Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
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Chapter 2.SE, Problem 61AP
Phenol, C6H5OH, is a stronger acid than methanol, CH3OH, even though both contain an Q-H bond. Draw the structures of the anions resulting from loss of H+ from phenol and methanol, and use resonance structures to explain the difference in acidity.
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Chapter 2 Solutions
Organic Chemistry
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Ch. 2.7 - Nitric acid (HNO3) reacts with ammonia (NH3) to...Ch. 2.8 - Prob. 12PCh. 2.8 - Amide ion, H2N-, is a much stronger base than...Ch. 2.9 - Prob. 14PCh. 2.9 - Prob. 15PCh. 2.9 - Prob. 16PCh. 2.11 - Using curved arrows, show how the species in part...Ch. 2.11 - Prob. 18PCh. 2.12 - Of the two vitamins A and C, one is hydrophilic...Ch. 2.SE - Prob. 20VCCh. 2.SE - The following model is a representation of...Ch. 2.SE - cis-l, 2-Dichloroethylene and trans-1,...Ch. 2.SE - The following molecular models are representations...Ch. 2.SE - Predict the product(s) of the acid/base reactions...Ch. 2.SE - Use curved arrows to draw the protonated form of...Ch. 2.SE - Prob. 26MPCh. 2.SE - Double bonds can also act like Lewis bases,...Ch. 2.SE - Prob. 28APCh. 2.SE - Use the electronegativity table given in Figure...Ch. 2.SE - Which of the following molecules has a dipole...Ch. 2.SE - Prob. 31APCh. 2.SE - Phosgene, C12C=O, has a smaller dipole moment than...Ch. 2.SE - Prob. 33APCh. 2.SE - Methanethiol, CH3SH, has a substantial dipole...Ch. 2.SE - Calculate the formal charges on the atoms shown in...Ch. 2.SE - Assign formal charges to the atoms in each of the...Ch. 2.SE - Which of the following pairs of structures...Ch. 2.SE - Prob. 38APCh. 2.SE - 1, 3-Cyclobutadiene is a rectangular molecule with...Ch. 2.SE - Alcohols can act either as weak acids or as weak...Ch. 2.SE - The O-H hydrogen in acetic acid is more acidic...Ch. 2.SE - Draw electron-dot structures for the following...Ch. 2.SE - Write the products of the following acid-base...Ch. 2.SE - Rank the following substances in order of...Ch. 2.SE - Which, if any, of the substances in Problem 2-44...Ch. 2.SE - The ammonium ion (NH4+, pKa = 9.25) has a lower...Ch. 2.SE - Prob. 47APCh. 2.SE - Prob. 48APCh. 2.SE - Calculate Ka values from the following pka’s:...Ch. 2.SE - Calculate pKa values from the following Ka’s:...Ch. 2.SE - What is the pH of a 0.050 M solution of formic...Ch. 2.SE - Prob. 52APCh. 2.SE - Maleic acid has a dipole moment, but the closely...Ch. 2.SE - Assume that you have two unlabeled bottles, one of...Ch. 2.SE - Identify the acids and bases in the following...Ch. 2.SE - Which of the following pairs represent resonance...Ch. 2.SE - Draw as many resonance structures as you can for...Ch. 2.SE - Carbocations, which contain a trivalent,...Ch. 2.SE - We’ll see in the next chapter that organic...Ch. 2.SE - The azide functional group, which occurs in...Ch. 2.SE - Phenol, C6H5OH, is a stronger acid than methanol,...Ch. 2.SE - Thiamin diphosphate (TPP), a derivative of vitamin...Ch. 2.SE - Determine if each compound or ion below has a...Ch. 2.SE - Prob. 64APCh. 2.SE - Prob. 65APCh. 2.SE - Draw the conjugate base for each compound below...Ch. 2.SE - 1, 1, 1-Trichloroethanol is an acid more than 1000...
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- Using a table of average bond enthalpies. Table 6.2 ( Sec. 6-6b), estimate the enthalpy change for the industrial synthesis of methanol by the catalyzed reaction of carbon monoxide with hydrogen.arrow_forwardValine is an amino acid with this Lewis structure: Write the Lewis structure for the zwitterion form of valine.arrow_forwardFormamide, HC(O)NH2, is prepared at high pressures from carbon monoxide and ammonia, and serves as an industrial solvent (the parentheses around the O indicate that it is bonded only to the carbon atom and that the carbon atom is also bonded to the H and the N atoms). Two resonance forms (one with formal charges) can be written for formamide. Write both resonance structures, and predict the bond angles about the carbon and nitrogen atoms for each resonance form. Are they the same? Describe how the experimental determination of the HNH bond angle could be used to indicate which resonance form is more important.arrow_forward
- Acetylene 1C2H22 and nitrogen 1N22 both contain a triplebond, but they differ greatly in their chemical properties.(a) Write the Lewis structures for the two substances. (b) Byreferring to Appendix C, look up the enthalpies of formationof acetylene and nitrogen. Which compound is more stable?(c) Write balanced chemical equations for the completeoxidation of N2 to form N2O51g2 and of acetylene to formCO21g2 and H2O1g2. (d) Calculate the enthalpy of oxidationper mole for N2 and for C2H2 (the enthalpy of formationof N2O51g2 is 11.30 kJ>mol). (e) Both N2 and C2H2 possesstriple bonds with quite high bond enthalpies (Table 8.3).Calculate the enthalpy of hydrogenation per mole for bothcompounds: acetylene plus H2 to make methane, CH4;nitrogen plus H2 to make ammonia, NH3.arrow_forward1. Write the ΔHf ̊ reaction for HNO3, accounting for the enthalpy term in your reaction.arrow_forwardChoose the best Lewis structure for phosphoric acid (H 3 PO 4 )? choose onearrow_forward
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