A solution of 5-methylcyclopenta-1,3-diene rearranges at roomtemperature to a mixture containing 1-methyl-, 2-methyl-, and 5-methylcyclopenta-1,3-diene. (a) Show how both isomeric products areformed from the starting material by a sigmatropic rearrangementinvolving a C–H bond. (b) Explain why 2-methylcyclopenta-1,3-diene isnot formed directly from 5-methylcyclopenta-1,3-diene by a [1,3]rearrangement.
A solution of 5-methylcyclopenta-1,3-diene rearranges at roomtemperature to a mixture containing 1-methyl-, 2-methyl-, and 5-methylcyclopenta-1,3-diene. (a) Show how both isomeric products areformed from the starting material by a sigmatropic rearrangementinvolving a C–H bond. (b) Explain why 2-methylcyclopenta-1,3-diene isnot formed directly from 5-methylcyclopenta-1,3-diene by a [1,3]rearrangement.
Chapter14: Conjugated Compounds And Ultraviolet Spectroscopy
Section14.SE: Something Extra
Problem 50AP: -Ocimene is a pleasant-smelling hydrocarbon found in the leaves of certain herbs. It has the...
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A solution of 5-methylcyclopenta-1,3-diene rearranges at room
temperature to a mixture containing 1-methyl-, 2-methyl-, and 5-
methylcyclopenta-1,3-diene. (a) Show how both isomeric products are
formed from the starting material by a sigmatropic rearrangement
involving a C–H bond. (b) Explain why 2-methylcyclopenta-1,3-diene is
not formed directly from 5-methylcyclopenta-1,3-diene by a [1,3]
rearrangement.
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