Dolbier HW Solutions 585

Dolbier HW Solutions 585 - 679 PHENOLS(d Friedel Crafts...

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( d ) Friedel Crafts acylation occurs ortho to the hydroxyl group. 24.7 ( b ) The hydroxyl group of 2-naphthol is converted to the corresponding acetate ester. ( c ) Benzoyl chloride acylates the hydroxyl group of phenol. 24.8 Epoxides are sensitive to nucleophilic ring-opening reactions. Phenoxide ion attacks the less hin- dered carbon to yield 1-phenoxy-2-propanol. 24.9 The aryl halide must be one that is reactive toward nucleophilic aromatic substitution by the addition elimination mechanism. p -Fluoronitrobenzene is far more reactive than f uorobenzene. The reaction shown yields p -nitrophenyl phenyl ether in 92% yield. 24.10 Substituted allyl aryl ethers undergo a Claisen rearrangement similar to the reaction described in text Section 24.13 for allyl phenyl ether. 2-Butenyl phenyl ether rearranges on heating to give
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