Bromination of Stilbene- (The melting point retrieved from melting the crystals

Question

Bromination of Stilbene-

(The melting point retrieved from melting the crystals might be what's messing me up since that doesn't relate to literature recorded melting points)

Cis-Stilbene Initial Mass stilbene 0.381 g #of mol 2.1x10 -3 Recovered mass stilbene dibromide 0.457 g # of mol 1.3x10 -3 percent yield 60% melting point temperature 62 C 2. From the melting points of your products, can you determine whether the racemic mixture or the meso compound was formed? 3, Based on your answer in question #2, did the experiment prove or disprove the proposed mechanism of bromination of alkenes? (Be specific about how you will know.)

Explanation / Answer

2. Yes, we can determine whether racemic or meso compound is formed from the melting points.

The meso compound melting point is 238oC for while melting point for the racemic mixture is 113oC.

3. Yes, the experiment approves the proposed mechanism for the bromination of alkenes. Since I have got a racemic mixture after the completion of an experiment which suggests that the bromination of alkene involves the formation of cyclic bromonium ion which can be attacked by either side to open the bromonium ion. one side will give the RR product while the attack from the other side will give the SS product. Both RR and SS will give the racemic mixture.

PS: I have assumed that you have got the racemic mixture but due to the presence of impurities your melting point has decreased from 114 to 620C and therefore I have written this answer considering the assumption that you have got a racemic mixture as a product after the completion of the reaction.

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