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When ethanolic silver nitrate is added, why does trans-stilbene not form a precipitate while cis-stilbene does...

When ethanolic silver nitrate is added, why does trans-stilbene not form a precipitate while cis-stilbene does form a precipiate. Explain how there different structures influence this observation.

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Answer #1

As off stilbeen directly donot react with AgNO3. The brominated product of stilbene reacts with AgNO3. The reaction would be .

Both the brominated products of cis and trans stilbene give precipitation with silver nitrate but trans stilbene brominated product give slow precipitation while cis stilbene brominated product gives fast precipitation. This is because reaction of a bromo compound with AgNO3 is a substitution reaction where a stable carbocation proceed the reaction towards the product successfully . In the dibromo compound formed by cis stilbene there is a formation of bromonium ion which is more stable. Hence precipitation occurs immediately. While in dibromo compound from trans stilbene there is no such bromonium ion formation which hinders the reaction time with silver nitarte hence precipitation is slow.

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