Dewar benzene was once proposed as the structure of benzene. How many different monosubstituted products would Dewar benzene give ?

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Dewar benzene (bicyclo[2.2.0]hexa-2,5-diene) has two kinds of hydrogen : the four vinylic CH and the two bridgehead CH. Replacing one H on each kind gives two different monosubstituted products. Real benzene gives only one, which is one reason Dewar benzene was rejected.

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