Chapter 8: Q48E (page 262)
Question:Predict the products of the following reactions. Don’t worry about thesize of the molecule; concentrate on the functional groups.
Short Answer
Answer
Products of the reactions are:
Step by step solution
Product of reaction (a)
In the first reaction reagent is bromine, and the reactant is cholesterol. In cholesterol, an alkene is a nucleophile, and it is reactive; therefore, double bonds of an alkene will react with the bromine and will for vicinal- dibromide or 1,2- dibromide.
Product of reaction (b)
In this reaction, the reactant is an unsymmetrical alkene. When treated with the reagent HBr, it will follow Markovnikov’s rule, and a hydrogen atom and bromine will attach on both sides of the double bond. According to Markovnikov’s rule, a hydrogen atom will attach to the carbon atom having more hydrogens, and bromine will attach to that carbon atom which is having less number of hydrogen atoms.
Hence, the product of the reaction is:
Product of reaction (c)
In this reaction, the reagent is osmium Tetraoxide, also known as osmic acid. When cholesterol is treated with this reagent, double bonds of reactant will react with the reagent and produce 1,2-diol.
Product of reaction (d)
When the reactant cholesterol is treated with the reagent, the double bond of the reactant will react with the reagent. This reaction is a hydroboration- oxidation reaction, and a hydrogen atom and hydroxide will add to both sides of the double bond according to anti- Markovnikov’s rule.
Product of reaction (e)
When our reactant, i.e., cholesterol, is reacted with the reagent, the alkene bond will be converted into a cyclopropane ring, and this reaction is known as Simmons- Smith reaction.
Hence, the product of the reaction is:
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