Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
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Chapter 2.SE, Problem 40AP
Alcohols can act either as weak acids or as weak bases, just as water can. Show the reaction of methanol, CH3OH, with a strong acid such as HCl and with a strong base such as Na+-NH2.
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Chapter 2 Solutions
Organic Chemistry
Ch. 2.1 - Prob. 1PCh. 2.1 - Prob. 2PCh. 2.1 - Use the electronegativity values shown in Figure...Ch. 2.1 - Look at the following electrostatic potential map...Ch. 2.2 - Ethylene glycol, HOCH2CH2OH, may look nonpolar...Ch. 2.2 - Make three-dimensional drawings of the following...Ch. 2.3 - Calculate formal charges for the nonhydrogen atoms...Ch. 2.3 - Organic phosphate groups occur commonly in...Ch. 2.6 - Which of the following pairs of structures...Ch. 2.6 - Draw the indicated number of resonance forms for...
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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- What is the freezing point of vinegar, which is an aqueous solution of 5.00% acetic acid, HC2H3O2, by mass (d=1.006g/cm3)?arrow_forward12.62 Write the formula of the conjugate acid of each of the following bases, (a) OH-, (b) NHj, (c) CHjNHt, (d) HPO/-, (e) CO.,2’arrow_forwardFor conjugate acidbase pairs, how are Ka and Kb related? Consider the reaction of acetic acid in water CH3CO2H(aq)+H2O(l)CH3CO2(aq)+H3O+(aq) where Ka = 1.8 105 a. Which two bases are competing for the proton? b. Which is the stronger base? c. In light of your answer to part b. why do we classify the acetate ion (CH3CO2) as a weak base? Use an appropriate reaction to justify your answer. In general, as base strength increases, conjugate acid strength decreases. Explain why the conjugate acid of the weak base NH3 is a weak acid. To summarize, the conjugate base of a weak acid is a weak base and the conjugate acid of a weak base is a weak acid (weak gives you weak). Assuming Ka for a monoprotic strong acid is 1 106, calculate Kb for the conjugate base of this strong acid. Why do conjugate bases of strong acids have no basic properties in water? List the conjugate bases of the six common strong acids. To tie it all together, some instructors have students think of Li+, K+, Rb+, Cs+, Ca2+, Sr2+, and Ba2+ as the conjugate acids of the strong bases LiOH, KOH. RbOH, CsOH, Ca(OH)2, Sr(OH)2, and Ba(OH)2. Although not technically correct, the conjugate acid strength of these cations is similar to the conjugate base strength of the strong acids. That is, these cations have no acidic properties in water; similarly, the conjugate bases of strong acids have no basic properties (strong gives you worthless). Fill in the blanks with the correct response. The conjugate base of a weak acid is a_____base. The conjugate acid of a weak base is a_____acid. The conjugate base of a strong acid is a_____base. The conjugate acid of a strong base is a_____ acid. (Hint: Weak gives you weak and strong gives you worthless.)arrow_forward
- For each substance below, write a complete reaction with water and identify its conjugate acid or base, whichever is appropriate. a. H2SO4, a strong acidb. HCO3–, a weak acidc. HCO3–, a weak based. CH3NH3+, a weak acide. KOH, a strong basearrow_forwardGiven that methylamine, CH3NH2, has a Kb of 4.4 x 10-4, what is the pH of a 0.20 M aqueous solution of methylamine?arrow_forwardThe substance trimethylamine is a weak nitrogenous base like ammonia.Write a net ionic equation to show how trimethylamine, (CH3)3N, behaves as a base in water.arrow_forward
- For each conjugate acid-base pair, identify the first species as an acid or a base and the second species as its conjugate acid or base. In addition, draw Lewis structures for each species, showing all valence electrons and any formal charge. (a) HCOOH HCOO-arrow_forwardIndicate whether the chemical species HC6H5O72- acts as an acid or base when added to water. Please justify your answer with QUANTITATIVE evidencearrow_forwardWhat is the Kw of pure water at 50.0 degrees Celsius, if the pH is 6.630?arrow_forward
- The organic bases cocaine pKb = 8.412 and codeine pKb = 7.952 react with hydrochloric acid to form salts (similar to the formation of NH4Cl by the reaction of NH3 and HCl). If solutions of the following salts have the same molarity, which solution would have the higher pH: cocaine hydrochloride, C H O NH+Cl-, or codeine hydrochloride, C H ClO NH+Cl-? Show your step by step solution and explanation of your solution.arrow_forwardThe organic bases cocaine pKb = 8.412 and codeine pKb = 7.952 react with hydrochloric acid to form salts (similar to the formation of NH4Cl by the reaction of NH3 and HCl). If solutions of the following salts have the same molarity, which solution would have the higher pH: cocaine hydrochloride, C H O NH+Cl-, or codeine hydrochloride, C H ClO NH+Cl-? Show your step by step solution and explanation of your solution. *either write pka=14-pkb, and explain why trend of pH is same as pka or from pKb explain how to get pH of conjugate acid from pOH trend of Kb of base.arrow_forwardWhat is the pOH of pure water at 40 oC? ( K w at 40 oC = 2.87 × 10 –14)arrow_forward
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General Chemistry | Acids & Bases; Author: Ninja Nerd;https://www.youtube.com/watch?v=AOr_5tbgfQ0;License: Standard YouTube License, CC-BY