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Magazine Chapter 8: Q22P. (page 425)
Question: Show how you would accomplish the following synthetic conversions.
- 3-methylpent-2-ene to 2-chloro-3-methylpentan-3-ol
- Chlorocyclohexane to trans-2-chlorocyclohexaol
- 1-methylcyclopentanol to 2-chloro-1-methylcyclopentanol
Short Answer
Answer:
(a) 3-methylpent-2-ene to 2-chloro-3-methylpentan-3-ol
(b) Chlorocyclohexane to trans-2-chlorocyclohexaol
(c) 1-methylcyclopentanol to 2-chloro-1-methylcyclopentanol
Step by step solution
Converting reactants to products
In order to convert reactants to a particular product different types of reagents are used.These types of conversion may take place in one step or more than one steps and more than one or more reagents are used.
Explanation of part (a)
(a) To convert 3-methylpent-2-ene to 2-chloro-3-methylpentan-3-ol the reagents used is hypochlorous acid (HOCl). In the first step electrophilic addition and reaction take place according to the below step.
Reaction (a)
Explanation of part (b)
(b) To convert Chlorocyclohexane to trans-2-chlorocyclohexaol, first step is conversion of chlorocyclohexane to chlorocyclohexene. After this chlorocyclohexene is treated with Cl2/H2O to get trans-2-chlorocyclohexanol.
Reaction (b)
Explanation of part (c)
(c) To convert1-methylcyclopentanol to 2-chloro-1-methylcyclopentanol, in first step conversion of 1-methylcyclopentanol to 1-methylcyclopentene take place in presence of POCl3.After this step 1-methylcyclopentene to 2-chloro-1-methylcyclopentanol using Cl2/H2O.
Reaction (c)
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