Question: Treatment of 3-methylcyclohexene with HCl yields two products, 1-chloro-3-methylcyclohexane and 1-chloro-1-methylcyclohexane. Draw a mechanism to explain this result.
The carbon atom with a higher number of hydrogen atoms in the bond gets the hydrogen atom from HX bonded to it.
The more substituted and stable carbocation is favored to form the major product. However, the products also contain some amount of that product that has resulted from a less substituted carbocation.
The addition of the hydrogen atom from HX to 3-methylcyclohexene leads to two carbocations. In one case, the carbocationic center is next to the carbon having a methyl group.
Hence, the carbocation undergoes a 1,2-H shift to form a carbocation, leading to the formation of two products.
Question: Eleostearic acid is an unsaturated fatty acid obtained from the seeds of the tung oil tree (Aleurites fordii), a deciduous tree native to China.
(a) Draw the structure of a stereoisomer that has a higher melting point than eleostearic acid.
(b) Draw the structure of a stereoisomer that has a lower melting point.
Question: Draw the structure of (2Z,6E)-3-ethyl-7-methyldeca-2,6-dien-1-ol, the sex pheromone of the codling moth, a common agricultural pest that destroys apple crops. By spraying an apple orchard with this pheromone, the mating of male and female moths is disrupted, and moth populations can be controlled.
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