Question

Draw the structure of the organic product(s) of the Grignard reaction between dimethyl carbonate (CH3OCO2CH3) and excess phenylmagnesium bromide, followed by aqueous workup. You do not have to consider stereochemistry. If a compound is formed more than once, add another sketcher and draw it again. Alternatively, you may use the square brackets tool to add stoichiometries greater than one. Draw one structure per sketcher. Add additional sketchers using the dropdown menu in the bottom right corner. Separate multiple products using the + sign from the dropdown menu.

Answer 1

dimethoxy(phenyl)methanol

Step-by-step explanation:

For this question, we have to remember the mechanism of the Grignard reaction. In this case, phenylmagnesium bromide is our nucleophile, a carbo-anion is produced (step 1). Then this carbo-anion can attack the carbonyl group in the dimethyl carbonate, the double bond is delocalized into the oxygen producing a negative charge (step 2). Finally, with the addition of the hydronium ion (
`H_3O^+`), the anion can be protonated to produce the alcohol (dimethoxy(phenyl)methanol) (step 3).

See figure 1

I hope it helps!