Which of the following compounds does not form an alcohol when it reacts with excess Grignard reagent?


A. CH3CH2(C=O)NHCH3


B. CH3CH2(C=O)OCH3


C. HOCH2CH2(C=O)OCH3

Verified step by step guidance

1. Identify the functional groups present in each compound.
2. Recall that Grignard reagents react with carbonyl groups to form alcohols.
3. Consider the reactivity of each functional group with Grignard reagents.
4. Analyze compound A: CH3CH2(C=O)NHCH3, which contains an amide group.
5. Understand that amides are less reactive with Grignard reagents compared to esters and ketones, and thus do not form alcohols.

Key Concepts

Grignard Reagents

Grignard reagents are organomagnesium compounds that are highly reactive and can form new carbon-carbon bonds. They are typically used to react with electrophiles, such as carbonyl compounds, to produce alcohols. Understanding how Grignard reagents interact with different functional groups is crucial for predicting the products of these reactions.

Carbonyl Compounds

Carbonyl compounds, characterized by the presence of a carbon-oxygen double bond (C=O), include aldehydes and ketones. When reacted with Grignard reagents, they can undergo nucleophilic addition, leading to the formation of alcohols. Identifying the type of carbonyl compound is essential for determining whether an alcohol will be produced.

Functional Groups and Reactivity

Different functional groups exhibit varying reactivities towards Grignard reagents. For instance, amides and esters can react differently compared to aldehydes and ketones. Recognizing the functional groups present in the compounds listed in the question helps in predicting whether they will yield alcohols upon reaction with Grignard reagents.