Q.What is the major product obtained when two moles of ethylmagnesium bromide are treated with methyl benzoate, followed by acid hydrolysis?

Step 1. Methyl benzoate, C6H5-COOCH3, reacting with the FIRST equivalent of C2H5MgBr displaces methoxide to give propiophenone (C6H5-CO-C2H5) as an intermediate ketone.

Step 2. The SECOND equivalent of ethylmagnesium bromide then adds to this ketone's carbonyl carbon, giving a magnesium alkoxide bearing the phenyl group, one original ethyl group (from the ketone) and the newly added ethyl group (from the second Grignard equivalent).

Step 3. Acid hydrolysis liberates the corresponding TERTIARY alcohol: the carbinol carbon carries a phenyl group and TWO identical ethyl groups. …

Work through the ester-to-ketone-to-tertiary-alcohol sequence for two equivalents of Grignard, then name the resulti …

• Stopping after only one equivalent of Grignard has added (which would just be the intermediate ketone, not the final major product when two moles are explicitly used). …