Concept explainers
Interpretation:
Drawing resonance structures why p-nitroaniline is less basic than m-nitroaniline by a factor of 30 is to be explained. Given that the pKa values of the corresponding ammonium ions are 1.0 and 2.5 respectively.
Concept introduction:
To account::
By drawing resonance structures why p-nitroaniline is less basic than m-nitroaniline by a factor of 30. Given that the pKa values of the corresponding ammonium ions are 1.0 and 2.5 respectively.
Answer:
p-Nitroaniline is less basic than m-nitroaniline by a factor of 30 since in p-nitroaniline the nitro group is in conjugation with the amino group and hence resonance delocalization as shown is possible.
In m-nitroaniline such delocalization to nitro group is not possible and only inductive effect operates. Thus m-nitroaniline can donate electron faster than p-nitroaniline. Hence p-nitroaniline is weaker than m-nitroaniline.
Explanation:
The electron withdrawing inductive effect of the nitro group reduces the availability of lone pair of electrons on N of the amino group. But in p-nitroaniline in addition to inductive effect electron delocalization of the lone pair of the amino group in to the nitro group also is possible. In m-nitroaniline such a delocalization to the nitro group is not possible. Thus in comparison, the lone pair on N of the amino group is less available for donation in p-nitroaniline than those in m-nitroaniline. Hence p-nitroaniline is less basic than m-nitroaniline.
Conclusion:
p-Nitroaniline is less basic than m-nitroaniline by a factor of 30 since in p-nitroaniline the nitro group is in conjugation with the amino group and hence resonance delocalization as shown is possible.
In m-nitroaniline such delocalization to nitro group is not possible. Thus m-nitroaniline can donate electron faster than p-nitroaniline. Hence p-nitroaniline is weaker than m-nitroaniline.
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Chapter 24 Solutions
OWLv2 with Student Solutions Manual eBook, 4 terms (24 months) Printed Access Card for McMurry's Organic Chemistry, 9th
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