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 42P
Phenols generally are not changed on treatment with sodium borohydride followed by acidification to destroy the excess, unreacted hydride. For example, the 1,2-, 1,3-, and 1,4-benzenediols and 1,2,3-benzenetriol are unchanged under these conditions. However, 1,3,5-benzenetriol (phloroglucinol) gives a high yield of a product A that has these properties:
MS (m/z): 110
IR (cm−1): 3250 (broad), 1613, 1485
1H NMR (δ in DMSO): 6.15 (m, 3H), 6.89 (t, 1H), and 9.12 (s, 2H)
(a) What is the structure of A?
(b) Suggest a mechanism by which the above reaction occurred. (1,3,5-Benzenetriol is known to have more tendency to exist in a ketotautomeric form than do simpler phenols.)
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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:
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