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In the following compounds, the decreasi...

In the following compounds, the decreasing order of basic strength will be :

A

`C_(2)H_(5)NH_(2)gtNH_(3)gt(C_(2)H_(5))_(2)NH`

B

`(C_(2)H_(5))_(2)NHgtNH_(3)gtC_(2)H_(5)NH_(2)`

C

`(C_(2)H_(5))_(2)NHgtC_(2)H_(5)NH_(2)gtNH_(3)`

D

`NH_(3)gtC_(2)H_(5)NH_(2)gt(C_(2)H_(5))_(2)NH`

Text Solution

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The correct Answer is:
To determine the decreasing order of basic strength among the given compounds (a primary amine, a secondary amine, and ammonia), we will analyze the basicity of these compounds in both the gas phase and aqueous solution. ### Step-by-Step Solution: 1. **Identify the Compounds**: - Primary amine: C2H5NH2 (ethylamine) - Secondary amine: C2H5NH (diethylamine) - Ammonia: NH3 2. **Understand Basicity**: Basicity refers to the ability of a compound to accept protons (H+ ions). The more readily a compound can donate its lone pair of electrons to bond with a proton, the stronger the base it is. 3. **Analyze Basicity in Gas Phase**: - In the gas phase, the basic strength is influenced primarily by the +I (inductive) effect of alkyl groups. Alkyl groups are electron-donating, which increases the electron density on the nitrogen atom, making it more basic. - **Order in Gas Phase**: - Tertiary amines > Secondary amines > Primary amines > Ammonia - For our specific case: - Diethylamine (C2H5)2NH has the most +I effect due to two ethyl groups. - Ethylamine (C2H5)NH2 has one ethyl group. - Ammonia (NH3) has no alkyl groups. 4. **Analyze Basicity in Aqueous Solution**: - In aqueous solution, other factors come into play, such as steric hindrance and hydration energy. - Steric hindrance can inhibit the approach of protons to the nitrogen atom, thus affecting basicity. - Hydration energy is the energy released when a solute is dissolved in water; more hydration generally means a stronger base. - **Order in Aqueous Solution**: - Primary amines are more basic than secondary amines due to less steric hindrance and greater hydration. - Ammonia is less basic than both primary and secondary amines. 5. **Final Order of Basic Strength**: - Considering both phases, the order of basic strength from strongest to weakest is: - Diethylamine (C2H5)2NH > Ethylamine (C2H5)NH2 > Ammonia (NH3) ### Conclusion: The decreasing order of basic strength is: **(C2H5)2NH > C2H5NH2 > NH3**
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