How will you synthesize by Hawworth synthesis
Answers
Haworth synthesis is a multistep preparation of phenanthrenes from naphthalenes by means of the Friedel–Crafts acylation with succinic anhydride, followed by a Clemmensen reduction or Wolff–Kishner reduction, cyclization, reduction, and dehydrogenation.
Naphthalene is an organic compound with formula C10H8. It is the simplest polycyclic aromatic hydrocarbon and a white crystalline solid with a characteristic odour that is detectable at concentrations as low as 0.08 ppm by mass.
As an aromatic hydrocarbon, naphthalene's structure consists of a fused pair of benzene rings. It is best known as the main ingredient of traditional mothballs.
It can be synthesized by Haworth synthesis, the steps are as follows:
1. The Friedel craft acylation reaction of benzene with succinic anhydride gives 3 benzoylpropionic acid.
2. Next is the Clemmenson’s reaction with 3-benzoylpropionic acid which gives 4-phenylebutanoic acid.
3. On heating this product in the presence of conc. sulfuric acid results in the formation of ring structure of α-tetralene by the ellimination of water molecule.
4. The Clemmenson reaction of α-tetralene gives tetrahydronaphthalene.
5. Dehydrogenation of tetrahydronaphthalene in the presence of selenium yields naphthalene.
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