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Practical Organic Chemistry question

2019 · 8 Apr · Shift 1 · Q1
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Practical Organic Chemistry question

2019 · 8 Apr · Shift 1 · Q1

JEE MainChemistryPractical Organic ChemistryMCQ+4 / −1
An organic compound neither reacts with neutral ferric chloride solution nor with fehling solution. it however, reacts with Grignard reagent and gives positive iodoform test. The compound is :
  1. A
    JEE Main 2019 (Online) 8th April Morning Slot Chemistry - Practical Organic Chemistry Question 78 English Option 1
  2. B
    JEE Main 2019 (Online) 8th April Morning Slot Chemistry - Practical Organic Chemistry Question 78 English Option 2
  3. C
    JEE Main 2019 (Online) 8th April Morning Slot Chemistry - Practical Organic Chemistry Question 78 English Option 3
  4. D
    JEE Main 2019 (Online) 8th April Morning Slot Chemistry - Practical Organic Chemistry Question 78 English Option 4
View written solutionFree

Correct answer: D

  1. Interpret each test given in the question

    We need a compound that:

    • does not react with neutral ferric chloride
    • does not react with Fehling solution
    • does react with Grignard reagent
    • gives positive iodoform test
  2. Neutral ferric chloride test

    Neutral FeCl3\text{FeCl}_3FeCl3​ gives a colored complex with phenols (and some enols).

    Since the compound does not react with neutral ferric chloride, it is not a phenol.

  3. Fehling solution test

    Fehling solution is reduced by aliphatic aldehydes.

    Since the compound does not react with Fehling solution, it is not an aliphatic aldehyde.

  4. Reaction with Grignard reagent

    Grignard reagents react with compounds having a polar carbonyl group such as:

    • aldehydes
    • ketones
    • esters, etc.

    So the compound likely contains a carbonyl group.

  5. Positive iodoform test

    Iodoform test is given by compounds containing either:

    • a methyl ketone group, RCOCH3\mathrm{RCOCH_3}RCOCH3​, or
    • a secondary alcohol of type CH3CH(OH)R\mathrm{CH_3CH(OH)R}CH3​CH(OH)R, or
    • ethanol / ethanal as special cases.
  6. Combine all conditions

    • Not phenol
    • Not aliphatic aldehyde
    • Must react with Grignard reagent ⇒\Rightarrow⇒ likely carbonyl compound
    • Must give iodoform test ⇒\Rightarrow⇒ likely methyl ketone

    Therefore the compound should be a methyl ketone, most simply acetone (CH3COCH3)\left(\mathrm{CH_3COCH_3}\right)(CH3​COCH3​) or generally any RCOCH3\mathrm{RCOCH_3}RCOCH3​.

  7. Check consistency

    • Ferric chloride: no reaction ✓\checkmark✓
    • Fehling solution: ketones do not reduce Fehling solution ✓\checkmark✓
    • Grignard reagent: ketones react with Grignard reagents ✓\checkmark✓
    • Iodoform test: methyl ketones give positive test ✓\checkmark✓
  8. Conclusion

    The correct compound is the methyl ketone option, which corresponds to Option D as per the stored answer.

Since the actual option texts are missing, the identifiable class is methyl ketone (e.g. acetone), and this matches the stored answer if option D is that compound.

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