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Interpretation:
- The strong acid has to be predicted.
Concept Introduction:
Electronic effect:
Electron donating groups decreases acidity by inductive effect (withdrawal of electrons through a sigma bond). Electron withdrawal increases acidity. Electron-donating substituents destabilize a base, and decrease the strength of its conjugate acid; electron-withdrawing substituents stabilize a base, which increase the strength of its conjugate base.
Effect of delocalized electrons on
Due to Inductive effect, an anion is stabilized by a nearby electronegative atom. In the same way, electron delocalization also effective on stabilization of anion.
Rule: The strength of an acid depends on the stability of its conjugate base.
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Chapter 19 Solutions
Organic Chemistry; Modified MasteringChemistry with Pearson eText -- ValuePack Access Card; Study Guide and Student Solutions Manual for Organic Chemistry, Books a la Carte Edition (7th Edition)
- 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: cyclohexanone (pKa = 16.7), and ethylammonium ion (pK = 10.8). CH5 NH2 CH3 NH3 A в D ethylamine cyclohexanone enolate cyclohexanone ethylammonium a) The stronger acid is D b) Its conjugate base is c) The species that predominate at equilibrium are (two letters, e.g. ac) ABarrow_forwardExplain each statement. a. The pKa of p-nitrophenol is lower than the pKa of phenol (7.2 vs. 10). b. The pKa of p-nitrophenol is lower than the pKa of m-nitrophenol (7.2 vs. 8.3).arrow_forwardExplain why p-nitrophenol is more acidic than 4- nitrocyclohexanol?arrow_forward
- what is the structure of o-methylphenoxide anion and what is its pKa?arrow_forwardDefine why are protons on an alpha carbon of an aldehyde or ketone more acidic than a proton on an alpha carbon of an ester? What are their pKa's?arrow_forwardIdentify the most and the least acidic compound in each of the following sets. Leave the remaining answer in each set blank. a) 2,4-dinitrobenzoic acid: v p-nitrobenzoic acid: p-bromobenzoic acid: b) benzoic acid: v formic acid: v propanoic acid: c) cyclohexanol: v phenol: v benzoic acid:arrow_forward
- (a) Label the acetal in salicin, a naturally occurring pain reliever isolated from the bark of the willow tree. (b) How many 1° OH groups does salicin contain?arrow_forwardThioglycolic acid, HSCH2CO2H, a substance used in depilatory agents (hair removers) has pKa = 3.42. What is the percent dissociation of thioglycolic acid in a buffer solution at pH = 3.0?arrow_forwardThe following pKa values have been measured. Explain why a hydroxyl group in the para position decreases the acidity while a hydroxyl group in the meta position increases the acidity.arrow_forward
- Although codeine occurs in low concentration in the opium poppy, most of the codeine used in medicine is prepared from morphine (the principal component of opium) by the following reaction. Explain why selective methylation occurs at only one OH in morphine to give codeine. Codeine is a less potent and less addictive analgesic than morphine. но. CH,0. [1 кон H [2] CH3I H. CH3 H Ho morphine H. CH3 Ho codeinearrow_forwardDraw the product formed when phenylacetic acid (C6H5CH2COOH) istreated with following reagent. With some reagents, no reaction occurs. NH3 , Δarrow_forwardWhich is more acidic, p-methylphenol or phenol? why? Why is water more acidic than ethanol but slightly less acidic than methanol? Explain the acidity trend of alcohols: 1>2 > 3arrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning
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