Portmess Homework Q&S 100

Portmess Homework Q&S 100 - 94 STRUCTURE AND...

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( b , c ) Both 1-propanol and 2-propanol give propene on acid-catalyzed dehydration. ( d ) Carbon-3 has no hydrogens in 2,3,3-trimethyl-2-butanol. Elimination can involve only the hydroxyl group at C-2 and a hydrogen at C-1. 5.13 ( b ) Elimination can involve loss of a hydrogen from the methyl group or from C-2 of the ring in 1-methylcyclohexanol. According to the Zaitsev rule, the major alkene is the one corresponding to loss of a hydrogen from the alkyl group that has the smaller number of hydrogens. Thus hydrogen is removed from the methylene group in the ring rather than from the methyl group, and 1-methylcyclo- hexene is formed in greater amounts than methylenecyclohexane. ( c ) The two alkenes formed are as shown in the equation. The more highly substituted alkene is formed in greater amounts, as predicted by Zaitsev s rule. 5.14 2-Pentanol can undergo dehydration in two different directions, giving either 1-pentene or
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This note was uploaded on 09/20/2011 for the course CHM 2210 taught by Professor Reynolds during the Spring '01 term at University of Florida.

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