Organic Chemistry
11th Edition
ISBN: 9781118133576
Author: T. W. Graham Solomons, Craig Fryhle
Publisher: Wiley, John & Sons, Incorporated
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Chapter 21, Problem 23P
Interpretation Introduction
Interpretation:
The structure of the product, dibenzo-18-crown-6 and the mechanism for the given reaction are to be provided.
Concept introduction:
Ethers are organic compounds in which an oxygen atom is attached to two alkyl or two aryl groups. These compounds are similar in structure to alcohols and phenols.
Crown ethers are large cyclic compounds, which consist of a ring containing several ether groups.
A class of organic compounds whose molecule are large rings containing a number of ether linkages. These ethers are called crown ether due to their shape.
They have
The name
They trapped metal ion into their cavity.
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we know that ethers, such as diethyl ether and tetrahydrofuran, are quite resistant to the action of dilute acids and require hot concentrated HI or HBr for cleavage. However, acetals in which two ether groups are linked to the same carbon undergo hydrolysis readily, even in dilute aqueous acid. How do you account for this marked difference in chemical reactivity toward dilute aqueous acid between ethers and acetals?
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
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(1)
(2)
(3)
OH
(4)
2-ethoxy-1-butanol
(racemic)
OH
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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
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(f) pyridinium chlorochromate) PBr3
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(h) NaOH
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5. Optically pure 2-octyl sulfonate was treated with varying mixtures of water and dioxane, and the
optical purity of the resulting product (2-octanol) was found to vary with the ratio of water to
dioxane, as shown in the following table (J. Am. Chem. Soc. 1965, 87, 287-291). Given that
dioxane possesses fairly nucleophilic oxygen atoms, provide a complete mechanism that
explains the variation in in the product's optical purity due to changes in solvent composition.
Hint, the solvent is doing more here than just dissolving.. it is partaking in the reaction.
Solvent Ratio (water : dioxane)
25:75
50: 50
75: 25
100 :0
Optical purity of (S)-2-octanol
77%
88%
95%
100%
H20
он
(R)-2-Octyl sulfonate
(optically pure)
(S)-2-Octanol
(dioxane)
Chapter 21 Solutions
Organic Chemistry
Ch. 21 - PRACTICE PROBLEM
21.1 If we examine Table 21.1, we...Ch. 21 - PRACTICE PROBLEM If we examine Table 21.1, we see...Ch. 21 - Prob. 3PPCh. 21 - PRACTICE PROBLEM
21.4 Predict the products of each...Ch. 21 - Prob. 5PPCh. 21 - PRACTICE PROBLEM
21.6 What are compounds A and B...Ch. 21 - Prob. 7PPCh. 21 - PRACTICE PROBLEM Outline a possible synthesis of...Ch. 21 - PRACTICE PROBLEM 1-Fluoro-2,4-dinitrobenzene is...Ch. 21 - PRACTICE PROBLEM
21.10 When o-chlorotoluene is...
Ch. 21 - PRACTICE PROBLEM When 2-bromo-1,3-dimethylbenzene...Ch. 21 - PRACTICE PROBLEM (a) Outline a step-by-step...Ch. 21 - Rank the following in order of increasing acidity.Ch. 21 - Prob. 14PCh. 21 - Prob. 15PCh. 21 - Describe a simple chemical test that could be used...Ch. 21 - Prob. 17PCh. 21 - Predict the product of the following reactions.Ch. 21 - 21.19 A synthesis of the β-receptor blocker called...Ch. 21 - Prob. 20PCh. 21 - When m-chlorotoluene is treated with sodium amide...Ch. 21 - Prob. 22PCh. 21 - Prob. 23PCh. 21 - Prob. 24PCh. 21 - Prob. 25PCh. 21 - Prob. 26PCh. 21 - Prob. 27PCh. 21 - Prob. 28PCh. 21 - Prob. 29PCh. 21 - Prob. 30PCh. 21 - Prob. 31PCh. 21 - 21.32 A compound X (C10H14O) dissolves in aqueous...Ch. 21 - 21.33 Compound Z (C5H10O) decolorizes bromine in...Ch. 21 - Explain why, in the case shown, the allyl group...Ch. 21 - In protic solvents the naphthoxide ion (I) is...Ch. 21 - Prob. 36PCh. 21 - Prob. 37PCh. 21 - Prob. 38PCh. 21 - Prob. 39PCh. 21 - Prob. 40PCh. 21 - 21.41 Compound W was isolated from a marine...Ch. 21 - 21.42 Phenols generally are not changed on...Ch. 21 - 21.43 Open the molecular model file for benzyne...Ch. 21 - Which of the following would be the strongest...Ch. 21 - What products would you expect from the following...Ch. 21 - Prob. 3QCh. 21 - Prob. 4QCh. 21 - 21.5 Complete the following synthesis:
Ch. 21 - Prob. 6QCh. 21 - 21.7 Select the stronger acid.
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