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Chapter 31: Q.30. (page 1231)

Question: Draw a stepwise mechanism for the conversion of neryl diphosphate to α-pinene, α-pineneis a component of pine oil and rosemary oil.

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Answer

A stepwise mechanism for the conversion of neryl diphosphate to α-pineneis:

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 α-pinene.

Stepwise mechanism

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Most popular questions from this chapter

Question: An isoprene unit can be thought of as having a head and a tail. The “head” of the isoprene unit is located at the end of the chain nearest the branch point, and the “tail” is located at the end of the carbon chain farthest from the branch point. Most isoprene units are connected together in a “head-to-tail” fashion, as illustrated. For both lycopene (Problem 31.26), and squalene (Figure 31.9), decide which isoprene units are connected in a head-to-tail fashion and which are not.

Draw the products formed when cholesterol is treated with each reagent. Indicate the stereochemistry around any stereogenic centers in the product.

  1. CH3COCl
  2. H2,Pd-C
  3. PCC
  4. oleicacid,H+
  5. [1]BH3·THF;[2]H2O2,-OH

Locate the isoprene units in each compound.

a.

b.

Question: Locate the isoprene units in biformene, a component of amber, and classify biformene as a monoterpene, sesquiterpene etc.

Draw all possible constitutional isomers of a triacylglycerol formed from one mole each of palmitic, oleic, and linoleic acids. Locate the tetrahedral stereogenic centers in each constitutional isomer.
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