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Chapter 11: Problem 45

Using your roadmap as a guide, show how to convert cyclohexanol into racemic trans-1,2cyclohexanediol. Show all required reagents and all molecules synthesized along the way.

Short Answer

Expert verified
Answer: The step-by-step process is as follows: 1. Identify the starting material (cyclohexanol) and target product (racemic trans-1,2-cyclohexanediol). 2. Choose an appropriate oxidizing agent (KMnO_4). 3. Perform the oxidation reaction with the selected oxidizing agent and any necessary additional reagents (NaIO_4). 4. Verify that the product has the desired trans configuration and is a racemic mixture.

Step by step solution

01

Identify the starting material and target product

In this exercise, the starting material is cyclohexanol, which has a chemical formula of C_6H_(11)OH. The target product is racemic trans-1,2-cyclohexanediol, with a chemical formula of C_6H_(10) (OH)_2.
02

Choose the appropriate oxidizing agent

One possible oxidizing agent that can convert an alcohol to a diol is potassium permanganate (KMnO_4). In this exercise, KMnO_4 will be used with a catalytic amount of sodium periodate (NaIO_4) in the presence of water as the solvent.
03

Perform the oxidation reaction

The oxidation reaction can be represented as follows: Cyclohexanol + KMnO_4 + NaIO_4 -> trans-1,2-cyclohexanediol Visually, this can be represented with the following reaction: C_6H_(11)OH + KMnO_4 + NaIO_4 -> C_6H_(10)(OH)_2
04

Verify the trans configuration and racemic mixture

In the product, trans-1,2-cyclohexanediol, the two hydroxyl groups are located on the opposite sides (trans) of the cyclohexane ring, as required. The reaction conditions ensure that both enantiomers are produced, leading to a racemic product. Overall, the step-by-step process to convert cyclohexanol into racemic trans-1,2-cyclohexanediol is: 1. Identify the starting material (cyclohexanol) and target product (racemic trans-1,2-cyclohexanediol) 2. Choose an appropriate oxidizing agent (KMnO_4) 3. Perform the oxidation reaction with the selected oxidizing agent and any necessary additional reagents (NaIO_4) 4. Verify that the product has the desired trans configuration and is a racemic mixture.

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Most popular questions from this chapter

Following are two reaction sequences for converting 1,2 -diphenylethylene into 2,3-diphenyloxirane. Suppose that the starting alkene is trans-1,2-diphenylethylene. (a) What is the configuration of the oxirane formed in each sequence? (b) Will the oxirane formed in either sequence rotate the plane of polarized light? Explain.

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