Practicing Success

Target Exam

CUET

Subject

Chemistry

Chapter

Organic: Aldehydes, Ketones and Carboxylic Acids

Question:

Which of these statements is false regarding the following reaction?

Options:

The reactant can be synthesized in a reaction between an alcohol and an acid chloride  

The product can react with SOCl2 to form 1-chloropropane 

The C-O bond in the product is longer than the C-O bond of the carbonyl in the reactant. 

The reactant has lower pKa than the product

Correct Answer:

The reactant can be synthesized in a reaction between an alcohol and an acid chloride  

Explanation:

The reaction is a reduction from a carboxylic acid to an alcohol. The carboxylic acid has a conjugate base that is stabilized by resonance . Therefore, carboxylic acids readily donate their H+ and thus have a lower pKa than alcohols.

 The bond length in a single bond is longer than the bond length in a double bond. The carbon-oxygen bond in the alcohol is therefore longer than the carbon-oxygen bond of the carbonyl in the carboxylic acid reactant. 

SOCl2  can convert alcohols to alkyl chlorides through a nucleophilic chloride atom. However, a reaction between an alcohol and an acid chloride does not produce a carboxylic acid, instead it produces an ester.