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Basics of Organic Chemistry question

2019 · 8 Apr · Shift 1 · Q8
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Basics of Organic Chemistry question

2019 · 8 Apr · Shift 1 · Q8

JEE MainChemistryBasics of Organic ChemistryMCQ+4 / −1
In the following compounds, the decreasing order of basic strength will be :
  1. A
    (C2H5)2NH(C_2H_5)_2NH(C2​H5​)2​NH > NH3NH_3NH3​ > C2H5NH2C_2H_5NH_2C2​H5​NH2​
  2. B
    NH3NH_3NH3​ > C2H5NH2C_2H_5NH_2C2​H5​NH2​ > (C2H5)2NH(C_2H_5)_2NH(C2​H5​)2​NH
  3. C
    ((C2H5)2NH(C_2H_5)_2NH(C2​H5​)2​NH > C2H5NH2C_2H_5NH_2C2​H5​NH2​ > NH3NH_3NH3​)
  4. D
    C2H5NH2C_2H_5NH_2C2​H5​NH2​ > NH3NH_3NH3​ > (C2H5)2NH(C_2H_5)_2NH(C2​H5​)2​NH
View written solutionFree

Correct answer: C

  1. Identify the compounds

We need the decreasing order of basic strength among:

  • NH3NH_3NH3​ (ammonia)
  • C2H5NH2C_2H_5NH_2C2​H5​NH2​ (ethylamine, a primary amine)
  • (C2H5)2NH(C_2H_5)_2NH(C2​H5​)2​NH (diethylamine, a secondary amine)
  1. Recall the factor affecting basic strength

A base is stronger if the lone pair on nitrogen is more easily available for donation.

Alkyl groups like C2H5−C_2H_5-C2​H5​− show a +I+I+I effect (electron-donating inductive effect), which increases electron density on nitrogen and makes the amine more basic than ammonia.

So, compared to NH3NH_3NH3​:

  • C2H5NH2C_2H_5NH_2C2​H5​NH2​ is more basic than NH3NH_3NH3​
  • (C2H5)2NH(C_2H_5)_2NH(C2​H5​)2​NH is generally more basic than C2H5NH2C_2H_5NH_2C2​H5​NH2​ in aqueous medium among these choices
  1. Compare the three compounds
  • NH3NH_3NH3​ has no alkyl group, so least electron donation.
  • C2H5NH2C_2H_5NH_2C2​H5​NH2​ has one ethyl group, so nitrogen gets more electron density.
  • (C2H5)2NH(C_2H_5)_2NH(C2​H5​)2​NH has two ethyl groups, so even greater +I+I+I effect, making the lone pair most available.

Hence,

(C2H5)2NH>C2H5NH2>NH3(C_2H_5)_2NH > C_2H_5NH_2 > NH_3(C2​H5​)2​NH>C2​H5​NH2​>NH3​
  1. Match with the options

Option C states:

(C2H5)2NH>C2H5NH2>NH3(C_2H_5)_2NH > C_2H_5NH_2 > NH_3(C2​H5​)2​NH>C2​H5​NH2​>NH3​

which matches our result.

  1. Final answer

The decreasing order of basic strength is:

(C2H5)2NH>C2H5NH2>NH3(C_2H_5)_2NH > C_2H_5NH_2 > NH_3(C2​H5​)2​NH>C2​H5​NH2​>NH3​

So, the correct option is C.

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