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Briefly explain how the experiment about the comparison of the heats of hydrogenation between cyclohexane, cyclohexene, 1,3-cyclohexadiene and benzene is able to indicate the unusual stability of benzene? (Hint: please refer to Slide 9 in "Benzene" chapter of the lecture notes.)

Briefly explain how the experiment about the comparison of the heats of hydrogenation between cyclohexane, cyclohexene, 1,3-cyclohexadiene and benzene is able to indicate the unusual stability of benzene? (Hint: please refer to Slide 9 in "Benzene" chapter of the lecture notes.)

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2. Briefly explain how the experiment about the comparison of the heats of hydrogenation between cyclohexane, cyclohexene, 1,3-cyclohexadiene and benzene is able to indicate the unusual stability of benzene? (Hint: please refer to Slide 9 in "Benzene" chapter of the lecture notes.) Heats of Hydrogenation as Indicators of Benzene's Unusual Stability Benzene's Unusual Structure General Chemistry 2 General Chemistry 2 • The addition of H, to C=C normally gives off about 118 klimol - 3 double bonds would give off 354kJimol • Two conjugated double bonds in cyclohexadiene add 2 H2 to give off 230 kJ/mol • Benzene has 3 unsaturation sites but gives off only 206 kJimol on reacting with 3 H, molecules Therefore it has about 150 kJ more "stability" than an isolated set of three double bonds Based on resonance theory, benzene's actual structure is a hybrid of 2 equivalent resonance forms All its C-C bonds are the same length: 139 pm - between single (154 pm) and double (134 pm) bonds Electron density in all six C-C bonds is identical Structure is planar, hexagonal C-C-C bond angles 120 Each C is sp hybridized and has a p orbital perpendicular to the plane of the six-membered ring 1.5 bonds on average Cyhe
Transcribed Image Text:2. Briefly explain how the experiment about the comparison of the heats of hydrogenation between cyclohexane, cyclohexene, 1,3-cyclohexadiene and benzene is able to indicate the unusual stability of benzene? (Hint: please refer to Slide 9 in "Benzene" chapter of the lecture notes.) Heats of Hydrogenation as Indicators of Benzene's Unusual Stability Benzene's Unusual Structure General Chemistry 2 General Chemistry 2 • The addition of H, to C=C normally gives off about 118 klimol - 3 double bonds would give off 354kJimol • Two conjugated double bonds in cyclohexadiene add 2 H2 to give off 230 kJ/mol • Benzene has 3 unsaturation sites but gives off only 206 kJimol on reacting with 3 H, molecules Therefore it has about 150 kJ more "stability" than an isolated set of three double bonds Based on resonance theory, benzene's actual structure is a hybrid of 2 equivalent resonance forms All its C-C bonds are the same length: 139 pm - between single (154 pm) and double (134 pm) bonds Electron density in all six C-C bonds is identical Structure is planar, hexagonal C-C-C bond angles 120 Each C is sp hybridized and has a p orbital perpendicular to the plane of the six-membered ring 1.5 bonds on average Cyhe
The addition of H, to C=C normally gives off about 118 kJ/mol – 3 double bonds would give off 354kJ/mol • Two conjugated double bonds in cyclohexadiene add 2 H2 to give off 230 kJ/mol Benzene has 3 unsaturation sites but gives off only 206 kJ/mol on reacting with 3 H, molecules Therefore it has about 150 kJ more "stability" than an isolated set of three double bonds Benzene 150 kJ/mol (difference) 1,3-Cyclohexadiene -356 kJ/mol (expected) Cyclohexene -230 kJ/mol -206 kJ/mol (actual) -118 kJ/mol Cyclohexane
Transcribed Image Text:The addition of H, to C=C normally gives off about 118 kJ/mol – 3 double bonds would give off 354kJ/mol • Two conjugated double bonds in cyclohexadiene add 2 H2 to give off 230 kJ/mol Benzene has 3 unsaturation sites but gives off only 206 kJ/mol on reacting with 3 H, molecules Therefore it has about 150 kJ more "stability" than an isolated set of three double bonds Benzene 150 kJ/mol (difference) 1,3-Cyclohexadiene -356 kJ/mol (expected) Cyclohexene -230 kJ/mol -206 kJ/mol (actual) -118 kJ/mol Cyclohexane
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