The product of the given reaction is to be predicted. Concept introduction: Terminal alkynes undergo alkoxymercuration-reduction reaction in the presence of ethanol-THF as a solvent to yield a vinyl ether as the final product. The reaction takes place in accordance to Markovnikov’s rule. The ethoxy group in ethanol is bonded to the carbon atom that can better stabilize a positive charge. In step 1 , the Hg atom is electron-poor which is attacked by an electron-rich triple bond. The result is a three-membered mercurium ion intermediate. In step 2 , the solvent acts as a nucleophile to open the ring. In step 3 , the positively charged O atom is deprotonated. Reduction then occurs when NaBH 4 is added, in which Hg containing the substituent is replaced by H . In the case of the terminal alkyne, the ethoxy group attacks the more substituted carbon to acquire more positive charge from Hg .

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Chapter 12, Problem 12.16P

Interpretation Introduction

Interpretation:

The product of the given reaction is to be predicted.

Concept introduction:

Terminal alkynes undergo alkoxymercuration-reduction reaction in the presence of ethanol-THF as a solvent to yield a vinyl ether as the final product. The reaction takes place in accordance to Markovnikov’s rule. The ethoxy group in ethanol is bonded to the carbon atom that can better stabilize a positive charge. In step 1, the Hg atom is electron-poor which is attacked by an electron-rich triple bond. The result is a three-membered mercurium ion intermediate. In step 2, the solvent acts as a nucleophile to open the ring. In step 3, the positively charged O atom is deprotonated. Reduction then occurs when NaBH4 is added, in which Hg containing the substituent is replaced by H. In the case of the terminal alkyne, the ethoxy group attacks the more substituted carbon to acquire more positive charge from Hg.

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