Organic Chemistry
12th Edition
ISBN: 9781118875766
Author: T. W. Graham Solomons, Craig B. Fryhle, Scott A. Snyder
Publisher: WILEY
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Question
Chapter 11, Problem 4PP
Interpretation Introduction
Interpretation:
The major product formed by the given reaction under the shown conditions is to be predicted and a detailed mechanism is to be written for the same. Also, the reaction conditions under which 3,3-dimethyl-2-butanol are synthesis is to be listed.
Concept Introduction:
Acid-catalyzed hydration of alkenesproceeds by Markovnikov’sregioselectivity method. Such reactions involves the formation of carbocation as the intermediate which may rearrange to a more stable carbocation by the hydride or alkanide migration.
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Show how the following ethers might be synthesized using (1) alkoxymercuration–demercuration and (2) the Williamson synthesis. (When one of these methods cannot beused for the given ether, point out why it will not work.)(a) 2-methoxybutane
Each of the following is a set of directions for carrying out a reaction or sequence of reactions. Rewrite each set ofdirections in the form of a synthesis.(a) To 2-ethylcyclohexanone, add lithium diisopropylamide, and when that reaction is complete, add bromoethane toyield 2,6-diethylcyclohexanone.(b) Add molecular bromine to 2,2-dimethylcyclohexanone in the presence of acetic acid to yield 6-bromo-2,2-dimethylcyclohexanone. To the resulting mixture, add sodium cyanide to yield 6-cyano-2,2-dimethyl-cyclohexanone.(c) Treat pent-4-ynoic acid with diazomethane to produce methyl pent-4-ynoate. Next, add sodium hydride, followed by(bromomethyl)benzene, to yield methyl 6-phenylhex-4-ynoate.
Predict the product(s) and provide the mechanism for each of the following reactions.
(a)
(b)
LOCH₂CH3
HI
HBr
?
?
Chapter 11 Solutions
Organic Chemistry
Ch. 11 - Prob. 1PPCh. 11 - Practice Problem 11.2 Give bond-line formulas and...Ch. 11 - Prob. 3PPCh. 11 - Prob. 4PPCh. 11 - Prob. 5PPCh. 11 - Prob. 6PPCh. 11 - Prob. 7PPCh. 11 - Practice Problem 11.8 Show how you would prepare...Ch. 11 - Prob. 9PPCh. 11 - Prob. 10PP
Ch. 11 - Practice Problem 11.11
An exception to what is...Ch. 11 - Prob. 12PPCh. 11 - Prob. 13PPCh. 11 - Prob. 14PPCh. 11 - Prob. 15PPCh. 11 - Prob. 16PPCh. 11 - Prob. 17PPCh. 11 - Prob. 18PPCh. 11 - Practice Problem 11.19
Propose structures for each...Ch. 11 - Prob. 20PPCh. 11 - Prob. 21PPCh. 11 - Prob. 22PPCh. 11 - Prob. 23PPCh. 11 - Prob. 24PPCh. 11 - Give an IUPAC substitutive name for each of the...Ch. 11 - Prob. 26PCh. 11 - Prob. 27PCh. 11 - Prob. 28PCh. 11 - Prob. 29PCh. 11 - 11.30. Show how you might prepare 2-bromobutane...Ch. 11 - Prob. 31PCh. 11 - Prob. 32PCh. 11 - Prob. 33PCh. 11 - Considering A-L to represent the major products...Ch. 11 - Write structures for the products that would be...Ch. 11 - Prob. 36PCh. 11 - Provide the reagents necessary for the following...Ch. 11 - 11.38. Predict the major product from each of the...Ch. 11 - Predict the products from each of the following...Ch. 11 - Provide the reagents necessary to accomplish the...Ch. 11 - 11.41. Provide reagents that would accomplish the...Ch. 11 - Prob. 42PCh. 11 - 11.43. A synthesis of the -receptor blocker called...Ch. 11 - Prob. 44PCh. 11 - Prob. 45PCh. 11 - 11.46. For each of the following, write a...Ch. 11 - 11.47. Vicinal halo alcohols (halohydrins) can be...Ch. 11 - Prob. 48PCh. 11 - Prob. 49PCh. 11 - Prob. 50PCh. 11 - Prob. 51PCh. 11 - Prob. 52PCh. 11 - Outlined below is a synthesis of the gypsy moth...Ch. 11 - Prob. 54PCh. 11 - Prob. 55PCh. 11 - Prob. 56PCh. 11 - 11.57. When the 3-bromo-2-butanol with the...Ch. 11 - 11.58. Reaction of an alcohol with thionyl...Ch. 11 - Prob. 59PCh. 11 - Prob. 60PCh. 11 - Prob. 1LGPCh. 11 - Prob. 2LGPCh. 11 - Synthesize the compound shown below from...
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