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NEET CHEMISTRYAldehydes, Ketones and Carboxylic AcidsMedium

Question

Propanoic acid with Br2/PBr_2/P yields a dibromo product. Its structure would be:

A

CH₂Br−CHBr−COOH

B

Option 2 (Image Missing)

C

CH₂Br−CH₂−COBr

D

CH₃−CBr₂−COOH

Step-by-Step Solution

The reaction of carboxylic acids having α\alpha-hydrogens with chlorine or bromine in the presence of small amount of red phosphorus is known as the Hell-Volhard-Zelinsky (HVZ) reaction.

  1. Specificity: This reaction results in the substitution of α\alpha-hydrogens (hydrogens attached to the carbon adjacent to the COOH-COOH group) by halogen atoms.
  2. Reactant: Propanoic acid is CH3CH2COOHCH_3-CH_2-COOH. The α\alpha-carbon is the CH2-CH_2- group, which contains two α\alpha-hydrogens.
  3. Product: If the reaction yields a 'dibromo' product, both α\alpha-hydrogens are replaced by bromine atoms.

CH3CH2COOHBr2/PCH3C(Br)2COOHCH_3-CH_2-COOH \xrightarrow{Br_2/P} CH_3-C(Br)_2-COOH

The product is 2,2-Dibromopropanoic acid (CH3CBr2COOHCH_3-CBr_2-COOH). Option 1 represents α,β\alpha,\beta-substitution which is incorrect for HVZ.

Exam Context & Concepts Covered

This question aligns with the NEET CHEMISTRY syllabus, specifically targeting concepts from Aldehydes, Ketones and Carboxylic Acids. Mastering this topic is crucial for scoring well in the upcoming medical entrance examinations. Solving conceptually related problems will help you understand the nuances of these concepts and improve your problem-solving speed.

CHEMISTRYAldehydes, Ketones and Carboxylic Acidspropanoicyieldsdibromoproductstructure

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