Early structural studies on benzene had to explain the following experimental evidence. When benzene was treated with Br2 (plus a Lewis acid), a single substitution product of molecular formula C6H5Br was formed. When this product was treated with another equivalent of Br2, three different compounds of molecular formula C6H4Br2 were formed.a. Explain why a single Kekulé structure is consistent with the first result, but does not explain the second result.b. Then explain why a resonance description of benzene is consistent with the results of both reactions.

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Asked Dec 29, 2019
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Early structural studies on benzene had to explain the following experimental evidence. When benzene was treated with Br2 (plus a Lewis acid), a single substitution product of molecular formula C6H5Br was formed. When this product was treated with another equivalent of Br2, three different compounds of molecular formula C6H4Br2 were formed.
a. Explain why a single Kekulé structure is consistent with the first result, but does not explain the second result.
b. Then explain why a resonance description of benzene is consistent with the results of both reactions.

 

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Expert Answer

Step 1

When benzene is treated with Br2, it forms a single substituted product. The bromine atom can replace any hydrogen atom on benzene ring.

When this monosubstituted benzene is further treated with Br2, it forms three different products.

Chemistry homework question answer, step 1, image 1
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Step 2

(a)

Kekule structure of benzene consists of three alternating double and single bonds.

According to Kekule structures, benzene has two structures which are in equilibrium with...

Chemistry homework question answer, step 2, image 1
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