Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
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Chapter 20.SE, Problem 39AP
Calculate the Ka's for the following acids:
(a) Citric acid, pKa = 3.14
(b) Tartaric acid, pKa = 2.98
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Calculate Ka values from the following pKa’s:(a) Acetone, pKa 5 19.3 (b) Formic acid, pKa 5 3.75
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 6.37
(b)Given the Ka and pKa values of the following compounds: Hydrobromic
acid (HBr), K= 1.0 x 10°; Acetic acid (CH3COOH), K. =1.75 x 10$; ethyl
alcohol (CH3CH;OH), pKa = 15.9 ; Ammonia (NH), pK = 36
%3D
%D
(1)
Calculate the Ka value of CH3CH:OH and NH3
(ii) Evaluate which of the conjugate base of the following acids in
Q1 (b) is the strongest base. Justify your answer
(iii) Calculate at what pH is the concentration of acetic acid
(CH3COOH), 10 times greater in its acidic form than basic form?
Chapter 20 Solutions
Organic Chemistry
Ch. 20.1 - Give IUPAC names for the following compounds:Ch. 20.1 - Draw structures corresponding to the following...Ch. 20.2 - Prob. 3PCh. 20.2 - The Ka for dichloroacetic acid is 3.32 Ă— 10-2....Ch. 20.3 - Calculate the percentages of dissociated and...Ch. 20.4 - Which would you expect to be a stronger acid, the...Ch. 20.4 - Dicarboxylic acids have two dissociation...Ch. 20.4 - The pKa of p-cyclopropylbenzoic acid is 4.45. Is...Ch. 20.4 - Prob. 9PCh. 20.5 - Prob. 10P
Ch. 20.6 - Prob. 11PCh. 20.6 - How might you carry out the following...Ch. 20.7 - Prob. 13PCh. 20.7 - Prob. 14PCh. 20.8 - Cyclopentanecarboxylic acid and...Ch. 20.8 - Prob. 16PCh. 20.SE - Prob. 17VCCh. 20.SE - Prob. 18VCCh. 20.SE - The following carboxylic acid can’t be prepared...Ch. 20.SE - Electrostatic potential maps of anisole and...Ch. 20.SE - Predict the product(s) and provide the mechanism...Ch. 20.SE - Predict the product(s) and provide the mechanism...Ch. 20.SE - Prob. 23MPCh. 20.SE - Predict the product(s) and provide the complete...Ch. 20.SE - Acid-catalyzed hydrolysis of a nitrile to give a...Ch. 20.SE - Prob. 26MPCh. 20.SE - Naturally occurring compounds called cyanogenic...Ch. 20.SE - 2-Bromo-6, 6-dimethylcyclohexanone gives 2,...Ch. 20.SE - Naturally occurring compounds called terpenoids,...Ch. 20.SE - In the Ritter reaction, an alkene reacts with a...Ch. 20.SE - Give IUPAC names for the following compounds:Ch. 20.SE - Prob. 32APCh. 20.SE - Prob. 33APCh. 20.SE - Prob. 34APCh. 20.SE - Prob. 35APCh. 20.SE - Prob. 36APCh. 20.SE - Prob. 37APCh. 20.SE - Prob. 38APCh. 20.SE - Calculate the Ka's for the following acids: (a)...Ch. 20.SE - Thioglycolic acid, HSCH2CO2H, a substance used in...Ch. 20.SE - Prob. 41APCh. 20.SE - Prob. 42APCh. 20.SE - How could you convert butanoic acid into the...Ch. 20.SE - How could you convert each of the following...Ch. 20.SE - How could you convert butanenitrile into the...Ch. 20.SE - How would you prepare the following compounds from...Ch. 20.SE - Prob. 47APCh. 20.SE - Using 13CO2 as your only source of labeled carbon,...Ch. 20.SE - Prob. 49APCh. 20.SE - Which method-Grignard carboxylation or nitrile...Ch. 20.SE - Prob. 51APCh. 20.SE - Prob. 52APCh. 20.SE - Propose a structure for a compound C6H12O2 that...Ch. 20.SE - Prob. 54APCh. 20.SE - How would you use NMR (either 13C or 1H) to...Ch. 20.SE - Prob. 56APCh. 20.SE - A chemist in need of 2,2-dimethylpentanoic acid...Ch. 20.SE - Prob. 58APCh. 20.SE - Prob. 59APCh. 20.SE - Prob. 60APCh. 20.SE - Prob. 61APCh. 20.SE - Prob. 62APCh. 20.SE - Prob. 63APCh. 20.SE - The following pKa values have been measured....Ch. 20.SE - Identify the missing reagents a-f in the following...Ch. 20.SE - Propose a structure for a compound, C4H7N, that...Ch. 20.SE - Prob. 67APCh. 20.SE - The 1H and 13C NMR spectra below belong to a...Ch. 20.SE - Propose structures for carboxylic acids that show...Ch. 20.SE - Carboxylic acids having a second carbonyl group...
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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
- Given the Ka values, estimate the pKa value of each of the following acids without using a calculator (that is, is it between 3 and 4, between 9 and 10, and so on?):arrow_forwardconjugate base acid Methyl Acetylene Isopropanol pKa pKa 1) Consider the reaction AH + H₂O ± A:0 + H3O+. For the following named acids: a) draw the structure of the acid, b) give the approximate pKa value of the acid in multiples of 5, c) give the name of the conjugate base, and d) draw the structure of the conjugate base. Ethyl Acetoacetate pKa Butanoic acid pKaarrow_forwardGiven the Ka values, estimate the pKa value of each of the following acids without using a calculator (that is, is it between 3 and 4, between 9 and 10,and so on?): 1. nitrous acid (HNO2), Ka = 4.0 * 10-4 2. nitric acid (HNO3), Ka = 22 3. bicarbonate (HCO3-), Ka = 6.3 * 10-11 4. hydrogen cyanide (HCN), Ka = 7.9 * 10-10 5. formic acid (HCOOH), Ka = 2.0 * 10-4 6. phosphoric acid (H3PO4), Ka = 2.1arrow_forward
- Give the Ka or pKą values that should be entered in the blanks below. pka = -log10 Ka; Ka = 10-pka (a) hydrocyanic acid: Ka = 4.92 x 10-10; pka = (b) acetic acid: Ka=;pka = 4.75 (c) lactic acid: Ka = 8.40 x 10-4; pka = (d) formic acid: Ka=;pKa = 3.75. (e) Which of these acids is the strongest?arrow_forwardMost of the pKa values given in this text were determined in water. How would the pKa values of carboxylic acids, alcohols, ammonium ions (RNH32) , phenol, and an anilinium ion (C6H5NH32) change if they were determined in a solvent less polar than water?arrow_forwardI mostly need help setting up how to do the math for these problems. I also need help with knowing how to find which acid is the strongest. Give the Ka or pKa values that should be entered in the blanks below. pKa = -log10ka ; Ka = 10-pKa (a) hydrocyanic acid: Ka = 4.92 x 10-10 ; pKa = (b) acetic acid: Ka = ; pKa = 4.75 (c) lactic acid: Ka = 8.40 x 10-4 ; pKa = (d) formic acid: Ka = ; pKa = 3.75 (e) Which of these acids is the strongest?arrow_forward
- Conjugate acid base pKa 2) Consider the reaction B: () + H3O+ →>> BH(+) + H2O. For the following named bases: 1) draw the structure of the base, 2) draw the structure of the conjugate acid, 3) give the name of the conjugate acid, and 4) give the approximate pKa of the conjugate acid (±1 pKa unit). For the purposes of answering this question you may use pKa values evenly divisible by 5. t-Butoxide anion p-Toluenesulfonate anion Triethylamine t-Butanol pKa pKa pKaarrow_forwardG.149.arrow_forwardThe pKa for Molecule A is 10 units lower than Molecule B. Molecule A Draw conjugate base of A :B H H pKa = 10 Molecule B Draw conjugate base of B OCH3 :B H H pКa 3 20 Please provide a brief explanation for the difference in pKa of these to molecules.arrow_forward
- Assign the pKa's 2.49 , 3.58 , and 4.78 to the compounds shown below. COOH СООН А: B: COOH C: Which of the compounds has the pKa = 2.49: O A OB Oc Which of the compounds has the pKa = 3.58 : O A Which of the compounds has the pKa = 4.78 : B 67%arrow_forwardExplain why the pKa of compound A is lower than the pKa’s of both compounds B and C.arrow_forwardWhich of the following is the primary and secondary species of EDTA at pH 2.05? (a) H6Y²+, HSY* (d) H3Y, H2Y2- EDTA: pK₂1 = 0.0 (b) HsY*, H4Y (e) HY³-, Y4- PK₁2 = 1.5 PK₂3 = 2.00 (c) H₂Y, H₂Y- nk = 760arrow_forward
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