Organic Chemistry, Books a la Carte Edition (8th Edition)
8th Edition
ISBN: 9780134074580
Author: Bruice, Paula Yurkanis
Publisher: PEARSON
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Chapter 19.7, Problem 17P
Interpretation Introduction
Interpretation:
The reason should be given for
Concept Introduction:
Imidazole is the
Pyrroles are the five membered rings containing nitrogen atom and the pi cloud contains three pairs of pi electrons.
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Provide an explanation without using the pka values :
Why is phenol stronger acid than butanoic acid?
Why is imidazole a stronger acid (pKa = 14.4) than pyrrole (pKa ~ 17)?
3. Which is the stronger acid:
(a) Benzoic acid with a Ka of 6.5 x10-5 or hydrocyanic acid with a Ka of 4.9 x 10-10?
(b) Boric acid with a pKa of 9.14 or carbonic acid with a pKa of 6.37
Chapter 19 Solutions
Organic Chemistry, Books a la Carte Edition (8th Edition)
Ch. 19.1 - Name the following:Ch. 19.2 - Prob. 3PCh. 19.2 - Prob. 4PCh. 19.3 - Draw the product of each of the following...Ch. 19.5 - Prob. 6PCh. 19.5 - Explain why cyclopentadiene (pKa = 15) is more...Ch. 19.5 - When pyrrole is added to a dilute solution of...Ch. 19.6 - Prob. 10PCh. 19.6 - How to the mechanisms of the following reactions...Ch. 19.6 - Prob. 12P
Ch. 19.6 - Rank the following compounds from easiest to...Ch. 19.7 - Prob. 14PCh. 19.7 - Prob. 15PCh. 19.7 - Prob. 16PCh. 19.7 - Prob. 17PCh. 19.7 - Prob. 18PCh. 19.7 - Prob. 19PCh. 19.7 - Prob. 20PCh. 19 - Name the following:Ch. 19 - Prob. 22PCh. 19 - Rank the following compounds from strongest acid...Ch. 19 - Which of the following compounds is easier to...Ch. 19 - Rank the following compounds from most reactive to...Ch. 19 - One of the following compounds undergoes...Ch. 19 - Benzene undergoes electrophilic aromatic...Ch. 19 - Pyrrole reacts with excess...Ch. 19 - The dipole moments of furan and tetrahydrofuran...Ch. 19 - Name the following:Ch. 19 - Prob. 31PCh. 19 - Prob. 32PCh. 19 - a. Draw resonance contributors to show why...Ch. 19 - The chemical shifts of the C-2 hydrogen in the...Ch. 19 - Explain why protonating aniline has a dramatic...Ch. 19 - Prob. 36PCh. 19 - Propose a mechanism for the following reaction:Ch. 19 - Prob. 38PCh. 19 - Propose a mechanism for the following reactions:Ch. 19 - Prob. 40PCh. 19 - Prob. 41PCh. 19 - Prob. 42PCh. 19 - Organic chemists work with tetraphenylporphyrins...Ch. 19 - Show how the following compounds can be prepared...
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- The pka for 2-hydroxybenzoic acid (i.e. salicylic acid, used in pain relief and a precursor for aspirin) is 2.98, while the pKa for 3-hydroxybenzoic acid (found in castoreum, a scent- marking substance secreted by beavers) is 4.08. What does this difference in pK₂ tell us about the relative acidities of these two compounds?, Why is there such a significant difference? OH OH 2-hydroxybenzoic acid (pKa = 2.98) OH OH 3-hydroxybenzoic acid (pKa 4.08)arrow_forwardTwo pKa values are reported for malonic acid, a compound with two COOH groups. Explain why one pKa is lower and one pKa is higher than the pKa of acetic acid (CH3COOH, pKa = 4.8).arrow_forwardWhat do you mean by carbon acid? What is the range of their pKa's?arrow_forward
- Draw acid-base equilibrium for sulfamethoxazole (pka 5.8), and suldapyridine (pKa 8.4).arrow_forwardWhat is the conjugate acid of acetamide and its pka value?arrow_forwardIf compound A has a ka of 3.0 x 10-11 , compound B has a ka of 1.1 x 10-10 and compound C has a ka of 1.8 x 10-5, which compound is the weakest acid?arrow_forward
- Using pKa Values to Determine Relative Acidity and Basicity Rank the following compounds in order of increasing acidity, and then rank their conjugate bases in order of increasing basicity.arrow_forwardThe pKa for Molecule A is 10 units lower than Molecule B. Molecule A Draw conjugate base of A :B H H pKa = 10 Molecule B Draw conjugate base of B OCH3 :B H H pКa 3 20 Please provide a brief explanation for the difference in pKa of these to molecules.arrow_forwardWhat is the ratio of ionized:unionized amine of glycine (pKa 9.60) in a solution at pH 8.0?arrow_forward
- For this assignment I want you to look up some of the following compounds with their conjugate acid or base. Look up the compounds pka. Draw each compound in a solution that has a pH of 1, a pH of 7 and a pH of 11. Acetic acid Acetylsalicylic acid Triethylamine Alanine (this compound is amphoteric and has multiple acidic protons)arrow_forwardNaming dicarboxylic acids and their pKa values:arrow_forwardDefine why are protons on an alpha carbon of an aldehyde or ketone more acidic than a proton on an alpha carbon of an ester? What are their pKa's?arrow_forward
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