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

9th Edition

ISBN:9781305080485

Author:John E. McMurry

Publisher:John E. McMurry

Chapter20: Carboxylic Acids And Nitriles

Section20.SE: Something Extra

Problem 54AP

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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
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.
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?
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
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
Propose a structure for an amine with molecular formula CfH7N by interpreting the given 1H and 13C NMR data below.14 NMR† 2.35 ppmò 7.10 ppmò8.46 ppmsinglet (3)doublet (2)doublet (2)
Propose a structure for an amine with molecular formula CGH7N by interpreting the given 'H and 13C NMR data below. 1H NMR O 2.35 ppm O7.10 ppm 8 8.46 ppm singlet (3) doublet (2) doublet (2) 13C NMR 2, 4 1,5 6.00- 5.00- 4.00- 3.00- 2.00- 1.00- 0.00- 200 120 100 8/ ppm 180 160 140 80 60 40 20
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Answer questions a-c about the Bronsted acid-base reaction below using the identifying letters A-D below each structure. The pka's for the acids of interest are: ethylammonium ion (pK₂ = 10.8), and hydrogen chloride (pK₂ = -7). NH₂ A ethylamine Submit Answer + H CI B hydrogen chloride CH3 NH3 с ethylammonium + CI D chloride a) The stronger acid is b) Its conjugate base is c) The species that predominate at equilibrium are (two letters, e.g. ac) Retry Entire Group 2 more group attempts remaining
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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