GOC Basicity

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iTeachChem Helper
@Dexter
iTeachChem Helper
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Xyphoes
XyphoesOP9mo ago
Isme if we look at the structure of the first compound in 3D, it's clear that the LP will be available as it will protrude from one end (tetrahedral ka vertex) Same with the second structure Then how come they've given that SIP effect acts in compound 1?
Comrade Rock Astley
three carbon atoms are large enough to provide steric hindrance think of them as large spheres, the spheres are large enough to be close to the LP
Xyphoes
XyphoesOP9mo ago
Wouldn't the tetrahedral shape enable the LP to stay away from the methyls? That would lead to the LP staying on one vertex of the tetrahedral, and the 3 methyls on the other vertices
Comrade Rock Astley
In a tertiary nitrogen atom, it turns out to not be enough
Comrade Rock Astley
they end up fairly close
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Xyphoes
XyphoesOP9mo ago
Hmm, okay then. They've also stated that the fourth compound will experience steric inhibition, but is that really true? From the data i've seen on google, aniline has a pKb of 9.38 while ortho-methyl aniline has a pKb of ~9.71. Im guessing the biggest contributor to this is the inductive effect of the methyl group I don't think a single methyl would be large enough to disturb the NH2 group enough to shift it out of the plane.
Xyphoes
XyphoesOP9mo ago
👍 I'm guessing they look at the proper data while making adv ka paper so that these mishaps dont happen lol +solved @Comrade Rock Astley
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