total synthesis of camphor with all the reagents shown.

Expert Solution

Steps in synthesis of Camphor from alpha-pinene.

1) alpha-pinene is treated with ethereal solution at -20 degree with HCl to give product pinene hydrochloride. It is unstable and at 10degree rearranges to bornyl chloride.

2) 1st wagner Meerwein arrangement takes place which is carbocation 1,2-rearrangement reaction in which alkyl, hydrogen or aryl group migrates from one carbon atom to neighbouring carbon atom.

3) Upon 2nd wagner meerwein arrangement Camphene is generated.

4) Camphene witb acetic acid and Sulphuric acid( dehydrating agent) produces isobornyl acetate. Methoxy group(OCH₃) is incorporated to the ring.

5) Isobornyl acetate reacts with strong base Sodium hydroxide (NaOH) giving Isoborneol. It is hydrolysis reaction.

6) Dehydrogenation of Isoborneol gives Camphor in high yield.

queen_honey_blossom answered 2 years ago

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