ORGANIC CHEMISTRY
5th Edition
ISBN: 9781259977596
Author: SMITH
Publisher: MCG
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Textbook Question
Chapter 19, Problem 19.36P
Draw the products of each acid-base reaction, and using the
a. 
c. 
b. 
d. 
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The conjugate base of benzoic acid is used as a
72
preservative. Write the equilibrium reaction for this
weak acid in aqueous solution.
ОН
Benzoic acid
a. What substances are present at equilibrium?
b. At equilibrium, are reactants or products favored,
and why?
c. Are the concentrations of benzoic acid and
benzoate constant or changing at equilibrium?
d. What happens to the equilibrium if more
hydronium ions are added to the reaction?
e. Label the conjugate acid-base pairs.
4. What is the conjugate acid of OH-
A. H2O
B. 0-2
c.02
D.O
Which compound is considered as the conjugate base? *
D. OH-
B. C2H5NH+3
C. H2O
A. C2H5NH2
Chapter 19 Solutions
ORGANIC CHEMISTRY
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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- Predict which of these acid-base reactions are product-favored and which are reactant-favored. In each case write a balanced equation for any reaction that might occur, even if the reaction is reactant-favored. Consult Table 14.2 if necessary. (a) NH4+(aq)+HPO42(aq) (b) CH3COOH(aq) + OH(aq) (c) HSO4(aq)+H2PO4(aq) (d) CH3COOH(aq) + F(aq)arrow_forwardSalicylic acid, HOC6H4CO2H, and its derivatives have been used as pain relievers for a long time. Salicylic acid occurs in small amounts in the leaves, bark, and roots of some vegetation (most notably historically in the bark of the willow tree). Extracts of these plants have been used as medications for centuries. The acid was first isolated in the laboratory in 1838. (a) Bath functional groups of salicylic acid ionize in water, with Ka=1.0103 for the—CO2H group and 4.201013 for the -OH group. What is the pH of a saturated solution of the acid (solubility = 1.8 g/L).. (b) Aspirin was discovered as a result of efforts to produce a derivative of salicylic acid that would not be irritating to the stomach lining. Aspirin is acetylsalicylic acid, CH3CO2C6H4CO2H. The -CO2H functional group is still present, but its acidity is reduced, Ka=3.0104. What is the pH of a solution of aspirin with the same concentration as a saturated solution of salicylic acid (See Part a). (c) Under some conditions, aspirin reacts with water and forms a solution of salicylic acid and acetic acid: CH3CO2C6H4CO2H(aq)+H2O(l)HOC6H4CO2H(aq)+CH3CO2H(aq) i. Which of the acids, salicylic acid or acetic acid, produces more hydronium ions in such a solution? ii. What are the concentrations of molecules and ions in a solution produced by the hydrolysis of 0.50 g of aspirin dissolved in enough water to give 75 mL of solution?arrow_forwardSulfanilic acid, which is used in making dyes, is made by reacting aniline with sulfuric acid. (a) Is aniline a Brnsted base, a Lewis base, or both? Explain, using its possible reactions with HCl, BF3, or other acid. (b) Sulfanilic acid has a pKa value of 3.23. The sodium salt of the acid, Na(H2NC6H4SO3), is quite soluble in water. If you dissolve 1.25 g of the salt in water to give 125 ml, of solution, what is the pH of the solution?arrow_forward
- How is acid strength related to the value of Ka? What is the difference between strong acids and weak acids (see Table 13-1)? As the strength of an acid increases, what happens to the strength of the conjugate base? How is base strength related to the value of Kb? As the strength of a base increases, what happens to the strength of the conjugate acid?arrow_forwardSeveral acids and their respective equilibrium constants are: Which is the strongest acid? Which is the weakest acid? Which acid has the weakest conjugate base? Which acid has the strongest conjugate base?arrow_forward2 Classify each compound as a Lewis base, a Brønsted-Lowry base, both, or neither. b. CH3-CI d. a. C. H.arrow_forward
- For each conjugate acid-base pair, identify the first species as an acid or base and the second species as the conjugate acid or base of the first. A) H₂CO3 and B) HCO3 A. is B. is C) CH3CH₂O and D) CH3CH₂OH C. is D. isarrow_forwarddentify the conjugate base in the reaction of propanoic acid CH3CH3COOH reacting with methyl amine, CH3NH2. a. CH3NH2 b. CH3CH3COOH c. CH3NH3+ d. OH-1 e. CH3CH3COO-1arrow_forwardWhat is the conjugate acid of NH 3? A. NH4 B. NH3 C. NH3* D. NH2*arrow_forward
- Which of the following aqueous solutions should demonstrate the most nonideal behavior? Select one: a. 0.1 M Nal b. 0.2 M CuSO4 c.0.5 M KBr d. 2.0 M CuCl₂ e. 2.5 M CSCI Xarrow_forward19. Which species is the conjugate base of NH3? A. NH4+ B. H2O C. NH4OH D. NH2 E. NH2-arrow_forwarda.Draw the conjugate acid of each base: NH3, Cl−, (CH3)2C=O b. Draw the conjugate base of each acid: HBr, HSO4−, CH3OH.arrow_forward
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