Organic Chemistry (8th Edition)
8th Edition
ISBN: 9780134042282
Author: Paula Yurkanis Bruice
Publisher: PEARSON
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Textbook Question
Chapter 2.9, Problem 38P
Using the table of pKa values given in Appendix I, answer the following:
- a. Which is the most acidic organic compound in the table?
- b. Which is the least acidic organic compound in the table?
- c. Which is the most acidic
carboxylic acid in the table? - d. Which is more electronegative: an sp3 oxygen or an sp2 oxygen? (Hint: Pick a compound in Appendix I with a hydrogen attached to an sp2 oxygen and one with a hydrogen attached to an sp3 oxygen and compare their pKa values.)
- e. Which compounds demons that the relative electronegativities of a hybridized nitrogen atom are sp > sp2 > sp3?
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thank you, I would like to have a follow-up question. Would you get an answer of 4.05 pH if the value of your formic acid is 0.050 M while your sodium formate is 0.10 M? and still the same pKa which is 3.75?
Chapter 2 Solutions
Organic Chemistry (8th Edition)
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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- Calculate the pKa of a acid at 25°C if its conjugate base has a pKb = 1.19arrow_forwardDicarboxylic acids have two pKa's.- For maleic acid (cis-2-butenedioic acid) these are pKa1 = 2.0, and pKa2 = 6.3- For fumaric acid (trans-2-butenedioic acid) these are pKa1 = 3.0, and pKa2 = 4.5 Which factor best explains why the cis-isomer has a smaller pKa1 and a larger pKa2 than the trans-isomer? a. Intramolecular hydrogen bonding b. Intramolecular steric hindrance c. Selective solvation in water d. Intramolecular dipole repulsionarrow_forwardexplain in great detail why the pKa values are what they are and compare them among the three compounds. The conjugate acids that are protonated are drawn in red for each compound. Which one based on the pKa is most acidic and what does that tell you about how basic their lone pairs are?arrow_forward
- Put the following compounds in order from weakest acid to strongest acid. Explain (pKa values are not enough and trends should be considered).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_forwardWhen water is the solvent, the pKa of acetic acid (CH3CO2H) is 4.75, but when DMSO is the solvent, the pKa is 12.6.Explain why. Hint: Review Section 2.9 and consider the ability of each solvent to solvate cations and anions.arrow_forward
- 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 percent of acetic acid is present in the acidic form at pH 5.0, assuming a pKa of 4.8?arrow_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_forward
- What is the approximate pKa value of acetic acid? Is it protonated or not at pH -10? At pH 7? Please explain your answer.arrow_forwardA 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)?arrow_forwardOrganic Chemistry help! Which compound has the conjugated base with higher pKa and why?arrow_forward
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