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Electrophilic Aromatic substitution (EAS) Reactions Bromination

CHEM 2211 Organic Chemistry I: Chapter 8 Summary of Reactions Know these!!!!! Slides 2-7 show the EAS reactions Slides 8-10 show the side chain reactions. Electrophilic Aromatic substitution (EAS) Reactions Bromination. Note: All species shown underneath the arrows

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Electrophilic Aromatic substitution (EAS) Reactions Bromination

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  1. CHEM 2211 Organic Chemistry I: Chapter 8 Summary of ReactionsKnow these!!!!!Slides 2-7 show the EAS reactionsSlides 8-10 show the side chain reactions

  2. Electrophilic Aromatic substitution (EAS) ReactionsBromination Note: All species shown underneath the arrows in these EAS reactions are catalytic in their activity.

  3. Electrophilic Aromatic substitution (EAS) ReactionsChlorination

  4. Electrophilic Aromatic substitution (EAS) ReactionsNitration

  5. Electrophilic Aromatic substitution (EAS) ReactionsSulfonation

  6. Electrophilic Aromatic substitution (EAS) ReactionsFriedel-Crafts Alkylation

  7. Electrophilic Aromatic substitution (EAS) ReactionsFriedel-Crafts Alkylation

  8. Reduction of aromatic nitro groups

  9. Oxidation of alkylbenzene side chains

  10. Reduction of aromatic alkyl ketones This is a useful method to place an alkyl group onto a benzene ring without the problems of rearrangement (which could be observed in F/C alkylation reactions).

  11. Other useful infomation • Make sure that you know the directing and activating/deactivating effects of • each different group in these reactions (Figure 8.15); This does not mean that • you need to memorize this whole table. • Remember that Friedel-Crafts reactions are somewhat limiting, in that they • will not work on a strongly deactivated benzene ring (Figure 8.12); this is of • high importance when developing a synthetic procedure. • Take a look at Table 8.2 for another representation of substituent effects in • EAS reactions.

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