Organic Chemistry (8th Edition)
8th Edition
ISBN: 9780134042282
Author: Paula Yurkanis Bruice
Publisher: PEARSON
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Textbook Question
Chapter 16, Problem 95P
The pKa values of the
- 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.
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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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- Calculate the percentages of dissociated and undissociated forms present in the following solutions: (a) 0.0010 M glycolic acid (HOCH2CO2H; pKa = 3.83) at pH = 4.50 (b) 0.0020 M propanoic acid (pKa = 4.87) at pH = 5.30arrow_forwardWhich has the larger numerical value? (a) The pKa of a strong acid or the pKa of a weak acid (b) The Ka of a strong acid or the Ka of a weak acidarrow_forwardWhich has the larger numerical value? Q.) The pKa of a strong acid or the pKa of a weak acidarrow_forward
- Which of the following functional groups will increase acidity? I. -NO2 II. -CH2CH3 III. -OCH3 IV. - Clarrow_forwardFor a solution of formic acid, a weak acid with a pKa of 8.74, at what pH will the concentration of formic acid be equal to the concentration of formate, the conjugate weak base of formic acid. Report the value using 3 significant figures.arrow_forwardQuestion 8. For each of following organic acids fill in the table: acid Draw the Mark by X the Estimate pka conjugated base strongest acidarrow_forward
- Arrange the compounds in order of increasing base strength. Consult the table for the pK, values of each conjugate acid pK, values of conjugate acids. a. Acid pKa Acid pKa CH3 CH3 51 H3PO, 2.1 H2 35 HNOS -1.5 H2O 15.7 H3O+ -1.74 H2CO3 10.33 H2SO4-5.2 H2S 7.04 HBr -8 C6 H5 COOH 4.19 (Suppose the strongest base is b, the base of intermediate strength is c, and the weakest base is a. Then this leads to the follow C H5 COO H2PO4 H aarrow_forwardMcq also give some explanationarrow_forwardArrange the following carboxylic acids in order of decreasing acid strength ( strongest to weakest). A. CICH2COOH B. BRCH2COOH C. FCH2COOH D. ICH2COOH OC>A> D> B O C> B> A> D OD>A> B >C O C>A> B> Darrow_forward
- The pka of butanoic acid is 4.82. butanoic acid a. Draw the structure that predominates at a pH of 1.50. b. Draw the structure that predominates at a pH of 9.40. c. Calculate the ratio of conjugate base to acid at a pH of 1.50 d. Calculate the ratio of conjugate base to acid at a pH of 9.40.arrow_forward2. Sulfurous acid is a diprotic acid that forms when SO2(g) dissolves in water A. Draw a principal species diagram for sulfurous acid B. At what pH is [H2A] = [HA¯]? C. At what pH is [HA¯] = [A?-]? D. Which is the principal species at pH 4? E. Which is the principal species at pH 10?arrow_forwardWrite equations for the reaction of each compound with BF3 a Lewis acid Q.CH3CH2NHCH2CH3arrow_forward
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