Predict the product of the following reactions.
(a)

A chemist failed to generate the alcohol using the reaction shown here.

(a) Suggest a reason why this reaction did not work as written.

In lieu of quenching the product of Grignard addition to a carbonyl with acid, alkyl halides can be added directly to generate ether products. Predict the product and show the mechanism of this process.

Predict the products formed when cyclohexanone reacts with the following reagents.

(f) PhMgBr and then mild H₃O⁺

Predict the products of the following reactions.

(d) product of (c) + cyclopentylmagnesium bromide, then acidic hydrolysis

You might expect that aldehydes and ketones could undergo the addition/elimination mechanism. With strong nucleophiles, however, nucleophilic addition is the only outcome. Why?

Beginning with an amide, two different pathways produce the same compound. Predict the product of these two pathways.

Which of the following solvents are reasonable choices for a Grignard reaction? Justify your choices. [Hint: Carbonyls are good electrophiles.]

A student, when solving the following 'predict-the-product' question, made a common mistake by writing the answer shown here. Explain why this reaction would not work as written.