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

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Chapter20: Carboxylic Acids And Nitriles

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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
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?
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
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?
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 (pK = 10.8), and hydrogen chloride (pKa = -7). CH3- NH2 CH3. NH3 cī H-CI H2 A в D chloride ethylamine hydrogen chloride ethylammonium a) The stronger acid is b) Its conjugate base is c) The species that predominate at equilibrium are (two letters, e.g. ac)
Rank the following benzoic acid derivatives from weakest (list first) to strongest (list last).
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The following three derivatives of succinimide are anticonvulsants and have found use in the treatment of epilepsy, particularly petit mal seizures. Ph Ph `N' `N' ČH3 ČH3 Methsuximide Ethosuximide Phensuximide Following is a synthesis of phensuximide. CN Ph CN Ph CN 1. NaOH, H2O 2. HC, Н20 NaOEt KCN Ph-CHO cOOEt H cOOEt NC COOEt 3. Нeat Ethyl cyanoacetate (A) (B) Benzaldehyde Ph Ph Ph CH;NH2 НООС СООН Et0oC COOEt `N' (C) (D) ČH3 Phensuximide Methsuximide is formed by a similar pathway to that shown for phensuximide. Draw the structure of the compound that reacts with ethyl cyanoacetate in the synthesis of methsuximide.
Ff.185.

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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