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As noted in Table 3.1, the
(a) Draw the bond-line formula of acetone and of any other contributing resonance form. (b) Predict and draw the structure of the conjugate base of acetone and of any other contributing resonance form.
(c) Write an equation for a reaction that could be used to synthesize
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Chapter 3 Solutions
Organic Chemistry, 12e Study Guide/Student Solutions Manual
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- The C-H bond in acetone, (CH3)C=O, has a pką of 19.2. Draw two resonance structures for its conjugate base. Then, explain why acetone is much more acidic than propane, CH;CH,CH3 (pKa = 50). %3Darrow_forwardHydroxide (-OH) can react as a Brønsted–Lowry base (and remove a proton), or a Lewis base (and attack a carbon atom). (a) What organic product is formed when -OH reacts with the carbocation (CH3)3C+ as a Brønsted–Lowry base? (b) What organic product is formed when -OH reacts with (CH3)3C+ as a Lewis base?arrow_forward2,4-Pentanedione is a considerably stronger acid than is acetone (Chapter 19). Write a structural formula for the conjugate base of each acid and account for the greater stability of the conjugate base from 2,4-pentanedione.arrow_forward
- (a) Given that Ka for acetic acid is 1.8 x 10-5 and that forhypochlorous acid is 3.0 x 10-8, which is the stronger acid?(b) Which is the stronger base, the acetate ion or the hypochloriteion? (c) Calculate Kb values for CH3COO- and ClO-.arrow_forwardThe disinfectant phenol, C₆H₅OH, has a pKₐ of 10.0 in wa-ter, but 14.4 in methanol. (a) Why are the values different? (b) Is methanol is a stronger or weaker base than water? (c) Write the dissociation reaction of phenol in methanol. (d) Write an expres-sion for the autoionization constant of methanol.arrow_forward(a) Predict the products of the following acid-base reactions using curved-arrow mechanisms to indicate electron flow. (b) Indicate the acid, base, conjugate acid, and conjugate base of each reaction. (c) Indicate whether the reactants or products are favored at equilibrium a) CH,COOH CH3O b) CH,CH,OH H2Narrow_forward
- Benzoic acid (C6H5COOH) and aniline (C6H5NH2) areboth derivatives of benzene. Benzoic acid is an acid withKa = 6.3 x10-5 and aniline is a base with Ka = 4.3 x10-10. (a) What are the conjugate base of benzoic acid andthe conjugate acid of aniline? (b) Anilinium chloride(C6H5NH3Cl) is a strong electrolyte that dissociates intoanilinium ions (C6H5NH3+) and chloride ions. Which willbe more acidic, a 0.10 M solution of benzoic acid or a 0.10M solution of anilinium chloride? (c) What is the value ofthe equilibrium constant for the following equilibrium?C6H5COOH(aq) + C6H5NH2(aq) ⇌ C6H5COO-(aq) + C6H5NH3+(aq)arrow_forward2-methylvaleric acid, CH3(CH2)2CH(CH3)COOH, has a pKa=4.9. draw the skeletal structure of the conjugate base of 2-methylvakeric acid and give the pH above which 90% of the compound will be in this conjugate base form.arrow_forward1) Complete the following reactions and identify the acid, base, conjugate acid and conjugate base. CH;CH,NH2 (aq) + H2O (1) a) CH;COOH (aq) + H,O (I) b) c) Identify the conjugate base and conjugate acid of each of the following. Conjugate Base Molecule Conjugate Acid HCO3 H20 HSO4- H2PO4arrow_forward
- Using pKa Values to Determine Relative Acidity and Basicity Rank the following compounds in order of increasing acidity, and then rank their conjugate bases in order of increasing basicity.arrow_forwardWhich of the following compounds are acidic (A), basic (B), or relatively neutral (N). CH;-CH-S-H CH;-CH2-CH3 CH;-CH=CH2 CH;-CH,-0-CH, CH;-CH2-O-Harrow_forward1/ Hydrolysis of CH;CH,NO, with 85% H,SO, gives? 2/ When benzyl alcohol is oxidised with KMNO4, the product obtained ? 3/ In the below sequence of reactions, A and B? NaCN (CH3),CO- (HCI) 4/ Which of the following is the strongest acid? CH;COOH , BRCH,COOH , CICH,COOH , FCH,COOH 5/ Which substituted benzoic acid is most acidic? .CO2H CH3 .co,H CO2H CI .CO2H CH, 6/ Which acid is strongest or Which is most acidic? а) Cl,CH.COOН b) CICH,COOН c) CH;COOH d) CI3C.COOH 71. In the anion HCOO- the two carbon-oxygen bonds are found to be of equal length. What is the reason for it?arrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning
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