Organic Chemistry
5th Edition
ISBN: 9780078021558
Author: Janice Gorzynski Smith Dr.
Publisher: McGraw-Hill Education
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Chapter 2, Problem 2.74P
Interpretation Introduction
Interpretation: The reason corresponding to the fact that one
Concept introduction: According to Bronsted-Lowry theory, the species that can easily accept the proton is known as base and the species that easily donate the proton is known as acid.
The species that donates the proton more readily is known to be a stronger acid. The stronger acid has a higher value of
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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 each statement as True or False.
a. is the...Ch. 2 - Label the acid and base, and the conjugate acid...Ch. 2 - Decide which compound is the acid and which is the...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 - Prob. 2.11PCh. 2 - Draw the products of each reaction and determine...Ch. 2 - Prob. 2.13PCh. 2 - Without reference to a pKa table, decide which...Ch. 2 - Rank the labeled H atoms in the following compound...Ch. 2 - Which hydrogen in each molecule is most...Ch. 2 - Which hydrogen in pseudoephedrine, the nasal...Ch. 2 - Which compound in each pair of isomers is the...Ch. 2 - Which compound in each pair is the stronger acid?...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 - Which anion A or B is the stronger base? ABCh. 2 - Prob. 2.28PCh. 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. 2.33PCh. 2 - Prob. 2.34PCh. 2 - Label the Lewis acid and base. Use curved arrow...Ch. 2 - 2.36 Propranolol is an antihypertensive agent—that...Ch. 2 - 2.37 Amphetamine is a powerful stimulant of the...Ch. 2 - 2.38 What is the conjugate acid of each base?
a....Ch. 2 - 2.39 What is the conjugate base of each acid?
a....Ch. 2 - 2.40 Draw the products formed from the acid-base...Ch. 2 - Draw the products formed from the acid-base...Ch. 2 - Draw the products of each proton transfer...Ch. 2 - Prob. 2.43PCh. 2 - Prob. 2.44PCh. 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 products of each reaction. Use the pKa...Ch. 2 - Rank the following compounds in order of...Ch. 2 - 2.51 Rank the following ions in order of...Ch. 2 - Prob. 2.52PCh. 2 - Prob. 2.53PCh. 2 - 2.54 The of three 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 - 2.59 Atenolol is a (beta) blocker, a drug used to...Ch. 2 - 2.60 Use the principles in Section 2.5 to label...Ch. 2 - 2.61 Label the three most acidic hydrogen atoms in...Ch. 2 - Prob. 2.62PCh. 2 - 2.63 Classify each compound as a Lewis base, a...Ch. 2 - 2.64 Classify each species as a Lewis acid, a...Ch. 2 - Label the Lewis acid and Lewis base in each...Ch. 2 - 2.66 Draw the products of each Lewis acid-base...Ch. 2 - Prob. 2.67PCh. 2 - 2.68 Answer the following questions about the four...Ch. 2 - Prob. 2.69PCh. 2 - 2.70 Hydroxide can react as a Brønsted-Lowry base...Ch. 2 - 2.71 Answer the following questions about esmolol,...Ch. 2 - 2.72 DBU, is a base we will encounter in...Ch. 2 - 2.73 Molecules like acetamide can be protonated...Ch. 2 - Prob. 2.74PCh. 2 - Prob. 2.75PCh. 2 - 2.76 Write a stepwise reaction sequence using...Ch. 2 - Prob. 2.77PCh. 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 K a of an acid whose pK a is 8.60?arrow_forwardWhich of the following bases can remove a proton from acetic acid in a reaction that favors products? HO− CH3NH2 HC =C- CH3OH H2O Cl-arrow_forwardWhat is the role of ammonium ion in the following reaction? NH3 H;0 H20 NHA + Select one: Conjugate acid Acid Conjugate base Basearrow_forward
- What is the major product of the following reaction? CEN HCI 40 °Carrow_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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