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 freeA 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.
Why was a deuterated compound used in the last reaction on the preceding page?
Draw the product formed when each of the following compounds undergoes an electrocyclic reaction
a. under thermal conditions.
b. under photochemical conditions.
a. Propose a mechanism for the following reaction. (Hint:An electrocyclic reaction is followed by a Diels–Alder reaction.)
b. What would be the product if trans-2-butene were used instead of ethene?
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).
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