Abstract
Rate data for alkaline hydrolysis of γ-butyrolactone, γ-valerolactone, phthalide, and 3-phenylphthalide and their open chain analogues, ethyl acetate, isopropyl acetate, methyl benzoate, and benzyl benzoate respectively have been evaluated in the mixed solvents dimethyl sulphoxide (DMSO)–water, ethanol–water, and acetone–water. The lactones are hydrolysed faster than the open chain esters in all the solvent systems, and the rate enhancements are higher in aqueous ethanol than in aqueous DMSO or aqueous acetone. This shows the minor importance of the electrostatic repulsion between the OH– ion and the ‘lone pair dipole’ of oxygen, the absence of which in the case of lactones was considered to cause their higher reactivity over open chain esters in BAC2 reactions.
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 callMore From: Journal of the Chemical Society, Perkin Transactions 2
Disclaimer: 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.
