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Chapter 16: PROBLEM 16.61 (page 638)

Question: Draw a stepwise mechanism for the biological conversion of linalyl diphosphate to limonene.

Short Answer

Expert verified

Answer

Intramolecular cyclization

Step by step solution

01

Intramolecular cyclization

The intramolecular cyclization occurs between the alkene and the empty alkene orbital.

It eliminates the group at the same time via the bimolecular substitution reaction

02

Explanation

The reaction mechanism of the given is shown as:

Mechanism of the conversion of linalyl diphosphate to limone

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Most popular questions from this chapter

Question:(a) Which triene has the largest heat of hydrogenation?(b) Which triene has the smallest heat of hydrogenation?(c) Which triene absorbs the longest wavelength of UV light?(d) Which triene is most reactive in the Diels-Alder reaction?

Question: The treatment of CH32C=CHCH2Brwith H2Oforms B (molecular formula C5H11O) as one of the products. Determine the structure of B from its 1H NMR and IR spectra.

Question: Draw the products of the following Diels–Alder reactions. Indicate stereochemistry where appropriate.

a.

b.

c.

d.

Question: Draw the structure of each compound

  1. (Z)-penta-1,3-diene in the s-trans conformation
  2. (2E,4Z)-1-bromo-3-methylhexa-2,4-diene
  3. (2E,4E,6E)-octa-2,4,6-triene
  4. (2E,4E)-3-methylhexa-2,4-diene in the s-cis conformation

Question: What diene and dienophile are needed to prepare each compound by a Diels-Alder reaction?

a.

b.
See all solutions

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