Ether, benzyl ethyl

Write equations describing two different ways in which benzyl ethyl ether could be prepared by a Williamson ether synthesis J... 

The use of an inadequate excess of Ra-Ni (170 mmol Ni/mmol) led to the isolation of a benzyl ethyl ether (37), which was hydrogenolyzed by Pd in the presence of acid (Scheme 4.121). 

Wesdemiotis, C. Feng, R. McLafferty, F.W. Distonic Radical Ions. Stepwise Elimination of Acetaldehyde From Ionized Benzyl Ethyl Ether. J. Am. Chem. Soc. 1985, 707,715-716. 

Barker et al. have demonstrated a vigorous benzyloxy-group participation for the ethanolysis of 4-0-benzyl-1-0-toluene-p-sulphonyl-pentane-l,4-diol to give 2-methyltetrahydrofuran, benzyl ethyl ether, and toluene- -sulphonic acid. Cyclization to 1,4-anhydropentitol deriv-... 

Acetals of aldehydes are usually stable to lithium aluminum hydride but are reduced to ethers with alane prepared in situ from lithium aluminum hydride and aluminum chloride in ether. Butyraldehyde diethyl acetal gave 47% yield of butyl ethyl ether, and benzaldehyde dimethyl acetal and diethyl acetal afforded benzyl methyl ether and benzyl ethyl ether in 88% and 73% yields, respectively [792]. 

Figure 11.38 (Left) Fourth generation monodendron with a hexaethylene glycol tail. (Right) Proposed conformations of poly(benzyl ethyl ether) monodendrons oriented at the air-water interface.

The oxidation of benzaldoxime with perchloryl fluoride (FClOj) has been reported [29 a) to give a complex mixture in which benzaldoxime benzoate and diphenyl oxadiazole are the main products. Sodium nitrohydroxamate [Na2(02NN0)] has been reported [99b) to oxidize benzyl chloride to a mixture of compounds from which benzyl alcohol, benzaldehyde, benzoic acid, 3,4,5-triphenylisoxazole, benzyl-ethyl-ether, phenylnitromethane and diphenyloxadiazole have been isolated. 

Benzyl ethyl ether FALSE FALSE FALSE FALSE... 

Benzyl ethyl ether [539-30-0] M 136.2, b 186°, 65°/10mm, d 0.949, n 14955. Dried with CaCl2 or NaOH, then fractionally distd. [JACS 78 6079 7956],... 

Phenyl n-propyl et.her. Phenyl n-butyl ether o-Cresyl methyl ether (1) m-Cresyl methyl ether. p-Cresyl methyl ether. o-Cresyl ethyl ether m-Cresyl ethyl ether p-Cresyl ethyl ether Benzyl methyl ether Benzyl ethyl ether Methyl a-naphthyl ether Methyl p-naphthyl ether Ethyl a-naphthyl ether Ethyl p-naphthyl ether Benzyl a-naphthyl ether Benzyl P-naphthyl ether o-Methoxydiphenyl p-Methoxydiphenyl. o-Chloroanisole. m-Chloroanisole. p-Chloroanisolc o-Bromoanisole m-Bromoanisole. p-Bromoanisole. o-Iodoanisole m-Iodoanisole p-Iodoanisole o-Nitroanisole... 

SAMPLE SOLUTION (a) Benzyl bromide is a primary bromide and undergoes SN2 reactions readily. It has no hydrogens 3 to the leaving group and so cannot undergo elimination. Ethoxide ion acts as a nucleophile, displacing bromide and forming benzyl ethyl ether. 

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