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Grade: 12th pass
        
A hydrocarbon A does not react with chlorine in the dark. When a mixture of A and chlorine is irradiated with ultraviolet light, two and only two monochlorinated products, B and C are obtained.  When B and C are treated separately with warm aqueous sodium hydroxide and then with potassium permanganate solution, B gives a acid D and C gives a ketone, E. Identify A, B, C, D, and E. Give your reasoning and draw their structural formulae. 
one year ago

Answers : (1)

Pooja
askIITians Faculty
478 Points
							Dear Student,
In your problem no where it stated the number of carbon atoms in the parent hydrocarbon.
On my assumption lets take the smallest hydrocabon which on irradiatin under sunlight gives two monochlorinated products.
The hydrocarbon be propane
Since the hydrocarbon does not react with Cl2 in dark means it lack unsaturation.
Propane on reaction with chlorine in the sunlight gives 1-chloropropane and 2-Chloropropane.
1- Chloropropane (B) on reaction with aq. NaOH gives 1-propanol which on further reaction with KMnO4 gives propanoic acid.
2-Chloropropane (C) on reaction with aq. NaOH gives 2-propanol which on further reaction with KMnO4 gives acetone.
one year ago
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