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Basicity Of Organic Compounds

Mediumchemistry

Comparing ammonia with methylamine in the gas-free conceptual sense of electron availability, why is methylamine the stronger base of the two?

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About This Question

Subject
chemistry
Chapter
some basic principles of organic chemistry
Topic
basicity of organic compounds
Difficulty
Medium
Year
2025
Tags
amine basicityplus I effectlone pair availabilityelectron donationalkyl substituent

Solution

Correct Answer:

The methyl group donates electron density to nitrogen by the +I effect

Basicity of an amine reflects how readily the lone pair on nitrogen is donated to a proton, which increases when the electron density on nitrogen is raised. In methylamine, the attached methyl group is electron-releasing and exerts a +I effect, pushing electron density toward nitrogen and making its lone pair more available for protonation than in ammonia, where nitrogen bears only hydrogens. Hence methylamine is the stronger base. The option claiming the methyl group withdraws electron density is wrong because alkyl groups are electron-donating, not withdrawing. The claim that methylamine has no lone pair is false; nitrogen retains its characteristic lone pair, which is the very source of basicity. The statement that nitrogen is sp hybridised is incorrect, since amine nitrogen is sp^3 with a lone pair in an sp^3 orbital. This explanation matches the NCERT discussion of the inductive effect on basicity in the gas phase and in dilute conditions where only electronic donation is considered. In aqueous solution the picture is complicated by solvation of the protonated cation, which is why the experimental order of amine basicity in water is not strictly monotonic; the question deliberately restricts attention to electron availability. Plausibility check: a more electron-rich nitrogen holds a proton more strongly, so increased electron donation must raise basicity, confirming methylamine as the stronger base.

This medium difficulty chemistry question is from the chapter some basic principles of organic chemistry, covering the topic of basicity of organic compounds. It appeared in the 2025 exam.

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