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    Benzene Rxns

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    This document summarizes important reactions of benzene including electrophilic aromatic substitution reactions and reductions. It notes that sulfonation can be used to block the para position on benzene rings with electron donating groups, forcing subsequent additions to the ortho position. Activators have a lone pair on the attached atom while deactivators do not. Halogens withdraw electron density through induction despite having a lone pair. Rings with activating OH and NH2 groups may require protection to prevent polysubstitution. The mnemonic mD opA poX remembers the directing effects in substitution reactions.

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    Benzene Rxns

    Uploaded by

    api-465421809
    443 views1 page
    This document summarizes important reactions of benzene including electrophilic aromatic substitution reactions and reductions. It notes that sulfonation can be used to block the para position on benzene rings with electron donating groups, forcing subsequent additions to the ortho position. Activators have a lone pair on the attached atom while deactivators do not. Halogens withdraw electron density through induction despite having a lone pair. Rings with activating OH and NH2 groups may require protection to prevent polysubstitution. The mnemonic mD opA poX remembers the directing effects in substitution reactions.

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    This document summarizes important reactions of benzene including electrophilic aromatic substitution reactions and reductions. It notes that sulfonation can be used to block the para position on benzene rings with electron donating groups, forcing subsequent additions to the ortho position. Activators have a lone pair on the attached atom while deactivators do not. Halogens withdraw electron density through induction despite having a lone pair. Rings with activating OH and NH2 groups may require protection to prevent polysubstitution. The mnemonic mD opA poX remembers the directing effects in substitution reactions.

    Copyright:

    © All Rights Reserved
    Download as PDF, TXT or read online from Scribd
    Download as pdf or txt
    443 views1 page

    Benzene Rxns

    Uploaded by

    api-465421809
    This document summarizes important reactions of benzene including electrophilic aromatic substitution reactions and reductions. It notes that sulfonation can be used to block the para position on benzene rings with electron donating groups, forcing subsequent additions to the ortho position. Activators have a lone pair on the attached atom while deactivators do not. Halogens withdraw electron density through induction despite having a lone pair. Rings with activating OH and NH2 groups may require protection to prevent polysubstitution. The mnemonic mD opA poX remembers the directing effects in substitution reactions.

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    Chemistry Specialist: Alicia Hart

    BENZENE RXNS UC Davis - SASC


    Br

    Br2
    FeBr3
    Cl Ex's: Sn, HCl or H2, raney Ni or Fe, HCl or Zn(Hg), HCl,
    Cl2
    AlCl3
    O
    NO2 NH2 O O or O
    HNO3 red. agent HN R
    R O R R Cl
    H2SO4
    pyridine
    mCPBA
    NaOH, H2O,
    (aka RCO3H)
    or
    1. H3O+,
    2. NaOH, H2O

    SO3H

    SO3 H+, H2O,


    H2SO4
    or
    H2SO4,
    CH2R
    RCH2X Clemmensen
    Issues?..polyalkylation and rearrangement Reduction
    lewis acid catalyst

    O R R
    O or O O
    1. R Cl Zn(Hg), HCl
    R O R , AlCl 3
    2. H3O+
    Jones
    Important things to note about benzene reactions: (p.750 and 22-2 in 6 ed.)

    SO3, H2SO4 is used to block the para position of a ring w/ an EDG on it (only a small percentage of the product adds SO3H
    ortho) forcing the next group to add exclusively ortho; remove the blocking group using acid and heat.

    Activators (EDG's through resonance) have a lone pair on the atom directly attached to benzene (exception: alkyl groups do
    not have a lone pair but are EDGs via induction)

    Deactivators (EWG's through resonance) do NOT have a lone pair on the atom directly attached to benzene (exception:
    halogens have a lone pair but withdraw via induction)
    no lone pair but alkyl lone pair but halogens
    EX's grps are the exception Cl are the exception O OH
    OCH3
    lone pair on the O no lone pair
    on the C

    Activator Activator Deactivator Deactivator


    (EDG) (EDG) (EWG) (EWG)

    Watch out for benzene rings with OH and NH2 grps on them; they are highly activated and need to be toned down prior to
    adding another grp on the ring. If you do not convert them into less activating groups, you will get polysubstitution at both
    ortho and para positions. To do this, use either an anhydride or acyl chloride: EX O
    OH O
    Cl O
    Directing Effects - mD opA poX is a helpful mnemonic to remember that
    pyridine
    Deactivators direct meta, Activators direct ortho and para, and halogens (X)
    direct ortho and para even though they are weakly deactivating.

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