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Why 2^@ amine is more basic than 1^@ and...

Why `2^@` amine is more basic than `1^@` and `3^@` amine ?

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Basic character of `1^(@), 2^(@) and 3^(@)` amines in aqueous solutions depend upon following two factors on the basis of electron donating effect of alkyl group :
1. On the basis of electron donating effect of alkyl group, the basic character of `1^(@), 2^(@)and3^(@)` amines should be in the order,

2. On the basis of H-bonding : Amines dissolve in water and ionise to give `OH^(-)` ions, which are responsible for their basic character in aqueous solutions. For example `1^(@)` amine dissolve in water and ionise as follows :
`underset(1^(@)"Amine")(R-oversetoverset(H)(|)underset(..)(N)-H)+H_(2)Orarr[R-underset(H)underset(|)overset(H)overset(|)NH]^(+ -)OHiffunderset("Intermadiate")([R-undersetunderset(H)(|)oversetoverset(H)(|)N-H]^(+))+OH^(-)`
The stability of the carbon so formed depends upon the extent of H-bonding. More the number of H-atoms bonded to N-atom, more is the H-bonding and hence more is the stability. A high stability of carbon means a more basic character. This make `1^(@)` amines most basic. Thus on the basis of H-bonding the basic character of amines should be in the order.
`3lt2^(@)lt1^(@)`
Combined effect of there two factors makes `2^(@)` amine more basic than `1^(@) and 3^(@)` amines.
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BETTER CHOICE PUBLICATION-AMINES -QUESTION BANK (13.3 CHEMICAL REACTIONS)
  1. Out of ammonia (NH(3)) and C(2)H(5)NH(2) which is more basic and why?

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  2. Why Methyl amine is stronger base than ammonia ?

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  3. Why 2^@ amine is more basic than 1^@ and 3^@ amine ?

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  4. Why benzylamine more basic than aniline?

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  5. The reaction of toluene with chlorine in the presence of ferric chlori...

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  6. Amino group in aniline is o, p-directing and activating in electroph...

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  7. Aniline does not undergo Friedel-Crafts reaction. Explain.

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  8. Acylation of —NH2 group in aniline reduces its reactivity in electroph...

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  9. What is Carbylamine reaction ? How is it used to distinguish primary a...

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  10. How will you convert ethylamine to ethyl alcohol?

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  11. How will you convert : Aniline into benzonitrile

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  12. How will you convert : Aniline into benzonitrile

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  13. How will you convert : Aniline into a acetanilide

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  14. Write short note on acetylation of amines.

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  15. How 1^@ amine reacts with nitrous acid ?

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  16. How 2^@ amine reacts with nitrous acid ?

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  17. How 3^(@) amine reacts with nitrous acid ?

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  18. Give one chemical test to distinguish between the following pairs of c...

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  19. Give one chemical test to distinguish between the following pairs of c...

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  20. Give one chemical test to distinguish between the following pairs of c...

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