EBK ORGANIC CHEMISTRY
8th Edition
ISBN: 8220102744127
Author: Bruice
Publisher: PEARSON
expand_more
expand_more
format_list_bulleted
Concept explainers
Videos
Textbook Question
Chapter 16, Problem 95P
The pKa values of the
- a. Which carboxyl group is the stronger acid?
- b. The amount of hydrate present in an aqueous solution of oxaloacetic acid depends on the pH of the solution: 95% at pH 0, 81% at pH 1.3, 35% at pH 3.1, 13% at pH 4.7, 6% at pH 6.7, and 6% at pH 12.7. Explain this pH dependence.
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solution
Students have asked these similar questions
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.
What is the second most abundant species of ethylenediamine at pH 9.250?
O H₂NCH₂CH₂NH₂
O HINCH₂CH₂NH
H₂NCH₂CH₂NH
Calculate the percentage of ethylenediamine in the predominant form at each pH.
pH 6.250:
pH 9.250:
%
%
What is the ratio of lactic acid (Ka = 1.37x10-4) to lactate in a solution with pH =4.09?
Write your ratio out as a number containing a decimal.
[lactic acid][lactate] =
Chapter 16 Solutions
EBK ORGANIC CHEMISTRY
Ch. 16.1 - Give two names for each of the following:Ch. 16.1 - Prob. 2PCh. 16.1 - Name the following:Ch. 16.2 - Prob. 4PCh. 16.4 - What products are formed when the following...Ch. 16.4 - We saw on the previous page that...Ch. 16.4 - a. How many stereoisomers are obtained from the...Ch. 16.4 - Prob. 9PCh. 16.4 - Write the mechanism for the reaction of acetyl...Ch. 16.4 - Prob. 11P
Ch. 16.4 - Show how the following compounds can be...Ch. 16.4 - Prob. 13PCh. 16.4 - Prob. 14PCh. 16.4 - In the mechanism for cyanohydrin formation, why is...Ch. 16.4 - Prob. 16PCh. 16.4 - Prob. 17PCh. 16.4 - Show two ways to convert an alkyl halide into a...Ch. 16.5 - Prob. 20PCh. 16.5 - Prob. 21PCh. 16.5 - Prob. 22PCh. 16.5 - Prob. 23PCh. 16.6 - Prob. 24PCh. 16.7 - What reducing agents should be used to obtain the...Ch. 16.7 - Prob. 26PCh. 16.8 - Prob. 27PCh. 16.8 - Prob. 28PCh. 16.8 - Prob. 29PCh. 16.8 - The pKa of protonated acetone is about 7.5. and...Ch. 16.8 - Prob. 31PCh. 16.8 - Prob. 32PCh. 16.8 - Prob. 33PCh. 16.8 - Excess ammonia must be used when a primary amine...Ch. 16.8 - The compounds commonly known as amino acids are...Ch. 16.9 - Hydration of an aldehyde is also catalyzed by...Ch. 16.9 - Which ketone forms the most hydrate in an aqueous...Ch. 16.9 - When trichloroacetaldehyde is dissolved in water,...Ch. 16.9 - Which of the following are a. hermiacetals? b....Ch. 16.9 - Prob. 40PCh. 16.9 - Explain why an acetal can be isolated but most...Ch. 16.10 - Prob. 42PCh. 16.10 - Prob. 43PCh. 16.10 - What products would be formed from the proceedings...Ch. 16.10 - a. In a six-step synthesis, what is the yield of...Ch. 16.10 - Show how each of the following compounds could be...Ch. 16.12 - Prob. 47PCh. 16.13 - Prob. 49PCh. 16.14 - Prob. 50PCh. 16.15 - Prob. 51PCh. 16.16 - Prob. 52PCh. 16 - Draw the structure for each of the following: a....Ch. 16 - Prob. 54PCh. 16 - Prob. 55PCh. 16 - Prob. 56PCh. 16 - a. Show the reagents required to form the primary...Ch. 16 - Prob. 58PCh. 16 - Prob. 59PCh. 16 - Using cyclohexanone as the starting material,...Ch. 16 - Propose a mechanism for each of the following...Ch. 16 - Show how each of the following compounds can be...Ch. 16 - Fill in the boxes:Ch. 16 - Prob. 64PCh. 16 - Identify A through O:Ch. 16 - Prob. 66PCh. 16 - Prob. 67PCh. 16 - Prob. 68PCh. 16 - How many signals would the product of the...Ch. 16 - Prob. 70PCh. 16 - Prob. 71PCh. 16 - Prob. 72PCh. 16 - Prob. 73PCh. 16 - Prob. 74PCh. 16 - Prob. 75PCh. 16 - Prob. 76PCh. 16 - Prob. 77PCh. 16 - Prob. 78PCh. 16 - Draw structure for A-D for each of the following:Ch. 16 - Prob. 80PCh. 16 - a. Propose a mechanism for the following reaction:...Ch. 16 - Prob. 82PCh. 16 - A compound gives the following IR spectrum. Upon...Ch. 16 - How can be following compounds be prepared from...Ch. 16 - Prob. 85PCh. 16 - Prob. 86PCh. 16 - Prob. 87PCh. 16 - In the presence of an acid catalyst, acetaldehyde...Ch. 16 - Prob. 89PCh. 16 - Prob. 90PCh. 16 - Prob. 91PCh. 16 - A compound reacts with methylmagnesium bromide...Ch. 16 - Show how each of the following compounds can be...Ch. 16 - Prob. 94PCh. 16 - The pKa values of the carboxylic acid groups of...Ch. 16 - The Baylis-Hillman reaction is a DABCO...Ch. 16 - Prob. 97PCh. 16 - Prob. 98P
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
- Calculate the percentages of dissociated and undissociated forms present in the following solutions: (a) 0.0010 M glycolic acid (HOCH2CO2H; pKa = 3.83) at pH = 4.50 (b) 0.0020 M propanoic acid (pKa = 4.87) at pH = 5.30arrow_forwardWhich 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_forwardA 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_forward
- At what pH will the concentration of a compound with a pK, 8,4 be 100 tímes greater in ita acidic form than in its basic form? Express your answer using one decimal place. pH= 7.9 At what pH will 50% of a compound with a pK, = 7.6 be in its basic form? Express your answer using one decimal place. pH = At what pH will the concentration of a compound with a pK = 4.6 be 10 times greater in its basic form than in its acidic form? Express your answer using one decimal place. pH = Submit Danunet Anenrarrow_forwardConsidering the acid-base reaction, which statement is not true?arrow_forwardWhich has the larger numerical value? Q.) The pKa of a strong acid or the pKa of a weak acidarrow_forward
- Which of the following functional groups will increase acidity? I. -NO2 II. -CH2CH3 III. -OCH3 IV. - Clarrow_forwardI need help with this problem. Compare the pH of propionic acid and nitric acid when they are dissolved in water at a concentration of 20 mM using the "Arrhenius Concept". Include:a balanced equation describing the acid-base reactions involvedThe calculation of the pKa for bothThe calculation of the two pH's (of propionic acid and nitric acid when they are dissolved in water at a concentration of 20 mM)and A calculation of the percent of dissociation of both propionic acid and nitric acid.The gibbs free energy ΔG are listed as the following:Nitric acid: -152 kJ/molPropionic Acid : -291 kJ/molPropionate: -361 kJ/molarrow_forwardThe dissociation of lactic acid to lactate is shown in the reaction. Lactic acid has a pk, of 3.86. + H* HO OH OH Lactic acid Lactate A solution containing a mixture of lactic acid and lactate was found to have a pH of 3.32. Calculate the ratio of the lactate concentration to the lactic acid concentration in this solution. [lactate] [lactic acid] 0.301 What fraction of the lactic acid/lactate mixture is lactic acid? fraction lactic acid =arrow_forward
- Question 8. For each of following organic acids fill in the table: acid Draw the Mark by X the Estimate pka conjugated base strongest acidarrow_forward3. What is observed when the H2O concentration in the acetic acid equilibrium becomes relatively low? Relatively high? 4. Humidity indicator cards (HIC) are commonly added to semiconductor shipments to document that the parts were not exposed to humidity. These cards are impregnated with cobalt(II) chloride, or an alternative, and change color to indicate the presence of water. Predict the color you would see if a cobalt(II) chloride HIC were exposed to moist, humid air?arrow_forwardAnswer the following question and show your full solution.arrow_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
Organic Chemistry: A Guided InquiryChemistryISBN:9780618974122Author:Andrei StraumanisPublisher:Cengage Learning
Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning
Organic Chemistry: A Guided Inquiry
Chemistry
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Cengage Learning
Enzymes - Effect of cofactors on enzyme; Author: Tutorials Point (India) Ltd;https://www.youtube.com/watch?v=AkAbIwxyUs4;License: Standard YouTube License, CC-BY
Enzyme Catalysis Part-I; Author: NPTEL-NOC IITM;https://www.youtube.com/watch?v=aZE740JWZuQ;License: Standard Youtube License