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acetic acid alkyl position allyl cation allylic rearrangement anion aqueous acetone brucine calculated carbon carbonium ion carbonyl labeled carbonyl position carbonyl-0 carboxyl group Chart VIII completely intramolecular corresponding d-enantiomer d-ester d-isomer d-trans determined dimethylallyl acid phthalate dimethylallyl alcohol dimethylallyl nitrobenzoate dimethylallyl p_-nitrobenzoate discretely labeled dissociated dl-XIV enantiomer enantiomeric acid phthalates ethanol ether ether-oxygen atoms ether-oxygen position excess experimental Fractional distil geometric isomerization hydroxylic solvent infrared spectra intermediate XV internal ion pair internal return intramolecular rearrangement inverse labeling ion-pair intermediate ionizing power isomer kinetics krac loss of optical mechanism melting point mole nitrobenzoic acid optical activity optical purity optically pure oxygen atoms oxygen-18 content oxygen-18 data oxygen-18 label oxygen-18 value polarimetric and titrimetric rate constants rate of racemization ratio reactant reaction rearrangement racemization recrystallization from pentane result in racemization rotation solvolysis products specific rotation titrimetric rate constants trans-o unsolvolyzed ester XIIa