13.4k views
3 votes
Draw the structure of the organic product(s) of the Grignard reaction between methyl benzoate 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 drop-down menu in the bottom right corner. Separate multiple products using the sign from the drop-down menu.

User Falstaff
by
4.4k points

1 Answer

1 vote

Answer:

See explanation and image attached

Step-by-step explanation:

The product of the Grignard reaction between methyl benzoate and excess phenylmagnesium bromide is triphenyl methanol.

The reaction proceeds by nucleophillic reaction as the carbonyl moiety is attacked. A tetrahedral intermediate is formed. Loss of the -OMe group is accompanied by the attack of the first molecule of PhMgBr.

Attack by a second PhMgBr molecule yields trimethyl phenoxide. Protonation of this specie yields the final product which is obtained by aqueous workup.

Draw the structure of the organic product(s) of the Grignard reaction between methyl-example-1
User Fredmaggiowski
by
4.1k points