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Chapter 31: Q40P (page 1260)

Draw a stepwise mechanism for the following reaction.

Short Answer

Expert verified

Answer

The mechanism of the reaction

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+ the given compound is rearranged and is treated with

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

Why are phospholipids, but not triacylglycerols, found in cell membranes?

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 a stepwise mechanism for the following conversion, which forms camphene. Camphene is a component of camphor and citronella oils.

Convert the ball-and-stick model of androsterone to (a) a skeletal structure using wedges and dashed wedges around all stereogenic centers; and (b) a three-dimensional representation using chair cyclohexane rings.

androsterone

Draw the structure of the following phospholipids:

a. a cephalin formed from two molecules of stearic acid

b. a sphingomyelin formed from palmitic acid.
See all solutions

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