Which of the following substituents will increase the acidity of a substituted benzoic acid (relative to the acidity of benzoic acid)?Select answer from the options belowNitroHydroxyl MethylMethoxy
Question
Which of the following substituents will increase the acidity of a substituted benzoic acid (relative to the acidity of benzoic acid)?Select answer from the options belowNitroHydroxyl MethylMethoxy
Solution
The acidity of a substituted benzoic acid is increased by electron-withdrawing groups, which stabilize the negative charge on the carboxylate ion formed after deprotonation.
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Nitro (-NO2) group: This is a strong electron-withdrawing group. It pulls electron density away from the benzene ring and stabilizes the negative charge on the carboxylate ion. Therefore, it increases the acidity of the benzoic acid.
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Hydroxyl (-OH) group: This group can donate a hydrogen bond to the carboxylate ion, stabilizing it and thus increasing the acidity of the benzoic acid.
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Methyl (-CH3) group: This is an electron-donating group. It pushes electron density towards the benzene ring and destabilizes the negative charge on the carboxylate ion. Therefore, it decreases the acidity of the benzoic acid.
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Methoxy (-OCH3) group: This is also an electron-donating group. It destabilizes the negative charge on the carboxylate ion and thus decreases the acidity of the benzoic acid.
So, the substituents that will increase the acidity of a substituted benzoic acid are the Nitro and Hydroxyl groups.
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