AAMC Practice Test 10

[cycloethane]

Does anyone know why 1-Fluoro-1-methylcyclohexane with tert-BuO'/tert-BuOH is preferable over 2-Fluoro-1-methylcyclohexane when forming a cyclohexyl-methene (I think this is right nomenclature: cyclohexane with a methyl group double bonded to it)? I thought that since primary and tertiary alkyl halides react as E2 with strong bulky bases, it can be either 1-Fluoro or 2-Fluoro... This is from Item 141 AAMC test 10.

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[mitchlucker]

Does anyone know why 1-Fluoro-1-methylcyclohexane with tert-BuO'/tert-BuOH is preferable over 2-Fluoro-1-methylcyclohexane when forming a cyclohexyl-methene (I think this is right nomenclature: cyclohexane with a methyl group double bonded to it)? I thought that since primary and tertiary alkyl halides react as E2 with strong bulky bases, it can be either 1-Fluoro or 2-Fluoro... This is from Item 141 AAMC test 10.

With 2 Fluoro 1 methylcyclohexene what will your products be? Your products will be 1 methylcyclohexene (very small yield) and 1 methyl cyclohex-2-ene....you won't get methylenecyclohexane...the only way to get it is with 1-Fluoro1 methylcyclohexane.

Plus the big bulky base will remove protons from primary carbons first, then secondary carbons.