1.

You are planning to carry out a reaction between propyne,CH3CCH and sodium amide,NaNH2.You also need to choose an appropriate solvent for carrying out the reaction.Would ethanol be suitable for this purpose? Explain your rationale clearly.

Answer»

No, ethanol would be unsuitable for carrying out the reaction between propyne and methyllithium. The pKa of ethanol is ~16,and sodium amide is strong enough a base to readily abstract a proton from the solvent (pKa of NH3 is ~38); in doing so,it becomes deactivated and is no longer available to react with propyne (pKa ~25).Typically, the selected solvent should be chemically inert toward all substances used in the reaction, so that it does not interfere with the desired reaction.



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