5. In the industrial synthesis of nylon, one of the starting materials, adipic
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Lowery-Bronsted theory is applied here. Acc. to this theory Base accepts protons and Acids donate proton.
Part 1:
Aniline is less basic than ethylamine because the lone pair on nitrogen (which accepts proton) is not localized. It resonates throughout the conjugated system of phenyl ring. Hence due to unavailability of electrons for accepting proton it is less basic compare to ethylamine. In ethyl amine the lone pair of electron is localized and available to abstract proton.
Part 2:
In this case the alkyl groups attached to -NH₂ (in ethylamine) and -O⁻ (in ethoxide are same (i.e. CH₃-CH₂-). Ethoxide is more basic than ethylamine because ethoxide is a conjugate base of ethanol (pKa value of ethanol = 15.9 very weak acid) and the conjugate base of weak acid is always a strong base. Secondly, the oxygen atom more Electronegative than Nitrogen atom can attract more electron cloud from alkyl group as compared to Nitrogen in ethylamine. Hence, oxygen in ethoxide attains greater electron cloud than the nitrogen in ethylamine. Therefore, it is more basic than ethylamine.
Part 1:
Aniline is less basic than ethylamine because the lone pair on nitrogen (which accepts proton) is not localized. It resonates throughout the conjugated system of phenyl ring. Hence due to unavailability of electrons for accepting proton it is less basic compare to ethylamine. In ethyl amine the lone pair of electron is localized and available to abstract proton.
Part 2:
In this case the alkyl groups attached to -NH₂ (in ethylamine) and -O⁻ (in ethoxide are same (i.e. CH₃-CH₂-). Ethoxide is more basic than ethylamine because ethoxide is a conjugate base of ethanol (pKa value of ethanol = 15.9 very weak acid) and the conjugate base of weak acid is always a strong base. Secondly, the oxygen atom more Electronegative than Nitrogen atom can attract more electron cloud from alkyl group as compared to Nitrogen in ethylamine. Hence, oxygen in ethoxide attains greater electron cloud than the nitrogen in ethylamine. Therefore, it is more basic than ethylamine.