The leaving group dependence in the rates of solvolysis of 1,2‐diphenylethyl system |
| |
Authors: | D Santhosh Kumar K P Jayakumar S Balachandran |
| |
Institution: | 1. Department of Chemistry, Government Arts College, Thiruvananthapuram, Kerala 695 014, India;2. Forensic Science Laboratory, Thiruvananthapuram, Kerala 695 014, India;3. Department of Chemistry, N. S. S. College, Cherthala, Alappuzha, Kerala 670 055, India |
| |
Abstract: | 1,2‐Diphenylethyl chloride undergoes solvolysis by SN1 mechanism in aqueous organic solvents. The α‐phenyl group of 1,2‐diphenylethyl chloride enters into conjugation with the developing carbocationic centre. The β‐phenyl group on the other hand was unable to extend its conjugation via neighbouring group participation due to steric inhibition of resonance in the formation of non‐classical carbocation. 1,2‐Diphenylethyl chloride thus behaves similar to 1‐phenylethyl chloride in its solvolysis pattern. The solvolytic rate studies of chloride and methanesulphonate of 1,2‐diphenylethyl alcohol in various aqueous organic solvents show that the dispersion observed in the Winstein–Grunwald plot is not due to a change in leaving group but due to the difference in solvation requirements of aromatic and aliphatic groups. Copyright © 2010 John Wiley & Sons, Ltd. |
| |
Keywords: | kinetics leaving group effect LFERS solvolysis solvent effect |
|
|