B. Modified from book problem 24-52: Explain in 1-2 sentences why p-nitroaniline (pKa = 1.0)is less basic than m-nitroaniline (pKa = 2.5). Draw resonance structures to support yourargument. (The pKa values refer to the corresponding ammonium ions.)NH2NH2NO2NO2m-nitroanilinep-nitroaniline

Step 1:The compound which tends to donate electrons is more basic. In the basicity of aniline…

Answered: B. Modified from book problem 24-52:…

Organic Chemistry: A Guided Inquiry

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ISBN:9780618974122

Author:Andrei Straumanis

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Chapter20: Acidity And Pka Of Phenols

Section: Chapter Questions

Problem 20CTQ

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19-33 Rank the amines in each set in order of increasing basicity. (b) sbims ne (a) NH2 NH2 N. H (c) H (d) NH2 NH2 NH2 H3C H2 (е) NH2 CH,NH, CONH,
2. Piperidine is an amine base used in organic reactions. The conjugate acid form of piperidine has a pka of 11.28. Which of the following compounds drawn here can be deprotonated by piperidine? Oethyl methanol DBU triethylamine acetate Oacetic O acid phthalimide H N. H. но .N. methanol аcetic acid pКa %3D 15.5 DBU pka = 4.76 pka = 13.5 NH ethyl acetate triethylamine pКa%3D 25 phthalimide pka = 10.75 pKa = 8.3
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Explain why pyrrole is a much WEAKER base than pyridine (pKa's for their conjugate acids shown to right).
Phenacetin, a substance formerly used in over-the-counter headache remedies, has the formula C10H13NO2. Phenacetin is neutral and does not dissolve in either acid or base. When warmed with aqueous NaOH, phenacetin yields an amine, C8H11NO, whose 1H NMR spectrum is shown. When heated with HI, the amine is cleaved to an aminophenol, C6H7NO. What is the structure of phenacetin, and what are the structures of the amine and the aminophenol?
16-26 The p/fb of amphetamine is approximately 3.2 Amphetamine (a) Which form of amphetamine (the free base or its conjugate acid) would you expect to be present at pH 1.0, the pH of stomach acid? (b ) Which form of amphetamine would you expect to be present at pH 7.40, the pH of blood plasma?
4 5 Arrange the following bases in increasing base strength. There is no partial credit on this problem. Weakest base 1 2 3 Pyridine (C5H5N), Kb = 1.7 x 10-⁹ Aniline (C6H5NH2), Kb = 3.9 x 10-10 Strongest base Methylamine (CH3NH₂), Kb = 4.4 x 10-4 Hydrazine (N2H4), Kb = 1.3 x 10-6 ⠀ Dimethylamine ((CH3)2NH), K₂ = 5.1 x 10-4
Br ||| Based on resonance and inductive effects, identify the strongest base among the aniline derivatives shown below. NH₂ NH₂ O₂N7 IV H3C NH₂ Question 30 of 30 NH₂ A) I B) II C) III D) IV
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Rank the nitrogens in order of decreasing basicity 1, 2, and 3
Amoxycillin is often adminisstered as the sodium salt. It is more soluble form that results from the reaction: Amoxycillin + NaOH --> Sodium-amoxycillin + H2O What functional grouo omn amoxycillin allows it to act as an acid in the reaction?

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B. Modified from book problem 24-52: Explain in 1-2 sentences why p-nitroaniline (pKa = 1.0) is less basic than m-nitroaniline (pKa = 2.5). Draw resonance structures to support your argument. (The pKa values refer to the corresponding ammonium ions.) NH2 NH2 NO2 NO2 m-nitroaniline p-nitroaniline