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EBK ORGANIC CHEMISTRY
- 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_forwardArrange the following compounds in the increasing order of their acid strength: p-cresol, p-nitrophenol, phenolarrow_forwarddraw the conjugate basearrow_forward
- Arrange the following organic molecules in order of increasing acidity, starting with the least acidic and explain your answer CH3CH3, HC≡CH and CH2=CH2arrow_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_forward2. Give the pK₂ values for the following compounds and then rank them in terms of increasing acidity. Explain why the values change so dramatically (each pKa unit is an order of magnitude) from one member of the series to the next. NH3 HF CH4 H₂Oarrow_forward
- The hydrocarbon fluorene was treated with potassium t-butoxide in an acid-base reaction, giving the fluorenide anion and t-butyl alcohol. (a) Which way does the equilibrium lie, and by how much? b) What is the proportion of the fluorenide anion to fluorene? (c) Why is fluorene so highly acidic, considering the pKa of an average alkane is above 50?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) (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) 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_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_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_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning