Essential Organic Chemistry, Global Edition
3rd Edition
ISBN: 9781292089034
Author: Paula Yurkanis Bruice
Publisher: PEARSON
expand_more
expand_more
format_list_bulleted
Concept explainers
Videos
Textbook Question
Chapter 2.5, Problem 15P
Ethyne has a pKa value of 25, water has a pKa value of 15.7, and ammonia (NH3) has a pKa value of 36. Draw the equation, showing equilibrium arrows that indicate whether reactants or products are favored, for the acid–base reaction of ethyne with
- a. HO−.
- b. -NH2.
- c. Which would be a better base to use if you wanted to remove a proton from ethyne, HO− or −NH2?
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solution
Students have asked these similar questions
Which of the following two acids has the stronger conjugate base?
Nitrous acid, Ka = 7.1 x 10–4 Phenol, Ka = 1.0 x 10–10
The strength of the conjugate base cannot be obtained from the information given.
Nitrous acid, because it has a larger Ka value.
Nitrous acid, because it has a smaller Ka value.
Phenol, because it has a larger Ka value.
Phenol, because it has a smaller Ka value.
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.
10. Given the pH of 1.5 M chloroacetic acid, CH2CICOOH solution is 1.96.
a. Write an equation to show the dissociation of CH2CICOOH in water.
b. Calculate the Ka of the acid.
c. Calculate the pKb of its conjugate base.
d. Which is a stronger base, acetate ion or the conjugate base of CH2CICOOH?
(Ka of acetic acid, CH3COOH = 1.8 x 105)
Chapter 2 Solutions
Essential Organic Chemistry, Global Edition
Ch. 2.1 - Which of the following are not acids? CH3COOH CO2...Ch. 2.1 - Draw the products of the acidbase reaction when a....Ch. 2.1 - a.What is the conjugate acid of each of the...Ch. 2.2 - a. Which is a stronger acid, one with a pKa of 5.2...Ch. 2.2 - Prob. 5PCh. 2.2 - Antacids are compounds that neutralize stomach...Ch. 2.2 - Are the following body fluids acidic or basic? a....Ch. 2.3 - Draw the conjugate acid of each of the following:...Ch. 2.3 - a. Write an equation showing CH3OH reacting as an...Ch. 2.3 - Prob. 10P
Ch. 2.3 - a. Which is a stronger base, CH3COO or HCOO? (The...Ch. 2.3 - Using the pKa values in Section 2.3, rank the...Ch. 2.4 - Prob. 13PCh. 2.5 - Prob. 14PCh. 2.5 - Ethyne has a pKa value of 25, water has a pKa...Ch. 2.5 - Which of the following bases can remove a proton...Ch. 2.6 - List the ions (CH3, NH2, HO, and F) in order from...Ch. 2.6 - List the carbanions shown in the margin in order...Ch. 2.6 - Which is a stronger acid?Ch. 2.6 - a. Draw the products of the following reactions: A...Ch. 2.6 - List the halide ions (F, Cl, Br, and I) in order...Ch. 2.6 - a. Which is more electronegative, oxygen or...Ch. 2.6 - Which is a stronger acid? a. HCl or HBr b....Ch. 2.6 - a. Which of the halide ions (F, Cl, Br, and I) is...Ch. 2.6 - Which is a stronger base? a. H2O or HO b. H2O or...Ch. 2.7 - Which is a stronger acid? a. CH3OCH2CH2OH or...Ch. 2.7 - Which is a stronger base?Ch. 2.8 - Fosamax has six acidic groups. The structure of...Ch. 2.8 - Which is a stronger acid? Why?Ch. 2.10 - For each of the following compounds (shown in...Ch. 2.10 - Prob. 33PCh. 2.11 - Write the equation that shows how a buffer made by...Ch. 2.11 - What products are formed when each of the...Ch. 2 - a. List the following alcohols in order from...Ch. 2 - Which is a stronger base? a. HS or HO b. CH3O or...Ch. 2 - Prob. 40PCh. 2 - a. List the following carboxylic acids in order...Ch. 2 - For the following compound, a. draw its conjugate...Ch. 2 - List the following compounds in order from...Ch. 2 - For each of the following compounds, draw the form...Ch. 2 - Give the products of the following acidbase...Ch. 2 - Prob. 46PCh. 2 - For each compound, indicate the atom that is most...Ch. 2 - Tenormin, a member of the group of drugs known as...Ch. 2 - From which acids can HO remove a proton in a...Ch. 2 - Prob. 50PCh. 2 - Which is a stronger acid? a. CH29CHCOOH or...Ch. 2 - Prob. 52PCh. 2 - Prob. 53PCh. 2 - How could you separate a mixture of the following...Ch. 2 - Prob. 1PCh. 2 - Prob. 2PCh. 2 - Draw the products of the following acidbase...Ch. 2 - Prob. 4PCh. 2 - Prob. 5PCh. 2 - Prob. 6PCh. 2 - Prob. 7PCh. 2 - Prob. 8PCh. 2 - Prob. 9PCh. 2 - Prob. 10PCh. 2 - Prob. 11PCh. 2 - Prob. 12PCh. 2 - Prob. 13PCh. 2 - Prob. 14P
Knowledge Booster
Learn more about
Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.Similar questions
- A carboxylic acid has a pKa of 6.00. Which of the following statements is true? O A. There is an equimolar ratio of the acid and its conjugate base when the pH is 6.00. B. Half of the acid will be deprotonated when the pH = 3. O C. Half of the acid will be protonated when the pH = 12. D. The acid will be completely neutralized when the pH = 7.00. %3!arrow_forwardWill 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_forwardAlkynes exhibit acidic properties because of the differences in the electronegativity of sp- hybridized carbons. Which of the following statements best explains the acidic property of acetylene? A. The electronegativity of sp hybridized carbon decreases bond dipole between C and H. B. Hydrogen atom becomes ionized due to sp-s repulsion. C. The sp-sp orbital overlap attracts the electron cloud between C and H. D. The pi bonds in the triple bond promote ionization of carbon into carbocationsarrow_forward
- Which acid do you think would have the lower pKa value: HBrO4, HBrO3, HBrO2, or HBrO? Explain your answer.arrow_forward2,4,6-Trinitrophenol is also called picric acid. Why is this substance called an acid? How is the acid strength affected by the substituting groups in this case? H NO₂ O₂N. NO₂arrow_forward61. Give the products of the following acid-base reactions and indicate whether reactants or products are favored at equilibrium. (Use the pk, values that are given in Section 2.3.) CH,NH; = a. CH,COH + CH;0 b. CH,CH,OH + NH, c. CH;COH + d. CH;CH,OH + HCI =arrow_forward
- Calculate the pH of an acetic acid solution, originally 0.25 M, in water. The pKa for acetic acid = 4.76.arrow_forwardEquilibrium of methyl orangea) Give a balanced reaction equation for the reaction of methyl orange with 6M HCl b) Give a balanced reaction equation for the reaction of methyl orange with 6M NaOHc) Use Le Chatelier’s Principle to explain the color change when acid or base is added to methyl Orange. Reaction: HMO = H^+ +MO^-arrow_forwardIdentify the acid and base in each reaction. Additionally, predict the product of the reaction. 1. Arrhenius reaction between KOH and HCIO2 2. Bronsted-Lowry acid-base reaction between HCIO4 and Br 3. Lewis reaction between Ag* and 2 cyanide ions (CN')arrow_forward
- 1. Fumaric acid and malonic acid are both diprotic acids. a. Sketch the general shape of the curve for a diprotic acid with Ka1 >> Ka2. Explain how to determine pKa1, pKa2, and the molecular weight.b. Sketch the general shape of the curve for a diprotic acid with Ka1 ≈ Ka2.c. Sketch the general shape of a curve for a triprotic acid with Ka1 >> Ka2 >> Ka3.arrow_forwardCalculate the pH of 1M solution of acedic acid (pKa = 4.76)?arrow_forwardThe acid dissociation constant K of trimethylacetic acid (HC(CH³)₂CO₂) is 9.33 × 10¯6. a Calculate the pH of a 3.6M solution of trimethylacetic acid. Round your answer to 1 decimal place. pH = - 0 X Śarrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning
Chemistry: The Molecular ScienceChemistryISBN:9781285199047Author:John W. Moore, Conrad L. StanitskiPublisher:Cengage Learning
Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning
Chemistry: The Molecular Science
Chemistry
ISBN:9781285199047
Author:John W. Moore, Conrad L. Stanitski
Publisher:Cengage Learning
General Chemistry | Acids & Bases; Author: Ninja Nerd;https://www.youtube.com/watch?v=AOr_5tbgfQ0;License: Standard YouTube License, CC-BY