3 or BCy2 (for alkynes); H2O2; another molecule with an alcohol group; alkene or alkyne</p><p>stereochemistry: syn addition</p><p>regiochemistry: Markovnikov addition</p>
12
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Hydrogenation

addition of H and H

occurs when: Pd or Pt; H2, alkene or alkyne

stereochemistry: syn addition

<p>addition of H and H</p><p>occurs when: Pd or Pt; H2, alkene or alkyne</p><p>stereochemistry: syn addition</p>
13
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Hydrogenation of alkynes w/ poisoned catalyst

addition of H and H on alkynes (cis product)

occurs when: Lindlar’s cat; H2; alkyne only

stereochemistry: syn addition

<p>addition of H and H on alkynes (cis product)</p><p>occurs when: Lindlar’s cat; H2; alkyne only</p><p>stereochemistry: syn addition</p>
14
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Dissolving metal reduction

addition of H and H on alkynes (trans product)

occurs when: Na˚ or Li˚; liquid NH3; H2

regiochemistry: anti addition

<p>addition of H and H on alkynes (trans product)</p><p>occurs when: Na˚ or Li˚; liquid NH3; H2</p><p>regiochemistry: anti addition</p>
15
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Epoxidation

addition of ether group

occurs when: mCPBA, alkene only

stereochemistry: syn addition

<p>addition of ether group</p><p>occurs when: mCPBA, alkene only</p><p>stereochemistry: syn addition</p>
16
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Dihydroxylation

addition of OH and OH

occurs when: KMnO4 or OsO4; NaOH & H2O or H2S; alkene only

stereochemistry: syn addition

<p>addition of OH and OH</p><p>occurs when: KMnO4 or OsO4; NaOH &amp; H2O or H2S; alkene only</p><p>stereochemistry: syn addition</p>
17
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Ozonolysis

division into two aldehydes and/or ketones

occurs when: O3; Zn & HOAc or DMS or PPh3; alkenes only

<p>division into two aldehydes and/or ketones</p><p>occurs when: O3; Zn &amp; HOAc or DMS or PPh3; alkenes only</p>
18
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Chain elongation

occurs when: alkyne w/ terminal H; strong base; LG on hydrocarbon

stereochemistry: inversion

<p>occurs when: alkyne w/ terminal H; strong base; LG on hydrocarbon</p><p>stereochemistry: inversion</p>
19
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Diels Alder reaction

formation of cyclohexene

occurs when: diene; dienophile w/ EWG; heat

<p>formation of cyclohexene</p><p>occurs when: diene; dienophile w/ EWG; heat</p>