ORGANIC CHEMISTRY-ETEXT REG ACCESS
12th Edition
ISBN: 9781119308362
Author: Solomons
Publisher: WILEY
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Chapter SRP, Problem 25P
The Dow process for synthesizing phenol, which involves reaction of chlorobenzene with aqueous sodium hydroxide at high temperature and pressure, produces both diphenyl ether (1) and 4-hydroxybiphenyl (2) as by-products. Write mechanisms that account for formation of 1 and 2.
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Develop syntheses for the following compounds. As starting materials, you may use cyclopentanol, alcohols containing no more than four carbon atoms, and any common reagents and solvents. (a) trans-cyclopentane-1,2-diol (b) 1-chloro-1-ethylcyclopentane
10c
Give reasons for the following:
(i) p-nitrophenol is more acidic than p-methylphenol.
(ii) Bond length of C—O bond in phenol is shorter than that in methanol.
(iii) (CH3)3C—Br on reaction with sodium methoxide (Na+ _OCH3) gives alkene as the main product and not an ether.
Chapter SRP Solutions
ORGANIC CHEMISTRY-ETEXT REG ACCESS
Ch. SRP - 1. Arrange the compounds of each of the following...Ch. SRP - 2. Arrange the compounds of each of the following...Ch. SRP - Predict the final product from each of the...Ch. SRP - Prob. 4PCh. SRP - Write detailed mechanisms for each of the...Ch. SRP - Prob. 6PCh. SRP - Prob. 7PCh. SRP - Prob. 8PCh. SRP - Prob. 9PCh. SRP - Give stereochemical structures for compounds AD:
Ch. SRP - Prob. 11PCh. SRP - The remaining steps in the industrial synthesis of...Ch. SRP - Prob. 13PCh. SRP - Prob. 14PCh. SRP - Prob. 15PCh. SRP - Prob. 16PCh. SRP - 17. Show how you would modify the synthesis given...Ch. SRP - Prob. 18PCh. SRP - Give structures for compounds AD. Compound D gives...Ch. SRP - The tranquilizing drug meprobamate (Equanil or...Ch. SRP - Prob. 21PCh. SRP - 22. Outlined here is the synthesis of a central...Ch. SRP - 23. What are compounds A and B? Compound B has a...Ch. SRP - Prob. 24PCh. SRP - 25. The Dow process for synthesizing phenol, which...Ch. SRP - Prob. 26PCh. SRP - Prob. 27PCh. SRP - 28. Compound Y shows prominent IR absorption...Ch. SRP - Prob. 29PCh. SRP - Consider this reaction involving peracetic acid:...Ch. SRP - 31. A compound (N) with the molecular formula...Ch. SRP - 32. Compound X is insoluble in aqueous sodium...Ch. SRP - Write the structures of the three products...Ch. SRP - Compound C (C9H11NO) gives a positive Tollens test...Ch. SRP - A compound X (C10H14O) dissolves in aqueous sodium...Ch. SRP - Compound Z (C5H10O) decolorizes bromine. The IR...Ch. SRP - 37. Compound W was isolated from a marine annelid...Ch. SRP - 38. Phenols generally are not changed on treatment...
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