Asked in ETEA MDCAT 2005 2005Moderate

Which one of the following is the strongest acid?

Correct answer: B. CHCl2COOH

  • A. CH2Cl-H2-COOH
  • B. CHCl2COOH
  • C. CH3 COOH
  • D. CH3- CH2-COOH

Explanation

Many concepts are required to be cleared while solving these types of MCQsFirst, we should know, those acids are the strongest which can lose hydrogen easily( specifically talking about organic acids)Oxygen in the functional group has lone pairs and has a partially negative charge, so it binds with hydrogen strongly having a partially positive charge, but when an electronegative atom ( such as halogen) will be present, this partially negative charge will be withdrawn by halogen,making oxygen less negative, so it will now not bind with hydrogen as strongly as it was, so hydrogen losing capacity will be increased making acid strongerSecondly, if that halogen is bonded to a carbon atom nearer to alpha carbon it will have more withdrawing effect on oxygen, making acid stronger, As in option A it is bound with C-2, while in option B it is bound to C-1 (nearer to alpha carbon), making acid in option B stronger, moreover in option B two Cl atoms are bonded having a more withdrawing effect, making it stronger acid.A: It is stronger than the one in option B.

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About Reactivity of Carboxylic Acids

Carboxylic acids show acidic behaviour because their carboxylate ions are resonance-stabilised, and electron-withdrawing groups can change their strength. Reactions include neutralisation, esterification, formation of acid chlorides and amides, reduction, decarboxylation and substitution at the acyl carbon, which differs from the reactions of phenols.

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