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In section 6.8, you learned that the hydroboration - oxidation of 1-methylcycloh

ID: 862645 • Letter: I

Question

In section 6.8, you learned that the hydroboration - oxidation of 1-methylcyclohexene will provide a racemic mixture of trans-2-methyl-1-cyclohexanol; the cis-diastereomer is not formed at all.

What is the major product arising from the reaction of trans-2-methyl-1-cyclohexanol with POCl3 in pyridine at 0 oC?

cis-1-chloro-2-methylcyclohexane

trans-1-chloro-2-methylcyclohexane

1-methylcyclohexene

3-methylcyclohexene

cis-1-chloro-2-methylcyclohexane

trans-1-chloro-2-methylcyclohexane

1-methylcyclohexene

3-methylcyclohexene

Explanation / Answer

POCl3 (phorphorus oxychloride) and a pyridine are mild reagents for dehydration. You will form the most stable alkene.

The answer to your question is 3-methylcyclohexene

It can also be written as 3-methylcyclohexene with the alkene understood to be at the one position.

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