Organic Chemistry (8th Edition)
8th Edition
ISBN: 9780134042282
Author: Paula Yurkanis Bruice
Publisher: PEARSON
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Chapter 16.8, Problem 28P
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It should be explained that why the
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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...”)
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)?
Two 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).
Chapter 16 Solutions
Organic Chemistry (8th Edition)
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
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- What is the ratio of ionized:unionized amine of glycine (pKa 9.60) in a solution at pH 8.0?arrow_forwardAt what pH will 25% of a compound with a pKa of 5.3 be in its basic form?arrow_forwardThe 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_forward
- Carnosine, 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_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_forwardRank the pKa values of the conjugate acids for nosylate, tosylate, and brosylatearrow_forward
- The simplest amino acid is glycine. The pKa value for its carboxylic acid group is 2.34 and the pKa value for the conjugate acid of the amino group is 9.60. Draw the product of the acid-base reaction that would take place when glycine reacts with itself..give a clear handwritten answerarrow_forwardThe pKa values of the conjugate acids of 2-aminopyridine (6.71) and 4- aminopyridine (9.11) are as shown. Why are these structures so much more basic than pyridine?arrow_forwardProvide an explanation without using the pka values : Why is phenol stronger acid than butanoic acid?arrow_forward
- Explain the reactions involved in separation of p-nitroaniline from mixture contain 3 components 1.Benzoic acid (acidic nature pKa=4.17) 2.Naphthalene (neutral compound) 3.paraNitroaniline(basic compound pKa=12.99arrow_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_forwardThe pKa values of the conjugate acids of 2-aminopyridine (6.71) and 4- aminopyridine (9.11) are as shown. Which nitrogen is the more basic in these structures and why?arrow_forward
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