Organic Chemistry - Standalone book
10th Edition
ISBN: 9780073511214
Author: Francis A Carey Dr., Robert M. Giuliano
Publisher: McGraw-Hill Education
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Chapter 22, Problem 30P
Interpretation Introduction
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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Aniline (conjugate acid pKa 4.63) is a considerably stronger base than diphenylamine (pKa 0.79). Account for these marked differences.
How do you account for the fact that N-phenylacetamide (acetanilide) is less reactive
toward electrophilic aromatic substitution than is aniline?
-NHCCH,
-NH,
N-Phenylacetamide
(Acetanilide)
Aniline
Arrange the members of each group in order of decreasing basicity: (a) Ammonia, aniline, methylamine (b) Acetanilide, aniline, N-methylaniline (c) 2,4-Dichloroaniline, 2,4-dimethylaniline, 2,4-dinitroaniline (d) 3,4-Dichloroaniline, 4-chloro-2-nitroaniline, 4-chloro-3-nitroaniline (e) Dimethylamine, diphenylamine, N-methylaniline
Chapter 22 Solutions
Organic Chemistry - Standalone book
Ch. 22.1 - Prob. 1PCh. 22.1 - Prob. 2PCh. 22.1 - Prob. 3PCh. 22.2 - Prob. 4PCh. 22.4 - Prob. 5PCh. 22.4 - Prob. 6PCh. 22.4 - Prob. 7PCh. 22.4 - Prob. 8PCh. 22.4 - Prob. 9PCh. 22.7 - Prob. 10P
Ch. 22.8 - Problem 22.11 Three of the following amines can be...Ch. 22.9 - Prob. 12PCh. 22.10 - Prob. 13PCh. 22.13 - Prob. 14PCh. 22.14 - Prob. 15PCh. 22.15 - Prob. 16PCh. 22.15 - Prob. 17PCh. 22.17 - Prob. 18PCh. 22.17 - Prob. 19PCh. 22.17 - Prob. 20PCh. 22.17 - Prob. 21PCh. 22.18 - Prob. 22PCh. 22 - Prob. 23PCh. 22 - Prob. 24PCh. 22 - Prob. 25PCh. 22 - Prob. 26PCh. 22 - Prob. 27PCh. 22 - Arrange the following compounds or anions in each...Ch. 22 - Prob. 29PCh. 22 - Prob. 30PCh. 22 - The compound shown is a somewhat stronger base...Ch. 22 - Prob. 32PCh. 22 - Prob. 33PCh. 22 - Prob. 34PCh. 22 - Prob. 35PCh. 22 - Prob. 36PCh. 22 - Write the structure of the product formed on...Ch. 22 - Prob. 38PCh. 22 - Prob. 39PCh. 22 - Prob. 40PCh. 22 - Prob. 41PCh. 22 - Prob. 42PCh. 22 - Prob. 43PCh. 22 - Prob. 44PCh. 22 - Devise efficient syntheses of each of the...Ch. 22 - Prob. 46PCh. 22 - Prob. 47PCh. 22 - Prob. 48PCh. 22 - Prob. 49PCh. 22 - Prob. 50PCh. 22 - Prob. 51PCh. 22 - Prob. 52PCh. 22 - Prob. 53PCh. 22 - Prob. 54PCh. 22 - Prob. 55PCh. 22 - Prob. 56DSPCh. 22 - Prob. 57DSPCh. 22 - Prob. 58DSPCh. 22 - Prob. 59DSPCh. 22 - Synthetic Applications of Enamines The formation...Ch. 22 - Prob. 61DSP
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- Rank the following compounds in terms of increasing acidity of the most acidic proton. Assume all conjugated atoms are coplanar.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_forwardRank each set of compounds in order of increasing basicity.aniline, p-methylaniline, p-nitroanilinearrow_forwardPyridine forms a stronger Lewis acid-base complex with SO3 than SO2. However, pyridine forms a weaker complex with SF6 than with SF4. Explain the difference.arrow_forwardWhy does cyclohexanol have a pK, of 18 and phenol, despite its similarities in structure, have a pK, of 10? Phenol has a resonance-stabilized conjugate base, which increases the stability of the base and favors its formation Cycohexanol has a resonance-stabilized structure, which increases its stability and reduces the likelihood that it will react to form a conjugate base Phenol has a resonance-stabilized conjugate base, which decreases the stability of the base and inhibits its formation Cycohexanol has a resonance-stabilized conjugate base, which increases the stability of the base and favors its formation Phenol has a resonance-stabilized conjugate base, which decreases the stability of the base and favors its formationarrow_forwardArrange the following in increasing order of boiling point. Give reason. Methylamine, trimethylamine, dimethylamine Arrange the following in increasing order of basicity. Give reason. Methylamine, trimethylamine, dimethylamine Arrange the following in increasing order of solubility in H2O. Give reason. Methylamine, trimethylamine, dimethylaminearrow_forwardReaction of p-nitroaniline with sodium nitrite and hydrochloric acid at 0°C, followed by treatment with N,N-diethylaniline.arrow_forwardPhenacetin is an analgesic compound having molecular formula C10H13NO2. Once a common component in over-thecounter pain relievers such as APC (aspirin, phenacetin, caffeine), phenacetin is no longer used because of its liver toxicity. Deduce the structure of phenacetin from its 1H NMR and IR spectra.arrow_forward(−)-Hyoscyamine, an optically active drug used to treat gastrointestinal disorders, is isolated from Atropa belladonna, the deadly nightshade plant, by a basic aqueous extraction procedure. If too much base is used during isolation, optically inactive material is isolated. (a) Explain this result by drawing a stepwise mechanism. (b) Explain why littorine, an isomer isolated from the tailflower plant in Australia, can be obtained optically pure regardless of the amount of base used during isolation.arrow_forwardarrow_back_iosSEE MORE QUESTIONSarrow_forward_ios
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