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
Choose the BEST reagent for carrying out the following conversion.
or
H
(A) NaOH, H₂O
B) NaBH4
C CH₂PPh3
All of the above
CH₂OH
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) Vinylcyclohexane
Draw structural formulas for the isomeric carbocation intermediates formed on treat-
ment of each alkene with HCl. Label each carbocation 1°, 2°, or 3° and state which of
the isomeric carbocations forms more readily.
CH₂CH3
(a) H₂C=C
(c)
CH3
CH3
(b)
(d) H₂C-CH=CH-CH3
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
- Complete the following multistep syntheses by showing the major intermediate products and the reagents necessary for each step. b) Br c) OH ONLYarrow_forwardDevise a synthesis for each compound, starting with methylenecyclohexane and any other reagents you need.(a) 1-methylcyclohexanol (b) cyclohexylmethanol(c) 1-(hydroxymethyl)cyclohexanol (d) trans-2-methylcyclohexanol(e) 2-chloro-1-methylcyclohexanol (f) 1-(phenylmethyl)cyclohexanolarrow_forwarda) Reaction of 2-methyl propene with methanol in acid-catalyzed medium step by step showing the mechanism, show the product to be formed. b) Starting from benzene, synthesize the following substances by choosing the appropriate reagents. 1) m-chloro benzoic acid 2) p-nitro phenolarrow_forward
- Devise a synthesis for each compound, starting with methylenecyclohexane and any other reagents you need.(a) 1-methylcyclohexanolarrow_forward18. Identify the products from each step in the following synthesis sequence of reactions. Show the structure of all reactants and products from each step. (a) 3-methyl-1-pentanol + PBr3 --------> A (b) A + Mg/ether-------->B (c) B + 1.CH3CH2C(O)H/2.H3O+ -------> C (d) C + Na2Cr2O7/H2SO4, H2O -----> Darrow_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.(a) 1-phenyl-1-bromobutanearrow_forward
- Devise synthetic routes that allow you to get from the reactant/starting material side of the reactions to the product side. More than one transformation may be needed in each case. (a) H3C₂ (b) OH mayon H3C₂ OH ? ? H3C₂ H3C OH SHarrow_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_forwardShow 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_forward
- The following series of reactions will yield 2) CI-CH2-CH2-C6H5 1) CH3CH2SH + N2OH O 2-chloro-4-ethyl-benzenesulfonic acid O CH;CH2-S-CH2CH2C6H5 O ortho-chloro-ethyl-benzene O 1-phenyl-3-chloro-propane O CH3CH2-O-CH2CH2C6H5arrow_forwardEthers/Aldehydes/Ketones SynthesisDraw and Prepare the following compounds from any simple alkyl halide having four carbons or less,cyclohexane, and/or benzene. You may also use ethylene oxide (oxacyclopropane). SHOW ALLSTEPS AND REAGENTS with arrows.arrow_forwardQuestion: Which reaction would be the best synthesis of the following compound? CH3-CH- NH- CH2- CH3 CH3 (a) (b) EtOH CH3-CH-Br + CH3-CH2- NH2 EtOH CH3-CH=CH2 + CH3-CH2- NH2 CH3 (c) (d) EtOH EtOH CH3-CH-Br + CH3-CEN CH3- CH-NH, + CH3-CHy- Br CH3 CH3 (A) (В) (D) Question: What is the IUPAC name for (СН3)3ССН(ОН)CH2CH(OH)CH2CH(C НЗ)2? * 1,1,1,6-tetramethyl-2,4-heptanediol 2,2,7-trimethyl-3,5-octanediol 2,2,6,6-tetramethyl-3,5-heptanediol 2,7,7-trimethyl-4,6-octanediol O Oarrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
ChemistryChemistryISBN:9781305957404Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCostePublisher:Cengage Learning
ChemistryChemistryISBN:9781259911156Author:Raymond Chang Dr., Jason Overby ProfessorPublisher:McGraw-Hill Education
Principles of Instrumental AnalysisChemistryISBN:9781305577213Author:Douglas A. Skoog, F. James Holler, Stanley R. CrouchPublisher:Cengage Learning
Organic ChemistryChemistryISBN:9780078021558Author:Janice Gorzynski Smith Dr.Publisher:McGraw-Hill Education
Chemistry: Principles and ReactionsChemistryISBN:9781305079373Author:William L. Masterton, Cecile N. HurleyPublisher:Cengage Learning
Elementary Principles of Chemical Processes, Bind...ChemistryISBN:9781118431221Author:Richard M. Felder, Ronald W. Rousseau, Lisa G. BullardPublisher:WILEY
Chemistry
Chemistry
ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Cengage Learning
Chemistry
Chemistry
ISBN:9781259911156
Author:Raymond Chang Dr., Jason Overby Professor
Publisher:McGraw-Hill Education
Principles of Instrumental Analysis
Chemistry
ISBN:9781305577213
Author:Douglas A. Skoog, F. James Holler, Stanley R. Crouch
Publisher:Cengage Learning
Organic Chemistry
Chemistry
ISBN:9780078021558
Author:Janice Gorzynski Smith Dr.
Publisher:McGraw-Hill Education
Chemistry: Principles and Reactions
Chemistry
ISBN:9781305079373
Author:William L. Masterton, Cecile N. Hurley
Publisher:Cengage Learning
Elementary Principles of Chemical Processes, Bind...
Chemistry
ISBN:9781118431221
Author:Richard M. Felder, Ronald W. Rousseau, Lisa G. Bullard
Publisher:WILEY
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