Abstract
A measure of the quantitative effect of proximate fluorine substituents on the rates of SN2 and E2 reactions has been obtained through a study mainly of reactions of fluorinated n-alkyl bromides with weak base, strong nucleophile azide ion and strong base/nucleophile methoxide ion in the protic solvent methanol and the aprotic solvent, DMSO. The order of reactivity for SN2 reactions of azide in methanol at 50°C was found to be: n-alkyl-Br>n-alkyl-CHFBr>n-perfluoroalkyl-CH2CH2Br≫n-perfluoroalkyl-CH2Br>n-alkyl-CF2Br. Approximate relative rates of reaction were: 1, 0.20, 0.12, 1×10−4, <7.7×10−5. The order of reactivity for E2 reactions was found to be: n-perfluoroalkyl-CH2CH2Br≫n-alkyl-CF2Br>n-alkyl-CHFBr>n-alkyl-Br. The approximate relative rates for reaction of methoxide in methanol at 50°C were: 1100, 4.4, 1.9, 1.
Sign-in/Register to access full text options 
Talk to us
Join us for a 30 min session where you can share your feedback and ask us any queries you have
Schedule a callDisclaimer: All third-party content on this website/platform is and will remain the property of their respective owners and is provided on "as is" basis without any warranties, express or implied. Use of third-party content does not indicate any affiliation, sponsorship with or endorsement by them. Any references to third-party content is to identify the corresponding services and shall be considered fair use under The CopyrightLaw.
