4-Chlorobutyl chloroformate (ClCH2CH2CH2CH2OCOCl) is an alkaloid precursor for fungal inhibitors and microbiocides. This undergraduate project specifically evaluates the impact of the chloro-substituent (in position 4) in comparison to its alkyl parent, n-butyl chloroformate. Employing the acid-base and conductometric titration methods, we followed the pseudo first-order kinetics of 4-chlorobutyl chloroformate and n-butyl chloroformate at 25.0 oC in a wide variety of pure and binary aqueous organic mixtures. Using the two-term Grunwald-Winstein equation, the mechanism of the reactions was determined and the solvolytic addition-elimination mechanism was found to be dominant. This project was funded by the Delaware INBRE IDeA program, with a grant from the National Institute of General Medical Sciences – NIGMS (8 P20 GM103446-16) from the National Institute of Health, and a National Science Foundation (NSF) EPSCoR grant IIA-1301765 (DE-EPSCoR program). Further scholarship support from the National Science Foundation S-STEM DUE grant 135554 (Cannon Scholar program) and the State of Delaware DEDO program is also acknowledged.

Impact of the position of the chloro-substituent in chloroformate reactivity

253rd National Meeting (2017)

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