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Chapter 11: Q.11-14P (page 335)

Question: Review the mechanism of geraniol biosynthesis shown in Figure 11-15, and propose a mechanism for the biosynthesis of limonene from linalyl diphosphate.

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01

Geraniol Biosynthesis

Geraniol is a monoterpenoid containing alcohol functionality. The biosynthesis of terpenes and terpenoids actually take place starting from isopropyl pyrophosphate and dimethylallyl pyrophosphate, then these two react to form geraniol pyrophosphate which then undergo hydrolysis to form geraniol.

02

Redraw lialyl diphosphate

Redraw the structure of lialyl diphosphateso that it has the same orientation as limonene.

03

 Step 3: Mechanism for the biosynthesis of limonene from linalyl diphosphate

Biosynthesis of Limonene

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Most popular questions from this chapter

Among the many examples of reactions that occur with incomplete racemization, the optically pure tosylate of 2,2-dimethyl-1-phenyl-1-propan([伪]D= 230.3) gives the corresponding acetate ([伪]D= 15.3) when heated inacetic acid. If complete inversion had occurred, the optically pure acetatewould have had[伪]D= 153.6. What percentage racemization and what percentageinversion occurred in this reaction?

Question: Order each of the following sets of compounds with respect to reactivity:

b. (CH3)3 CCI (CH3)3 CBr (CH3)3 COH

Predict the product(s) for each elimination reaction below. In each case show the mechanism. What do the mechanisms have in common? Why?

a.

b.

c.

Which reaction in each of the following pairs would you expect to be faster?

(b) Thedisplacement byon bromoethane or on bromocyclohexane

Which compound in each of the following pairs will react faster in an SN2reaction with OH-?

(c)(CH3)3CClorCH3Cl
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