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Multiple Choice
Which of the following functional groups is most likely to act as a nucleophile in organic reactions?
A
Carbonyl group (C=O)
B
Amide group (-CONH2)
C
Nitro group (-NO2)
D
Hydroxyl group (-OH)
Verified step by step guidance
1
Understand the concept of a nucleophile: A nucleophile is a chemical species that donates an electron pair to form a chemical bond in reaction. Nucleophiles are typically rich in electrons and have a negative charge or lone pairs of electrons.
Analyze the functional groups: Consider the electron density and availability of lone pairs in each functional group. The carbonyl group (C=O) has a polarized double bond, but the oxygen is more electronegative, making it less likely to donate electrons. The amide group (-CONH2) has resonance stabilization, reducing its nucleophilicity. The nitro group (-NO2) is electron-withdrawing, making it a poor nucleophile.
Focus on the hydroxyl group (-OH): The hydroxyl group has a lone pair of electrons on the oxygen atom, which can be readily donated in a reaction, making it a good nucleophile.
Consider the electronegativity and resonance effects: The oxygen in the hydroxyl group is less hindered and more available to participate in nucleophilic reactions compared to the other groups listed.
Conclude that the hydroxyl group (-OH) is the most likely to act as a nucleophile due to its electron-rich nature and availability of lone pairs for bonding.