lecture notes 15_bruice

lecture notes 15_bruice - !-conjugation A Look to the...

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Chapter 15 Reactions of Substituted Benzenes • Nomenclature • Substituent Effects on the Reactivity • Effect on Orientation • o/p-Ratio • pK a values • Di- and Trisubstituted Benzenes • Name Reactions
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Nomenclature
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Nomenclature If substituents are different list in alphabetic order
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Nomenclature Incorporated name is given first position
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Once more
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Trivial Names
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What Do We Know from Chapter 14?
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We have to Work out the Electron Demand Rate of electrophilic substitution is different!
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Donation by Resonance
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Hyperconjugation, a Special Case
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We can also Withdraw Density by Hyperconjugation
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Electron Withdrawal by Resonance
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The Scaling
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Strong Donation vs. Weak Donation Amino > methoxy > -NHCO- > -COOR
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Strong Donation Electron density is shifted from the substituents into the ring system. --> increases the reactivity towards electrophiles
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Weaker Donation
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We also can Define Deactivation Weakly deactivating are the halogens
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Moderately Deactivating Aldehydes, ketones, esters, acids
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Strongly Deactivating Withdrawal of electron density via
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Unformatted text preview: !-conjugation A Look to the Electron Distributions How to Conduct Disubstitution? We want the different isomers! Positive Hyperconjugation Negative Hyperconjugation A Tricky Case Different Ring Activation What would Happen with Bromination This is a classical electrophilic aromatic substitution Exercise Acids of Benzene Derivatives Exercise o-, p-Direction 2 ortho-positions, 1 para-position stronger steric hindrance for ortho The Influence of Steric Hindrance More para product Bromination Benzene is already activated by -OCH 3 , no Lewis acid necessary Further Activation with Lewis Acid Deactivation, No Reaction Exercise Synthesis of disubstituted benzenes Answer Friedel-Crafts has always to be done first! 1) First example a) Friedel-Crafts of ben ! zene with acyl chloride, b) nitration 2) a) acylation, b) sulfonation 3) a) acylation, b) oxidation with NaCr 2 O 7 , c) nitration...
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lecture notes 15_bruice - !-conjugation A Look to the...

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