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Propose mechanisms for the following reactions. (a) (a) H2SO4 heat cyclopentanol

Chapter 7, Problem PROBLEM 7-34

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QUESTION:

Propose mechanisms for the following reactions. (a) (a) H2SO4 heat cyclopentanol cyclopentene OH (b) (b) H2SO4 OH pentan-2-ol pent-1-ene pent-2-ene (cis + trans) heat + (c) (c) H2SO4 heat 2-methylcyclohexanol OH CH3 1-methylcyclohexene CH3 3-methylcyclohexene CH3 methylenecyclohexane CH2 + + (d) (d) H2SO4/H2O heat OH (an interesting minor product)

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QUESTION:

Propose mechanisms for the following reactions. (a) (a) H2SO4 heat cyclopentanol cyclopentene OH (b) (b) H2SO4 OH pentan-2-ol pent-1-ene pent-2-ene (cis + trans) heat + (c) (c) H2SO4 heat 2-methylcyclohexanol OH CH3 1-methylcyclohexene CH3 3-methylcyclohexene CH3 methylenecyclohexane CH2 + + (d) (d) H2SO4/H2O heat OH (an interesting minor product)

ANSWER:

Step 1 of 4

(a)

The dehydration of cyclopentanol can be carried out through sulfuric acid at a high temperature. Sulfuric acid removes water from cyclopentanol. The product formed will be cycloalkene.

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