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Magazine Chapter 20: Q63 (page 813)
Convert propan-2-ol into each compound. You may use any other organic or inorganic compounds
a.
b.
Short Answer
a. Propan-2-ol is oxidized to propanone, which undergoes a Grignard reaction with cyclohexyl magnesium bromide to get the desired product.
b. Propan-2-ol is halogenated and then converted to isopropyl magnesium bromide. This reagent undergoes a Grignard reaction with cyclohexanone to get the desired product.
Step by step solution
Organic synthesis
Organic synthesis is a stepwise conversion of simple organic molecules to complex molecules using organic or organic reagents.
It generally involves oxidation reactions, reduction reactions, and the forming or breaking of C-C bonds.
The reagents and conditions for organic synthesis are selected such that the yield is maximum.
Formation of C-C bonds n organic synthesis
Reactions involving the formation of C-C bonds are an important part of organic synthesis
One of the widely used reactions to form a C-C bondis the Grignard reaction.
It involves the use of alkyl magnesium bromide to react with electrophilic carbon, which is a part of a polar bond. The C-Mg bond in the reagent is polar and can be cleaved to form a carbanion species highly nucleophilic in nature.
Synthesis of given compounds from propan-2-ol
a. In the first step, propan-2-ol is oxidized to propanone using PCC.
Oxidation ofpropan-2-ol
The propanone thus formed is reacted with cyclohexyl magnesium bromide in a Grignard reaction to form 2-cyclohexyl-2-propanol.
Synthesis of 2-cyclohexyl-2-propanol
b. Propan-2-ol is converted into a Grignard reagent by halogenation followed by a reaction with magnesium.
Preparation of isopropyl magnesium bromide
The Grignard reagent thus formed is added to cyclohexanone to form 1-isopropyl cyclohexanol.
Synthesis of 1-isopropylcyclohexanol
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