DMF was used in the experiment for alkylation of saccharin. Why is ethanol/water
ID: 1040841 • Letter: D
Question
DMF was used in the experiment for alkylation of saccharin. Why is ethanol/water chosen as the solvent for "Bridgehead Reactivity in an Sn1 Solvolysis Reaction" experiment?
?THIS IS THE QUESTION GIVEN TO ME, DO NOT HAVE MORE INFORMATION. AS FAR AS SIMPLIFYING GOES - DMF WAS USED IN THE EXPERIMENT FOR ALKYLATION OF SACCHARIN. WE ARE PERFORMING AN SN1 SOLVOLYSIS REACTION INVOLVING 1-BROMOADAMANTANE AND AMANTADINE. WHY IS ETHANOL/WATER CHOSEN AS THE SOLVENT FOR THIS REACTION. HAVE NO OTHER WAY TO EXPLAIN IT
Explanation / Answer
To understand this you need to know 2 basic things:
1) SN2 reactions are favored in polar aprotic solvents like DMSO, DMF, Ethers etc which do not release H+ .
2)SN1 reactions are favored in polar protic solvents like H20, Ethanol, Propanol etc which release H+. Such solvents stabilise the carbocation formed in SN1 reactions.
- Alkylation of Saccharin follows SN2 reaction mechanism, thus DMF was used.
-Solvolysis at bridgehead leads to carbocation fomation which is stabilised by polar protic solvent, in this case it was water and ethanol.
CHeers!!
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