Organic Chemistry
6th Edition
ISBN: 9781936221349
Author: Marc Loudon, Jim Parise
Publisher: W. H. Freeman
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Chapter 26, Problem 26.32AP
Interpretation Introduction
Interpretation:
The structure of the conjugate acid for the given compound and the resonance stabilization are to be shown.
Concept introduction:
Resonance is a phenomenon in which polarity is generated in a molecule by the interaction of the conjugated
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Arrange the following compounds in the increasing order of their acid strength: p-cresol, p-nitrophenol, phenol
4-Methylphenol is more acidic than ethanol (pKa 10.36 vs 16.0) , even though both contain an OH group and a methyl group. Draw the structures of the anions formed from loss of the alcoholic protons from both compounds. Use resonance to explain the difference in their respective acidities.
Provide an explanation without using the pka values :
Why is phenol stronger acid than butanoic acid?
Chapter 26 Solutions
Organic Chemistry
Ch. 26 - Prob. 26.1PCh. 26 - Prob. 26.2PCh. 26 - Prob. 26.3PCh. 26 - Prob. 26.4PCh. 26 - Prob. 26.5PCh. 26 - Prob. 26.6PCh. 26 - Prob. 26.7PCh. 26 - Prob. 26.8PCh. 26 - Prob. 26.9PCh. 26 - Prob. 26.10P
Ch. 26 - Prob. 26.11PCh. 26 - Prob. 26.12PCh. 26 - Prob. 26.13PCh. 26 - Prob. 26.14PCh. 26 - Prob. 26.15PCh. 26 - Prob. 26.16PCh. 26 - Prob. 26.17PCh. 26 - Prob. 26.18PCh. 26 - Prob. 26.19PCh. 26 - Prob. 26.20PCh. 26 - Prob. 26.21PCh. 26 - Prob. 26.22PCh. 26 - Prob. 26.23PCh. 26 - Prob. 26.24PCh. 26 - Prob. 26.25PCh. 26 - Prob. 26.26APCh. 26 - Prob. 26.27APCh. 26 - Prob. 26.28APCh. 26 - Prob. 26.29APCh. 26 - Prob. 26.30APCh. 26 - Prob. 26.31APCh. 26 - Prob. 26.32APCh. 26 - Prob. 26.33APCh. 26 - Prob. 26.34APCh. 26 - Prob. 26.35APCh. 26 - Prob. 26.36APCh. 26 - Prob. 26.37APCh. 26 - Prob. 26.38APCh. 26 - Prob. 26.39APCh. 26 - Prob. 26.40APCh. 26 - Prob. 26.41APCh. 26 - Prob. 26.42APCh. 26 - Prob. 26.43APCh. 26 - Prob. 26.44APCh. 26 - Prob. 26.45APCh. 26 - Prob. 26.46APCh. 26 - Prob. 26.47APCh. 26 - Prob. 26.48APCh. 26 - Prob. 26.49APCh. 26 - Prob. 26.50APCh. 26 - Prob. 26.51APCh. 26 - Prob. 26.52APCh. 26 - Prob. 26.53AP
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- Which 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(a) Rank the following compounds in order of increasing acidity. (b) Which compound forms the strongest conjugate base?arrow_forwardWhy are carboxylic acids more acidic than alcohols? The increased inductive effect of the alkyl group of the carboxylic acid resonance stabilization of the carboxylate ion (conjugate base of carboxylic acids) Due to hydrogen bonding They have high pKa valuesarrow_forward
- Sodium hydroxide is used to partially neutralize sulfuric acid from the one-pot Friedel-Crafts and amide hydrolysis reactions. Which bases can deprotonate a phenol that has a pKa of 10.0? Consider the pKa of the conjugate acid of each base. OH NaH NaOH Na2CO3 NaHCO3arrow_forwardDraw the structure of the predominant form of CF3CH2OH (pK a = 12.4) at pH = 6.arrow_forwardGive reasons for the following :(i) Phenol is more acidic than methanol.(ii) The C—O—H bond angle in alcohols is slightly less than the tetrahedral angle (190°28′).(iii) (CH3)3C—O—CH3 on reaction with HI gives (CH3)3C—I and CH3—OH as the main products and not (CH3)3C—OH and CH3—I.arrow_forward
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