Organic Chemistry
12th Edition
ISBN: 9781118875766
Author: T. W. Graham Solomons, Craig B. Fryhle, Scott A. Snyder
Publisher: WILEY
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Chapter 11, Problem 11PP
Practice Problem 11.11
An exception to what is stated above has to do with syntheses of unsymmetrical ethers in which one alkyl group is a tert-butyl group and the other group is primary. For example, this synthesis can be accomplished by adding tm-butyl alcohol to a mixture of the primary alcohol and
Give a likely mechanism for this reaction and explain why it is successful.
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Using your reaction roadmap as a guide, show how to convert 1-butanol and ethanol into racemic 2-ethoxy-1-butanol. You must use 1-butanol and ethanol as the source of
all carbon atoms in the ether product.
(1)
(2)
(3)
OH
(4)
2-ethoxy-1-butanol
(racemic)
OH
Suggest reagents and experimental conditions for each step in this synthesis.
From the choices provided, suggest appropriate reagents for each step. More than one reagent may be necessary. Use the minimum number of steps possible. Enter your
answer as a letter, or a series of letters, in the order necessary to bring about the steps shown.
Reagents:
OH
(c) ethylene oxide
(a) (CH3)3CO¯K+, THF (d) H₂SO4, H₂O
(b) OsO4, H₂O2
Br
OH
+
(9) H₂ SO4 (anhydrous) Na, NH3 (1)
(k) NBS, heat
(e) m-chloroperoxybenzoic acid
(mCPBA)
(f) pyridinium chlorochromate) PBr3
(PCC)
(h) NaOH
(N-bromosuccinimide)
Previous
Next
Using your reaction roadmap as a guide, show how to convert 1-butanol and ethanol into racemic 2-ethoxy-1-butanol. You must use 1-butanol and ethanol as the source of
all carbon atoms in the ether product.
(1)
(2)
(3)
OH
(4)
2-ethoxy-1-butanol
(racemic)
OH
OH
(c) ethylene oxide
Suggest reagents and experimental conditions for each step in this synthesis.
From the choices provided, suggest appropriate reagents for each step. More than one reagent may be necessary. Use the minimum number of steps possible.
Enter your answer as a letter, or a series of letters, in the order necessary to bring about the steps shown.
Reagents:
(a) (CH3)3 CO K+, THF (d) H₂SO4, H₂O
(b) OsO4, H₂O2
1
Br
(e) m-chloroperoxybenzoic acid
OH
(mCPBA)
(f) pyridinium chlorochromate
(PCC)
+
le
2
(9) H₂SO4 (anhydrous) (j) Na, NH3 (1)
(h) NaOH
(k) NBS, heat
(i) PBr3
(N-bromosuccinimide)
Previous
Next
Using your reaction roadmap as a guide, show how to convert 1-butanol and ethanol into racemic 2-ethoxy-1-butanol. You must use 1-butanol and ethanol as the source of
all carbon atoms in the ether product.
(1)
(2)
(3)
OH
(4)
2-ethoxy-1-butanol
(racemic)
OH
OH
Suggest reagents and experimental conditions for each step in this synthesis.
From the choices provided, suggest appropriate reagents for each step. More than one reagent may be necessary. Use the minimum number of steps possible.
Enter your answer as a letter, or a series of letters, in the order necessary to bring about the steps shown.
Reagents:
(c) ethylene oxide
(a) (CH3)3 COK, THF (d) H₂SO4, H₂O
(b) OsO4, H₂O2
Br
OH
(e) m-chloroperoxybenzoic acid
(mCPBA)
(f) pyridinium chlorochromate
(PCC)
+
2
(9) H₂SO4 (anhydrous)
(h) NaOH
(i) PBr3
(j) Na, NH3 (1)
(k) NBS, heat
(N-bromosuccinimide)
Previous
Next
Chapter 11 Solutions
Organic Chemistry
Ch. 11 - Prob. 1PPCh. 11 - Practice Problem 11.2 Give bond-line formulas and...Ch. 11 - Prob. 3PPCh. 11 - Prob. 4PPCh. 11 - Prob. 5PPCh. 11 - Prob. 6PPCh. 11 - Prob. 7PPCh. 11 - Practice Problem 11.8 Show how you would prepare...Ch. 11 - Prob. 9PPCh. 11 - Prob. 10PP
Ch. 11 - Practice Problem 11.11
An exception to what is...Ch. 11 - Prob. 12PPCh. 11 - Prob. 13PPCh. 11 - Prob. 14PPCh. 11 - Prob. 15PPCh. 11 - Prob. 16PPCh. 11 - Prob. 17PPCh. 11 - Prob. 18PPCh. 11 - Practice Problem 11.19
Propose structures for each...Ch. 11 - Prob. 20PPCh. 11 - Prob. 21PPCh. 11 - Prob. 22PPCh. 11 - Prob. 23PPCh. 11 - Prob. 24PPCh. 11 - Give an IUPAC substitutive name for each of the...Ch. 11 - Prob. 26PCh. 11 - Prob. 27PCh. 11 - Prob. 28PCh. 11 - Prob. 29PCh. 11 - 11.30. Show how you might prepare 2-bromobutane...Ch. 11 - Prob. 31PCh. 11 - Prob. 32PCh. 11 - Prob. 33PCh. 11 - Considering A-L to represent the major products...Ch. 11 - Write structures for the products that would be...Ch. 11 - Prob. 36PCh. 11 - Provide the reagents necessary for the following...Ch. 11 - 11.38. Predict the major product from each of the...Ch. 11 - Predict the products from each of the following...Ch. 11 - Provide the reagents necessary to accomplish the...Ch. 11 - 11.41. Provide reagents that would accomplish the...Ch. 11 - Prob. 42PCh. 11 - 11.43. A synthesis of the -receptor blocker called...Ch. 11 - Prob. 44PCh. 11 - Prob. 45PCh. 11 - 11.46. For each of the following, write a...Ch. 11 - 11.47. Vicinal halo alcohols (halohydrins) can be...Ch. 11 - Prob. 48PCh. 11 - Prob. 49PCh. 11 - Prob. 50PCh. 11 - Prob. 51PCh. 11 - Prob. 52PCh. 11 - Outlined below is a synthesis of the gypsy moth...Ch. 11 - Prob. 54PCh. 11 - Prob. 55PCh. 11 - Prob. 56PCh. 11 - 11.57. When the 3-bromo-2-butanol with the...Ch. 11 - 11.58. Reaction of an alcohol with thionyl...Ch. 11 - Prob. 59PCh. 11 - Prob. 60PCh. 11 - Prob. 1LGPCh. 11 - Prob. 2LGPCh. 11 - Synthesize the compound shown below from...
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