Chapter 28: Q26P (page 1237)
Show how norbornane can be prepared from cyclopentadiene.
Short Answer
Conversion ofcyclopentadiene to norbornane
Chapter 28: Q26P (page 1237)
Show how norbornane can be prepared from cyclopentadiene.
Conversion ofcyclopentadiene to norbornane
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Get started for freeTwo 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.
Problem:a. Under thermal conditions, will ring closure of (2E,4Z,6Z,8E)-2,4,6,8-decatetraene be conrotatory or disrotatory?
b. Will the product have the cis or the trans configuration?
c. Under photochemical conditions, will ring closure be conrotatory or disrotatory?
d. Will the product have the cis or the trans configuration?
If isomer A is heated to about 100 °C, a mixture of isomers A and B is formed. Explain why there is no trace of isomer C or D.
a. Draw the product of the following reaction:
b. If the terminal sp2 carbon of the substituent attached to the benzene ring is labeled with 14C, where will the label be in the product?
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