Organic Chemistry - Access
7th Edition
ISBN: 9780321820020
Author: Bruice
Publisher: PEARSON
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Chapter 20.7, 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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A naturally occurring amino acid such as alanine has a group that is a carboxylic acid and a group that is a protonated amine. The pKa values of the two groups are shown.(a). If the pKa value of a carboxylic acid such as acetic acid is about 5, 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)?
Provide an explanation without using the pka values :
Why is phenol stronger acid than butanoic acid?
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...”)
Chapter 20 Solutions
Organic Chemistry - Access
Ch. 20.1 - Name the following:Ch. 20.2 - Prob. 2PCh. 20.2 - Prob. 3PCh. 20.3 - Draw the product of each of the following...Ch. 20.5 - Prob. 6PCh. 20.5 - When pyrrole is added to a dilute solution of...Ch. 20.5 - Explain why cyclopentadiene (pKa = 15) is more...Ch. 20.6 - Prob. 10PCh. 20.6 - How to the mechanisms of the following reactions...Ch. 20.6 - Prob. 12P
Ch. 20.6 - Rank the following compounds from easiest to...Ch. 20.7 - Prob. 14PCh. 20.7 - Prob. 15PCh. 20.7 - Prob. 16PCh. 20.7 - Prob. 17PCh. 20.7 - Prob. 18PCh. 20.7 - Prob. 19PCh. 20.7 - Prob. 20PCh. 20 - Name the following:Ch. 20 - Prob. 22PCh. 20 - Prob. 23PCh. 20 - Which of the following compounds is easier to...Ch. 20 - Rank the following compounds from most reactive to...Ch. 20 - One of the following compounds undergoes...Ch. 20 - Benzene undergoes electrophilic aromatic...Ch. 20 - The dipole moments of furan and tetrahydrofuran...Ch. 20 - Prob. 29PCh. 20 - Prob. 30PCh. 20 - The chemical shifts of the C-2 hydrogen in the...Ch. 20 - Explain why protonating aniline has a dramatic...Ch. 20 - Prob. 33PCh. 20 - Propose a mechanism for the following reaction:Ch. 20 - Prob. 35PCh. 20 - Propose a mechanism for the following reactions:Ch. 20 - Prob. 37PCh. 20 - a. Draw resonance contributors to show why...Ch. 20 - Prob. 39PCh. 20 - Pyrrole reacts with excess...Ch. 20 - Prob. 41PCh. 20 - Prob. 42PCh. 20 - Organic chemists work with tetraphenylporphyrins...
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- 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 6.37arrow_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_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_forward
- The side chain of acetyl-L-lysine-OMe has a pKa=10.5 and its acid-dissociation reaction is shown below. C. what is the pH of a solution wherein the ration of [A-]/[HA]=1:10?arrow_forwardWhich of the following acid/conjugate base pairs has a pKa value of 9.44? A. Ammonium/ammonia B. carboxylic acid/carboxylate C. imidazolium/imidazolearrow_forwardThe 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?arrow_forward
- Calculate the pKa of a acid at 25°C if its conjugate base has a pKb = 1.19arrow_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_forwardAt what pH will 25% of a compound with a pKa of 5.3 be in its basic form?arrow_forward
- What is the conjugate acid of acetamide and its pka value?arrow_forwardThe side chain of acetyl-L-lysine-OMe has a pKa=10.5 and its acid-dissociation reaction is shown below. B. At what pH does [A-]=[HA]?arrow_forwardPhthalic acid and isophthalic acid have protons on two carboxy groups that can be removed with base. (a) Explain why the pKa for loss of the first proton (pKa1) is lower for phthalic acid than isophthalic acid. (b) Explain why the pKa for loss of the second proton (pKa2) is higher for phthalic acid than isophthalic acid.arrow_forward
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