Concept explainers
Interpretation: The nitrogen atom that is more basic in
Concept introduction:
According to Lewis acid-base theory, the compounds which can donate its lone pair of electron are termed as bases and the electron acceptors are known as acids.
Most of the organic structures cannot be represented using single Lewis structure. Therefore, there exists more than one Lewis structure for representing a molecule or ion. These structures are known as resonance structures. These resonance structure combine together to give resonance hybrid that is lower in energy and is the most stable structure.
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Loose Leaf for Organic Chemistry
- which of the following compounds would be the most basic? A. p-methoxyaniline B. p-nitroaniline C. p-toluidine D. aniline E. All would have the same basicityarrow_forwardOne of the heptanedione isomers below has a pka of approximately 9 rather than 20. Which isomer? Why? Draw its conjugate base and offer a full explanation of its acidity.arrow_forwardWhether the ortho-carboxy substituent acts as an intramolecular general-base catalyst or as an intramolecular nucleophilic catalyst can be determined by carrying out the hydrolysis of aspirin with 18O-labeled water and determining whether 18O is incorporated into ortho-carboxy-substituted phenol. Explain the results that would be obtained with the two types of catalysis.arrow_forward
- Substituted phenols show substituent effects similiar to substituted benzoic acids. Should the pKa of phenol A, one of the naturally occurring phenols called urushiols isolated from poison ivy, be higher or lower than the pKa of phenol (C6H5OH, pKa = 10)? Explain.arrow_forwardExplain why a base can remove a proton from the a-carbon of N,N-dimethylethanamide but not from the α-carbon of either N-methylethanamide or ethanamide.arrow_forwardWould you expect 2-Chlorobutanoic acid to have higher or lower pka than 4-Chlorobutanoic acid?arrow_forward
- Give reasons for the following:(i) Aniline does not undergo Friedal-Crafts reaction.(ii) (CH3)2 NH is more basic than (CH3)3 N in an aqueous solution.(iii) Primary amines have higher boiling point than tertiary amines.arrow_forwardwhat is the structure of o-methylphenoxide anion and what is its pKa?arrow_forwardExplain how benzaldehyde and dimedone reacts with each other, and then with the aminotriazole to form compound 1a in the presence of an acid catalyst. Provide a detailed reaction mechanism. During the development of the optimized procedure for the experiment, it was found out that compound 1b can also be produced from the same set of starting materials. Propose a detailed reaction mechanism for the formation of 1b. Explain your answer. What factor/s may drive the formation of 1b over 1a?arrow_forward
- Rank the following compounds in order of increasing basicity: I. p-nitroaniline III. N-methylaniline II. p-aminobenzaldehyde IV. p-methylanilinearrow_forwardConsider the tetracyclic aromatic compound drawn below, with rings labeled as A, B, C, and (a) Which of the four rings is most reactive in electrophilic aromatic substitution? (b) Which of the four rings is least reactive in electrophilic aromatic substitution? (c) What are the major produces) formed when this compound is treated with one equivalent of Br2?arrow_forwardPlace the binders below in descending order of acidity (pi) and justify your choice: CH3CN; (C2H5)2O; PCl3; As(C6H5)3; (C2H5)3Narrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning