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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Provide an explanation without using the pka values :
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Calculate the ratio of ethyl amine (CH3CH2NH2) to the ethyl ammonium ion (CH3CH2NH3+) in a solution with a pH of 11.0. pKa for CH3CH2NH3+ = 10.636.
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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- The pkb of methylamine, CH3NH2, is 3.36. Calculate the pka of its conjugate acid, CH3NH3*. pka =arrow_forward3. 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_forwardWhat is the ratio of ionized:unionized amine of glycine (pKa 9.60) in a solution at pH 8.0?arrow_forward
- The 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_forwardAt what pH will 25% of a compound with a pKa of 5.3 be in its basic form?arrow_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_forward
- 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_forwardThe pKas of the conjugate acids of -OH (conjugate acid H2O) and HPO42- (conjugate acid H2PO4-) are 15.7 and 6.8, respectively. First, identify which is the strong base, and which is the weak base. Then, explain how you can use these pKa values to help you identify which compounds will be separated at each step.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. 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)?arrow_forward
- assign the acid its appropriate pKaarrow_forwardCan any functional groups on Risperidone ionize? If so, which ones? Under what conditions? What are the pKa values of these functional groups? Write the structures in their correct ionization state at physiological pH.arrow_forwardI mostly need help setting up how to do the math for these problems. I also need help with knowing how to find which acid is the strongest. Give the Ka or pKa values that should be entered in the blanks below. pKa = -log10ka ; Ka = 10-pKa (a) hydrocyanic acid: Ka = 4.92 x 10-10 ; pKa = (b) acetic acid: Ka = ; pKa = 4.75 (c) lactic acid: Ka = 8.40 x 10-4 ; pKa = (d) formic acid: Ka = ; pKa = 3.75 (e) Which of these acids is the strongest?arrow_forward
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