1 2008 Lecture 21 Aromatic Compounds Part III [Compatibility Mode]

1 2008 Lecture 21 Aromatic Compounds Part III [Compatibility Mode]

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Chem 2203/2207 Tuesday Nov. 25 – Aromatic compounds Part III Thursday Nov. 27 - Review lecture on final exam ssignments on Dienes and Aromatics have been Assignments on Dienes and Aromatics posted on http://http-server.carleton.ca/~pbuist/ • 1995 final exam with answers as well as the 2007 final exam without answers is posted on http://http- server.carleton.ca/~pbuist/ Tutorial This Friday at 12:30 – 3:30 UC 282
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Aromatic Compounds •Benzene –the prototypical aromatic compound •Introduction to the concept of Aromaticity •Chemistry of Benzene •Reactions of MonoSubstituted Aromatics. •Synthesis of Drugs, Dyes and Antioxidants
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Reactions of Monosubstituted Aromatics with Electrophile (E + ) Subs’t E Subs’t “ortho” “meta” “para” E E Subs’t Subs’t
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Reactions of Monosubstitued Aromatics Three classes of substituents: 1) Activating; ortho , para directing 2) Deactivating; meta directing 3) Deactivating; ortho , para directing
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1. Activating, ortho- , para- directing substituents CH 3 OH NH 2 H : .. : • Activation through donation of electron density into ring through a pi resonance effect (lone pair, pi electrons) or hyperconjugation (C-H sigma bonds). Increasing Rate of reaction
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Mechanism of Activation to Electrophilic Attack • Electron rich substituent stabilizes positively charged intermediate and thus speeds up rate determining first step. NH 2 E+ NH 2 E H NH 2 E : slow : + fast : -H + Carbocation – stabilized by substituent
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How does the amino substituent stabilize the carbocation derived from electrophilic attack? NH
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1 2008 Lecture 21 Aromatic Compounds Part III [Compatibility Mode]

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