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 6PP
Interpretation Introduction
Interpretation:
The
Concept introduction:
The negative logarithm of
The larger the value of
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(a) Rank the following compounds in order of increasing acidity. (b) Which compound forms the strongest conjugate base?
но
HO
но
он
The pK, of ascorbic acid (vitamin C) is 4.17, showing that it is slightly more acidic
than acetic acid (CH3CO0H, pKa 4.74).
(a) Show the fou
r different conjugate bases that would be formed by deprotonation
of the four different OH groups in ascorbic acid.
(b)
Compare the stabilities of these four conjugate bases, and predict which OH
group of ascorbic acid is the most acidic.
(c) Compare the most stable conjugate base of ascorbic acid with the conjugate base
of acetic acid, and suggest why these two compounds have similar acidities, even
though ascorbic acid lacks the carboxylic acid (COOH) group.
19.39 (a) Rank the following compounds in order of increasing acidity. (b)
Which compound forms the strongest conjugate base?
O₂N.
OH
A
B
OH
C
OH
D
OH
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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- Which nitrogen-containing compound of each pair would you expect to be stronger base?Indicate (a) or (b)arrow_forwarda.) Rank the attached compounds in order of increasing acidity. (b)Which compound forms the strongest conjugate base?arrow_forwardWhich is the conjugate base in each of the pairs below?arrow_forward
- The C-H bond in acetone, (CH3)C=O, has a pką of 19.2. Draw two resonance structures for its conjugate base. Then, explain why acetone is much more acidic than propane, CH;CH,CH3 (pKa = 50). %3Darrow_forward(a) Predict the products of the following acid-base reactions using curved-arrow mechanisms to indicate electron flow. (b) Indicate the acid, base, conjugate acid, and conjugate base of each reaction. (c) Indicate whether the reactants or products are favored at equilibrium a) CH,COOH CH3O b) CH,CH,OH H2Narrow_forward3.41 Write an equation for the proton transfer reaction that occurs when each of the following acids reacts with water. In each case, draw curved arrows that show a mechanism for the proton transfer: (a) HBr (b) O=S=O H-O-S-O-H (c) L -Harrow_forward
- What is the conjugate acid of each of the following? What is the conjugate Dase of eacn? (a) NH Parts of the formula in your answer are transposed. Your answer appears to be missing a charge. Conjugate acid (b ) (CH₂)₂NH \table[[chemPad, (9) Help], [xlx =larr|l, Greek -],[(CH),NH,N What is the conjugate acid of each of the following? What is the conjugate base or eacn (UTIL SOLES- (a) NH3 Conjugate acid Conjugate base (b) (CH3)2NH Conjugate acid Conjugate base chemPad XX→→ chemPad XX→ NH₂ NH 2 NH4 NH 4 Parts of the formula in your answer are transposed. Your answer appears to be missing a charge. chemPad XX→ (CH4)2NH2 (CH_4)_2NH_2 chemPad XX→= Greek (CH₂)2N (CH_2) 2N Help Greek Help Greek X Help Greek juur Helparrow_forward4. The pk, of vanillin is about 9, which is much more acidic than a normal alcohol. Draw a reaction showing the deprotonation of vanillin with NaOH, and then draw six resonance structures of the conjugate base. Draw the hybrid structure and clearly indicate how the negative charge is distributed in the compound.arrow_forwardI) The following reaction runs as written therefore... 1HClO2 +1NH3 ==>1ClO2- +1NH4+ (a)HClO2 is a weaker Bronsted base than NH4+(b)ClO2- is a stronger Bronsted base than NH3(c)HClO2 is a stronger Bronsted Acid than NH4+(d)None of those is correct.arrow_forward
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