Organic Chemistry-Package(Custom)
4th Edition
ISBN: 9781259141089
Author: SMITH
Publisher: MCG
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Chapter 2, Problem 2.51P
Interpretation Introduction
Interpretation: An explanation regarding the correct choice of
Concept introduction: According to Bronsted-Lowry theory, when an acid donates a proton the species formed is known as conjugate base and when the base accepts a proton the species formed is known as conjugate acid.
The equilibrium constant of an acid dissociation reaction depends on the strength of an acid involved in the reaction. The
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Another way to express acid strength is by using pk b:pK a =−logK a Another way to express base strength is by using pK b pK b =−logK b A new potential heart medicine, code-named X-281, is being tested by a pharmaceutical company, Pharma-pill. As a research technician at Pharma-pill, you are told that X-281 is a monoprotic weak acid, but because of security concerns, the actual chemical formula must remain top secret. The company is interested in the drug's K a value because only the dissociated form of the chemical is active in preventing cholesterol buildup in arteries.To find the pK a of X-281, you prepare a 0.079 M M test solution of X-281 at 25.0 ∘ C The pH of the solution is determined to be 3.00. What is the pK a of X-281?
NaHCO3 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 > II
What is the role of ammonium ion in the following reaction?
NH3
H;0
H20
NHA
+
Select one:
Conjugate acid
Acid
Conjugate base
Base
Chapter 2 Solutions
Organic Chemistry-Package(Custom)
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 has the larger numerical value? (a) The pKa of a strong acid or the pKa of a weak acid (b) The Ka of a strong acid or the Ka of a weak acidarrow_forwardFor each value of Ka, calculate the corresponding value of pKa. Which compound is the stronger acid? (a) Acetic add, Ka = 1.74 105 (b) Chloroacetic acid, Ka= 1.38 103arrow_forwardIn each pair, select the stronger acid. (a) Pyruvic acid (pKa 2.49) or lactic acid (pKa 3.08) (b) Citric acid (pKa1 3.08) or phosphoric acid (pKa1 2.10)arrow_forward
- Will acetylene react with sodium hydride according to the following equation to form a salt and hydrogen, H2? Using pKa values given in Table 4.1, calculate Keq for this equilibrium.arrow_forwardWhat is the relative trend in acidity and pKa of the two compounds? a. Structure I is the most acidic, and Structure I has the highest pKa. b. Structure I is the most acidic, and Structure I has the lowest pKa. c. Structure II is the most acidic, and Structure I has the highest pKa. d. Structure II is the most acidic, and Structure I has the lowest pKa.arrow_forwardConsider these acids (a) Arrange the acids in order of increasing acid strength from weakest to strongest. (b) Which acid has the smallest pKa value?arrow_forward
- Calculate Ka for the weak acids that have the following PKa values. (a) 3.9(b) 10.12 (c) 13.07arrow_forwardFind the value of Kb for the conjugate base of the following organic acids. (a) picric acid used in the manufacture of explosives; Ka = 0.16 (b) trichloroacetic acid used in the treatment of warts; Ka = 0.20arrow_forwardDefine or illustrate the meaning of the following terms: a. Ka reaction b. Ka equilibrium constant c. Kb reaction d. Kb equilibrium constant e. conjugate acidbase pairarrow_forward
- What is the percent dissociation of acetic acid if the solution has a pH = 4.74 and a pK a = 4.74? What is the percent dissociation of acetic acid if the solution has a pH = 4.74 and a pK a = 4.74? 100% 10% 1% 50%arrow_forwardPlace the following fictitious monoprotic acids in order of decreasing acidity.HX 2 (pk a = 5.5408)HE 5 (pk a = 3.0557)HT (pk a = 5.1609)arrow_forwardQ)7arrow_forward
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