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 12P
Bromination of 2-methylbutane yields predominantly one product with the formula
(a) 2-Methyl-2-butene
(b) 2-Methyl-2-butanol
(c) 3-Methyl-2-butanol
(d) 3-Methyl-1-butyne
(e) 1-Bromo-3-methylbutane
(f) 2-Chloro-3-methylbutane
(g) 2-Chloro-2-methylbutane
(h) 1-Iodo-3-methylbutane
(i)
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How could you convert butanoic acid into the following compounds?
Write each step showing the reagents needed.
(a) 1-Butanol (b) 1-Bromobutane (c) 1-Butene
2-bromo-2-methylbutane undergoes hydrolysis reaction with water, H2O toform compound W. Compound X and compound Y are produced when 2-bromo-2-methylbutane undergoes elimination reaction with alcoholic ofsodium hydroxide, NaOH.
(i) Draw the structural formula of compounds W, X and Y
(a) Why is the following reaction a poor method for the synthesis of t-butyl
propyl ether?
(b) What would be the major product from this reaction?
(c) Propose a better synthesis of r-butyl propyl ether.
ÇH,
does not
give
ÇH,
CH,CH,CH,-O: *Na + CH,-C-Br
> CH,-C-o-CH,CH,CH,
CH,
CH,
t-butyl propyl ether
sodium propoxide
1-butyl bromide
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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