Textbook Question
Predict the product for the acid-catalyzed pinacol rearrangement of the following diols.
(a)
21. Aldehydes and Ketones: Nucleophilic Addition
Ketone and Aldehyde Synthesis Reactions
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Provide the major product for the following reaction dealing with the Grignard reagent.
A
B
C
D
Verified step by step guidance1
Identify the Grignard reagent in the reaction, which is CH₃CH₂MgBr. Grignard reagents are organomagnesium compounds that act as nucleophiles.
Recognize the functional group in the substrate molecule. The substrate contains a nitrile group (C≡N), which is a carbon-nitrogen triple bond.
Understand that Grignard reagents react with nitriles to form ketones. The nucleophilic carbon of the Grignard reagent attacks the electrophilic carbon in the nitrile group.
The reaction proceeds with the addition of the Grignard reagent to the nitrile, forming an intermediate imine. This intermediate is then hydrolyzed in the presence of H₃O⁺ to yield a ketone.
Consider the structure of the final product. The ethyl group from the Grignard reagent will be attached to the carbon originally part of the nitrile group, resulting in a ketone with an additional ethyl group.
Related Practice
Ketone and Aldehyde Synthesis Reactions practice set
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