Why is benzyl‐gem‐diacetate remarkably stable in aqueous solution? |
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| Authors: | V Jagannadham D Annapurna Padmavathi R Sanjeev |
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| Institution: | 1. Department of Chemistry, Osmania University, Hyderabad 500 007, India;2. Department of Chemistry, Osmania University College for Women, Koti, Hyderabad 500 001, India;3. Department of Chemistry, Lovely Professional University, Phagwara 144 402, Punjab, India |
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| Abstract: | Benzyl‐gem‐diacetate is synthesized and performed its solvolysis in water at 25°C. It did not solvolize even for a year, whereas its counterparts benzyl‐gem‐diazide and dihalides underwent spontaneous cleavage through a SN1 mechanism in aqueous solution to give benzaldehydes as the final product through α‐azido benzyl and α‐halo benzyl carbocation intermediates, respectively. The possible explanations are offered for the extraordinary stability of the benzyl‐gem‐diacetate in water. © 2009 Wiley Periodicals, Inc. Int J Chem Kinet 41: 554–557, 2009 |
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