ARKIVOC

The reactions of 4-chloro-2-butanol and 3-chloro-1-butanol with aqueous sodium hydroxide, and 1-chloro-2-propanol and 2-chloro-1-propanol with isopropyl …

…, K Aaljoki, MR Lyytinen, ML Huusko, M Hotokka

Index: Pihlaja, Kalevi; Aaljoki, Kari; Lyytinen, Maija-Riitta; Huusko, Marja-Liisa; Hotokka, Marjut Arkivoc, 2011 , vol. 2011, # 5 p. 188 - 199

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Abstract

Abstract The total reaction of 4-chloro-2-butanol 1 with NaOH (aq) is dominated (74%) by intramolecular substitution (SNi), besides which bimolecular substitution (SN2, 12%) and 1, 4-elimination (ie fragmentation, contrary to earlier arguments) exhibit a significant contribution (11%). The total reaction of 3-chloro-1-butanol 2 instead is dominated by 1, 4- (72%) and 1, 2-elimination (25%), the substitution reactions being just observable (SNi 2 ...