A student added an equivalent of 3,4-epoxy-4-methylcyclohexanol to a solution of methylmagnesium bromide in diethyl ether, and then added dilute hydrochloric acid. He expected that the product would be 1,2-dimethyl-1,4-cyclohexanediol. He did not get any of the expected product. What product did he get?
Using the given starting material, any necessary inorganic reagents and catalysts, and any carbon-containing compounds with no more than two carbons, indicate how each of the following compounds can be prepared:
c. 
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Concetti chiave
Organometallic Reagents
Nucleophilic Addition Reactions
Stereochemistry
What are the products of the following reactions?
d.
Using the given starting material, any necessary inorganic reagents and catalysts, and any carbon-containing compounds with no more than two carbons, indicate how each of the following compounds can be prepared:
b.
Using the given starting material, any necessary inorganic reagents and catalysts, and any carbon-containing compounds with no more than two carbons, indicate how each of the following compounds can be prepared:
a.
Dimerization is a side reaction that occurs during the preparation of a Grignard reagent. Propose a mechanism that accounts for the formation of the dimer.
Using the given starting material, any necessary inorganic reagents, and any carbon-containing compounds with no more than two carbons, indicate how each of the following compounds can be prepared:
b.
