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Organic Synthesis

Condensation

Mechanism:



First of all, one equivalent of alcohol is protonated to its conjugate acid which has the good leaving group, OH2 (water, a weak base).

Next, another equivalent of the alcohol can now perform nucleophilic attack at carbon (SN2), leading to displacement of OH2 (water) and formation of a new C-O bond. This is an SN2 reaction.

The final step is deprotonation of the product by another equivalent of solvent (or other weak base), resulting in our ether product.

Conditions:
Care must be taken with the temperature. Too high and the primary product produced is an alkene.



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