Problem: 4-Bromo-5-methyhex-2-yne (shown below) undergoes a metal ammonia reduction to form an alkene product. Two hydrogen atoms add to the triple bond with the help of sodium metal in liquid ammonia. Draw the vinyl radical intermediate of this reaction that leads to the major alkene.

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4-Bromo-5-methyhex-2-yne (shown below) undergoes a metal ammonia reduction to form an alkene product. Two hydrogen atoms add to the triple bond with the help of sodium metal in liquid ammonia. Draw the vinyl radical intermediate of this reaction that leads to the major alkene.

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What scientific concept do you need to know in order to solve this problem?

Our tutors have indicated that to solve this problem you will need to apply the Dissolving Metal Reduction Mechanism concept. If you need more Dissolving Metal Reduction Mechanism practice, you can also practice Dissolving Metal Reduction Mechanism practice problems.

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Based on our data, we think this problem is relevant for Professor Roslaniec's class at Modesto Junior College.