Benzene Substitution Reactions

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Last updated 2:44 PM on 9/17/26
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18 Terms

1
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<p>Reagents? Mechanism? </p>

Reagents? Mechanism?

Form electron:

(O-H) O grabs proton from H2SO4

HSO4- & H2NO3

-O donates electrons to N, kicking H2O off

O=N+=O and H2O

<p>Form electron:</p><p> (O-H) O grabs proton from H2SO4 </p><p> HSO4- &amp; H2NO3 </p><p> -O donates electrons to N, kicking H2O off </p><p>O=N+=O and H2O </p>
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<p>Friedel-Crafts Alkylation</p>

Friedel-Crafts Alkylation

NO REACTION IF:

  • mod/ strong EWG on ring

  • NH2 on ring

NO CH3 / primary Carbocation ONLY 2ary


<p>NO REACTION IF: </p><ul><li><p>mod/ strong EWG on ring </p></li><li><p>NH2 on ring </p></li></ul><p>NO CH3 / primary Carbocation ONLY 2ary </p><p></p>
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<p>Friedel-Crafts Acylation </p>

Friedel-Crafts Acylation

NO REACTION IF :

  • NH2 present on ring

  • mod/ strong EWG on ring


<p>NO REACTION IF : </p><ul><li><p>NH2 present on ring </p></li><li><p>mod/ strong EWG on ring </p></li></ul><p></p>
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Gilman Reagent

inside the () can be C, H, and OR

<p>Gilman Reagent </p><p>inside the () can be C, H, and OR </p>
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Clemmensen Reduction

Completely Removes =O

<p>Clemmensen Reduction </p><p>Completely Removes =O </p>
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Any carbon directly attached to the benzene ring with at least one hydrogen will be oxidized all the way to –COOH


  • Side chains without benzylic hydrogens DONT oxidize


<p>Any carbon directly attached to the benzene ring with at least <strong>one hydrogen</strong> will be oxidized all the way to <strong>–COOH</strong></p><p></p><ul><li><p>Side chains without benzylic hydrogens <strong>DONT oxidize</strong></p></li></ul><p></p>
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aka: Hot NaOH and H3O+

<p>aka: Hot NaOH and H3O+ </p>
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15
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16
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PCC

OH → =O

<p>OH → =O</p>
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NBS / hv

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sulfonation mechanism

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