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Practical Organic Chemistry question

2019 · 9 Jan · Shift 2 · Q3
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Practical Organic Chemistry question

2019 · 9 Jan · Shift 2 · Q3

JEE MainChemistryPractical Organic ChemistryMCQ+4 / −1
The tests performed on compound X and their inferences are :

Test Inference
(a) 2, 4 - DNP test Coloured precipitate
(b) Idoform test Yellow precipitate
(c) Azo-dye test No dye formation

Compound 'X' is :
  1. A
    JEE Main 2019 (Online) 9th January Evening Slot Chemistry - Practical Organic Chemistry Question 81 English Option 1
  2. B
    JEE Main 2019 (Online) 9th January Evening Slot Chemistry - Practical Organic Chemistry Question 81 English Option 2
  3. C
    JEE Main 2019 (Online) 9th January Evening Slot Chemistry - Practical Organic Chemistry Question 81 English Option 3
  4. D
    JEE Main 2019 (Online) 9th January Evening Slot Chemistry - Practical Organic Chemistry Question 81 English Option 4
View written solutionFree

Correct answer: B

  1. Interpret each test result

    We are given:

    • 2,4-DNP test: coloured precipitate
    • Iodoform test: yellow precipitate
    • Azo-dye test: no dye formation
  2. Inference from 2,4-DNP test

    The 2,42,42,4-dinitrophenylhydrazine test is given by aldehydes and ketones.

    So, compound XXX must contain a carbonyl group (>C=O)\left(>C=O\right)(>C=O) of an aldehyde or ketone.

  3. Inference from iodoform test

    A positive iodoform test is given by compounds containing either:

    • the methyl ketone group, \ceCH3CO−\ce{CH3CO-}\ceCH3CO−, or
    • alcohols of type \ceCH3CH(OH)−\ce{CH3CH(OH)-}\ceCH3CH(OH)−, which get oxidized to methyl ketones.

    But from step 2, since XXX already gives 2,4-DNP, it must itself be a carbonyl compound, not just an alcohol.

    Therefore, XXX should be a methyl ketone: \ceR−CO−CH3\ce{R-CO-CH3}\ceR−CO−CH3

  4. Inference from azo-dye test

    The azo-dye test is given by phenols (and certain aromatic amines after diazotization/coupling).

    Since there is no dye formation, XXX is not a phenol.

  5. Combine all observations

    So XXX must be:

    • a ketone,
    • specifically a methyl ketone,
    • and not a phenol.

    Hence the correct option must be the one corresponding to a simple methyl ketone such as acetone / methyl ketone, which is given as Option B.

  6. Conclusion

    Therefore, compound XXX is Option B.

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