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Chapter 31: Question 31.13 (page 1250)

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

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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 to伪-terpinene

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Most popular questions from this chapter

Draw the enantiomer and any two diastereomers of cholesterol. Does the OH group of cholesterol occupy an axial or equatorial position?

Question: A difficult problem in the synthesis of PGF2伪 is the introduction of the OH group at C15 in the desired configuration.

  1. Label this stereogenic center as R or S.
  2. A well known synthesis of PGF2伪involves reaction of A with Zn(BH4)2, a metal hydride reagent similar in reactivity to NaBH4, to form two isomeric products, B and C. Draw their structures and indicate their stereochemical relationship.
  3. Suggest a reagent to convert A to the single stereoisomer X.

Write a stepwise mechanism for the following reaction.

Crocin, which occurs naturally in crocus and gardenia flowers, is primarily responsible for the color of saffron.

(a) What lipid and monosaccharides are formed by the hydrolysis of crocin?

(b) Classify the lipid as a monoterpenoid, diperpenoid, etc., and locate the isoprene units.

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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