ORGANIC CHEMISTRY W/ST.GDE W/ACCESS
8th Edition
ISBN: 9780134892566
Author: Bruice
Publisher: PEARSON
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Textbook Question
Chapter 2.10, Problem 45P
a. At what pH is the concentration of a compound, with a pKa = 8.4. 100 times greater in its acidic form than in its basic form?
b. At what pH is 50% of a compound, with a pKa = 7.3 in its basic form?
c. At what pH is the concentration of a compound, with a pKa = 4.6, 10 times greater in its basic form than in its acidic form?
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A naturally occurring amino acid such as alanine has a group that is a carboxylic acid and a group that is a protonated amine. a. If the pKa value of a carboxylic acid such as acetic acid is about 5 (see Table 2.1), then why is the pKa value of the carboxylic acid group of alanine so much lower? b. Draw the structure of alanine in a solution at pH = 0. c. Draw the structure of alanine in a solution at physiological pH (pH 7.4). d. Draw the structure of alanine in a solution at pH = 12. e. Is there a pH at which alanine is uncharged (that is, neither group has a charge)? f. At what pH does alanine have no net charge (that is, the amount of negative charge is the same as the amount of positive charge)?
Which acid do you think would have the lower pKa value: HBrO4, HBrO3, HBrO2, or HBrO? Explain your answer.
Given the following information determine which of these acids is the strongest?
Ka for boric acid is 7.3 x 10–10
pKa of acetic acid is 4.75
Ka for lactic acid is 8.4 x 10–4
pKa of phenol is 9.89
A
acetic acid
B
formic acid
C
lactic acid
D
phenol
Chapter 2 Solutions
ORGANIC CHEMISTRY W/ST.GDE W/ACCESS
Ch. 2.1 - Which of the following are not acids? CH3COOH CO2...Ch. 2.1 - Consider the following reaction: a. What is the...Ch. 2.1 - Draw the products of the addbase renc1 ion when a....Ch. 2.1 - a. What is the conjugate acid of each or the...Ch. 2.2 - a. Which is a stronger acid: one with a pKa of 5.2...Ch. 2.2 - An acid has a Ka of 4.53 106 in water. What is...Ch. 2.2 - Prob. 7PCh. 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 - Estimate the pKa values of the following...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. 15PCh. 2.5 - a. For each of the acid-base reactions in Section...Ch. 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. 2.5 - Calculate the equilibrium constant for the...Ch. 2.6 - Rank the ions (CH3, NH2, HO, and F) from most...Ch. 2.6 - Rank the carbanions shown in the margin from most...Ch. 2.6 - Which is the stronger acid?Ch. 2.6 - Prob. 23PCh. 2.6 - What reaction in Problem 23 has the smallest...Ch. 2.6 - Rank the halide ions (F, Cl, Br, and l) from...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 l) is...Ch. 2.6 - Which is a stronger base? (The potential maps in...Ch. 2.7 - What is a stronger acid? a. CH3OCH2CH2OH or...Ch. 2.7 - Rank the following compounds from strongest add to...Ch. 2.7 - What is a stronger base?Ch. 2.8 - For each of the following compounds, indicate the...Ch. 2.8 - Prob. 35PCh. 2.8 - Which is a stronger acid? Why?Ch. 2.8 - Fosamax (shown on the previous page) has six...Ch. 2.9 - Using the table of pKa values given in Appendix I,...Ch. 2.10 - For each of the following compounds (here shown in...Ch. 2.10 - As long as the pH is not less than _______, at...Ch. 2.10 - a. Indicate whether a protonated amine (RN+H3)...Ch. 2.10 - A naturally occurring amino acid such as alanine...Ch. 2.10 - a. At what pH is the concentration of a compound,...Ch. 2.10 - For each of the following compounds, indicate the...Ch. 2.10 - Given the data in Problem 47: a. What pH would you...Ch. 2.11 - Write the equation that shows how a buffer made by...Ch. 2.12 - Draw the products of the following react ions. Use...Ch. 2.12 - What product are formed when each of the following...Ch. 2 - Which is a stronger base? a. HS or HO b. CH3O or...Ch. 2 - According to the explanations by Lewis, if a...Ch. 2 - a. Rank the following alcohols from strongest to...Ch. 2 - a. Rank the following carboxylic acids from...Ch. 2 - Prob. 57PCh. 2 - For the following compound. a. draw its conjugate...Ch. 2 - Rank the following compounds from strongest to...Ch. 2 - Prob. 60PCh. 2 - Prob. 61PCh. 2 - a. Rank the following alcohols from strongest to...Ch. 2 - A single bond between two carbons with different...Ch. 2 - For each compound, indicate the atom that is most...Ch. 2 - a. Given the Ka values, estimate the pKa value of...Ch. 2 - Tenormin, a member of the group of drugs known as...Ch. 2 - From which of the following compounds can HO...Ch. 2 - a. For each of the following pairs of reactions,...Ch. 2 - Prob. 69PCh. 2 - Which is a stronger acid? a. b. c. d.Ch. 2 - Prob. 71PCh. 2 - Prob. 72PCh. 2 - Given that pH+ pOH = 14 and that the concentration...Ch. 2 - How could you separate a mixture of the following...Ch. 2 - Prob. 75PCh. 2 - a. If an add with a pKa of 5.3 is in an aqueous...Ch. 2 - Calculate the pH values of the following...Ch. 2 - Prob. 1PCh. 2 - Prob. 2PCh. 2 - Prob. 3PCh. 2 - Which of the reactions in Problem 3 favor...Ch. 2 - Prob. 5PCh. 2 - Prob. 6PCh. 2 - Prob. 7PCh. 2 - Which is the stronger acid? a. ClCH2CH2OH or...Ch. 2 - Prob. 9PCh. 2 - Prob. 10PCh. 2 - Which is a more stable base? Remembering that the...Ch. 2 - Which is the Stronger acid?Ch. 2 - Prob. 13PCh. 2 - a. Draw the structure of (CH3COOH (pKa = 4.7) at...
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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
- Ethyne (HC‚CH) 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?arrow_forwardWhat is the K a of an acid whose pK a is 8.60?arrow_forwardA weak acid has a pKa of 7.58. What is the proportion of A- to HA if pH is 9.42? Round to one decimal place Thank you!arrow_forward
- What fraction of iminodiacetic acid is in each of its four forms (H3AH3A H2A−H2A−, HA2−HA2−, A3−A3−) at pH 3.519? The p?apKa values for iminodiacetic acid are 1.85 (p?a1pKa1), 2.84 (p?a2pKa2) and 9.79 (p?a3pKa3).arrow_forward3. Rank the following acids in order from strongest to weakest.HA (pKa = 2.55) H2Z (pKa1 = 4.35) H3X (pKa1 = 3.17) HY (pKa = 5.72) 4. Rank each base in order from strongest to weakest.B (pKb = 4.12) Y– (pKa = 5.72 for conjugate acid) A– (pKa = 2.55 for conjugate acid)E (pKb = 8.12)arrow_forwardNitric acid (HNO3) is a strong acid that completely ionizes when dissolved in water (pKa = -1.30). Calculate the pH of 10 mg/L HNO3. a. Unlike nitric acid, butyric acid (CH3CH2CH2COOH) is a weak acid (pKa = 4.8). Calculate the pH of a solution when 90% of the CH3CH2CH2COOH is dissociated. b. Briefly explain how you can use the pKa values of these two molecules to determine that nitric acid is a strong acid, while butyric acid is a weak acid.arrow_forward
- Using their Ka values, what is the pKb1 of 0.10 M chloroacetic acid 0.20 M carbonic acid 0.40 M citric acidarrow_forward1.95 grams of ethanolamine were dissolved in water, and the pH of the solution was adjusted with HCl until 62% of the molecules were in their protonated (conjugate acid) state. The pKa of ethanolaminium (the conjugate acid of ethanolamine) is 9.5. What is the pH of the final solution? Round your answer to one decimal place (e.g., 2.3) using standard rounding conventions for the last digit.arrow_forwardAt what pH will 25% of a compound with a pKa of 5.3 be in its basic form?arrow_forward
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