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Chapter 31: Q30P. (page 1259)

Draw a stepwise mechanism for the conversion of neryl diphosphate to is a component of pine oil and rosemary oil.

Short Answer

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A stepwise mechanism for the conversion of neryl diphosphate tois:

Step by step solution

01

Biosynthesis of terpenes and terpenoids

A diphosphate is a leaving group in the biosynthesis of terpenes and terpenoids.There are two main steps: one is forming a new sigma bond between two carbon atoms, and the other is forming a new pi bond.

02

Stepwise mechanism for the conversion of neryl diphosphate to α-pinene

In the first step, diphosphate loss occurs, forming a resonance stabilized carbocation.

In the second step, a pi bond is formed by the proton loss (with a base B), forming a 伪-pinene.

Stepwise mechanism

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Most popular questions from this chapter

Draw the structure of the following phospholipids:

a. a cephalin formed from two molecules of stearic acid

b. a sphingomyelin formed from palmitic acid.

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

a. Draw a three-dimensional structure for the following steroid.

b. What is the structure of the single stereoisomer formed by reduction of this ketone with H2 , Pd-C? Explain why only one stereoisomer is formed.

Axial alcohols are oxidized faster than equatorial alcohols by PCC and other oxidants. Which OH group in each compound is oxidized faster?

a.

b.

One component of lanolin, the wax that coats sheep鈥檚 wool, is derived from cholesterol and stearic acid. Draw its structure, including the correct stereochemistry of all stereogenic centers.
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