1. If the reaction gave a mixture of products, could you distinguish between Mec

Question

1. If the reaction gave a mixture of products, could you distinguish between Mechanisms 1 and 4? If so, how?

2. In the yield calculation, it is not necessary to calculate the number of moles of bromine added. Why id this so?

3. What product would a student obtain if he attempted the brominatio of cis-stilbene (also known as (Z)-stilbene) Explain your reasoning.

4. A student attempts the chlorination of trans-stilbene. A solid product was obtained. Would you expect it to be the racemic product, the meso compound or a mixture of the two? Explain your reasoning.

Explanation / Answer

1. This could or can be be determined experimentally. It is either Mechanism 1 yielded to a high mixture or formation of products or Machnism 4 gave the mixture of the product. Temperature or catalyst could also be another factor. Some temperatures or catalyst may favor the mechanism and vice versa.

2. This is because the addition or removal of bromide didnt affect the mechanism. This time the bromide is acting as a spectator ion or reactants. Shortage or excess of it wouldnt bring any change. The reaction is going to be the same as it was before unless otherwise stated.

3.The student will obtain dibromostilbene. The addition of bromine is another widely-used reaction.

4. Meso Compounds. This is because, it contain two or more identical substituted stereocenters. Also, it has an internal symmetry plane that divides the compound in half. These two halves reflect each other by the internal mirror. The stereochemistry of stereocenters should "cancel out". This means, when we have an internal plane that splits the compound into two symmetrical sides, the stereochemistry of both left and right side should be opposite to each other, and therefore, result in optically inactive. Cyclic compounds may also be meso.

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