week 4 - 1 - Week 4 July 12, 2010 Benzene and its...

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Week 4 July 12, 2010 Benzene and its Derivatives Draw the structures of the following molecules: toluene m -chlorophenol nitrobenzene p -nitroaniline o -chloroanisole Reading : Section 16.1 1
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Week 4 July 12, 2010 Electron Donating and Withdrawing Groups Match the chemical shift with the highlighted protons in the compounds shown below. Explain why these trends are observed. H OR H NR 2 H R RO C H 3 R 2 N C H 3 R C H 3 Chemical Shifts (ppm): Compounds: 1.0 2.2 2.5 3.8 4.6 5.4 5.7 6.9 R C H 3 O H C R O Reading : Section 16.5 2
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Week 4 July 12, 2010 Inductive vs. Resonance Effects Complete the following table. Be sure to indicate the relative magnitude of the various effects. ( D = donating, W = withdrawing) Functional Group Inductive Effect ( ! -bonds) Resonance Effect ( -bonds) —NMe 2 —OH —CH 3 —Cl —COOEt —CN + NMe 3 —NO 2 Reading : Section 16.5 3
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July 12, 2010 Application of Substituent Effects: The Acidity of Phenols, Part 1 Explain the observed p K a
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week 4 - 1 - Week 4 July 12, 2010 Benzene and its...

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