Organic Chemistry
12th Edition
ISBN: 9781118875766
Author: T. W. Graham Solomons, Craig B. Fryhle, Scott A. Snyder
Publisher: WILEY
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Chapter 3, Problem 1LGP
List all the chemical species likely to be present at the end of the reaction but before adding aqueous
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CH3CH2COOH
Draw the Lewis structure of the acid and mark the acidic hydrogen with an asterisk (*).
Draw a Lewis structure of the conjugate base of the acid.
Suppose the acid is neutralized with a strong base.
a) Which of the two structures you drew in 6 and 7 would be the predominant form of the species at a pH well above that at the equivalence point?
b) Which of the two structures would be the predominant form of the species at a very low pH, well below that at the equivalence point and similar to the pH near the start of the titration?
c) At what point in the titration, if any, would there be equal amounts of the two forms?
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drawing complete Lewis structures for both reactants and products, along with arrows to show the
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and justify your answer. (c) Calculate the pK, values for the conjugate bases of the acids in
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NH t H20 H30®
CHy Cita OH +Ho 1300 + CHzchb0s pka =15:9
+ NH3 pkw =9.24
Predict whether aqueous solutions of the following substances are acidic, basic, or neutral and write hydrolysis equations for the acidic and basic solutions.
(a) CsBr; (b) Al(NO3)3; (c) KCN; (d) CH3NH3Cl
Chapter 3 Solutions
Organic Chemistry
Ch. 3 - Prob. 1PPCh. 3 - PRACTICE PROBLEM 3.2
Write equations showing the...Ch. 3 - PRACTICE PROBLEM 3.3 Which of the following are...Ch. 3 - Prob. 4PPCh. 3 - PRACTICE PROBLEM 3.5 Formic acid (HCO2H) has...Ch. 3 - Prob. 6PPCh. 3 - Prob. 7PPCh. 3 - Prob. 8PPCh. 3 - PRACTICE PROBLEM 3.9 Predict the outcome of the...Ch. 3 - Prob. 10PP
Ch. 3 - Prob. 11PPCh. 3 - Prob. 12PPCh. 3 - Prob. 13PPCh. 3 - Prob. 14PPCh. 3 - PRACTICE PROBLEM 3.15 Nitro groups have a large...Ch. 3 - PRACTICE PROBLEM 3.16
Your laboratory instructor...Ch. 3 - Prob. 17PPCh. 3 - Prob. 18PPCh. 3 - Prob. 19PPCh. 3 - What is the conjugate base of each of the...Ch. 3 - List the bases you gave as answers to Problem 3.20...Ch. 3 - 3.22 What is the conjugate acid of each of the...Ch. 3 - List the acids you gave as answers to Problem 3.22...Ch. 3 - Rank the following in order of increasing acidity.Ch. 3 - Without consulting tables, select the stronger...Ch. 3 - Designate the Lewis acid and Lewis base in each of...Ch. 3 - Prob. 27PCh. 3 - Prob. 28PCh. 3 - Write an equation, using the curved-arrow...Ch. 3 - 3.30 What reaction will take place if ethyl...Ch. 3 - 3.31 (a) The of formic acid. What is the? (b)...Ch. 3 - Acid HA has pKa=20; acid HB has pKa=10. (a) Which...Ch. 3 - Prob. 33PCh. 3 - 3.34 (a) Arrange the following compounds in order...Ch. 3 - 3.35 Arrange the following compounds in order of...Ch. 3 - 3.36 Arrange the following in order of increasing...Ch. 3 - Prob. 37PCh. 3 - 3.38 Supply the curved arrows necessary for the...Ch. 3 - Glycine is an amino acid that can be obtained from...Ch. 3 - 3.40 Malonic acid, , is a diprotic acid. The for...Ch. 3 - 3.41 The free-energy change, , for the ionization...Ch. 3 - 3.42 At the enthalpy change, , for the ionization...Ch. 3 - The compound at right has (for obvious reasons)...Ch. 3 - 3.44.
(a) Given the above sequence of...Ch. 3 - Prob. 45PCh. 3 - Prob. 46PCh. 3 - 3.47 As noted in Table 3.1, the of acetone, , is...Ch. 3 - Formamide (HCONH2) has a pKa of approximately 25....Ch. 3 - List all the chemical species likely to be present...Ch. 3 - Prob. 2LGPCh. 3 - Prob. 3LGPCh. 3 - Prob. 4LGP
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- Weak base B has a pKb of 6.78 and weak acid HA has a pKa of 5.12. a Which is the stronger base, B or A? b Which is the stronger acid, HA or BH+? c Consider the following reaction: B(aq)+HA(aq)BH+(aq)+A(aq) Based on the information about the acid/base strengths for the species in this reaction, is this reaction favored to proceed more to the right or more to the left? Why? d An aqueous solution is made in which the concentration of weak base B is one half the concentration of its acidic salt, BHCl, where BH+ is the conjugate weak add of B. Calculate the pH of the solution. e An aqueous solution is made in which the concentration of weak acid HA twice the concentration of the sodium salt of the weak acid, NaA. Calculate the pH of the solution. f Assume the conjugate pairs B/BH+ and HA/A are capable of being used as color-based end point indicators in acidbase titrations, where B is the base form indicator and BH is the acid form indicator, and HA is the acid form indicator and A is the base form indicator. Select the indicator pair that would be best to use in each of the following titrations: (1) Titration of a strong acid with a strong base. (i) B/BH+ (ii) HA/A (2) Titration of a weak base with a strong acid. (i) B/BH+ (ii) HA/Aarrow_forwardWhat are the products of each of the following acid-base reactions? Indicate the acid and its conjugate base and the base and its conjugate acid. (a) HCIO4 + H2O (b) NH4 ++ H2O (c) HCO3 + OHarrow_forwardAmino acids are an important group of compounds. At low pH, both the carboxylic acid group (CO2H) and the amine group (NHR) are protonated. However, as the pH of the solution increases (say, by adding base), the carboxylic acid proton is removed, usually at a pH between 2 and 3. In a middle range of pHs, therefore, the amine group is protonated, but the carboxylic acid group has lost the proton. (This is called a zwitterion.) At more basic pH values, the amine proton is dissociated. What is the pH of a 0.20 M solution of alanine hydrochloride, [NH3CHCH3CO2H]Cl?arrow_forward
- Most naturally occurring acids are weak acids. Lactic acid is one example. CH3CH(OH)CO2H(s)+H2O(l)H3O+(aq)+CH3CH(OH)CO2(aq) If you place some lactic acid in water, it will ionize to a small extent, and an equilibrium will be established. Suggest some experiments to prow that this is a weak acid and that the establishment of equilibrium is a reversible process.arrow_forwardIonization of the first proton from H2SO4 is complete (H2SO4 is a strong acid); the acid-ionization constant for the second proton is 1.1 102. a What would be the approximate hydronium-ion concentration in 0.100 M H2SO4 if ionization of the second proton were ignored? b The ionization of the second proton must be considered for a more exact answer, however. Calculate the hydronium-ion concentration in 0.100 M H2SO4, accounting for the ionization of both protons.arrow_forward8-112 Consider an initial 0.040 M hypobromous acid (HOBr) solution at a certain temperature. At equilibrium after partial dissociation, its pH is found to be 5.05. What is the acid ionization constant, Ka, for hypobromous acid at this temperature?arrow_forward
- Write the chemical equation and the expression for the equilibrium constant, and calculate Kb for the reaction of each of the following ions as a base. (a) sulfate ion (b) citrate ionarrow_forwardWrite a balanced molecular equation for the preparation of each of the following salts, using an acidbase neutralization reaction. a. LiNO3 (lithium nitrate) b. BaCl2 (barium chloride) c. K3PO4 (potassium phosphate) d. Na2SO4 (sodium sulfate)arrow_forwardTable 13-4 lists the stepwise Ka values for some polyprotic acids. What is the difference between a monoprotic acid, a diprotic acid, and a triprotic acid? Most polyprotic acids are weak acids; the major exception is H2SO4. To solve for the pH of a solution of H2SO4, you must generally solve a strong acid problem as well as a weak acid problem. Explain. Write out the reactions that refer to Ka1 and Ka2 for H2SO4. For H3PO4, Ka1 = 7.5 103, Ka2 = 6.2 108, and Ka3= 4.8 1013. Write out the reactions that refer to the Ka1, Ka2and Ka3equilibrium constants. What are the three acids in a solution of H3PO4? Which acid is strongest? What are the three conjugate bases in a solution of H3PO4? Which conjugate base is strongest? Summarize the strategy for calculating the pH of a polyprotic acid in water.arrow_forward
- The pigment cyanidin aglycone is one of the anthocyanin molecules that gives red cabbage (Brassica oleracea var. capitata f. rubra) its characteristic red coloration. Many chemistry students have used this red cabbage indicator to study acid-base chemistry. Estimate tire pH range at which cyanidin agly-cone shows a color change. Anth-H(aq) Anth(aq) + H+ (aq) Ka = 1.3 107arrow_forward8-14 Write an equation for the reaction that takes place when each acid is added to water. (a) HNO3 (b) HBr (c) HCO3- (d) NH4+arrow_forwardWrite chemical equations showing the individual proton-transfer steps that occur in aqueous solution for each of the following acids. a. H2C2O4 (oxalic acid) b. H2C4H4O6 (tartaric acid)arrow_forward
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