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Haloalkanes and Haloarenes question

2021 · 17 Mar · Shift 1 · Q14
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Haloalkanes and Haloarenes question

2021 · 17 Mar · Shift 1 · Q14

JEE MainChemistryHaloalkanes and HaloarenesMCQ+4 / −1
Which of the following reaction is an example of ammonolysis?
  1. A
    C6H5COClC_6H_5COClC6​H5​COCl + C6H5NH2C_6H_5NH_2C6​H5​NH2​ →\to→ C6H5CONHC6H5C_6H_5CONHC_6H_5C6​H5​CONHC6​H5​
  2. B
    C6H5CH2CNC_6H_5CH_2CNC6​H5​CH2​CN →[H]\xrightarrow{[H]}[H]​ C6H5CH2CH2NH2C_6H_5CH_2CH_2NH_2C6​H5​CH2​CH2​NH2​
  3. C
    C6H5CH2CNC_6H_5CH_2CNC6​H5​CH2​CN →HCl\xrightarrow{HCl}HCl​ C6H5C_6H_5C6​H5​ N+\mathop N\limits^ +N+​ H3Cl −-−
  4. D
    C6H5CH2ClC_6H_5CH_2ClC6​H5​CH2​Cl + NH3NH_3NH3​ →\to→ C6H5CH2NH2C_6H_5CH_2NH_2C6​H5​CH2​NH2​
View written solutionFree

Correct answer: D

  1. Meaning of ammonolysis

    Ammonolysis is a reaction in which a compound reacts with ammonia (NH3)\left(NH_3\right)(NH3​) and a group is replaced by an amino group.

    In organic chemistry, a common example is: R−X+NH3→R−NH2R-X + NH_3 \rightarrow R-NH_2R−X+NH3​→R−NH2​ where XXX is a leaving group such as halogen.

  2. Check each option

    Option A: C6H5COCl+C6H5NH2→C6H5CONHC6H5C_6H_5COCl + C_6H_5NH_2 \rightarrow C_6H_5CONHC_6H_5C6​H5​COCl+C6​H5​NH2​→C6​H5​CONHC6​H5​ This is reaction of an acid chloride with aniline to form an amide. It is amidation/acylation, not ammonolysis.

    Option B: C6H5CH2CN→[H]C6H5CH2CH2NH2C_6H_5CH_2CN \xrightarrow{[H]} C_6H_5CH_2CH_2NH_2C6​H5​CH2​CN[H]​C6​H5​CH2​CH2​NH2​ This is reduction of nitrile to a primary amine. It is not ammonolysis.

    Option C: C6H5CH2CN→HClC6H5N+H3Cl−C_6H_5CH_2CN \xrightarrow{HCl} C_6H_5\overset{+}{N}H_3Cl^-C6​H5​CH2​CNHCl​C6​H5​N+H3​Cl− This corresponds to formation of an amine salt under acidic conditions, not reaction with ammonia replacing a leaving group. So this is not ammonolysis.

    Option D: C6H5CH2Cl+NH3→C6H5CH2NH2C_6H_5CH_2Cl + NH_3 \rightarrow C_6H_5CH_2NH_2C6​H5​CH2​Cl+NH3​→C6​H5​CH2​NH2​ Here benzyl chloride reacts with ammonia, and ClClCl is replaced by NH2NH_2NH2​. This is the standard example of ammonolysis.

  3. Conclusion

    The correct option is: D\boxed{D}D​

  4. Comparison with stored answer

    Stored correct answer: DDD

    My derived answer is also DDD, so they agree.

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