Dolbier HW Solutions 320

Dolbier HW Solutions 320 - propyl alcohol: 2-Propanol...

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( b ) All the methods that we have so far discussed for the preparation of epoxides are based on alkenes as starting materials. This leads us to consider the partial retrosynthesis shown. The key intermediate, 1-phenylcyclohexene, is both a proper precursor to the desired epoxide and readily available from the given starting materials. A reasonable synthesis is Preparation of the required tertiary alcohol, 1-phenylcyclohexanol, completes the synthesis. ( c ) The necessary carbon skeleton can be assembled through the reaction of a Grignard reagent with 1,2-epoxypropane. The reaction sequence is therefore The epoxide required in the f rst step, 1,2-epoxypropane, is prepared as follows from iso-
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Unformatted text preview: propyl alcohol: 2-Propanol (isopropyl alcohol) Propene H 2 SO 4 heat CH 3 COOH O CH 3 CH CH 2 CH 3 CHCH 3 OH 1,2-Epoxypropane CH 3 CH CH 2 O 1 C 6 H 5 MgBr Phenylmagnesium bromide (from bromobenzene and magnesium) C 6 H 5 CH 2 CHCH 3 OH 1-Phenyl-2-propanol 1,2-Epoxypropane H 2 C CHCH 3 O C 6 H 5 C 6 H 5 CH 2 CHCH 3 OH H 2 C CHCH 3 2 1 O 1. Mg, diethyl ether 3. H 3 O 1 2. cyclohexanone C 6 H 5 Br Bromobenzene OH C 6 H 5 1-Phenylcyclohexanol K 2 Cr 2 O 7 H 2 SO 4 , H 2 O OH Cyclohexanol O Cyclohexanone O C 6 H 5 C 6 H 5 H 1 heat CH 3 COOH OH C 6 H 5 O OH C 6 H 5 O C 6 H 5 Target molecule C 6 H 5 Key intermediate 414 ETHERS, EPOXIDES, AND SULFIDES...
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This note was uploaded on 09/28/2011 for the course CHM 2210 taught by Professor Reynolds during the Fall '01 term at University of Florida.

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