Organic - Must Do for JEE Advanced!

Chemistry Level 2

The basicity of following amines is measured in water and in chlorobenzene.

i) C H 3 N H 2 CH_3NH_2

ii) ( C H 3 ) 2 N H (CH_3)_2NH

iii) ( C H 3 ) 3 N (CH_3)_3N

The correct statement regarding the most basic compound in respective solvent is:

ii) in water, iii) in chlorobenzene ii) in water, i) in chlorobenzene ii) in water, ii) in chlorobenzene iii) in water, ii) in chlorobenzene

Sahil Bansal by Sahil Bansal , 21, India

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1 solution

Pradeep Tripathi
May 7, 2020

In water, * N-methylmethanamine * is the most basic of all due to +I effect of methyl groups and enhanced solubility in water as it has a hydrogen atom ( also think about hydrogen bonding) in place of methyl group.( A substance will show its basic character in solution only if it has greater solubility and localized electron density within it).

Whereas, in chlorobenzene; which is a non-polar solvent , N,N-dimethyl methanamine will be most basic because of +I effect of methyl groups and mainly maximum solubility in the non-polar solvent.

CRUX OF THE SOLUTION: Solubility of a substrate in a solvent affects most of its physical and chemical properties.

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