Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
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Textbook Question
Chapter 18.SE, Problem 59GP
Meerwein's reagent, triethyloxonium tetrafluoroborate, is a powerful ethylating agent that converts alcohols into ethyl ethers at neutral pH. Show the reaction of Meerwein’s reagent with cyclohexanol, and account for the fact that trialkyloxonium salts are much more reactive alkylating agents than alkyl iodides.
(CH 3CH 2) 3O + BF 4 - Meerwein's reagentExpert Solution & Answer
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1. (a) Oxidation of 1-butanol with PCC will produce which of the following?
2-chlorobutanal
butanone
butanoic acid
butanal
(b) Which synthetic route is the best way to prepare ethyl isopropyl ether?
CH3CH2OH + (CH3)2CHOH + H2SO4, 140 oC
CH3CH2ONa + (CH3)2CHOH
CH3CH2ONa + (CH3)2CHBr
(CH3)2CHONa + CH3CH2Br
Phenols (pKa ≈ 10) are more acidic than other alcohols, so they are easily deprotonated bysodium hydroxide or potassium hydroxide. The anions of phenols (phenoxide ions) can beused in the Williamson ether synthesis, especially with very reactive alkylating reagents suchas dimethyl sulfate. Using phenol, dimethyl sulfate, and other necessary reagents, show howyou would synthesize methyl phenyl ether.
Choose the best reagents from the list provided below for carrying out the following conversion. Match the reagent with the step number.
HCl (aq), Zn(Hg)
Br2, FeBr3
Na/NH3, -33 degrees C
NBS, light
KMnO4, H3O+
Mg metal, ether
KOH, EtOH, heat
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...
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- When warmed in dilute sulfuric acid, 1-phenyl-1,2-propanediol undergoes dehydration and rearrangement to give 2-phenylpropanal. (a) Propose a mechanism for this example of a pinacol rearrangement (Section 10.7). (b) Account for the fact that 2-phenylpropanal is formed rather than its constitutional isomer, 1-phenyl-1-propanone.arrow_forwardThe base-promoted rearrangement of an -haloketone to a carboxylic acid, known as the Favorskii rearrangement, is illustrated by the conversion of 2-chlorocyclohexanone to cyclopentanecarboxylic acid. It is proposed that NaOH first converts the a-haloketone to the substituted cyclopropanone shown in brackets and then to the sodium salt of cyclopentanecarboxylic acid. (a) Propose a mechanism for base-promoted conversion of 2-chlorocyclohexanone to the proposed intermediate. (b) Propose a mechanism for base-promoted conversion of the proposed intermediate to sodium cyclopentanecarboxylate.arrow_forwardUsing your reaction roadmap as a guide, show how to convert 1-butanol and ethanol into racemic 2-ethoxy-1-butanol. You must use 1-butanol and ethanol as the source of all carbon atoms in the ether product. Show all required reagents and all molecules synthesized along the way.arrow_forward
- Treating a Grignard reagent with carbon dioxide followed by aqueous HCl gives a carboxylic acid. Propose a structural formula for the bracketed intermediate and a mechanism for its formation.arrow_forwardPropose two different methods to synthesize oct-1 -en-3-ol [CH3(CH2)4CH(OH)CH = CH2] using a Grignard reagent and a carbonyl compound. Oct-1-en-3-ol is commonly called matsutake alcohol because it was rst isolated from the Japanese matsutake mushroom.arrow_forwardShow and explain reagents and expiramental conditions to synthesize each compound from 1- propanol.arrow_forward
- When 1-butanol is treated with conc. H2SO4 and heat .A product 'A' is formed from the reaction. Treatment of 'A' with HCl/H2O gives 'B'. Treatment of 'A' with cold KMnO4/OH- gives 'C' Treatment of 'A' with hot KMnO4 /OH- gives 'D' followed by acidification of the mixture to give 'E' 1. identify the compounds represented by A,B,C,D and E.arrow_forwardPredict the products formed when cyclohexanecarbaldehyde reacts with the following reagents.(a) PhMgBr, then H3O+ (b) Tollens reagent (c) semicarbazide and weak acid(d) excess ethanol and acid (e) propane-1,3-diol, H+ (f) zinc amalgam and dilute hydrochloric acidarrow_forwardWhat is the products you expect from oxidation of 2-Hexanol with CrO3 and H3O+?arrow_forward
- Starting with cyclohexanone, show how to prepare these compounds. In addition to the given starting material, use any other organic or inorganic reagents as necessary. Q.) 1-Methylcyclohexenearrow_forwardWrite the formula of reagents used in the following reactions:(i) Bromination of phenol to 2,4,6-tribromophenol(ii) Hydroboration of propene and then oxidation to propanol.(b) Arrange the following compound groups in the increasing order of their property indicated:(i) p-nitrophenol, ethanol, phenol (acidic character)(ii) Propanol, Propane, Propanal (boiling point)arrow_forwardDraw a structural formula for the product formed by treating butanal with each reagent. (a) LiA1H4LiA1H4 followed by H2OH2O (b) NaBH4NaBH4 in CH3OH/H2O (c) H2/Pt (d) Ag(NH3)2+in NH3/H2O (e) H2CrO4, heat (f) HOCH2CH2OH,HClarrow_forward
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