Competing Fragmentation, Substitution and Elimination in the Solvolysis of Alkylated 3??Chloropropanols and their Ethers. Fragmentation reactions no. 28
Abstract The unstrained 3-chloroalcohols 1a, 2a and 3a do not undergo solvolytic fragmentation in neutral and weakly acidic 80% ethanol, only substitution and elimination products being formed by the limiting SN 1-E1 mechanisms. This also applies to the corresponding ethers 1b and 3b. Addition of sodium hydroxide causes the observed rate constants for the 3-chloroalcohols to rise steeply by factors of at least 10 3 to 10 5. These ...
