Essential Organic Chemistry (3rd Edition)
3rd Edition
ISBN: 9780321937711
Author: Paula Yurkanis Bruice
Publisher: PEARSON
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Chapter 11.4, Problem 6P
- 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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Briefly explain how the products were obtained in the following reaction.
NaOP
70 °C
Using 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?
12.
Bicine is an organic compound used
as a buffering agent. It is one of Good's buffers and
has a pKa of 8.354 at 25 °C. The molecular formula of
bicine is C6H13NO4. Bicine can react with Ba(OH)2
according to the following reaction.
2 C6H13NO4 + Ba(OH)2 → Ba(C6H12NO4)2 + 2 H₂O
It took a student worker 3 steps to make a buffer
solution. First, a bicine solution is made by
dissolving 37.47 grams bicine in enough water. The
total volume is 200.00 mL. Then 250.00 mL Ba(OH)2
solution is prepared by adding 36.57 grams Ba(OH)2
solid and enough water. At the end, a buffer solution
is made by mixing 157.89 mL of the above bicine
solution and 89.32 mL of the above Ba(OH)2 solution.
A.
B.
C.
Determine the equilibrium concentration
of bicine in the buffer solution.
Please provider your answer below.
A
of Ba(C6H12NO4)2 in the buffer solution.
Check answer
Determine the equilibrium concentration
M
Please provider your answer below.
A
pH =
Please provider your answer below.
A
$
Check answer…
Chapter 11 Solutions
Essential Organic Chemistry (3rd Edition)
Ch. 11.1 - The aromas of many flowers and fruits are due to...Ch. 11.1 - Name the following compounds:Ch. 11.1 - Prob. 3PCh. 11.2 - Prob. 4PCh. 11.2 - Prob. 5PCh. 11.4 - a. What is the product of the reaction of acetyl...Ch. 11.4 - Prob. 7PCh. 11.5 - Using the pKa values listed in Table 11.1, predict...Ch. 11.6 - Starting with acetyl chloride, what neutral...Ch. 11.6 - Prob. 10P
Ch. 11.7 - Prob. 11PCh. 11.8 - Prob. 13PCh. 11.8 - Using the mechanism for the acidcatalyzed...Ch. 11.8 - Prob. 15PCh. 11.8 - Prob. 16PCh. 11.8 - Prob. 17PCh. 11.9 - Prob. 18PCh. 11.10 - Show how each of the following esters could be...Ch. 11.11 - Which of the following reactions would lead to the...Ch. 11.12 - Prob. 22PCh. 11.12 - Prob. 23PCh. 11.13 - Prob. 24PCh. 11.13 - Prob. 25PCh. 11.14 - Prob. 26PCh. 11.14 - Prob. 27PCh. 11.14 - Prob. 28PCh. 11.15 - Prob. 29PCh. 11.15 - How would you synthesize the following compounds...Ch. 11 - Write a structure for each of the following a. N,N...Ch. 11 - Prob. 32PCh. 11 - Which ester is more reactive, methyl acetate or...Ch. 11 - What products would be formed from the reaction of...Ch. 11 - What products would be obtained from the following...Ch. 11 - Prob. 36PCh. 11 - a. Which compound would you expect to have a...Ch. 11 - a. List the following esters in order of...Ch. 11 - D. N. Kursanov, a Russian chemist, proved that the...Ch. 11 - Prob. 40PCh. 11 - Using an alcohol for one method and an alkyl...Ch. 11 - Prob. 42PCh. 11 - Prob. 44PCh. 11 - Prob. 45PCh. 11 - Prob. 46PCh. 11 - Prob. 47PCh. 11 - Prob. 48PCh. 11 - Prob. 49PCh. 11 - Show how the following compounds could be prepared...Ch. 11 - Prob. 51PCh. 11 - Prob. 52PCh. 11 - Prob. 53P
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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
- Dicarboxylic acids have two dissociation constants, one for the initial dissociation into a monoanion and one for the second dissociation into a dianion. For oxalic acid, HO2C—CO2H, the first ionization constant is pKal = 1.2 and the second ionization constant is pKa2 = 4.2. Why is the second carboxyl group far less acidic than the first?arrow_forwardWhich of the following will have the highest pka? A. Co3?. B, HCO31 C. H2CO3 D. H2SO3 E. HCIO3arrow_forward12. Bicine is an organic compound used as a buffering agent. It is one of Good's buffers and has a pKa of 8.354 at 25 °C. The molecular formula of bicine is C6H13NO4. Bicine can react with Ba(OH)₂ according to the following reaction. 2 C6H13NO4 + Ba(OH)2 → Ba(C6H12NO4)2 + 2 H₂O It took a student worker 3 steps to make a buffer solution. First, a bicine solution is made by dissolving 37.47 grams bicine in enough water. The total volume is 200.00 mL. Then 250.00 mL Ba(OH)2 solution is prepared by adding 36.57 grams Ba(OH)2 solid and enough water. At the end, a buffer solution is made by mixing 157.89 mL of the above bicine solution and 89.32 mL of the above Ba(OH)₂ solution. A. B. Determine the equilibrium concentration of bicine in the buffer solution. Please provider your answer below. Determine the equilibrium concentration of Ba(C6H₁2NO4)2 in the buffer solution. Please provider your answer below. Determine the pH of the buffer solution. pH = Please provider your answer below. 0² 0₂…arrow_forward
- 3. Which is the stronger acid: (a) Benzoic acid with a Ka of 6.5 x10-5 or hydrocyanic acid with a Ka of 4.9 x 10-10? (b) Boric acid with a pKa of 9.14 or carbonic acid with a pKa of 6.37arrow_forwardHow will the acid be deprotonated if the pH of the solution is adjusted so that the pH> pKa? 4 methylhexanoic acidarrow_forwardNaming dicarboxylic acids and their pKa values:arrow_forward
- MCQ 112: Cagy + H,Oo→ Ca(OH)2) + Hz- The product Ca(OH), is A. highly soluble in water B. sparingly soluble in water C. insoluble in water D. sparingly insoluble in waterarrow_forwardDoes water behave as an acid or a base when it reacts with deprotonated methylamine? Water acts as a base because its pKa is greater than that of deprotonated methylamine. Water acts as an acid because its pKa is less than that of deprotonated methylamine. O Water acts as an acid because its pKa is greater than that of deprotonated methylamine. Water acts as a base because its pKa is less than that of deprotonated methylamine.arrow_forwardTwo pKa values are reported for malonic acid, a compound with two COOH groups. Explain why one pKa is lower and one pKa is higher than the pKa of acetic acid (CH3COOH, pKa = 4.8).arrow_forward
- Instruction: And put the COMPLETE THE FOLLOWING REACTIONS: condensed E.g. REACTION OF AMMONIA WITH HCHO formula 6HCHO + 4NH3 =(CH2)&N4 + Answer: 6H20arrow_forwardRank the basic sites in each of the following molecules from most (1) to least (5) basic. HO A D E В E A > > >arrow_forward1. Dimethyl disulfide, CH,S-SCH, found in the vaginal secretions of female hamsters, acts as a sexual attractant for the male hamster. Write an equation for its synthesis from methanethiol. 2. Write an equation for the reaction of ethylene oxide with a. I mole of HCI b. excess HCI c. phenol +H d. phenylmagnesium bromidearrow_forward
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