Organic Chemistry
11th Edition
ISBN: 9781118133576
Author: T. W. Graham Solomons, Craig Fryhle
Publisher: Wiley, John & Sons, Incorporated
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Textbook Question
Chapter 8, Problem 65P
(a) Based on the following information, draw three-dimensional formulas for A, B, and C.
Reaction of cyclopentene with bromine in water gives A.
Reaction of A with aqueous NaOH (1 equivalent, cold) gives B, C5H8O (no 3590–3650-cm−1 infrared absorption). (See the squalene cyclization discussion in “The Chemistry of…Cholesterol Biosynthesis” in WileyPLUS for a hint.)
Heating of B in methanol containing a catalytic amount of strong acid gives C, C6H12O2, which does show 3590–3650-cm−1 infrared absorption.
(b) Specify the (R) or (S) configuration of the chirality centers in your predicted structures for C. Would C be formed as a single stereoisomer or as a racemate?
(c) How could you experimentally confirm your predictions about the stereochemistry of C?
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Chapter 8 Solutions
Organic Chemistry
Ch. 8 - Prob. 1PPCh. 8 - PRACTICE PROBLEM Outline mechanisms for the...Ch. 8 - Practice Problem 8.3 Provide mechanistic...Ch. 8 - Prob. 4PPCh. 8 - PRACTICE PROBLEM
8.5 In one industrial synthesis...Ch. 8 - Prob. 6PPCh. 8 - Prob. 7PPCh. 8 - Prob. 8PPCh. 8 - Prob. 9PPCh. 8 - PRACTICE PROBLEM (a) Outline a likely mechanism...
Ch. 8 - Prob. 11PPCh. 8 - Prob. 12PPCh. 8 - Practice Problem 8.13
Specify the appropriate...Ch. 8 - Prob. 14PPCh. 8 - Practice Problem 8.15 Write a mechanism to explain...Ch. 8 - Prob. 16PPCh. 8 - Prob. 17PPCh. 8 - Prob. 18PPCh. 8 - Practice Problem 8.19 Treating cyclohexene with l,...Ch. 8 - Prob. 20PPCh. 8 - Practice Problem 8.21
Predict the products of the...Ch. 8 - Prob. 22PPCh. 8 - Prob. 23PPCh. 8 - Prob. 24PPCh. 8 - Prob. 25PPCh. 8 - Write structural formulas for the products that...Ch. 8 - Prob. 27PCh. 8 - Prob. 28PCh. 8 - 8.29. Give the structure of the products that you...Ch. 8 - Give the structure of the products you would...Ch. 8 - Prob. 31PCh. 8 - Prob. 32PCh. 8 - Prob. 33PCh. 8 - Prob. 34PCh. 8 - Prob. 35PCh. 8 - Prob. 36PCh. 8 - Prob. 37PCh. 8 - When 3, 3-dimethyl-2-butanol is neared with...Ch. 8 - Prob. 39PCh. 8 - Prob. 40PCh. 8 - Prob. 41PCh. 8 - The reaction of bromine with cyclohexene involves...Ch. 8 - Prob. 43PCh. 8 - Internal alkynes can be isomerized to terminal...Ch. 8 - 8.43. Write a mechanism that explains the...Ch. 8 - 8.44. Write a mechanism for the following...Ch. 8 - Write a mechanism that explains formation of the...Ch. 8 - Prob. 48PCh. 8 - 8.49 Farnesene (below) is a compound found in the...Ch. 8 - Prob. 50PCh. 8 - Limonene is a compound found in orange oil and...Ch. 8 - Prob. 52PCh. 8 - Synthesize the following compound starting with...Ch. 8 - Prob. 54PCh. 8 - Predict features of their IR spectra that you...Ch. 8 - Deduce the structures of compounds A, B, and C,...Ch. 8 - Ricinoleic acid, a compound that can be isolated...Ch. 8 - 8.54. There are two dicarboxylic acids with the...Ch. 8 - Prob. 59PCh. 8 - Prob. 60PCh. 8 - Prob. 61PCh. 8 - Prob. 64PCh. 8 - Prob. 66PCh. 8 - Prob. 62PCh. 8 - Prob. 63PCh. 8 - 8.65
(a)Based on the following information, draw...Ch. 8 - Triethylamine, (C2H5)3N, like all amines, has a...Ch. 8 - (a) Synthesize (3S, 4R)-3,...Ch. 8 - Prob. 2LGPCh. 8 - Prob. 3LGPCh. 8 - Prob. 4LGPCh. 8 - 8.1 A hydrocarbon whose molecular formula is...Ch. 8 - Prob. 2QCh. 8 - Give the major product of the reaction of...Ch. 8 - The compound shown here is best prepared by which...Ch. 8 - 8.5 A compound whose formula is C6H10 (Compound A)...Ch. 8 - Prob. 6QCh. 8 - 8.7 Which reaction sequence converts cyclohexene...Ch. 8 - Which of the following sequences leads to the best...
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