Concept explainers
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
Want to see the full answer?
Check out a sample textbook solutionChapter 3 Solutions
Organic Chemistry, 12e Study Guide/Student Solutions Manual
Additional Science Textbook Solutions
General, Organic, and Biological Chemistry: Structures of Life (5th Edition)
General Chemistry: Principles and Modern Applications (11th Edition)
Chemistry & Chemical Reactivity
Chemistry: Structure and Properties (2nd Edition)
Fundamentals of Heat and Mass Transfer
Chemistry: The Molecular Nature of Matter
- 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_forward5. (a) HF is an acid. What is it's conjugate base ? (b) CIO₂ is a base. What is it's conjugate acid ? (c) What is the conjugate base of H₂PO4¹ ? (d) What is the conjugate acid of H₂PO4-¹ ?arrow_forwardConsider the two following nitrophenol structures: OH OH `NO2 NO2 p-nitrophenol m-nitrophenol Predict which will be the stronger acid. (Hint: Consider possible resonance structures analogous to those given in the text for phenol.)arrow_forward
- Carboxylic Acid Derivatives Resolve by synthesis, step by step.arrow_forwardFrom pair, select the stronger base. For stronger base, write a structural formula of its conjugate acid.arrow_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
- The pKa of ascorbic acid (vitamin C, page 55) is 4.17, showing that it is slightly more acidic than acetic acid (CH3COOH, pKa 4.74).Compare the stabilities of these four conjugate bases, and predict which OH group of ascorbic acid is the most acidicarrow_forwardWrite equations for the following acid-base reactions. Label the conjugate acids and bases, and show any inductive stabilization. Predict whether the equilibrium favors the reactants or products. Try to do this without using a table of pKa values, (a) CH3CH2OH + CH3NH- (b) F3CCOONa + Br3C¬COOH(c) CH3OH + H2SO4 (d) NaOH + H2S(e) CH3NH3+ + CH3O- (f) BrCH2CH2OH + F3C¬CH2O-(g) NaOCH2CH3 + Cl2CHCH2OH (h) H2Se + NaNH2(i) CH3CHFCOOH + FCH2CH2COO- (j) CF3CH2O- + FCH2CH2OHarrow_forwardDraw the products of each proton transfer reaction. Label the acid and base in the starting materials, and the conjugate acid and base in the products. (c) + H2SO4arrow_forward
- 3. For the following acid - base reaction, (a) predict the products; (b) identify the Bronsted acid, Bronsted base, conjugate acid, and conjugate base; (c) use curved arrows to show the flow of electron pairs in the reaction. CH3 CH2C-OH + NaNHaarrow_forwardAcid-Base Equilibria Many factors contribute to the acidity of organic compounds. Electronegativity, resonance, induction, hybridization, aromaticity, and atomic size, all play a role. In the following comparisons, you are asked to identify the factor(s) that would be most important to analyze when predicting relative acidity, and then to predict the trend in acidity and pKa values. For each of the following pairs of compounds answer the following two multiple-choice questions. 1. What factor(s) are the most important to consider when predicting the relative acidity of the two compounds? a. Electronegativity of the atom possessing the hydrogen. b. Resonance stabilization of the anionic conjugate base. c. Inductive stabilization of the anionic conjugate base. d. Hybridization of the atom possessing the hydrogen. e. The atomic size of the atom possessing the hydrogen.arrow_forwardNaHCO3 can deprotonate benzoic acid but cannot deprotonate phenol. On the other hand, NaOH can deprotonate both benzoic acid and phenol. Given this information, rank the molecules numbered I to V in order of decreasing acidity. COH cOH он H,0 H,CO, IV CH3 II I II (A) V > II >I > III > IV (В) II > 1 > V > III IV (C) II > V >I > IV > IIarrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage LearningChemistry: The Molecular ScienceChemistryISBN:9781285199047Author:John W. Moore, Conrad L. StanitskiPublisher:Cengage Learning