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Chapter 31: Question 31.13 (page 1250)

Draw a stepwise mechanism for the conversion of geranyldiphosphateto α-terpinene .

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Answer

Step by step solution

01

Synthesis of α-terpinene from geranyldiphosphate.

In the organic synthesis of , different steps are involved, starting with isomerization, cyclization, and nucleophilic attack. In between the mechanism, a resonance stabilized carbocation is formed.

02

Stepwise mechanism

  • In the first step, loss of OPP occurs.
  • The resonance stabilized carbocation is formed by single bond-free rotation.
  • Attack of the nucleophile with diphosphate.
  • The leaving group OPP is removed, and the double bond present at the other end is used for intramolecular cyclization.
  • By 1,2-H shift, carbocation is stabilized, and we get the desired .

Conversion of geranyldiphosphate toα-terpinene

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Most popular questions from this chapter

Treatment of cholesterol with mCPBA results in formation of a single epoxide A, with the stereochemistry drawn. Why isn’t the isomeric epoxide B formed to any extent?

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Question: Flexibilene is a terpene isolated from Sinulariaflexibilis, a soft coral found in the Indian Ocean. Draw a stepwise mechanism for the formation of flexibilene from farnesyl diphosphate and isopentenyl diphosphate. What is unusual about the cyclization that forms the 15-membered ring of flexibilene?

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(a)(b)

(c)

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