Organic Chemistry
4th Edition
ISBN: 9780073402772
Author: Janice G. Smith
Publisher: MCG
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Textbook Question
Chapter 2, Problem 2.13P
Without reference to a pKa table, decide which compound in each pair is the stronger acid.
a. NH3 or H20 b. H2S or HBr
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Chapter 2 Solutions
Organic Chemistry
Ch. 2 - a. Which compounds are Bronsted-Lowry acids:...Ch. 2 - a. Draw the conjugate acid of each base:...Ch. 2 - Label the acid and base, and the conjugate acid...Ch. 2 - Draw the products of each proton transfer...Ch. 2 - Draw the products formed from the acid-base...Ch. 2 - Which compound in each pair is the stronger acid?...Ch. 2 - Use a calculator when necessary to answer the...Ch. 2 - Rank the conjugate bases of each of group of acids...Ch. 2 - Problem-2.10 Considers two acids: (formic acid,)...Ch. 2 - Estimate the pKa of each of the indicated bonds.
Ch. 2 - Draw the products of each reaction and determine...Ch. 2 - Prob. 2.12PCh. 2 - Without reference to a pKa table, decide which...Ch. 2 - which compound in each pair of isomers is the...Ch. 2 - Prob. 2.15PCh. 2 - Which hydrogen in pseudoephedrine, the nasal...Ch. 2 - whichcompound in each pair is the stronger acid? a...Ch. 2 - Glycolic acid, HOCH2CO2H, is the simplest member...Ch. 2 - Explain the apparent paradox. HBr is a stronger...Ch. 2 - The CH bond in acetone, (CH3)2C=O, has a pKa of...Ch. 2 - Acetonitrile (CH3CN) has a pKa of 25, making it...Ch. 2 - For each pair of compounds: [1] Which indicated H...Ch. 2 - Rank the compounds in each group in order of...Ch. 2 - Which proton in each of the following drugs is...Ch. 2 - Prob. 2.25PCh. 2 - Problem 2.29
Compounds like amphetamine that...Ch. 2 - Problem 2.30 Which species are Lewis bases?
a. b....Ch. 2 - Which species are Lewis acids?
a. b. c. d.
Ch. 2 - For each reaction, label the Lewis acid and base....Ch. 2 - Prob. 2.30PCh. 2 - Prob. 2.31PCh. 2 - Prob. 2.32PCh. 2 - 2.36 Propranolol is an antihypertensive agent—that...Ch. 2 - 2.37 Amphetamine is a powerful stimulant of the...Ch. 2 - Prob. 2.35PCh. 2 - Prob. 2.36PCh. 2 - a Draw the conjugate acid of ethylene, CH2 = CH2....Ch. 2 - 2.40 Draw the products formed from the acid-base...Ch. 2 - Draw the products formed from the acid-base...Ch. 2 - Prob. 2.40PCh. 2 - Draw the product of acid-base reaction. a. c. b....Ch. 2 - Prob. 2.42PCh. 2 - Prob. 2.43PCh. 2 - What is Ka for each compound? Use a calculator...Ch. 2 - What is the pKa for each compound? a. b. c.Ch. 2 - Which of the following bases are strong enough to...Ch. 2 - Which compounds can be deprotonated by OH, so that...Ch. 2 - Draw the product of each reaction. Use the pKa...Ch. 2 - Rank the following compounds in order of...Ch. 2 - Rank the following ions in order of increasing...Ch. 2 - Prob. 2.51PCh. 2 - Prob. 2.52PCh. 2 - The pKa of three CH bonds is given below. a. For...Ch. 2 - a. What is the conjugate acid of A? b. What is the...Ch. 2 - 2.56 Draw the structure of a constitutional isomer...Ch. 2 - 2.57 Many drugs are Bronsted-Lowry acids or...Ch. 2 - Dimethyl ether (CH3OCH3) and ethanol (CH3CH2OH)...Ch. 2 - Prob. 2.58PCh. 2 - Ethyl butanoate, CH3CH2CH2CO2CH2CH3, is one of the...Ch. 2 - Prob. 2.60PCh. 2 - 2.61 Label the three most acidic hydrogen atoms in...Ch. 2 - Prob. 2.62PCh. 2 - 2.64 Classify each species as a Lewis acid, a...Ch. 2 - Prob. 2.64PCh. 2 - Draw the products of each Lewis acid-base...Ch. 2 - Prob. 2.66PCh. 2 - Prob. 2.67PCh. 2 - 2.70 Hydroxide can react as a Brønsted-Lowry base...Ch. 2 - 2.71 Answer the following questions about esmolol,...Ch. 2 - Prob. 2.70PCh. 2 - 2.72 DBU, is a base we will encounter in...Ch. 2 - 2.73 Molecules like acetamide can be protonated...Ch. 2 - Two pKa values are reported for malonic acid, a...Ch. 2 - Prob. 2.74PCh. 2 - 2.76 Write a stepwise reaction sequence using...Ch. 2 - Prob. 2.76PCh. 2 - 2.78 Which compound, M or N, is the stronger acid?...
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- Which of each pair of acids is stronger? Why? (a) HClO3, HClO4 (b) H2S, H2Searrow_forwardConsider the following four biological solutions: (1) bile, pH 8.0, (2) blood, pH 7.4, (3) urine, pH 6.0, and (4) gastric juice, pH 1.6. a. Which solution has the lowest [H3O+]? b. Which solution has the lowest [OH]? c. List the solutions in order of decreasing acidity. d. List the solutions in order of increasing basicity.arrow_forwardPredict whether each of these is a Lewis acid or a Lewis base. (Hint: Drawing a Lewis structure for a molecule or ion often helps to make such predictions.) (a) PH3 (b) BCl3 (c) H2S (d) NO2 (e) Ni2+ (f) COarrow_forward
- . For each pair of concentrations, tell which represents the more basic solution. a. [H+]=2.02107Mor[OH-]=5.05105M b. [H+]=1.79105Mor[OH-]=4.21106M c. [H+]=1.251012Mor[OH-]=6.51103Marrow_forwardUse Table 14.3 to help order the following acids from strongest to weakest HNO3,H2O,NH4+,C5H5NH+arrow_forwardConsider the following four solutions: (1) apple juice, pH 3.8, (2) pickle juice, pH 3.5, (3) carbonated beverage, pH 3.0, and (4) drinking water, pH 7.2. a. Which solution has the highest [H3O+]? b. Which solution has the highest [OH]? c. List the solutions in order of increasing acidity. d. List the solutions in order of decreasing basicity.arrow_forward
- . A strong acid has a weak conjugate base, whereas a weak acid has a relatively strong conjugate base. Explain.arrow_forwardCoal and other fossil fuels usually contain sulfur compounds that produce sulfur dioxide, SO2, when burned. One possible way to remove the sulfur dioxide is to pass the combustion gases into a tower packed with calcium oxide, CaO. Write the equation for the reaction. Identify each reactant as either a Lewis acid or a Lewis base. Explain how you arrived at your answer.arrow_forwardHow is acid strength related to the value of Ka? What is the difference between strong acids and weak acids (see Table 13-1)? As the strength of an acid increases, what happens to the strength of the conjugate base? How is base strength related to the value of Kb? As the strength of a base increases, what happens to the strength of the conjugate acid?arrow_forward
- Are solutions of the following salts acidic, basic, or neutral? For those that are not neutral, write balanced chemical equations for the reactions causing the solution to be acidic or basic. The relevant Ka and Kb values are found in Tables 13-2 and 13-3. a. NaNO3 b. NaNO2 c. C5H5NHClO4 d. NH4NO2 e. KOCl f. NH4OClarrow_forwardSeveral acids are listed here with their respective equilibrium constants: HF(aq) + H2O() H3O+(aq) + F(aq) Ka = 7.2 104 HPO42(aq) + H2O() H3O+(aq) + PO43(aq) Ka = 3.6 1013 CH3CO2(H) + H2O() H3O+(aq) + CH3CO2(aq) Ka = 1.8 105 (a) Which is the strongest acid? Which is the weakest acid? (b) What is the conjugate base of the acid I IF? (c) Which acid has the weakest conjugate base? (d) Which acid has the strongest conjugate base?arrow_forwardSeveral acids and their respective equilibrium constants are: Which is the strongest acid? Which is the weakest acid? Which acid has the weakest conjugate base? Which acid has the strongest conjugate base?arrow_forward
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