Try it on paper first. A hint, the key idea and the worked solution are here when you need them.
The heat given out in hydrogenation to cyclohexane is for cyclohexene, for cyclohexa-1,3-diene and for benzene.
How does the first compare with the second, and what does this say about the pi electrons of benzene?
A compound is aromatic when its molecule is cyclic, planar, fully conjugated and has pi electrons. Benzene is about more stable than three separate double bonds, which we find from the heats of hydrogenation. Disubstituted benzenes have three isomers: ortho, meta and para.
Have you tried it?
Work it out on paper first. It is fine to get stuck or make a mistake: that is how we learn. When you are ready, go through the solution one step at a time, and check each step against your own.
Step 1. Benzene. Expected for three separate double bonds: . Measured: . Stabilisation: .
Step 2. The diene. Expected for two separate double bonds: . Measured: . Stabilisation: .
Step 3. Compare. is about nineteen times as large as . Two conjugated double bonds gain a little. A ring of six pi electrons all sharing one cloud gains far more. That is the special stability of an aromatic ring.
Answer: and .
Source. The heats of hydrogenation are standard values from reference tables, for example Clayden, Greeves and Warren, Organic Chemistry.
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