Organic Chemistry
8th Edition
ISBN: 9781305580350
Author: William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher: Cengage Learning
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Textbook Question
Chapter 4.6, Problem 2Q
What 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.
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pKa of CF3CH2OH is higher than the pKa of a CCl3CO2H. Provide the reason
Group of answer choices
a) The conjugate base of CCl3CO2H is more stabilized than the conjugate base of CF3CH2OH
b) The conjugate base of CCl3COH is stabilized by type of atom
c) CF3CH2OH is stronger acid
d) The conjugate base of CCl3CO2H is less stabilized than the conjugate base of CF3CH2OH
e) Fluorine is more electronegative than Cl
Arrange the compounds in each set in order of increasing acid strength. consult Table 4.1 for pKa values of each acid.
Which compound would be more basic or weaker, a compound with a pka of -3.5 or a compound with a pja of -1.7
Chapter 4 Solutions
Organic Chemistry
Ch. 4.2 - For each conjugate acid-base pair, identify the...Ch. 4.2 - Write these reactions as proton-transfer...Ch. 4.2 - Following is a structural formula for guanidine,...Ch. 4.2 - Write an equation to show the proton transfer...Ch. 4.3 - For each value of Ka, calculate the corresponding...Ch. 4.4 - Predict the position of equilibrium and calculate...Ch. 4.5 - Calculate Keq for a reaction with G0 = 17.1 kJ/mol...Ch. 4.6 - Acid-Base Equilibria Many factors contribute to...Ch. 4.6 - What is the relative trend in acidity and pKa of...Ch. 4.7 - Write an equation for the reaction between each...
Ch. 4 - For each conjugate acid-base pair, identify the...Ch. 4 - Complete a net ionic equation for each...Ch. 4 - Arrange the compounds in each set in order of...Ch. 4 - Prob. 4.12PCh. 4 - In acetic acid, CH3COOH, the OH hydrogen is more...Ch. 4 - Which has the larger numerical value? (a) The pKa...Ch. 4 - In each pair, select the stronger acid. (a)...Ch. 4 - Arrange the compounds in each set in order of...Ch. 4 - Arrange the compounds in each set in order of...Ch. 4 - If the G for a reaction is 4.5 kcal/mol at 298 K,...Ch. 4 - Calculate the Keq for the following reactions from...Ch. 4 - Prob. 4.20PCh. 4 - Answer true or false to the following statements...Ch. 4 - In each of the following three reaction coordinate...Ch. 4 - The acid-base chemistry reaction of barium...Ch. 4 - Unless under pressure, carbonic acid (H2CO3) in...Ch. 4 - Prob. 4.25PCh. 4 - Acetic acid, CH3COOH, is a weak organic acid, pKa...Ch. 4 - Benzoic acid, C6H5COOH (pKa 4.19), is only...Ch. 4 - Prob. 4.28PCh. 4 - One way to determine the predominant species at...Ch. 4 - Will acetylene react with sodium hydride according...Ch. 4 - Prob. 4.31PCh. 4 - For each equation, label the Lewis acid and the...Ch. 4 - Complete the equation for the reaction between...Ch. 4 - Each of these reactions can be written as a Lewis...Ch. 4 - The sec-butyl cation can react as both a...Ch. 4 - Prob. 4.36APCh. 4 - Prob. 4.37APCh. 4 - Prob. 4.38APCh. 4 - Explain why the hydronium ion, H3O+, is the...Ch. 4 - What is the strongest base that can exist in...Ch. 4 - Prob. 4.42APCh. 4 - Prob. 4.43APCh. 4 - Methyl isocyanate, CH3N=C=O, is used in the...Ch. 4 - Offer an explanation for the following...Ch. 4 - Prob. 4.46APCh. 4 - Alcohols (Chapter 10) are weak organic acids, pKa...Ch. 4 - As we shall see in Chapter 19, hydrogens on a...Ch. 4 - 2,4-Pentanedione is a considerably stronger acid...Ch. 4 - Write an equation for the acid-base reaction...Ch. 4 - Prob. 4.51APCh. 4 - Prob. 4.52APCh. 4 - Prob. 4.53APCh. 4 - Following is a structural formula for imidazole, a...
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- If compound A has a ka of 3.0 x 10-11 , compound B has a ka of 1.1 x 10-10 and compound C has a ka of 1.8 x 10-5, which compound is the weakest acid?arrow_forwardWhich is a stronger base: H2O or CH3OH? (The pKa of H3O+ is -1.7; the pKa of CH3O+H2 is -2.5.)arrow_forwardPhthalic acid and isophthalic acid have protons on two carboxy groups that can be removed with base. (a) Explain why the pKa for loss of the first proton (pKa1) is lower for phthalic acid than isophthalic acid. (b) Explain why the pKa for loss of the second proton (pKa2) is higher for phthalic acid than isophthalic acid.arrow_forward
- Nepheliosyne B is a novel acetylenic fatty acid isolated from a New Caledonian marine sponge. (a) Label the most acidic H atom. (b) Which carbon–carbon σ bond is shortest? (c) How many degrees of unsaturation does nepheliosyne B contain? (d) How many bonds are formed from Csp–Csp3? (e) Label each triple bond as internal or terminal.arrow_forwardorganic chemistry 30) Which compound is the strongest acid?arrow_forward3. Rank the following acids in order from strongest to weakest.HA (pKa = 2.55) H2Z (pKa1 = 4.35) H3X (pKa1 = 3.17) HY (pKa = 5.72) 4. Rank each base in order from strongest to weakest.B (pKb = 4.12) Y– (pKa = 5.72 for conjugate acid) A– (pKa = 2.55 for conjugate acid)E (pKb = 8.12)arrow_forward
- The pKa of three CH bonds is given below.a.For each compound, draw the conjugate base, including all possible resonance structures. b. Explain the observed trend in pKaarrow_forwardDicarboxylic acids have two pKa's.- For maleic acid (cis-2-butenedioic acid) these are pKa1 = 2.0, and pKa2 = 6.3- For fumaric acid (trans-2-butenedioic acid) these are pKa1 = 3.0, and pKa2 = 4.5 Which factor best explains why the cis-isomer has a smaller pKa1 and a larger pKa2 than the trans-isomer? a. Intramolecular hydrogen bonding b. Intramolecular steric hindrance c. Selective solvation in water d. Intramolecular dipole repulsionarrow_forwardWhich of the following will be the most basic? Select one: a. 1.0M NO3- b. 1.0M PO43- c. 1.0M SO42- d. 1.0M CO32-arrow_forward
- Draw the structure of a constitutional isomer of compound B that fits each description. a. an isomer that is at least 105 times more acidic than B b. an isomer that is at least 105 times less acidic than B c. an isomer that is comparable in acidity to Barrow_forwardWhat percent of acetic acid is present in the acidic form at pH 5.0, assuming a pKa of 4.8?arrow_forwardArrange the compounds in each set in order of increasing base strength. consult Table 4.1 for pKa values of the conjugate acid of each base.arrow_forward
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