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Organic Chemistry
- The pKa values of a few ortho-, meta-, and para-substituted benzoic acids are shown below: The relative pKa values depend on the substituent. For chloro-substituted benzoic acids, the ortho isomer is the most acidic and the para isomer is the least acidic; for nitro-substituted benzoic acids, the ortho isomer is the most acidic and the meta isomer is the least acidic; and for amino-substituted benzoic acids, the meta isomer is the most acidic and the ortho isomer is the least acidic. Explain these relative acidities. a. Cl: ortho > meta > para b. NO2: ortho > para > meta c. NH2: meta > para > orthoarrow_forwardArrange the following compounds in the increasing order of their acid strength: p-cresol, p-nitrophenol, phenolarrow_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
- The pKa of phenol is 10.0 and the pKa of para-nitrophenol is 7.2. Given this information, one knows that The conjugate base of para-nitrophenol must be less stable than the conjugate base of phenol The conjugate acid of para-nitrophenol must be more stable than the conjugate base of phenol The conjugate base of para-nitrophenol must be more stable than the conjugate base of phenol Both acids are basesarrow_forwardRank the following compounds in their correct order of acidity. 1=Most acidic and 4=least acidic.arrow_forwardArrange the following organic molecules in order of increasing acidity, starting with the least acidic and explain your answer CH3CH3, HC≡CH and CH2=CH2arrow_forward
- (a) Tsomane and Nyiko were given a task of synthesising methylenecyclohexane 2. After a brief discussion with each other, Tsomane proposed Method A to synthesise 2 from cyclohexanone 1 while Nyiko proposed Method B that started from hydroxymethylcyclohexane 3. Each student believed that their proposed method is better than the other. (Scheme below) (1) 1 Ph THF A Ph Ph B H₂SO4 100 °C 3 OH What is the name of the reaction that is followed by reaction Method A?arrow_forward(a) Tsomane and Nyiko were given a task of synthesising methylenecyclohexane 2. After a brief discussion with each other, Tsomane proposed Method A to synthesise 2 from cyclohexanone 1 while Nyiko proposed Method B that started from hydroxymethylcyclohexane 3. Each student believed that their proposed method is better than the other. (Scheme below) (1) Ph Ph 836 Ph THF A 1 B H₂SO4 100 °C 3 OH Which of the two methods (A or B) is more likely give high yield of methylenecyclohexane 2? Briefly explain.arrow_forward(a) Tsomane and Nyiko were given a task of synthesising methylenecyclohexane 2. After a brief discussion with each other, Tsomane proposed Method A to synthesise 2 from cyclohexanone 1 while Nyiko proposed Method B that started from hydroxymethylcyclohexane 3. Each student believed that their proposed method is better than the other. (Scheme below) Ph THF A Ph Ph B H₂SO4 100 °C 3 OH (iii) In analysing both these methods, are there other possible alkene products other than methylenecyclohexane 2? Use mechanistic details to support your answer.arrow_forward
- Consider the following compounds that vary from nearly nonacidic to strongly acidic. Draw the conjugate bases of these compounds, and explain why the acidity increases so dramatically with substitution by nitro groups.refer to the photoarrow_forwardTrifluoroethanol (CF3CH2OH, pKa = 12.5) is more acidic than ethanol (CH3CH2OH, pKa = 16). Provide a three-dimensional structure for each conjugate base and draw the orbitals for all lone pairs. Provide a succinct explanation for the greater acidity of trifluoroethanol.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
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning