Dolbier HW Solutions 321

Dolbier HW Solutions 321 - CH 3 CH 2 Br PBr 3 Ethanol Ethyl...

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( d ) Because the target molecule is an ether, it ultimately derives from two alcohols. Our f rst task is to assemble 3-phenyl-1-propanol from the designated starting material benzyl alcohol. This requires formation of a primary alcohol with the original carbon chain extended by two carbons. The standard method for this transformation involves reaction of a Grignard reagent with ethylene oxide. After 3-phenyl-1-propanol has been prepared, its conversion to the corresponding ethyl ether can be accomplished in either of two ways: or alternatively The reagents in each step are prepared from ethanol. ( e ) The target epoxide can be prepared in a single step from the corresponding alkene. Disconnections show that this alkene is available through a Diels Alder reaction. 1 H 2 CC H 2 CH 3 COOH O Bicyclo[2.2.2]oct-2-ene O 2,3-Epoxybicyclo[2.2.2]octane
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Unformatted text preview: CH 3 CH 2 Br PBr 3 Ethanol Ethyl bromide CH 3 CH 2 OH or HBr CH 3 CH 2 ONa Na Ethanol Sodium ethoxide CH 3 CH 2 OH C 6 H 5 CH 2 CH 2 CH 2 OCH 2 CH 3 1. Na 3-Phenyl-1-propanol Ethyl 3-phenylpropyl ether C 6 H 5 CH 2 CH 2 CH 2 OH 2. CH 3 CH 2 Br C 6 H 5 CH 2 CH 2 CH 2 Br PBr 3 3-Phenyl-1-propanol 1-Bromo-3-phenylpropane Ethyl 3-phenylpropyl ether (1-ethoxy-3-phenylpropane) C 6 H 5 CH 2 CH 2 CH 2 OH C 6 H 5 CH 2 CH 2 CH 2 OCH 2 CH 3 or HBr NaOCH 2 CH 3 ethanol C 6 H 5 CH 2 Br PBr 3 Benzyl alcohol Benzyl bromide 3-Phenyl-1-propanol C 6 H 5 CH 2 OH C 6 H 5 CH 2 CH 2 CH 2 OH or HBr 1. Mg, diethyl ether 3. H 3 O 1 2. H 2 C CH 2 O C 6 H 5 CH 2 CH 2 CH 2 OCH 2 CH 3 C 6 H 5 CH 2 CH 2 CH 2 OH CH 3 CH 2 OH 1 ETHERS, EPOXIDES, AND SULFIDES 415...
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