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Chapter 28: Q26P (page 1237)

Show how norbornane can be prepared from cyclopentadiene.

Short Answer

Expert verified

Conversion ofcyclopentadiene to norbornane

Step by step solution

01

React with acryl molecule

When molecules of diene and acryl react with one another, the resulting product is:

02

Formation of norbornane

Cyclopentadiene and ethylene are combined in a Diels鈥揂lder process to produce norbornene. Many substitutes for norbornenes may be made in the same way. Norbornadiene, a bicyclic molecule with the same carbon skeleton as norbornene but two additional double bonds, and norbornane, a product of hydrogenation of norbornene, are related.

(norbornene)

03

Norbornane is used for

Antivibration (rail, building, industrial) and anti-impact (personal protective equipment (PPE), shoe parts, bumpers) and grip enhancement) are the primary uses of norbornene in the rubber industry (toy tires, racing tires, transmission systems, transports systems for copiers, feeders, etc.)

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Most popular questions from this chapter

Two products are formed in the following [1,7] sigmatropic rearrangement, one due to hydrogen migration and the other to deuterium migration. Show the configuration of the products by replacing A and B with the appropriate atoms (H or D).

A student found that heating any one of the isomers shown here resulted in scrambling of the deuterium to all three positions on the five-membered ring. Propose a mechanism to account for this observation.

a. Propose a mechanism for the following reaction. (Hint:An electrocyclic reaction is followed by a Diels鈥揂lder reaction.)

b. What would be the product if trans-2-butene were used instead of ethene?

Problem:a. For conjugated systems with two, three, four, five, six, and seven conjugated蟺 bonds, construct quick MOs (just draw the lobes at the ends of the conjugated system as they are drawn on pages 1220 and 1221) to show whether the HOMO is symmetric or antisymmetric.

b. Using these drawings, convince yourself that the Woodward鈥揌offmann rules in Table 28.1 are valid.

Propose a mechanism for the following reaction:
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