Organic Chemistry (8th Edition)
8th Edition
ISBN: 9780134042282
Author: Paula Yurkanis Bruice
Publisher: PEARSON
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Chapter 15.4, Problem 7P
- a. What is the product of the reaction of acetyl chloride with HO-? The pKa of HCl is −7; the pKa of H2O is 15.7.
- b. What is the product of the reaction of acetamide with HO-? The pKa of NH3 is 36; the pKa of H2O is 15.7.
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Chapter 15 Solutions
Organic Chemistry (8th Edition)
Ch. 15.1 - The aromas of many flowers and fruits are due to...Ch. 15.1 - Name the following:Ch. 15.1 - Prob. 3PCh. 15.2 - Which is longer, the carbon-oxygen single bond in...Ch. 15.2 - There are three carbon-oxygen bonds in methyl...Ch. 15.2 - Prob. 6PCh. 15.4 - a. What is the product of the reaction of acetyl...Ch. 15.4 - What is the product of an acyl substitution...Ch. 15.5 - a. Which compound has the stretching vibration for...Ch. 15.5 - Using the pKa values listed in Table 15.1, predict...
Ch. 15.5 - Is the following statement true or false? If the...Ch. 15.6 - Starting with acetyl chloride, what neutral...Ch. 15.6 - Prob. 13PCh. 15.7 - Starting with methyl acetate, what neutral...Ch. 15.7 - We saw that it is necessary to use excess amine in...Ch. 15.7 - Prob. 17PCh. 15.7 - Which ester hydrolyzes more rapidly? a. methyl...Ch. 15.7 - a. state three factors that cause the uncatalyzed...Ch. 15.8 - Prob. 21PCh. 15.8 - Using the mechanism for the acid-catalyzed...Ch. 15.8 - Prob. 23PCh. 15.8 - Show the mechanism for the acid-catalyzed...Ch. 15.8 - Prob. 25PCh. 15.8 - Write the mechanism for the acid-catalyzed...Ch. 15.8 - Write the mechanism for the acid-catalyzed...Ch. 15.9 - Prob. 28PCh. 15.9 - Prob. 29PCh. 15.10 - Show how each of the following esters could he...Ch. 15.10 - Prob. 32PCh. 15.11 - Prob. 33PCh. 15.11 - Which of the following reactions leads to the...Ch. 15.12 - Prob. 35PCh. 15.12 - Prob. 36PCh. 15.13 - Prob. 37PCh. 15.14 - Prob. 38PCh. 15.14 - Prob. 39PCh. 15.15 - Prob. 40PCh. 15.15 - Which alkyl halides from the carboxylic acids...Ch. 15.16 - Prob. 43PCh. 15.16 - Prob. 44PCh. 15.16 - Prob. 45PCh. 15.17 - Prob. 46PCh. 15.18 - How could you synthesize the following compounds...Ch. 15 - Prob. 48PCh. 15 - Name the following:Ch. 15 - Prob. 50PCh. 15 - What compound are obtained from the fallowing...Ch. 15 - a. Rank the following esters in order of...Ch. 15 - Because bromocyclohexane is a secondary alkyl...Ch. 15 - a. Which compound would you expect to have a...Ch. 15 - How could you use 1H NMR spectroscopy to...Ch. 15 - Rank the following compounds in order of...Ch. 15 - Prob. 57PCh. 15 - Prob. 58PCh. 15 - Prob. 59PCh. 15 - A compound with molecular formula C5H10O2 gives...Ch. 15 - Prob. 61PCh. 15 - Prob. 62PCh. 15 - Prob. 63PCh. 15 - Prob. 64PCh. 15 - Prob. 65PCh. 15 - Prob. 66PCh. 15 - Two products, A and B, are obtained from the...Ch. 15 - Prob. 68PCh. 15 - Prob. 69PCh. 15 - Prob. 70PCh. 15 - Prob. 71PCh. 15 - Prob. 72PCh. 15 - When treated with an equivalent of methanol,...Ch. 15 - a. Identify the two products obtained from the...Ch. 15 - Prob. 75PCh. 15 - Prob. 76PCh. 15 - a. When a carboxylic acid is dissolved in...Ch. 15 - Prob. 78PCh. 15 - Identity the major and minor products of the...Ch. 15 - When a compound with molecular formula C11H14O2...Ch. 15 - Prob. 81PCh. 15 - Prob. 82PCh. 15 - Prob. 83PCh. 15 - The 1H NMR spectra for two esters with molecular...Ch. 15 - Show how the following compounds could be prepared...Ch. 15 - Prob. 86PCh. 15 - Prob. 87PCh. 15 - The intermediate shown here is formed during the...Ch. 15 - Prob. 89PCh. 15 - Propose a mechanism that accounts for the...Ch. 15 - Catalytic antibodies catalyze a reaction by...Ch. 15 - Prob. 92P
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Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.Similar questions
- mention the conjugate bases and use structures to explain the following: a. why is the alpha proton of a ketone (pKa ~ 16) is more acidic than the protons in CH3CH3? b. why is the alpha proton of a ketone (pKa ~ 16) is more acidic than the protons in a ester (pKa ~ 35)? c. why are the hydrogens in a C-H bond like CH3CH3 difficult to remove?arrow_forwardDimethyl ether (CH,OCH) and ethanol (CH,CH,OH) are isomers, but CH,OCH, has a pka of 40 and CH,CH2OH has a pka of 16. Why are these pKa values so different?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
- The pKa values of the carboxylic acid groups of oxaloacetic acid are 2.22 and 3.98. 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.arrow_forwardExplain the difference in acidity between p-methoxybenzoic acid (pKa = 4.46) and m-methoxybenzoic acid (pKa = 4.09)arrow_forwardThe pK, of H2O is 15.7 and the pKa of CH3COOH is 4.8. What label and reason correctly describe a reaction between H20 and CH3COOH? CH3COOH will be the base because its pKa is lower. O H20 will be the acid because its pKa is greater. CH3COOH will be the acid because it is the stronger acid. H20 will be the acid because it is the stronger acid.arrow_forward
- Draw the product formed when phenylacetic acid (C6H5CH2COOH) is treated with each reagent. With some reagents, no reaction occurs. a. NaHCO3 b. NaOH c. SOCl2 d. NaCl e. NH3(1equiv) f. NH3, ∆ g. CH3OH, H2SO4 h. CH3OH, −OH i. [1] NaOH; [2] CH3COCl j. CH3NH2, DCC k. [1] SOCl2; [2] CH3CH2CH2NH2 (excess) l. [1] SOCl2; [2] (CH3)2; [2] (CHarrow_forwardCalculate the Ka's for the following acids: (a) Citric acid, pKa = 3.14 (b) Tartaric acid, pKa = 2.98arrow_forwardThe pKa values of the carboxylic acid groups of oxaloacetic acid are 2.22 and 3.98.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 pH3.1, 13% at pH 4.7, 6% at pH 6.7, and 6% at pH 12.7. Explain this pH dependence.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_forwardWhy does the Ka values decrease at each deprotonation in the reaction between naoh and h3po4?arrow_forwardUsing the table of pKa values given in Appendix I, answer the following: a. Which is the most acidic organic compound in the table? b. Which is the least acidic organic compound in the table? c. Which is the most acidic carboxylic acid in the table? d. Which is more electronegative: an sp3 oxygen or an sp2 oxygen? (Hint: Pick a compound in Appendix I with a hydrogen attached to an sp2 oxygen and one with a hydrogen attached to an sp3 oxygen and compare their pKa values.) e. Which compounds demonstrate that the relative electronegativities of a hybridized nitrogen atom are sp 7 sp2 7 sp3?arrow_forward
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