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Portmess Homework Q&S 85

Portmess Homework Q&S 85 - 79 ALCOHOLS AND ALKYL...

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( c ) The starting material is a tertiary alcohol and reacted readily with hydrogen chloride to form the corresponding chloride in 67% yield. ( d ) Both primary alcohol functional groups were converted to primary bromides; the yield was 88%. ( e ) This molecule is called adamantane. It has six equivalent CH 2 groups and four equivalent CH groups. Bromination is selective for tertiary hydrogens, so a hydrogen of one of the CH groups is replaced. The product shown was isolated in 76% yield. 4.33 The order of reactivity of alcohols with hydrogen halides is tertiary . secondary . primary . methyl. Reactivity of Alcohols with Hydrogen Bromide:
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