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 FRP, Problem 30P
In addition to more highly fluorinated products, fluorination of 2-methylbutane yields a mixture of compounds with the formula
(a) How many different isomers with the formula
(b) If the mixture of
(c) Which fractions would be optically inactive?
(d) Which would you be able to resolve into enantiomers?
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For each alkane, which mono brominated derivatives could you form in good yield by free-radical bromination?(a) cyclopentane (b) methylcyclopentane(c) 2-methylpentane (d) 2,2,3,3-tetramethylbutane
1. Deduce the structure of each compound from the information given. All unknowns in this problem have molecular formula C8H12.
(a) Upon catalytic hydrogenation, unknown W gives cyclooctane. Ozonolysis of W, followed by reduction with dimethylsulfide, gives octanedioic acid, HOOC—(CH2)6—COOH. Draw the structure of W.
(b) Upon catalytic hydrogenation, unknown X gives cyclooctane. Ozonolysis of X, followed by reduction with dimethyl sulfide, gives two equivalents of butanedial,
O=CH—CH2CH2—CH=O. Draw the structure of X.
Give reasons: (i) C—Cl bond length in chlorobenzene is shorter than C—Cl bond length in CH3—Cl.(ii) The dipole moment of chlorobenzene is lower than that of cyclohexyl chloride.(iii) SN1 reactions are accompanied by racemization in optically active alkyl halides
Chapter FRP Solutions
Organic Chemistry
Ch. FRP - Prob. 1PCh. FRP - 2. Which member of these pairs is the more polar?...Ch. FRP - 5. Though they each contain only one type of...Ch. FRP - Predict the products from each of the following...Ch. FRP - Prob. 5PCh. FRP - Prob. 6PCh. FRP - Prob. 7PCh. FRP - Prob. 8PCh. FRP - Predict the products from each of the following...Ch. FRP - Prob. 10P
Ch. FRP - 13. Starting with propyne and using any other...Ch. FRP - Bromination of 2-methylbutane yields predominantly...Ch. FRP - An alkane (A) with the formula C6H14 reacts with...Ch. FRP - Prob. 14PCh. FRP - Prob. 15PCh. FRP - Dehydrohalogenation of meso-1, 2-dibromo-1,...Ch. FRP - Prob. 17PCh. FRP - Prob. 18PCh. FRP - 27. (R)-3-Methyl-1-pentene is treated separately...Ch. FRP - Prob. 20PCh. FRP - Prob. 21PCh. FRP - Prob. 22PCh. FRP - Prob. 23PCh. FRP - Synthesize the following compound by a method that...Ch. FRP - Provide three methods that employ Grignard...Ch. FRP - 34. Compound Yexhibits one NMR signal at (a...Ch. FRP - Prob. 27PCh. FRP - 36. Compound X shows a strong IR absorption band...Ch. FRP - Prob. 29PCh. FRP - 38. In addition to more highly fluorinated...Ch. FRP - Fluorination of (R)-2-flurobutane yields a mixture...Ch. FRP - Prob. 32PCh. FRP - Prob. 33P
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