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

2nd Edition

ISBN:9780618974122

Author:Andrei Straumanis

Publisher:Andrei Straumanis

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
Basicity of Amines Table 9.6 Observations on the basicity of each test sample. Sample Observations +/- Test tube 1: NaOH Test tube 2: Ethylamine Test tube 3: Aniline Arrange the test samples in order of increasing basicity? Explain briefly. Ferric Chloride Test Table 9.7 Observations on the reaction of each test sample with ferric chloride. Sample Observations +/- Test tube 1: NaOH logy Environment Scienc Test tube Ethylamine Test tube 3: Aniline Based on the test result, what is the structural requirement for a substance to react with the ferric chloride?
Identify the stronger and weaker Bronsted acid, assign the smaller and largerpKa, identify the stronger and weaker Bronsted conjugate base give an explanation thatincludes resonance contributors if relevant.
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
Using pKa Values to Determine Relative Acidity and Basicity Rank the following compounds in order of increasing acidity, and then rank their conjugate bases in order of increasing basicity.
Identify the most and the least acidic compound in each of the following sets. Leave the remaining answer in each set blank. a) 2,4-dinitrobenzoic acid: v p-nitrobenzoic acid: p-bromobenzoic acid: b) benzoic acid: v formic acid: v propanoic acid: c) cyclohexanol: v phenol: v benzoic acid:
Rank the nitrogens in order of decreasing basicity 1, 2, and 3
1) Consider the reaction AH+ H₂O A:+H3O¹. For the following named acids: 1) draw the structure of the acid, 2) give the approximate pKa value of the acid in multiples of 5, 3) give the name of the conjugate base, and 4) draw the structure of the conjugate base. m-Chlorophenol 3-Pentanone acid Conj. base acid Conj. base pKa Benzoic acid pka_ iso-Butyl ammonium ion pka_ Diethyl Malonate pka_ Benzyl oxonium ion pka_ 1-pentyne pKa pKa Ethyl Acetate pKa

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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