ORGANIC CHEM.(LL)-W/OWL V2 >CUSTOM<
9th Edition
ISBN: 9781337034623
Author: McMurry
Publisher: CENGAGE C
expand_more
expand_more
format_list_bulleted
Concept explainers
Textbook Question
Chapter 18.2, Problem 5P
How would you prepare the following ethers? Use whichever method you think is more appropriate, Williamson synthesis or the alkoxymercuration reaction.
(a) Butyl cyclohexyl ether
(b) Benzyl ethyl ether (C6H5CH2OCH2CH3)
(c) sec-Butyl tert-butyl ether
(d) Tetrahydrofuran
Expert Solution & Answer
Trending nowThis is a popular solution!
Students have asked these similar questions
3
Provide the appropriate reagents or product in the following examples
In which case would a Williamson ether synthesis fail? a. sodium ethoxide + iodomethane c. sodium ethoxide +1-iodo-2-methylpropane b. sodium ethoxide + iodoethane d. sodium ethoxide + 2-iodo-2-methylpropane
How would you prepare the following ethers? Use whichever method you think is more appropriate, the Williamson synthesis or the alkoxymercuration reaction.(a) Butyl cyclohexyl ether(b) Benzyl ethyl ether (C6H5CH2OCH2CH3)(c) sec-Butyl tert-butyl ether(d) Tetrahydrofuran
Chapter 18 Solutions
ORGANIC CHEM.(LL)-W/OWL V2 >CUSTOM<
Ch. 18.1 - Name the following ethers:Ch. 18.2 - Why do you suppose only symmetrical ethers are...Ch. 18.2 - How would you prepare the following ethers using a...Ch. 18.2 - Review the mechanism of oxymercuration shown in...Ch. 18.2 - How would you prepare the following ethers? Use...Ch. 18.2 - Prob. 6PCh. 18.3 - Prob. 7PCh. 18.3 - Write the mechanism of the acid-induced cleavage...Ch. 18.3 - Why are HI and HBr more effective than HCl in...Ch. 18.4 - What product would you expect from Claisen...
Ch. 18.5 - Prob. 11PCh. 18.6 - Predict the major product of each of the following...Ch. 18.6 - Prob. 13PCh. 18.6 - Predict the major product of the following...Ch. 18.7 - 15-Crown-5 and 12-crown-4 ethers complex Na+ and...Ch. 18.8 - Prob. 16PCh. 18.8 - 2-Butene-l-thiol is one component of skunk spray....Ch. 18.9 - The 1H NMR spectrum shown is that of a cyclic...Ch. 18.SE - Give IUPAC names for the following compounds...Ch. 18.SE - Show the product, including stereochemistry, that...Ch. 18.SE - Prob. 21VCCh. 18.SE - Treatment of the following alkene with a...Ch. 18.SE - Prob. 23MPCh. 18.SE - Prob. 24MPCh. 18.SE - Predict the product(s) and provide the mechanism...Ch. 18.SE - The alkoxymercuration of alkenes involves the...Ch. 18.SE - Predict the product(s) and provide the mechanism...Ch. 18.SE - Predict the product(s) and provide the mechanism...Ch. 18.SE - Prob. 29MPCh. 18.SE - Ethers undergo an acid-catalyzed cleavage reaction...Ch. 18.SE - Treatment of 1, 1-diphenyl-l, 2-epoxyethane with...Ch. 18.SE - Fluoxetine, a heavily prescribed antidepressant...Ch. 18.SE - When 2-methyl-2, 5-pentanediol is treated with...Ch. 18.SE - Prob. 34MPCh. 18.SE - Prob. 35MPCh. 18.SE - Aldehydes and ketones undergo acid-catalyzed...Ch. 18.SE - Propose a mechanism to account for the following...Ch. 18.SE - Prob. 38APCh. 18.SE - Prob. 39APCh. 18.SE - How would you prepare the following ethers?Ch. 18.SE - Prob. 41APCh. 18.SE - tert-Butyl ethers can be prepared by the reaction...Ch. 18.SE - Treatment of trans-2-chlorocyclohexanol with NaOH...Ch. 18.SE - Predict the products of the following ether...Ch. 18.SE - Prob. 45APCh. 18.SE - Prob. 46APCh. 18.SE - Write the mechanism of the hydrolysis of cis-5,...Ch. 18.SE - Prob. 48APCh. 18.SE - Acid-catalyzed hydrolysis of a 1,...Ch. 18.SE - Prob. 50APCh. 18.SE - Epoxides are reduced by treatment with lithium...Ch. 18.SE - Prob. 52APCh. 18.SE - The red fox (Vulpes vulpes) uses a chemical...Ch. 18.SE - Anethole, C10H12O, a major constituent of the oil...Ch. 18.SE - Propose structures for compounds that have the...Ch. 18.SE - Prob. 56GPCh. 18.SE - How would you synthesize anethole (Problem 18-54)...Ch. 18.SE - How could you prepare benzyl phenyl ether from...Ch. 18.SE - Meerwein's reagent, triethyloxonium...Ch. 18.SE - Prob. 60GPCh. 18.SE - Prob. 61GPCh. 18.SE - The Zeisel method is an old analytical procedure...Ch. 18.SE - Prob. 63GPCh. 18.SE - Prob. 64GPCh. 18.SE - Prob. 65GPCh. 18.SE - Identify the reagents a-e in the following scheme:Ch. 18.SE - Propose structures for compounds that have the...Ch. 18.SE - Prob. 68GPCh. 18.SE - Prob. 69GPCh. 18.SE - Predict the product(s) if the starting materials...
Knowledge Booster
Learn more about
Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.Similar questions
- Provide a stepwise synthesis for benzyl alcohol to sodium benzoate with reagents KMnO4 and NaOH (including arrow-pushing mechanisms) Please show all the arrow push with the given reagents above.arrow_forwardShow how you would synthesize the following compounds, starting with benzene or toluene and any necessary acyclicreagents. Assume para is the major product (and separable from ortho) in ortho, para mixtures.3-nitro-5-bromobenzoic acidarrow_forwardShow how you would synthesize the following compounds, starting with benzene or toluene and any necessary acyclicreagents. Assume para is the major product (and separable from ortho) in ortho, para mixtures. 4-butylphenolarrow_forward
- how how you would synthesize the following compounds, starting with benzene or toluene and any necessary acyclicreagents. Assume para is the major product (and separable from ortho) in ortho, para mixtures. 1-phenylpropan-2-olarrow_forwardA key step in the synthesis of naproxen, an NSAID more commonly known by its brand name, Aleve (Section 3.9), is a coupling reaction of 2-bromo-6-methoxynaphthalene to form 2-methoxy-6-vinylnaphthalene. Show three different coupling reactions, and the required reagents, that could be used tocarry out this step.arrow_forwardChoose the right reagent or series of reagents from the ones listed below to prepare 2-pentanone from acetylene. NaNH2NaNH2 followed by CH3CH2CH2BrCH3CH2CH2Br, then disiamylborane followed by H2O2H2O2, HO−HO− H2H2, Lindlar followed by H2OH2O, H+H+ NaNH2NaNH2 and CH3CH2CHOCH3CH2CHO NaNH2NaNH2 followed by H2OH2O, H+H+ NaNH2NaNH2 followed by CH3CH2CH2BrCH3CH2CH2Br, then H2OH2O, H2SO4H2SO4, HgSO4 Choose one.arrow_forward
- Below are two potential methods for preparing the same ether (Option A and B), but only one of them is actually successful. Identify the successful approach (A or B)arrow_forwardEach 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.arrow_forwardPropose a stepwise mechanism that accounts for the transformations below.arrow_forward
- Show how you would synthesize the following compounds, starting with benzene or toluene and any necessary reagents. Assume para is the major product (and separable from ortho) in ortho, para mixtures. a) 1-phenypentane b) p- bromobenzene sulfonic acid c) o- chlorobenzonic acid d) m- chloronitrobenzenearrow_forwardBrevicomin, the aggregation pheromone of the western pine bark beetle, contains a bicyclic bridged ring system and is prepared by the acid-catalyzed cyclization of 6,7-dihydroxynonan- 2-one. a. Suggest a structure for brevicomin. b. Devise a synthesis of 6,7-dihydroxynonan-2-one from 6-bromohexan-2-one. You may also use three-carbon alcohols and any required organic or inorganic reagents.arrow_forward
arrow_back_ios
arrow_forward_ios
Recommended textbooks for you
- Organic Chemistry: A Guided InquiryChemistryISBN:9780618974122Author:Andrei StraumanisPublisher:Cengage Learning
Organic Chemistry: A Guided Inquiry
Chemistry
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Cengage Learning
Alcohols, Ethers, and Epoxides: Crash Course Organic Chemistry #24; Author: Crash Course;https://www.youtube.com/watch?v=j04zMFwDeDU;License: Standard YouTube License, CC-BY