Isomerism and StereochemistryhardNUMERICAL

Calculate the total number of distinct geometrical isomers possible for the linear, unsymmetrical poIsomerism and Stereochemistry Chemistry Question

Question

Calculate the total number of distinct geometrical isomers possible for the linear, unsymmetrical polyene chain given by the structure: $C_6H_5-CH=CH-CH=CH-CH=N-OH$.

Answer: 8

💡 Solution & Explanation

The molecule contains 3 stereogenic centers capable of restricted rotation and Geometrical Isomerism: two $C=C$ double bonds and one $C=N$ imine/oxime bond ($n=3$). Because the terminal structural ends of the chain are entirely different (a Phenyl group vs. an $-OH$ group), the molecule is stereochemically unsymmetrical. The formula for unsymmetrical systems is $2^n$. Therefore, $2^3 = 8$ total geometrical isomers exist.

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