Answer:
Here's what I get
Explanation:
pKₐ of o-vanillin = 7.81; pKₐ of p-toluidine = 4.44
The higher the pKₐ, the weaker the acid.
Thus, o-vanillin is the weaker acid and has a stronger conjugate base.
The conjugate acid of p-toluidine is the stronger and has the weaker conjugate base.
The equation for the equilibrium is
H-OC₆H₃(OCH₃)CHO + CH₃C₆H₄NH₂ ⇌ ⁻OC₆H₃(OCH₃)CHO + CH₃C₆H₄NH₃⁺
weaker acid weaker base stronger base stronger acid
The reaction between the stronger acid and the stronger base pushes the position of equilibrium to the left.
Thus, o-vanillin does not fully protonate p-toluidine.
O-vanillin is a weaker acid than p-toluidine and has a more stable conjugate base; hence, o-vanillin does not fully protonate p-toluidine.
The pKa is defined as the negative logarithm of Ka. The dissociation constant of an acid Ka shows the extent of dissociation of an acid in solution. The higher the pKa, the lower the Ka and the weaker the acid.
The pKₐ of o-vanillin is 7.81 while the pKₐ of p-toluidine is 4.44. This means that o-vanillin is a weaker acid than p-toluidine and has a more stable conjugate base. Hence, o-vanillin does not fully protonate p-toluidine.
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