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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