week 4 - 2 - Week 4 July 13, 2010 Electrophilic Aromatic...

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Week 4 July 13, 2010 Electrophilic Aromatic Substitution: Direction When anisole is nitrated, the ortho and para products predominate. Why? OCH 3 HNO 3 H 2 SO 4 OCH 3 OCH 3 NO 2 NO 2 ortho para (primary product) + When acetophenone is nitrated, the meta product predominates. Why? HNO 3 H 2 SO 4 meta CH 3 O CH 3 O NO 2 Reading : Section 16.5 13
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Week 4 July 13, 2010 Electrophilic Aromatic Substitution: Activation Explain the observed trend in the rate of nitration of the following compounds: OCH 3 CH 3 O relative rate of reaction with HNO 3 / H 2 SO 4 fast normal slow In general, ortho, para -directing groups are activating , while meta -directing groups are deactivating . Why? However, halogen substituents are deactivating but are ortho, para -directors. Why? Reading : Section 16.5 14
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Week 4 July 13, 2010 Synthesis Using Electrophilic Aromatic Substitution Starting from benzene , provide a synthesis of the following compound: NO 2 OH Reading : Section 16.5 15
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Week 4 July 13, 2010 Reactivity of Vinylic Halides Draw an example of a vinylic halide. Why does that halide
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This note was uploaded on 07/21/2010 for the course CHEM S20ab taught by Professor Mccarty during the Summer '10 term at Harvard.

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week 4 - 2 - Week 4 July 13, 2010 Electrophilic Aromatic...

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