Organic Chemistry
7th Edition
ISBN: 9780321803221
Author: Paula Y. Bruice
Publisher: Prentice Hall
expand_more
expand_more
format_list_bulleted
Concept explainers
Textbook Question
Chapter 9, Problem 43P
The pKa of acetic acid in water is 4.76. What effect will a decrease in the polarity of the solvent have on the pKa? Why?
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solutionStudents have asked these similar questions
The pKa of acetic acid in water is 4.76. What effect will a decrease in the polarity of the solvent have on the pKa? Why?
The pKa of salicylic acid is 2.97 whereas the pKa of benzoic acid is 4.19. Why is salycilic acid a much stronger acid compared to benzoic acid? (It is not enough to say “because the pKa is lower...”)
Calculate the percentage of free acid for (a) phenobarbital (it is an acid with pKa = 7.40) and (b) hexobarbital (also an acid with pKa = 8.4) at the physiological condition of pH 7.4.
Chapter 9 Solutions
Organic Chemistry
Ch. 9.1 - Prob. 3PCh. 9.1 - Does increasing the energy barrier for an SN2...Ch. 9.1 - Rank the following alkyl bromides from most...Ch. 9.2 - Prob. 8PCh. 9.2 - Prob. 9PCh. 9.2 - Prob. 10PCh. 9.2 - Prob. 11PCh. 9.2 - Which substitution reaction lakes place more...Ch. 9.2 - Prob. 14PCh. 9.2 - Prob. 16P
Ch. 9.3 - Prob. 17PCh. 9.4 - Prob. 18PCh. 9.5 - Prob. 19PCh. 9.5 - Prob. 20PCh. 9.5 - Prob. 21PCh. 9.5 - Prob. 22PCh. 9.6 - Prob. 23PCh. 9.6 - Prob. 24PCh. 9.6 - Which of the following reactions take place more...Ch. 9.7 - Prob. 26PCh. 9.7 - Prob. 27PCh. 9.7 - Prob. 28PCh. 9.7 - Prob. 30PCh. 9.7 - Under which of the following reaction conditions...Ch. 9.8 - After a proton is removed from the OH group, which...Ch. 9.8 - Prob. 33PCh. 9.9 - Prob. 34PCh. 9 - Prob. 1PCh. 9 - Methoxychlor is an insecticide that was intended...Ch. 9 - Prob. 35PCh. 9 - Prob. 36PCh. 9 - Prob. 37PCh. 9 - Prob. 38PCh. 9 - Prob. 39PCh. 9 - Prob. 40PCh. 9 - Starting with cyclohexene, how can the following...Ch. 9 - Prob. 42PCh. 9 - The pKa of acetic acid in water is 4.76. What...Ch. 9 - Prob. 44PCh. 9 - Prob. 45PCh. 9 - Prob. 46PCh. 9 - Prob. 47PCh. 9 - Prob. 48PCh. 9 - Prob. 49PCh. 9 - Prob. 50PCh. 9 - Prob. 51PCh. 9 - tert-Butyl chloride undergoes solvolysis in both...Ch. 9 - Prob. 53PCh. 9 - Prob. 54PCh. 9 - In which solventethanol or diethyl etherwould the...Ch. 9 - Prob. 56PCh. 9 - Two bromoethers are obtained from the reaction of...Ch. 9 - Prob. 58PCh. 9 - Prob. 59PCh. 9 - Prob. 60PCh. 9 - Propose a mechanism for the following reaction:Ch. 9 - Prob. 62PCh. 9 - Prob. 63PCh. 9 - Prob. 64PCh. 9 - Prob. 65PCh. 9 - When equivalent amounts of methyl bromide nod...Ch. 9 - Prob. 67PCh. 9 - The reaction of chloromethane with hydroxide ion...
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
- Provide an explanation without using the pka values : Why is phenol stronger acid than butanoic acid?arrow_forwardThe pKa values of the carboxylic acid groups of oxaloacetic acid are 2.22 and 3.98. 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.arrow_forwardThe pKa values of the carboxylic acid groups of oxaloacetic acid are 2.22 and 3.98.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 pH3.1, 13% at pH 4.7, 6% at pH 6.7, and 6% at pH 12.7. Explain this pH dependence.arrow_forward
- What is the lowest pH buffer that could effectively be made with a weak acid that has a pK a of 5.418?arrow_forwardTwo pKa values are reported for malonic acid, a compound with twoCOOH groups. Explain why one pKa is lower and one pKa is higher thanthe pKa of acetic acid (CH3COOH, pKa = 4.8).arrow_forwardCalculate the pH of 1.25x10^-2 M of the decongestantephedrine hydrochloride if the pKb of ephedrine (itsconjugate base) is 3.86.arrow_forward
- Most of the pKa values given in this text were determined in water. How would the pKa values of carboxylic acids, alcohols, ammonium ions (RN+H3) , phenol, and an anilinium ion (C6H5N+H3) + change if they were determined in a solvent less polar than waterarrow_forwardWhat is the pKa of a weak acid with a Ka of 4.7 X 10-6?arrow_forwardAt what pH will 25% of a compound with a pKa of 5.3 be in its basic form?arrow_forward
- Find the pH of 0.051 M trimethylammomium chloride solution given a pKa of 9.799 for the trimethylammonium ion.arrow_forwardCarnosine, found in muscle and brain tissue, acts as a buffer to neutralize small amounts of acid. The pKa of the conjugate acid of carnosine is close to 7.0. What is its structure?arrow_forwardConsider the properties of sodium carbonate (Na2CO3), potassium carbonate (K2CO3), andsodium hydroxide (NaOH). How do they differ by pKa? Nucleophilicity? Solubility?arrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
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