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+ Aniline
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+ Organic chemistry
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Ken Westmoreland

Which compound is a better base, aniline or para-fluoroaniline? Why?

Bernard Peter Gore  Follow

BASE=>Ability to donate electron easily.

Refer the pic attached.

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Dan Dunay  Follow

Aniline is better base because first of all according to lewis acid and base thoery , base is lone pair donor and acid is lone pair acceptor,so in anilne their is involvement of lone pair of the NH2 grp into the resonance with the benzene ring,but in pera fluro aniline their is a minus induction effect of fluorene which make the benzene ring more electron deficient,so for maintaining the aeromaticity of benzene ring it attract the lone pair of electron from NH2 group more forcibly so lone pair of electron is lesser available for donation to a acceptor in comparison to aniline because their is no minus induction effect so lone pair of electron have more chances to donate.

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