ORG.CHEMISTRY W/ACCESS+MODEL KIT PKG
5th Edition
ISBN: 9781260701128
Author: SMITH
Publisher: MCG
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Chapter 19, Problem 19.53P
The
why acetamide is less acidic than
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Using pKa Values to Determine Relative Acidity and Basicity Rank the following compounds in order of increasing acidity, and then rank their conjugate bases in order of increasing basicity.
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Chapter 19 Solutions
ORG.CHEMISTRY W/ACCESS+MODEL KIT PKG
Ch. 19 - Prob. 19.1PCh. 19 - Problem 19.2 Give the structure corresponding to...Ch. 19 - Problem 19.3 Draw the structure corresponding to...Ch. 19 - Prob. 19.4PCh. 19 - Prob. 19.5PCh. 19 - Problem 19.6 Rank the following compounds in order...Ch. 19 - Problem 19.7 Explain how you could use IR...Ch. 19 - Prob. 19.8PCh. 19 - Problem 19.9 How many tetrahedral stereogenic...Ch. 19 - Problem 19.10 What alcohol can be oxidized to each...
Ch. 19 - Problem 19.11 Identify A-D in the following...Ch. 19 - Problem 9.12 Draw the cation that results when a...Ch. 19 - Problem 19.13 Draw the products of each acid-base...Ch. 19 - Problem 19.14 Given the values in Appendix A,...Ch. 19 - Problem 19.15 Rank the labeled protons in...Ch. 19 - Problem 19.16 Match each of the following values ...Ch. 19 - Problem 19.17 Rank the compounds in each group in...Ch. 19 - Problem 19.18 Rank the compounds in each group in...Ch. 19 - Prob. 19.19PCh. 19 - Problem 19.20 Which of the following pairs of...Ch. 19 - Problem 19.21 Two other commonly used sulfonic...Ch. 19 - Problem 19.22 Draw both enantiomers of each amino...Ch. 19 - Problem 19.23 Explain why amino acids, unlike most...Ch. 19 - Problem 19.24 Draw the positively charged,...Ch. 19 - Prob. 19.25PCh. 19 - Problem 19.26 Explain why the of the group of...Ch. 19 - Answer each question for A and B depicted in the...Ch. 19 - Prob. 19.28PCh. 19 - 19.29 Give the IUPAC name for each compound.
a....Ch. 19 - 19.30 Draw the structure corresponding to each...Ch. 19 - Prob. 19.31PCh. 19 - 19.32 Rank the following compounds in order of...Ch. 19 - 19.33 Draw the organic products formed in each...Ch. 19 - 19.34 Identify the lettered compounds in each...Ch. 19 - 19.35 Using the table in Appendix A, determine...Ch. 19 - 19.36 Draw the products of each acid-base...Ch. 19 - 19.37 Which compound in each pair has the lower ?...Ch. 19 - 19.38 Rank the compounds in each group in order of...Ch. 19 - 19.39 Rank the compounds in each group in order of...Ch. 19 - 19.40 Match the values to the appropriate...Ch. 19 - Prob. 19.41PCh. 19 - 19.42 Which carboxylic acid has the lower ,...Ch. 19 - Prob. 19.43PCh. 19 - 19.44 Explain the following statement. Although...Ch. 19 - Prob. 19.45PCh. 19 - 19.46 Explain why the of compound A is lower than...Ch. 19 - 19.47 Rank the following compounds in order of...Ch. 19 - Prob. 19.48PCh. 19 - Prob. 19.49PCh. 19 - 19.50 Draw all resonance structures of the...Ch. 19 - As we will see in Chapter 23, CH bonds are...Ch. 19 - Prob. 19.52PCh. 19 - The pKa of acetamide (CH3CONH2) is 16. Draw the...Ch. 19 - 19.54 Write out the steps needed to separate...Ch. 19 - Prob. 19.55PCh. 19 - Can octane and octan -1- ol be separated using an...Ch. 19 - 19.57 Identify each compound from its spectral...Ch. 19 - 19.58 Use the NMR and IR spectra given below to...Ch. 19 - 19.59 An unknown compound (molecular formula )...Ch. 19 - 19.60 Propose a structure for (molecular formula...Ch. 19 - 19.61 Match the data to the appropriate...Ch. 19 - Prob. 19.62PCh. 19 - Prob. 19.63PCh. 19 - Prob. 19.64PCh. 19 - 19.65 For each amino acid ,draw its neutral,...Ch. 19 - Calculate the isoelectric point for each amino...Ch. 19 - 19.67 Lysine and tryptophan are two amino acids...Ch. 19 - Prob. 19.68PCh. 19 - Prob. 19.69PCh. 19 - Prob. 19.70PCh. 19 - 19.71 Hydroxy butanedioic acid occurs naturally in...Ch. 19 - 19.72 Although it was initially sold as a rat...
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- In each pair, select the stronger acid. (a) Pyruvic acid (pKa 2.49) or lactic acid (pKa 3.08) (b) Citric acid (pKa1 3.08) or phosphoric acid (pKa1 2.10)arrow_forwardRank the following substances in order of increasing acidity: (a) (CH3)2CHOH, HC≡CH, (CF3)2CHOH, CH3OH (b) Phenol, p-methylphenol, p-[trifluoromethyl) phenol (c) Benzyl alcohol, phenol, p-hydroxybenzonic acidarrow_forwardWhat is the relative trend in acidity and pKa of the two compounds? a. Structure I is the most acidic, and Structure I has the highest pKa. b. Structure I is the most acidic, and Structure I has the lowest pKa. c. Structure II is the most acidic, and Structure I has the highest pKa. d. Structure II is the most acidic, and Structure I has the lowest pKa.arrow_forward
- 18-28 Arrange these compounds in order of increasing acidity: benzoic acid, benzyl alcohol, phenol.arrow_forward18-31 Formic acid is one of the components responsible for the sting of biting ants and is injected under the skin by bee and wasp stings. The pain can be relieved by rubbing the area of the sting with a paste of baking soda (NaHCO3) and water, which neutralizes the acid. Write an equation for this reaction.arrow_forwardThe following pKa values have been measured. Explain why a hydroxyl group in the para position decreases the acidity while a hydroxyl group in the meta position increases the acidity.arrow_forward
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