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cricket20 [7]
3 years ago
11

Explain why o-vanillin does not fully protonate p-toluidine. Reference appropriate pKa values and include a balanced chemical re

action and an appropriate reaction arrow in your answer.
Chemistry
1 answer:
Sholpan [36]3 years ago
8 0

Answer:

Here's what I get  

Explanation:

pKₐ of <em>o</em>-vanillin = 7.81; pKₐ of p-toluidine = 4.44

The higher the pKₐ, the weaker the acid.

Thus, <em>o</em>-vanillin is the weaker acid and has a stronger conjugate base.

The conjugate acid of <em>p</em>-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, <em>o</em>-vanillin does not fully protonate <em>p</em>-toluidine.

 

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