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Chapter 19: Problem 78

Using your roadmaps as a guide, show how to convert cyclohexane and ethanol into racemic 2-acetylcyclohexanone. You must use ethanol and cyclohexane as the source of all carbon atoms in the target molecule. Show all reagents and all molecules synthesized along the way.

Short Answer

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Question: Describe the step-by-step process of synthesizing racemic 2-acetylcyclohexanone using cyclohexane and ethanol as the sources of all carbon atoms. Answer: To synthesize racemic 2-acetylcyclohexanone using cyclohexane and ethanol as the carbon sources, the following steps need to be performed: 1. Oxidize cyclohexane into cyclohexanone using a strong oxidizing agent like potassium permanganate (KMnO4). 2. Convert ethanol into acetyl chloride by reacting it with thionyl chloride (SOCl2) or phosphorus trichloride (PCl3). 3. Form 2-acetylcyclohexanone by reacting cyclohexanone with acetyl chloride in the presence of a base such as pyridine.

Step by step solution

01

Identify the functional groups of starting materials and target molecule

Cyclohexane is an alkane with the molecular formula C6H12, ethanol is an alcohol with the molecular formula C2H5OH, and 2-acetylcyclohexanone is a ketone with the molecular formula C8H12O. The target molecule contains an acetyl group and a cyclohexanone group.
02

Oxidation of cyclohexane into cyclohexanone

First, we will oxidize cyclohexane to get cyclohexanone. This can be done using an oxidation reaction with a strong oxidizing agent such as potassium permanganate (KMnO4) or chromium trioxide (CrO3) in an acidic medium. Reaction: Cyclohexane + KMnO4 -> Cyclohexanone
03

Acetylation of ethanol

Next, we will convert ethanol into acetyl chloride, which can be used to form an acetyl group in the target molecule. This can be done by reacting ethanol with thionyl chloride (SOCl2) or phosphorus trichloride (PCl3). Reaction: Ethanol + PCl3 -> Acetyl chloride + HCl
04

Formation of 2-acetylcyclohexanone

Finally, we will form the target molecule, racemic 2-acetylcyclohexanone, by reacting cyclohexanone with acetyl chloride in the presence of a base, such as pyridine. Reaction: Cyclohexanone + Acetyl chloride -> 2-Acetylcyclohexanone So, the overall process to convert cyclohexane and ethanol into racemic 2-acetylcyclohexanone is as follows: 1. Oxidation of cyclohexane to cyclohexanone with KMnO4. 2. Acetylation of ethanol with PCl3 to form acetyl chloride. 3. Reaction of cyclohexanone with acetyl chloride in the presence of a base to form the desired product, racemic 2-acetylcyclohexanone.

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