Synthesis of Diphenylacetylene This synthesis requires two reactions. The first results in the debromination of trans-stilbene. In the first reaction, glacial acetic acid will be used as the solvent. What is glacial acetic acid? Why are we using pyridinium hydrobromide perbromide instead of bromine in this experiment? What is the name of this reaction and what intermediate is formed?

Organic Chemistry: A Guided Inquiry
2nd Edition
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Andrei Straumanis
Chapter24: Carboxylic Acids & Derivatives
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Synthesis of Diphenylacetylene

This synthesis requires two reactions. The first results in the debromination of trans-stilbene. In the first reaction, glacial acetic acid will be used as the solvent.

What is glacial acetic acid?

Why are we using pyridinium hydrobromide perbromide instead of bromine in this experiment?

What is the name of this reaction and what intermediate is formed?

In the second reaction, we are going to see stilbene dibromide undergo two eliminations to form the alkene. Provide the structure of diphenylacetylene. In each elimination the starting material will lose HBr. What is the name of this type of reaction?

Assuming you began this reaction with 1.035 g of trans-stilbene, and your final weight of diphenylacetylene is 0.377g, what is your percent yield? Which spectrometry would you use to verify that your product no longer contained any bromine, and had been completely converted to the alkyne? Sketch the spectrum of your product.

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