Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
expand_more
expand_more
format_list_bulleted
Concept explainers
Videos
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
Can you provide steps and explanations? When to use each reagents?
Focus on B and C
Provide examples and rules
Can you provide steps and explanations? When to use each reagents?
Can I use BH3 for the second one as well?
Rules? Examples
This is not A or C.
The second one is not A or D
Chapter 18 Solutions
Organic Chemistry
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
- How will you synthesize cyclohexanecarboxaldehyde (cyclohexylmethanal) from the following reagents? (There are no restrictions on the reagents or the number of steps). (a) Cyclohexanone (b) Ethynylcyclohexane (c) Methyl cyclohexylformate (Remember: Formic acid is the IUPAC recognized name for Methanoic acid) (d) Cyclohexanecarboxylic acid (Cyclohexylmethanoic acid) (e) Vinylcyclohexanearrow_forwardplease explainarrow_forward(a) Why is the following reaction a poor method for synthesizing tert-butyl propyl ether? (b) What would be the major product of this reaction? (c) Propose a better synthesis of tert-butyl propyl ether. does not give CH3 CH,CH,CH,—O: Na + CH;–c–Br CH3 tert-butyl bromide odium propoxide CH3 CH₂-C-0-CH₂CH₂CH T CH3 tert-butyl propyl etherarrow_forward
- Show how you would use the Williamson ether synthesis to prepare the following ether. you may use any alcohols as your organic starting materials (a) cyclohexyl propyl ether (b) isopropyl methyl ether (d) ethyl n-propyl ether (two ways) (C) 3-butoxy-1,1-dimethy lcyclohexane from 3,3-dimethyl-cyclohexanol and butanol.arrow_forwarda) b) 1. Provide the necessary reagents to carry out the following transformations. 왜 H H OMearrow_forwardA chemist needs an ether to use as a solvent for a reaction and wants to synthesize it in one step from two of the following available reagents: sodium ethoxide, bromomethane, potassium tert-butoxide, and 2-bromo-2-methylpropane. i) Which combination(s) will give a good yield of an ether? Illustrate, showing the mechanism of the reaction. ii) Illustrate with a mechanism the reaction of one of the combinations that will not yield an ether?arrow_forward
- I need help with this organic synthesis problemarrow_forwardShow how you would synthesize octan-2-one from each compound. You may use any necessary reagents.(a) heptanalarrow_forwardConsider the following reaction. + PhLi (2 eq.) then water a) Propose a structure for the final product. b) Give a complete mechanism for the transformation. c) Draw an energy diagram of the transformation and briefly comment on the relative energies of the starting material, final product, and any intermediate(s), and about the rate determining step.arrow_forward
- Which of the following reactions provides iso-propyl methyl ether in a high yield? A) potassium iso-propoxide + iodomethane B) sodium methoxide + iso-propyl bromide C) methanol + iso-propyl alcohol in the presence of KOH D) iodomethane + iso-propyl bromide in the presence of KOHarrow_forward(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 bromidearrow_forwardShow how you would synthesize the following ethers in good yield from the indicated starting materials and anyadditional reagents needed.(a) cyclopentyl n-propyl ether from cyclopentanol and propan-1-ol(b) n-butyl phenyl ether from phenol and butan-1-olarrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning
Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
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