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Chapter 31: Question 31.40 (page 1256)

Draw a stepwise mechanism for the following reaction.

Short Answer

Expert verified

Answer

The mechanism of the reaction

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Step by step solution

01

About the given reaction

The given starting material consists of a five-membered cyclic ring, double bonds, and a triple bond. It is treated with an acid that gives rise to a network of cyclic rings.

02

About the mechanism of the reaction

The given compound is rearranged and is treated with H3O+that will result in the formation of a species in which the oxygen atom has a positive charge. This species is rearranged, which gives rise to a resonance structure.

03

About the mechanism

The obtained cation is rearranged and treated with water. The process is repeated several times, resulting in the formation of the final product. The overall mechanism is shown below.

Mechanism of the reaction

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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.

A flask contains 1/3 mole of H2 and 2/3 mole of He. Compare the force on the wall per impact of H2 relative to that for He.

Draw the products formed when triacylglycerol A is treated with each reagent. Rank compounds A, B and C in order of increasing melting point.

  1. H2O,H+
  2. data-custom-editor="chemistry" H2(excess),data-custom-editor="chemistry" Pd-C→B
  3. H2(1 equiv), Pd-C→C

Locate the isoprene units in each compound.

a.

b.

c.

d.

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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