Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
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Chapter 24.SE, Problem 70AP
Interpretation Introduction
Interpretation:
To suggest a reason for this behavior of a protonation of an amide using strong acid occurs on oxygen rather than on nitrogen.
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Aniline (conjugate acid pKa 4.63) is a considerably stronger base than diphenylamine (pKa 0.79). Account for these marked differences.
A carboxylic acid has two oxygen atoms, each with two nonbonding pairs of electrons. (b) Compare the resonance forms with those given previously for an acid protonated on thecarbonyl oxygen atom.(c) Explain why the carbonyl oxygen atom of a carboxylic acid is more basic than thehydroxy oxygen.
Show how acid derivatives hydrolyze to carboxylic acids under either acidic or basicconditions. Explain why some acid derivatives (amides, for example) require muchstronger conditions for hydrolysis than other derivatives.
Chapter 24 Solutions
Organic Chemistry
Ch. 24.1 - Name the following compounds:Ch. 24.1 - Prob. 2PCh. 24.1 - Prob. 3PCh. 24.3 - Prob. 4PCh. 24.3 - The benzylammonium ion (C6H5CH2NH3+) has pKa =...Ch. 24.4 - Prob. 6PCh. 24.5 - Prob. 7PCh. 24.6 - Prob. 8PCh. 24.6 - Prob. 9PCh. 24.6 - Show two methods for the synthesis of dopamine, a...
Ch. 24.6 - Prob. 11PCh. 24.6 - Prob. 12PCh. 24.6 - Prob. 13PCh. 24.7 - Prob. 14PCh. 24.7 - Prob. 15PCh. 24.8 - Prob. 16PCh. 24.8 - Propose syntheses of the following compounds from...Ch. 24.8 - How would you prepare the following compounds from...Ch. 24.8 - Prob. 19PCh. 24.9 - Draw an orbital picture of thiazole. Assume that...Ch. 24.9 - Prob. 21PCh. 24.9 - Prob. 22PCh. 24.9 - Which nitrogen atom in the hallucinogenic indole...Ch. 24.9 - Prob. 24PCh. 24.10 - Prob. 25PCh. 24.SE - Name the following amines, and identify each as...Ch. 24.SE - The following compound contains three nitrogen...Ch. 24.SE - Name the following amine, including R, S...Ch. 24.SE - Prob. 29VCCh. 24.SE - Predict the product(s) for each reaction below and...Ch. 24.SE - Predict the product(s) and provide the complete...Ch. 24.SE - Prob. 32MPCh. 24.SE - Predict the product(s) and provide the mechanism...Ch. 24.SE - The diazotization of aniline first involves the...Ch. 24.SE - Prob. 35MPCh. 24.SE - Prob. 36MPCh. 24.SE - Prob. 37MPCh. 24.SE - Prob. 38MPCh. 24.SE - Choline, a component of the phospholipids in cell...Ch. 24.SE - Prob. 40MPCh. 24.SE - -Amino acids can be prepared by the Strecker...Ch. 24.SE - Prob. 42MPCh. 24.SE - Prob. 43MPCh. 24.SE - Prob. 44MPCh. 24.SE - Propose a mechanism for the following reaction:Ch. 24.SE - Prob. 46MPCh. 24.SE - Name the following compounds:Ch. 24.SE - Prob. 48APCh. 24.SE - Prob. 49APCh. 24.SE - Prob. 50APCh. 24.SE - Histamine, whose release in the body triggers...Ch. 24.SE - Prob. 52APCh. 24.SE - Prob. 53APCh. 24.SE - Prob. 54APCh. 24.SE - Prob. 55APCh. 24.SE - Prob. 56APCh. 24.SE - Prob. 57APCh. 24.SE - Prob. 58APCh. 24.SE - Prob. 59APCh. 24.SE - Prob. 60APCh. 24.SE - Show the products from reaction of p-bromoaniline...Ch. 24.SE - Prob. 62APCh. 24.SE - How would you prepare the following compounds from...Ch. 24.SE - Prob. 64APCh. 24.SE - Phenacetin, a substance formerly used in...Ch. 24.SE - Prob. 66APCh. 24.SE - Draw the structure of the amine that produced the...Ch. 24.SE - Fill in the missing reagents a-e in the following...Ch. 24.SE - Prob. 69APCh. 24.SE - Prob. 70APCh. 24.SE - Deduce the structure of the compound with formula...Ch. 24.SE - Prob. 72APCh. 24.SE - Prob. 73APCh. 24.SE - Prob. 74APCh. 24.SE - Prob. 75APCh. 24.SE - Prob. 76APCh. 24.SE - Propose a structure for the product with formula...Ch. 24.SE - Prob. 78APCh. 24.SE - Prob. 79APCh. 24.SE - Prob. 80APCh. 24.SE - Prob. 81APCh. 24.SE - Prob. 82APCh. 24.SE - Prob. 83APCh. 24.SE - Prob. 84AP
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- Histamine, whose release in the body triggers nasal secretions and constricted airways, has three nitrogen atoms. List them in order of increasing basicity and explain your ordering.arrow_forwardCarbonyl compounds can be protonated on the carbonyl oxygen. Protonation of the carbonyl oxygen gives a species whose positive charge is delocalized by resonance. Explain why acetic acid (ethanoic acid) is more readily protonated than acetone (propanone).arrow_forwardComplete the following acid-base reactions and predict the direction of equilibrium (to the right or to the left) for each. Justify your prediction by citing values of pKa for the stronger and weaker acid in each equilibrium. For values of acid ionization constants, consult Table 23.2 (Acid Strengths, pKa, of the Conjugate Acids of Selected Amines) and Appendix 2 (Acid Ionization Constants for the Major Classes of Organic Acids). Where no ionization constants are given, make the best estimate from the information given in the reference tables and sections.arrow_forward
- Complete the following acid-base reactions and predict the direction of equilibrium (to the right or to the left) for each. Justify your prediction by citing values of pKa for the stronger and weaker acid in each equilibrium. For values of acid ionization constants, consult Table 23.2 (Acid Strengths, pKa, of the Conjugate Acids of Selected Amines) and Appendix 2 (Acid Ionization Constants for the Major Classes of Organic Acids). Where no ionization constants are given, make the best estimate from the information given in the reference tables and sections.arrow_forwardComplete the following acid-base reactions and predict the direction of equilibrium (to the right or to the left) for each. Justify your prediction by citing values of pKa for the stronger and weaker acid in each equilibrium. For values of acid ionization constants, consult Table 23.2 (Acid Strengths, pKa, of the Conjugate Acids of Selected Amines) and Appendix 2 (Acid Ionization Constants for the Major Classes of Organic Acids). Where no ionization constants are given, make the best estimate from the information given in the reference tables and sections.arrow_forwardComplete the following acid-base reactions and predict the direction of equilibrium (to the right or to the left) for each. Justify your prediction by citing values of pKa for the stronger and weaker acid in each equilibrium. For values of acid ionization constants, consult Table 23.2 (Acid Strengths, pKa, of the Conjugate Acids of Selected Amines) and Appendix 2 (Acid Ionization Constants for the Major Classes of Organic Acids). Where no ionization constants are given, make the best estimate from the information given in the reference tables and sections.arrow_forward
- (D)The best route to synthesise aromatic primary amines is by reduction of the corresponding nitro compounds. Draw the reaction scheme for the preparation of p-toluidine.arrow_forwardWhen acetophenone, hydroxelamine hydrochloride, and sodium hydroxide are reacted to synthesize acetophenone oxime, why is it necessary to add hydrochloric acid after the reaction to make it acidic?arrow_forwardRank the following in order of decreasing basicity and explain why (based on their structures). hydroxide ion, ethoxide ion, phenoxide ion, and carboxylate ionarrow_forward
- Although acetanilide and phenacetin are not appreciably acidic, aceta- minophen (like aspirin) is a stronger acid than water. What problem would you encounter if the unknown component were acetaminophen rather than acetanilide or phenacetin, and you extracted the aspirin with 5% NaOH? Explain, giving equations for any relevant reactions.arrow_forwardA precursor for para-aminophenol, para-nitrophenol, can be obtained by the nitration of phenol using nitric acid and sulfuric acid. a) What is (are) the major product(s) of the nitration reaction. Explain this selectivity, and support your answer with an appropriate drawing. b) Rank the following compounds in decreasing order of expected acidity (i.e. from strongest to weakest) of the phenol group, and briefly explain your answer: phenol, 4- nitrophenol, 4-aminophenol, 4-bromophenol.arrow_forward3. Rationalize the substantial differences in relative rates of alkaline hydrolysis for the following pair of amides: Ph N7 105 > Ph NH₂arrow_forward
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