Organic Chemistry
4th Edition
ISBN: 9780073402772
Author: Janice G. Smith
Publisher: MCG
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Textbook Question
Chapter 2, Problem 2.73P
Two
Explain why one
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Students have asked these similar questions
Acid Base Reaction
Consider the following acid-base reaction.
HSO4 + CN-HCN + SO4²-
Which compound is the conjugate base of the Bronsted-Lowry acid?
HCN
HSO4
CN
SO4²-
0 0 0 0
ξ0000
Which compound is the conjugate acid of the Bronsted-Lowry base?
CN
SO4²-
HSO4
HCN
D
Weak Base
NH
(CH) N
(CH3)2NH
H₂NNH₂
Which one of the following is the strongest weak base?
A
NH3
Kb
B
1.8 x 10-5
(CH3) N
6.4 x 10-5
5.4 x 10-4
C
(CH3)2NH
1.3 x 10-6
D
H₂NNH₂
The conjugate base of benzoic acid is used as a
72
preservative. Write the equilibrium reaction for this
weak acid in aqueous solution.
ОН
Benzoic acid
a. What substances are present at equilibrium?
b. At equilibrium, are reactants or products favored,
and why?
c. Are the concentrations of benzoic acid and
benzoate constant or changing at equilibrium?
d. What happens to the equilibrium if more
hydronium ions are added to the reaction?
e. Label the conjugate acid-base pairs.
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 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_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_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_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_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_forwardLactic acid, CH3CH(OH)COOH, is a weak monoprotic acid with a melting point of 53 C. It exists as two enantiomers (Sec. 7-2f) that have slightly different Ka values. The D form has a Ka of 1.5 104 and the L form has a Ka of 1.6 104. The D form is synthesized by some bacteria. The L form is produced in muscle cells during anaerobic metabolism in which glucose molecules are broken down into lactic acid and molecules of adenosine triphosphate (ATP) are formed. When lactic acid builds up too rapidly in muscle tissue, severe pain results. (a) Which form of lactic acid (D or L) is the stronger acid? Explain your answer. (b) Determine the pKa that would be measured for a 50:50 mixture of the two forms of lactic acid in aqueous solution, pKa = log Ka (c) A solution of D-lactic acid is prepared. Use HL as a general formula for lactic acid, and write the equation for the ionization of lactic acid in water. (d) If 0.100-M solutions of these two acids (D and L) were prepared, calculate what the pH of each solution would be. (e) Before any lactic acid dissolves in the water, what reaction determines the pH? (f) Calculate the pH of a solution made by dissolving 4.46 g D-lactic acid in 500. mL of water. (g) Calculate the volume (mL) of 1.15-M NaOH(aq) required to completely neutralize 4.46 g of pure lactic acid. (h) Calculate the pH of the solution when exactly enough NaOH was added to neutralize all of the lactic acid for (i) the D form; (ii) the L form; and (iii) a 50:50 mixture of the two forms.arrow_forward
- What is the role of ammonium ion in the following reaction? NH3 H;0 H20 NHA + Select one: Conjugate acid Acid Conjugate base Basearrow_forwardDescribe the acidity/basicity of each species and estimate the position of each equilibrium. CH3CH₂O + CH3C=CH CH3CH₂OH + H3CC=C b d a On the left, a is the and b is th✓ On the right, c is the and d is tl The species favored at equilibrium are those stronger acid stronger base weaker acid weaker base C Carrow_forwardGive the major product of the following reaction. HBr Ph-C C-Ph НООН There is no reaction under these conditions or the correct product is not listed here. Br Ph Ph Br Br Ph Ph Br Br Ph Ph Br Br Ph Ph Br Br J Ph Ph Br Br Ph Ph Brarrow_forward
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