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Identify Major Product P in Multistep Organic Reaction Sequence

Complete the following reaction sequence and give the name of major product 'PP'.

Question Diagram 1

Options

A

2-Chloropropanoic acid

Correct
B

3-Chloropropanoic acid

C

1-Chloropropane

D

2-Chloropropane

Step-by-Step Solution

To determine the major product PP in the given reaction sequence, we can break down the process into individual chemical steps:

Step 1 & 2: Hydrolysis of Propanenitrile

The starting material is propanenitrile (CH3CH2CN\text{CH}_3\text{CH}_2\text{C}\equiv\text{N}).

  • (i) Reaction with OH/H2O\text{OH}^-/\text{H}_2\text{O} and heat (Δ\Delta) causes alkaline hydrolysis of the nitrile group (CN-\text{C}\equiv\text{N}) to form propanoate ion (CH3CH2COO\text{CH}_3\text{CH}_2\text{COO}^-).
  • (ii) Acidification with H3O+\text{H}_3\text{O}^+ protonates the carboxylate ion to yield propanoic acid (CH3CH2COOH\text{CH}_3\text{CH}_2\text{COOH}).

CH3CH2CNΔ(i) OH/H2OCH3CH2COO(ii) H3O+CH3CH2COOH\text{CH}_3\text{CH}_2\text{C}\equiv\text{N} \xrightarrow[\Delta]{(i)\ \text{OH}^-/\text{H}_2\text{O}} \text{CH}_3\text{CH}_2\text{COO}^- \xrightarrow{(ii)\ \text{H}_3\text{O}^+} \text{CH}_3\text{CH}_2\text{COOH}


Step 3 & 4: Hell-Volhard-Zelinsky (HVZ) Reaction

  • (iii) & (iv) Propanoic acid (CH3CH2COOH\text{CH}_3\text{CH}_2\text{COOH}) is reacted with Cl2\text{Cl}_2 in the presence of red phosphorus (Red P\text{Red P}), followed by treatment with H2O\text{H}_2\text{O}.
  • This is the Hell-Volhard-Zelinsky (HVZ) reaction, which selectively substitutes an α\alpha-hydrogen atom of carboxylic acids with a halogen atom (Cl\text{Cl}).

CH3CH2COOH(iii) Cl2/Red PCH3CH(Cl)COCl(iv) H2OCH3CH(Cl)COOH\text{CH}_3\text{CH}_2\text{COOH} \xrightarrow{(iii)\ \text{Cl}_2/\text{Red P}} \text{CH}_3\text{CH(Cl)}\text{COCl} \xrightarrow{(iv)\ \text{H}_2\text{O}} \text{CH}_3\text{CH(Cl)}\text{COOH}

The final major product PP is 2-Chloropropanoic acid.


Conclusion:

The correct IUPAC name of the major product PP is 2-Chloropropanoic acid, which corresponds to Option A.

Identify Major Product P in Multistep Organic Reaction Sequence | Chemistry PYQ Solution - JEE Challenger