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Compounds Containing Nitrogen question

2021 · 25 Jul · Shift 2 · Q6
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  5. /2021 · 25 Jul · Shift 2 · Q6

Compounds Containing Nitrogen question

2021 · 25 Jul · Shift 2 · Q6

JEE MainChemistryCompounds Containing NitrogenMCQ+4 / −1
A reaction of benzonitrile with one equivalent CH3MgBrCH_3MgBrCH3​MgBr followed by hydrolysis produces a yellow liquid "P". The compound "P" will give positive ‾\underline{\hspace{2cm}}​.
  1. A
    Iodoform test
  2. B
    Schiff's test
  3. C
    Ninhydrin's test
  4. D
    Tollen's test
View written solutionFree

Correct answer: A

  1. Identify the reaction of nitrile with Grignard reagent

A nitrile reacts with one equivalent of Grignard reagent to give an imine magnesium salt, which on hydrolysis gives a ketone.

For benzonitrile: C6H5CN+CH3MgBr→C6H5C(=N ⁣MgBr)CH3C_6H_5CN + CH_3MgBr \rightarrow C_6H_5C(=N\!MgBr)CH_3C6​H5​CN+CH3​MgBr→C6​H5​C(=NMgBr)CH3​ On hydrolysis: C6H5C(=N ⁣MgBr)CH3→H3O+C6H5COCH3C_6H_5C(=N\!MgBr)CH_3 \xrightarrow{H_3O^+} C_6H_5COCH_3C6​H5​C(=NMgBr)CH3​H3​O+​C6​H5​COCH3​

So the product PPP is: P=C6H5COCH3P = C_6H_5COCH_3P=C6​H5​COCH3​ This is acetophenone (methyl phenyl ketone), a yellow liquid.


  1. Test the product against the given options

(A) Iodoform test

Iodoform test is given by compounds containing the group: −COCH3-COCH_3−COCH3​ Acetophenone has the structure: C6H5−CO−CH3C_6H_5-CO-CH_3C6​H5​−CO−CH3​ So it contains a methyl ketone group and gives positive iodoform test.

(B) Schiff's test

Schiff's reagent gives positive test mainly with aldehydes. Acetophenone is a ketone, so this is negative.

(C) Ninhydrin's test

Ninhydrin test is given by amino acids / primary amines in special cases, not by acetophenone. So negative.

(D) Tollen's test

Tollen's reagent is reduced by aldehydes (and a few special compounds like formic acid, alpha-hydroxy ketones). Acetophenone does not give this test. So negative.


  1. Conclusion

The product PPP is acetophenone, which gives a positive iodoform test.

Therefore, the correct option is: A: Iodoform test\boxed{A\text{: Iodoform test}}A: Iodoform test​


  1. Comparison with stored correct answer

Stored correct answer: A

My derived answer: A

They agree.

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