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Chapter 31: Question 31.12 (page 1250)

Write a stepwise mechanism for the following reaction.

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01

Diphosphate

Diphosphate is the oxyanion of phosphorus, and this compound contains two phosphate groups. It acts as a good leaving group (-OPP), and when two diphosphates are added, it forms geranyl diphosphate (10-C compound).

02

Stepwise mechanism

In the first step, the formation of a new C-C sigma bond occurs by the loss of diphosphate and then attack by isopentenyl diphosphate (nucleophile) on allylic carbocation.

In the second step, a new bond is formed by losing a proton.

Stepwise mechanism

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Most popular questions from this chapter

Unlike many fats and oils, the cocoa butter used to make chocolate is remarkably uniform in composition. All triacylglycerols contain oleic acid esterified to the ยฐ2OH group of glycerol, and either palmitic acid or stearic acid esterified to theยฐ1 OH groups. Draw the structures of two possible triacylglycerols that compose cocoa butter.

Convert each ball-and-stick model to a skeletal structure that clearly shows the stereochemistry at the ring fusion of these decalin derivatives.

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The biosynthesis of lanosterol from squalene has intrigued chemists since its discovery. It is now possible, for example, to synthesize polycyclic compounds from acyclic or monocyclic precursors by reactions that form several C-C bonds in a single reaction mixture.

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