Dolbier HW Solutions 364

Dolbier HW Solutions 364 - C(CH 2 ) 3 CH CH 3 OH CH 3 CH 2...

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Acid-catalyzed dehydration yields the more highly substituted alkene, the desired product, in accordance with the Zaitsev rule. ( c ) Analyzing the transformation retrosynthetically, keeping in mind the starting materials stated in the problem, we see that the carbon skeleton may be constructed in a straightforward manner. Proceeding with the synthesis in the forward direction, reaction between the Grignard reagent of o -bromotoluene and 5-hexenal produces most of the desired carbon skeleton. Oxidation of the resulting alcohol to the ketone followed by a Wittig reaction leads to the f nal product. Acid-catalyzed dehydration of the corresponding tertiary alcohol would not be suitable, be- cause the major elimination product would have the more highly substituted double bond. H 1 heat 2-( o- Methylphenyl)-6-hepten-2-ol 6-( o- Methylphenyl)-1,5-heptadiene
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Unformatted text preview: C(CH 2 ) 3 CH CH 3 OH CH 3 CH 2 C CH 3 CH 3 CHCH 2 CH 2 CH CH 2 PCC CH 2 Cl 2 1-( o-Methylphenyl)-5-hexen-1-ol 1-( o-Methylphenyl)-5-hexen-1-one CH(CH 2 ) 3 CH OH CH 3 CH 2 C(CH 2 ) 3 CH O CH 3 CH 2 2-( o-Methylphenyl)-1,6-heptadiene C(CH 2 ) 3 CH CH 2 CH 3 CH 2 (C 6 H 5 ) 3 P CH 2 1 2 1. diethyl ether 2. H 3 O 1 o-Methylphenylmagnesium bromide 5-Hexenal 1-( o-Methylphenyl)-5-hexen-1-ol MgBr CH 3 O H 2 C CHCH 2 CH 2 CH 2 CH CH(CH 2 ) 3 CH OH CH 3 CH 2 1 CH 3 CH(CH 2 ) 3 CH OH CH 2 CH 3 MgBr HC(CH 2 ) 3 CH O CH 2 1 CH 3 C(CH 2 ) 3 CH CH 2 CH 2 CH 3 C(CH 2 ) 3 CH (C 6 H 5 ) 3 P O CH 2 1 1 CH 2 2 C 6 H 5 C OH CH 3 C 6 H 5 H 3 C 1-Cyclopentyl-1-phenylethanol (1-Phenylethylidene)cyclopentane H 3 PO 4 heat 458 ALDEHYDES AND KETONES: NUCLEOPHILIC ADDITION TO THE CARBONYL GROUP...
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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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