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Dolbier HW Solutions 273 - 267 ARENES AND AROMATICITY(f...

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( f ) This reaction illustrates identical reactivity at two equivalent sites in a molecule. Both alcohol functions are tertiary and benzylic and undergo acid-catalyzed dehydration readily. ( g ) The compound shown is DDT (standing for the nonsystematic name dichlorodiphenyl- trichloroethane ). It undergoes -elimination to form an alkene. ( h ) Alkyl side chains on naphthalene undergo reactions analogous to those of alkyl groups on benzene. ( i ) Potassium carbonate is a weak base. Hydrolysis of the primary benzylic halide converts it to an alcohol. 11.33 Only benzylic (or allylic) hydrogens are replaced by N -bromosuccinimide. Among the four bromines in 3,4,5-tribromobenzyl bromide, three are substituents on the ring and are not capable of being introduced by benzylic bromination. The starting material must therefore have these three
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