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Basics of Organic Chemistry question

2017 · 8 Apr · Shift 1 · Q8
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Basics of Organic Chemistry question

2017 · 8 Apr · Shift 1 · Q8

JEE MainChemistryBasics of Organic ChemistryMCQ+4 / −1
A mixture containing the following four compounds is extracted with 1MHCl.1MHCl.1MHCl. The compound that goes to aqueous layer is : JEE Main 2017 (Online) 8th April Morning Slot Chemistry - Basics of Organic Chemistry Question 219 English
  1. A
    (I)
  2. B
    (II)
  3. C
    (III)
  4. D
    (IV)
View written solutionFree

Correct answer: B

  1. Principle of extraction with 1 M HCl1\text{ M HCl}1 M HCl

    Dilute hydrochloric acid extracts basic compounds into the aqueous layer by converting them into their water-soluble hydrochloride salts.

    So, among the given compounds, we must identify the one that behaves as a base and gets protonated by HCl\text{HCl}HCl.

  2. Which type of compound goes into aqueous layer?

    • Amines are basic due to the lone pair on nitrogen.
    • On treatment with HCl\text{HCl}HCl: RNH2+HCl→RNH3+Cl−RNH_2 + HCl \rightarrow RNH_3^+Cl^-RNH2​+HCl→RNH3+​Cl−
    • The resulting ammonium salt is ionic and dissolves in water, so it moves to the aqueous layer.
  3. Examine the four compounds

    From the given set, compound (II) is the one containing the basic amine functionality capable of forming a salt with HCl\text{HCl}HCl.

    The other compounds do not form stable water-soluble salts under these conditions and therefore remain in the organic layer.

  4. Conclusion

    Therefore, the compound that goes to the aqueous layer on extraction with 1 M HCl1\text{ M HCl}1 M HCl is: (II)\boxed{\text{(II)}}(II)​

  5. Comparison with stored answer

    Stored correct answer = B

    Our derived answer = B

    Hence, they agree.

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