Organic Chemistry
7th Edition
ISBN: 9780321803221
Author: Paula Y. Bruice
Publisher: Prentice Hall
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Textbook Question
Chapter 2.5, Problem 15P
a. For each of the acid-base reactions in Section 2.3. compare the pKa values of the acids on either side of the equilibrium arrows to prove that the equilibrium lies in the direction indicated. (The pKa values you need are found in Section 2.3 or in Problem 13.)
b. Do the same for the add-base reactions in Section 2. 1.
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where does the equilibrium lay for this reaction? and by how much? please show arrow pushing. I know I need to use pKa values to find out the equilibrium but I am having trouble finding these values so if you could please help!
H
Benzoic Acid
pka =
O
3-Hydrox
pKa =_
HO
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Q16. Identify the two acid/conjugate base and base/conjugate acid pairs in the following
acid/base reaction: ] Using Evan's pka table, assign a pka value to the acid and conjugate acid
species on the opposite side of the reaction arrow. Use the assigned pKa values to predict if
the preferred direction for this reaction is forward or backwards.
or
Et;N
MeO
EtzNH +
OMe
MeO
OMe
5
Chapter 2 Solutions
Organic Chemistry
Ch. 2.1 - Which of the following are not acids? CH3COOH CO2...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. 6PCh. 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. 14PCh. 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. 22PCh. 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 - Prob. 27PCh. 2.7 - What is a stronger acid? a. CH3OCH2CH2OH or...Ch. 2.7 - Prob. 29PCh. 2.7 - What is a stronger base?Ch. 2.8 - Fosamax (shown on the previous page) has six...Ch. 2.8 - Which is a stronger acid? Why?Ch. 2.8 - Prob. 34PCh. 2.9 - Using the table of pKa values given in Appendix I,...Ch. 2.10 - Prob. 36PCh. 2.10 - As long as the pH is not less than _______, at...Ch. 2.10 - A naturally occurring amino acid such as alanine...Ch. 2.10 - For each of the following compounds, indicate the...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 - a. Rank the following alcohols from strongest to...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 carboxylic acids from...Ch. 2 - Prob. 51PCh. 2 - For the following compound. a. draw its conjugate...Ch. 2 - Rank the following compounds from strongest to...Ch. 2 - Prob. 54PCh. 2 - Prob. 55PCh. 2 - a. Rank the following alcohols from strongest to...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 - A single bond between two carbons with different...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. 63PCh. 2 - Which is a stronger acid? a. b. c. d.Ch. 2 - Prob. 65PCh. 2 - Given that pH+ pOH = 14 and that the concentration...Ch. 2 - How could you separate a mixture of the following...Ch. 2 - Prob. 68PCh. 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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- Q16. Identify the two acid/conjugate base and base/conjugate acid pairs in the following acid/base reaction: ] Using Evan's pKa table, assign a pka value to the acid and conjugate acid species on the opposite side of the reaction arrow. Use the assigned pka values to predict if the preferred direction for this reaction is forward or backwards. Et;N or + + MeO OMe Et,NH MeO OMearrow_forward8. Consider each reaction below carefully. Identify the acid and base on the reactant side of the reaction. Draw the expected product of a proton transfer between the acid and base. Estimate the pka of the acid and conjugate acid. Determine whether the reaction is product or reactant favored. a. b. C. d. OH @O HICI HO NaH 39arrow_forwardDraw the Lewis structure of the 1:1 adduct that forms in the Lewis acid-base reaction between boron trifluoride (BF3) and dimethyl ether ((CH3)20). . Explicitly draw all H atoms. . Include all valence lone pairs in your answer. . Do not include charges in your answer. They will not be considered in the grading. . In cases where there is more than one answer, just draw one. O Q [ ] در ? Ⓡ ChemDoodlearrow_forward
- Which statement about the pKa value is false? * A- The pKa value is calculated from the equilibrium constant for the dissociation of the acid. B- The pKa value is a measure of the strength of an acid. C- The pKa value of a given acid gives an indication of the strength of the conjugate base of that acid. D- A larger pKa value indicates a stronger acid and a weaker associated conjugate base. E- All of these statements are correct.arrow_forwardhe pka of MOPS is 7.20. Draw the equilibrium involved in the dissociation of the proton. f. Suppose you dissolve 0.200 mol of MOPS in 1.00 L of water. Calculate the pH of the solution. g. Use the pka of MOPS to determine the ratio [A']/[HA] at pH 6.95.arrow_forward6. For each of the following acid base reactions shown below, draw curved arrows to show proton transfer. Use ARIO to predict if the equilibrium lies to the left or right. Na HO :O: Na® Hol HO töh töm .H :O: H Na Na Na HN :OH :0: H e.. :OH :O: SH *carbonic acid H₂CO3 has a pKa value of 6.3arrow_forward
- 1. For each statement, pick the correct answer. a. In the reaction below, SO,2 is Select] v (an acid, a base), H3O* is [ Select ] HSO4 is ( Select] , and H2O is [ Select ] H,0* = HSO; H20 b. For this reaction, the conjugate of SO, is ISelect] v and the conjugate of H3O* is (Select] C. According to Table 2, the stronger of the two acids in this reaction is [ Select ) and the weaker of the two acids is ( Select ] d. At equilibrium, there will be more SO42- and H30+ than Iarrow_forwardMolecule A below has a pka of 4.54 and B has a pka of 2.97. i. Which is more acidic? Explain. ii. Use resonance/equilibria structures and explain the difference in pka's. LOH OH A || C-OH B OHarrow_forwardSome weak acids and their pKa values are given below. Which one of these acids will have the STRONGEST conjugate base? Select one: a. Phenol; pKa = 10.00 b. Methanoic acid; pKa = 3.75 c. Bromoethanoic acid; pKa = 2.9 d. Methanol; pKa = 15.54arrow_forward
- 3. Identify the more acidic compound AND explain why. Draw the conjugate base of each compound. If your answer is "resonance", draw at least 1 resonance structure. H₂S a.) Hz Ot + b.) OH SH US US US GH CH 8arrow_forwardhe pka of MOPS is 7.20. Draw the equilibrium involved in the dissociation of the proton. f. Suppose you dissolve 0.200 mol of MOPS in 1.00 L of water. Calculate the pH of the solution. g. Use the pKa of MOPS to determine the ratio [A]/[HA] at pH 6.95. h. If you have 0.200 mol of MOPS dissolved in water, would you add NaOH or HCI to reach a pH of 6.95? And how many moles of the acid or base would you need to add? If you use a 100 mM MOPS buffer at pH 6.95 for a biochemical reaction which produces a maximum of 10 mM H*, which pH would you predict at the end of the reaction? i.arrow_forwardB. Using two acids, HF and CH;CO,H, and their conjugate bases, write a Bronsted Lowry acid-base reaction that has an equilibrium constant greater than one. pka of HF: 3.2 pka of CH;CO,H: 4.75arrow_forward
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