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Which of the following is more acidic: CH3COOH or CH3CH2COOH ? Explain on the basis of inductive effect.

Which of the following is more acidic: CH3COOH or CH3CH2COOH ? Explain on the basis of inductive effect.

Grade:11

1 Answers

Arun
25757 Points
4 years ago
CH3OOH is more acidic.  

Acidity is the tendency of a compound to lose a proton. When a carboxylic acid loses a proton, it leaves a negatively charged carboxylate group (COO-). The negative charge is spread over the entire group. The tendency of a carboxylic acid to lose the proton and form the carboxylate group depends on how stable the carboxylate group is.  

Now, alkyl groups are electron donating groups, meaning they push electron density onto the atoms they are adjacent to. The larger the alkyl group, the more electron donating it is. So CH3CH2- is more electron donating than CH3-. 

Having an electron donating group next to a carboxylate group destabilises it. A carboxylate group is already negatively charged, so it's not happy taking on more electron density from these electron donating alkyl groups. The larger CH3CH2- group on CH3CH2COOH will destabilise the carboxylate group more than the simple CH3- group. Thus CH3CH2COOH is less willing to lose a proton and therefrore is less acidic.

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