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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.

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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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