Warning: foreach() argument must be of type array|object, bool given in /var/www/html/web/app/themes/studypress-core-theme/template-parts/header/mobile-offcanvas.php on line 20

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?

Short Answer

Expert verified

Answer

The unusual feature of the cyclization is the generation of 2°carbocation instead of 3°carbocation.

Step by step solution

01

Flexibilene

Flexibilene is a diterpene with a chemical formula C20H32 , and its structure has a 15-membered ring.It is obtained from farnesyl diphosphate and isopentenyl diphosphate.

02

Stepwise mechanism of flexibilene

The unusual feature of cyclization is the generation of 2°carbocation instead of 3° carbocation. The cyclization at the other end of the C=C bond will give 3°carbocation, and a 14-membered ring will be formed.

Moreover, the rearrangement of 2°carbocation into 3°carbocation does not occur.

Stepwise mechanism of flexibilene

Unlock Step-by-Step Solutions & Ace Your Exams!

  • Full Textbook Solutions

    Get detailed explanations and key concepts

  • Unlimited Al creation

    Al flashcards, explanations, exams and more...

  • Ads-free access

    To over 500 millions flashcards

  • Money-back guarantee

    We refund you if you fail your exam.

Over 30 million students worldwide already upgrade their learning with Vaia!

One App. One Place for Learning.

All the tools & learning materials you need for study success - in one app.

Get started for free

Study anywhere. Anytime. Across all devices.

Sign-up for free