Organic Chemistry
4th Edition
ISBN: 9780073402772
Author: Janice G. Smith
Publisher: MCG
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Textbook Question
Chapter 2, Problem 2.47P
Which compounds can be deprotonated by
(a).
(b).
(c). 
(d).
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4. Consider the following bases: Which of the following bases is strong enough to deprotonate
CH4? Explain based on the direction of equilibrium:
a
b
H
H
·3.
Consider the following equilibrium reaction: 2 CH3OH + CH2O ⇌CH2(OCH3)2+ H2O ΔH = + 46 cal
Indicate the direction that the equilibrium will shift when the following changes are made.(No states are provided because the solvent for the reaction is not water, so aq for aqueous would not be appropriate.)
(d)How does the equilibrium constant (Keq) change when temperature is decreased?
a3
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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- Most naturally occurring acids are weak acids. Lactic acid is one example. CH3CH(OH)CO2H(s)+H2O(l)H3O+(aq)+CH3CH(OH)CO2(aq) If you place some lactic acid in water, it will ionize to a small extent, and an equilibrium will be established. Suggest some experiments to prow that this is a weak acid and that the establishment of equilibrium is a reversible process.arrow_forwardPlease explain it. ASAParrow_forwardYou are on one of Saturn's many moons and discover a substance, Y2O that undergoes autoionization just like water on Earth. Y2O + Y2O ⇌ Y3O+ + OY– Through a series of experiments, you determine the equilibrium constant (Keq) for this autoionization reaction at various temperatures. The value of Keq at 28.7ºC is 7.6 x 10-14. What is the pY of the pure substance at this temperature? Report your answer to the hundreths placearrow_forward
- Please explainarrow_forwardWhen the reversible reaction HC2H;O2 (aq) E> H(aq) + C2H3O2 (aq) is at equilibrium at room temperature, pH of the reaction mixture is 5. What will be the change in pH when you add a large amount of NaOH (aq) to the reaction mixture? a) pH will not change because NaOH is not a part of the reaction equation. b) pH will not change because acetic acid and NaOH form a buffer. c) pH will increase because NaOH will completely neutralize acetic acid. d) pH will decrease because NaOH will completely neutralize acetic acid. In the reversible reaction A (aq) + B(aq) E > C(aq), reactant A is very expensive. What are two ways to get it to react as fully as possible to form as much C as possible? a) remove C as it forms, and use an excess of A b) add another reactant that will form a precipitate with B c) remove C as it forms, and use an excess of B d) add another reactant that will form a precipitate with Aarrow_forwardSwimming pool disinfectants produce hypochlorous acid upon dissolution. The weak acid ionizes as follows: HClO (aq) ⇄ H+ (aq) + ClO‒ (aq) Ka=3.0 x 10 ‒8 As strong oxidizing agents, both acid and its conjugate base kill bacteria. However, too high [HClO] is irritating to swimmers’ eyes and too high [ClO‒] will cause the ions to decompose in sunlight. The recommended pH to circumvent both problems is 7.8. Determine the ratio of the weak acid and its conjugate base at this pH.arrow_forward
- How (which direction: right or left) will the equilibrium shift if Cl3 is added? Why will it shift in that direction? PCl5 (g) + heat ⇌ PCl3 (g) + Cl2 (g)arrow_forwardWrite the equilibrium constant expression, K, for the following reaction taking place in dilute aqueous solution.ClO- (aq) + H2O (l)HClO (aq) + OH- (aq)arrow_forwardWrite K expression for the following reaction: 2H2O2(aq) ↔ 2H2O(l) + O2(g)arrow_forward
- Organic chemistry:Hydrochloric acid is about as strong a mineral acid as sulfuric acid .Why would HCL not be a satisfactory catalyst in the synthesis of an aspirin?arrow_forward3. A 0.0560 g quantity of acetic acid is dissolved in enough water to make 50.0 mL of solution. Calculate the concentrations of H;O*, CH;COO and CH;COOH at equilibrium. What is the pH of the solution? (Ka = 1.8x10) CH;COOH(aq) = CH;COO (aq) + H;O* (aq) a) Calculate the initial concentration of CH;COOH. (C:12; H:1; 0:16) b) Calculate the concentration of CH;CoO (aq) and H;O* (aq) at equilibrium. c) Calculate pH of the solution.arrow_forwardDear hand written solution is not allowed.arrow_forward
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