Between 1865 and 1890, other structures were proposed for benzene, including Dewar benzene and Ladenburg benzene (prismane). Considering what nineteenth-century chemists knew about benzene (one monosu

Question

Between 1865 and 1890, other structures were proposed for benzene, including Dewar benzene and Ladenburg benzene (prismane). Considering what nineteenth-century chemists knew about benzene (one monosubstituted derivative and three disubstituted isomers), which is the better proposal ?

(I) Dewar benzene structure (II) Ladenburg benzene

TestHub · Accepted Answer

Known facts : C 6 ​ H 5 ​ X exists as only one compound and C 6 ​ H 4 ​ X 2 ​ as three isomers. In Ladenburg benzene (prismane) all six carbons are equivalent, so it gives 1 mono and 3 di isomers. Dewar benzene has two kinds of carbon, so it would give 3 monosubstituted isomers and more disubstituted ones. Ladenburg benzene is the better proposal.

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