Dolbier HW Solutions 360

Dolbier HW Solutions 360 - 3 Mg diethyl ether Ethanol...

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Then ( e ) The target aldehyde may be prepared from the corresponding alcohol. The best route to this alcohol is through reaction of an acetylide ion with ethylene oxide. Oxidation with PCC or PDC is appropriate for the f nal step. ( f ) The target molecule has four carbon atoms, suggesting a route involving reaction of an ethyl Grignard reagent with ethylene oxide. Ethylmagnesium bromide is prepared in the usual way. Reaction of the Grignard reagent with ethylene oxide, prepared in part ( b ), completes the synthesis. CH 3 CH 2 CH 2 CH 2 OH CH 3 CH 2 MgBr H 2 C CH 2 1 2. H 3 O 1 1. diethyl ether Ethylmagnesium bromide Ethylene oxide 1-Butanol O CH 3 CH 2 OH CH 3 CH 2 Br CH 3 CH 2 MgBr HBr or PBr
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Unformatted text preview: 3 Mg diethyl ether Ethanol Bromoethane Ethylmagnesium bromide CH 3 CH 2 CH 2 CH 2 OH CH 3 CH 2 H 2 C CH 2 1 2 3-Butyn-1-ol 3-Butynal CCH 2 CH 2 OH HC PCC or PDC CH 2 Cl 2 CCH 2 CH HC O 1 1. diethyl ether 2. H 3 O 1 H 2 C CH 2 O Ethylene oxide [prepared in part ( b )] HC CCH 2 CH 2 OH 3-Butyn-1-ol HC CNa Sodium acetylide [prepared in part ( d )] 3-Butynal O HCCH 2 C CH 3-Butyn-1-ol HOCH 2 CH 2 C CH NaNH 2 Acetylene HC CH Sodium acetylide HC CNa 3-Butyn-2-ol HC OH CCHCH 3 1. CH 3 CH O 2. H 3 O 1 454 ALDEHYDES AND KETONES: NUCLEOPHILIC ADDITION TO THE CARBONYL GROUP...
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