Q.How would you convert the following compounds into benzene?
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Start your 14-day free trial to unlock the full solution →The key idea is to use cyclic trimerisation reactions — three molecules of a suitable precursor cyclise to form the six‑membered aromatic ring. Ethyne trimerises directly over a hot metal catalyst; ethene must first be dehydrogenated to ethyne; hexane must be aromatised via catalytic reforming (dehydrocyclisation). The final product in each case is benzene, .
The Concept: Building an Aromatic Ring from Small Molecules
Benzene is a flat, hexagonal ring of six carbons with alternating single and double bonds (delocalised electrons). To make it from smaller compounds, we need to join three two‑carbon units (or rearrange a six‑carbon chain) and then create the conjugated ‑system. The reactions that do this are all examples of cyclisation — but the starting material determines the exact path.
Let’s take each compound in turn.
1. From Ethyne ()
Ethyne is the simplest alkyne. Three molecules of ethyne can be passed through a red‑hot iron tube (or over a catalyst like or ) at about . The triple bonds break and the six carbons join head‑to‑tail to form a ring. The driving force is the enormous stability of the aromatic ring compared to three isolated triple bonds.
The reaction is called cyclic trimerisation of alkynes:
This is the most direct route — no extra steps, no by‑products (except sometimes a little hydrogen). It works because each ethyne molecule contributes two ‑bonds that can overlap to form the delocalised ring.
2. From Ethene ()
Ethene is an alkene — it has a double bond, not a triple bond. It cannot trimerise directly to benzene because the ‑bonds are not reactive enough to cyclise without first being converted to a more unsaturated form.
The standard industrial route is:
- Dehydrogenate ethene to ethyne by passing it over a hot catalyst (e.g., at ):
- Then trimerise the ethyne as in step 1.
Alternatively, ethene can be passed over a platinum‑alumina catalyst at high temperature — this simultaneously dehydrogenates and cyclises, but the net reaction is the same:
A common mistake is to think ethene trimerises like ethyne. It does not — the double bond is too strong and too localised. You must first make a triple bond (or use a catalyst that strips hydrogen in situ).
3. From Hexane ()
Hexane is a straight‑chain alkane — no multiple bonds at all. To get benzene, we need to dehydrogenate (remove hydrogen) and cyclise (form a ring) in one step. This is called catalytic reforming or dehydrocyclisation. …
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