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Chapter 19

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CHEM 2020
Rajeshwari Iyer

,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,, -- when is nitrogen chiral.  To be none resolvable the nitrogen must be able to freely rotate, the nitrogen is symmetric, or the nitrogen has one proton and no lone pairs. ,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,   Alkyl amines are stronger (more basic) than ammonia, because the R group donates electrons and thus the nitrogen lone pair is more available for proton abstraction.  The more stable amine the less basic. (less stable=more basic). EX: aniline is less basic than aliphatic amines. -Also, the more ‘s’ character the lone pairs have the less basic. Ranked according to increasing basicisity (the more the electrons are drawn the more stable, =least basic)  Amines are soluble in ether, not in water. But protonated amines are soluble in water, not in ether. Salts are soluble in water, protonated amines are salts.
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