Organic Chemistry
11th Edition
ISBN: 9781118133576
Author: T. W. Graham Solomons, Craig Fryhle
Publisher: Wiley, John & Sons, Incorporated
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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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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.
(a) Explain how NaBH, in CH;OH can reduce hemiacetal A to 1,4-butanediol (HOCH,CH,CH,CH,OH). (b) What product is
formed when A is treated with Ph;P=CHCH,CH(CH),? (c) The drug isotretinoin is formed by reaction of X and Y. What is the
structure of isotretinoin? Although isotretinoin (trade name Accutane or Roaccutane) is used for the treatment of severe acne, it
is dispensed under strict controls because it also causes birth defects.
PPha
NaOCH,CH3
HO-
isotretinoin
HO
A
Br
X
Y
Which nitrogen-containing compound of each pair would you expect to be stronger base?Indicate (a) or (b)
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 - Prob. 15PPCh. 3 - Prob. 16PPCh. 3 - Prob. 17PPCh. 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 - Designate the Lewis acid and Lewis base in each of...Ch. 3 - Prob. 23PCh. 3 - Prob. 24PCh. 3 - Write an equation, using the curved-arrow...Ch. 3 - When methyl alcohol is treated with NaH, the...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. 30PCh. 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. 34PCh. 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. 42PCh. 3 - Prob. 43PCh. 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. 4LGPCh. 3 - Prob. 1QCh. 3 - Which of the following is the strongest base? (a)...Ch. 3 - Prob. 3QCh. 3 - Prob. 4QCh. 3 - Prob. 5QCh. 3 - Which would be the weakest base? (a) CH3CO2Na (b)...Ch. 3 - What acid-base reaction (if any) would occur when...Ch. 3 - The pKa of CH3NH3+ equals 10.6; the pKa of...Ch. 3 - 3.9 Supply the missing reagents.
Ch. 3 - 3.10 Supply the missing intermediates and...
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- 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_forward2.) Draw the products of the following reactions. Provide an arrow-pushing mechanism for each reaction. Label the acid, base, conjugate base, and conjugate acid. Finally, indicate the direction of equilibrium. 요요 + NaHarrow_forward2 Rank the following compounds with increasing acidity: (1 = least acidic; 3 = most acidic) (a) HH (b) (c) (d) HoHarrow_forward
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