Alpha Pinene Essay

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A functional group is an identity of a certain family compound. It decides compound's chemical properties and how the compounds in the family will react. In this experiment, we study about alkenes, a functional group that consists of one double bond. Specifically, we will learn about hydration of (+) - α - pinene, an alkene by hydroboration-oxidation reaction. Also, we will discover its regiochemistry and stereochemistry. Hydration reaction is a process that gives a alcohol functional group and a hydrogen to a carbon-carbon double bond of an alkene. According to Markovnikov's rule the -OH group will be attached to the most substituted carbon which is a carbon connected to the most branches. As the result, in normal hydration reaction of (+)-α-Pinene, the -OH group will attach the carbon attaching to a methyl group. However, the desired product is (-)-Isopinocampheol, in which the -OH group need to attach to the less substituted carbon instead. In order to form (-)-Isopinocampheol, we need to do hydroboration-oxidation reaction, in which (+)-α-Pinene will react with borane-tetrahydrofuran complex as hydroborating reagent to form an intermediate that have -OH group in anti-Markovnikov position. First of all, the carbon-carbon double bond in (+)-α-PInene will connect with H-BH group. Based on anti-Markovnikov rule, the H ion which has partial positive charge will connect to the most substituted carbon while -B which has partial negative charge will connect to the less substituted carbon. Since (+)-α-Pinene's double bond is trisubstituted and sterically hindered, only two compounds will reaction with borane to form dialkylborane as intermediate. After we get borane in the desired position, we will need to do oxidation process to replace borane by -OH group. Treat dialkylborane with NaOH and H202 to form alcohol and boric acid. Oxygen in hydrogen peroxide will attach to

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