The protonated form of aniline has a pk, of about 4.6.At what pH would you expect the species to existpredominantly in the protonated (cationic) form? At whatpH would you expect it to exist predominantly in theuncharged form? At what pH would you expect an equalNH3pKa = 4.6mixture of the two forms?

Aniline is a six-membered ring (Benzene) attached to an amine functional group. The Amine group is a…

Answered: The protonated form of aniline has a…

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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но HO но он The pK, of ascorbic acid (vitamin C) is 4.17, showing that it is slightly more acidic than acetic acid (CH3CO0H, pKa 4.74). (a) Show the fou r different conjugate bases that would be formed by deprotonation of the four different OH groups in ascorbic acid. (b) Compare the stabilities of these four conjugate bases, and predict which OH group of ascorbic acid is the most acidic. (c) Compare the most stable conjugate base of ascorbic acid with the conjugate base of acetic acid, and suggest why these two compounds have similar acidities, even though ascorbic acid lacks the carboxylic acid (COOH) group.
(a) Explain how NaBH, in CH;OH can reduce hemiacetal A to 1,4-butanediol (HOCH,CH,CH,CH,OH). (b) What product is formed when A is treated with Ph;P=CHCH,CH(CH),? (c) The drug isotretinoin is formed by reaction of X and Y. What is the structure of isotretinoin? Although isotretinoin (trade name Accutane or Roaccutane) is used for the treatment of severe acne, it is dispensed under strict controls because it also causes birth defects. PPha NaOCH,CH3 HO- isotretinoin HO A Br X Y
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.
(a) Rank the following compounds in order of increasing acidity. (b) Which compound forms the strongest conjugate base?
(a) Tsomane and Nyiko were given a task of synthesising methylenecyclohexane 2. After a brief discussion with each other, Tsomane proposed Method A to synthesise 2 from cyclohexanone 1 while Nyiko proposed Method B that started from hydroxymethylcyclohexane 3. Each student believed that their proposed method is better than the other. (Scheme below) (1) Ph Ph 836 Ph THF A 1 B H₂SO4 100 °C 3 OH Which of the two methods (A or B) is more likely give high yield of methylenecyclohexane 2? Briefly explain.
Which proton in ketamine (C13H16ClNO) is the most acidic and what is the structure of its conjugate base?
5. Which of the following equations shows that isoquinoline, C9H;N, behaves as a Bronsted-Lowry base in water? a) CóH;N(aq) + H2O(1) = b) CH;N(aq) + H2O(1) c) C9H;N(aq) + OH¯(aq) = d) CoH;N(aq) + H;O*(aq) e) CoH;NH*(aq) + H2O(!) C9H;NH*(aq) + OH (aq) = C9H&N°(aq) + H;O*(aq) C9HN¯(aq) + H;O(!) = C9H;NH*(aq) + H2O(1) = C9H;N(aq) + H;O*(aq)
Describe the trends in the acidityand physical properties of carboxylicacids, and explain how their acidityvaries with their substituents.
At pH 3.0, what percentage (in %) of lactic acid is in its deprotonated form? Hint: The pka of lactic acid is 3.86.
(i) Identify the acidic proton(s) for each of the following carbonyl compounds: O O ( CHỊCH, CÁCH, BỊ CHỊCHỊCH, CÁCH, (2) || (3) CHy-O-C-CH,-C-O-CH, (4) CH,-C-CH, (ii) Rank the compounds (in part (i) above) in the order of increasing or decreasing acidity by using the symbol "" in your answer.
(a) Tsomane and Nyiko were given a task of synthesising methylenecyclohexane 2. After a brief discussion with each other, Tsomane proposed Method A to synthesise 2 from cyclohexanone 1 while Nyiko proposed Method B that started from hydroxymethylcyclohexane 3. Each student believed that their proposed method is better than the other. (Scheme below) Ph THF A Ph Ph B H₂SO4 100 °C 3 OH (iii) In analysing both these methods, are there other possible alkene products other than methylenecyclohexane 2? Use mechanistic details to support your answer.
Write the equilibrium-constant expressions and obtainnumerical values for each constant in. (a) the basic dissociation of aniline, C6H5NH2. (b) the acidic dissociation of hypochlorous acid,HClO. (c) the acidic dissociation of methyl ammoniumhydrochloride, CH3NH3Cl. (d) the basic dissociation of NaNO2. (e) the dissociation of H3AsO3to H3O+and AsO33-. (f) the reaction of C2O42-with H2O to give H2C2O4and OH-. show solution

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