JEE Main · 2025 · Shift-ImediumHALO-130

The products A and B in the following reactions, respectively are: A Ag-NO2 CH3-CH2-CH2-Br AgCN B

Haloalkanes & Haloarenes · Class 12 · JEE Main Previous Year Question

Question

The products A and B in the following reactions, respectively are:

AAg-NO2\ceCH3CH2CH2BrAgCNB\text{A} \xleftarrow{\text{Ag-NO}_2} \ce{CH3-CH2-CH2-Br} \xrightarrow{\text{AgCN}} \text{B}

Options
  1. a

    \ceCH3CH2CH2ONO\ce{CH3CH2CH2-ONO}, \ceCH3CH2CH2NC\ce{CH3CH2CH2-NC}

  2. b

    \ceCH3CH2CH2ONO\ce{CH3CH2CH2-ONO}, \ceCH3CH2CH2CN\ce{CH3CH2CH2-CN}

  3. c

    \ceCH3CH2CH2NO2\ce{CH3CH2CH2-NO2}, \ceCH3CH2CH2CN\ce{CH3CH2CH2-CN}

  4. d

    \ceCH3CH2CH2NO2\ce{CH3CH2CH2-NO2}, \ceCH3CH2CH2NC\ce{CH3CH2CH2-NC}

Correct Answerb

\ceCH3CH2CH2ONO\ce{CH3CH2CH2-ONO}, \ceCH3CH2CH2CN\ce{CH3CH2CH2-CN}

Detailed Solution

Reaction with \ceAgNO2\ce{AgNO2}:

\ceAgNO2\ce{AgNO2} is an ionic silver salt. The \ceNO2\ce{NO2^-} ion is an ambident nucleophile (can attack through N or O).

With \ceAgNO2\ce{AgNO2}: The silver coordinates with oxygen, making O the attacking end → alkyl nitrite (\ceRON=O\ce{R-O-N=O}) is the major product.

\ceCH3CH2CH2Br+AgNO2>CH3CH2CH2ONO\ce{CH3CH2CH2Br + AgNO2 -> CH3CH2CH2-ONO} (propyl nitrite) → A = \ceCH3CH2CH2ONO\ce{CH3CH2CH2-ONO}

Reaction with AgCN:

\ceAgCN\ce{AgCN} is a covalent silver compound. The \ceCN\ce{CN^-} is an ambident nucleophile (attacks through C or N).

With \ceAgCN\ce{AgCN}: Silver coordinates with N, making C the attacking end → nitrile (\ceRCN\ce{R-CN}) is the major product.

\ceCH3CH2CH2Br+AgCN>CH3CH2CH2CN\ce{CH3CH2CH2Br + AgCN -> CH3CH2CH2-CN} (butanenitrile) → B = \ceCH3CH2CH2CN\ce{CH3CH2CH2-CN}

Answer: A = \ceCH3CH2CH2ONO\ce{CH3CH2CH2-ONO}, B = \ceCH3CH2CH2CN\ce{CH3CH2CH2-CN} → Option (b)

Key Points:

  • \ceAgNO2\ce{AgNO2} (ionic) → O-attack → alkyl nitrite (\ceRONO\ce{R-ONO})
  • \ceAgCN\ce{AgCN} (covalent) → C-attack → nitrile (\ceRCN\ce{R-CN})
  • \ceNaNO2\ce{NaNO2} (ionic) → N-attack → nitroalkane (\ceRNO2\ce{R-NO2})
  • \ceKCN\ce{KCN} (ionic) → C-attack → nitrile (\ceRCN\ce{R-CN})

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