**Synthesis Challenge:**Propose a method of synthesis for the compound below, starting from methylcyclopentane. Name and draw all known intermediates, and indicate the optimum conditions for the most effective yield of the product in each reaction.**Target Compound Structure:**- The compound depicted is a β-hydroxy-ketone with a molecular framework consisting of a six-carbon chain.- The structure features a hydroxyl (-OH) group attached to a secondary carbon (position 2) and a ketone (C=O) group at the terminal methyl end (position 1).- An additional keto group is present at the opposite terminal of the chain (position 6).**Diagram Explanation:**- The chemical structure is represented in a skeletal formula.- The chain is denoted as linear with bends indicating the position of carbon atoms.- Functional groups are labeled in red: an alcohol (-OH) group is shown connected to the second carbon, while the carbonyl (C=O) groups are located at the first and sixth carbon positions.- Methyl group (CH₃) is attached to the carbon adjacent to the primary ketone group.Your task is to derive this structure from methylcyclopentane using viable organic synthesis routes.

Answered: Propose a method of synthesis of the…

Chemistry

10th Edition

ISBN:9781305957404

Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste

Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste

Chapter1: Chemical Foundations

Section: Chapter Questions

Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...

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Question

**Synthesis Challenge:**

Propose a method of synthesis for the compound below, starting from methylcyclopentane. Name and draw all known intermediates, and indicate the optimum conditions for the most effective yield of the product in each reaction.

**Target Compound Structure:**

- The compound depicted is a β-hydroxy-ketone with a molecular framework consisting of a six-carbon chain.
- The structure features a hydroxyl (-OH) group attached to a secondary carbon (position 2) and a ketone (C=O) group at the terminal methyl end (position 1).
- An additional keto group is present at the opposite terminal of the chain (position 6).

**Diagram Explanation:**

- The chemical structure is represented in a skeletal formula.
- The chain is denoted as linear with bends indicating the position of carbon atoms.
- Functional groups are labeled in red: an alcohol (-OH) group is shown connected to the second carbon, while the carbonyl (C=O) groups are located at the first and sixth carbon positions.
- Methyl group (CH₃) is attached to the carbon adjacent to the primary ketone group.

Your task is to derive this structure from methylcyclopentane using viable organic synthesis routes.

Expert Solution

Step 1

First step : Methyl cyclopentane contains primary, secondary and tertiary hydrogens. Bromination under photolytic condition is less reactive and more selective reaction. That's why when methyl cyclopentane reacts with Br2 in presence of photon then 1-Bromo-1-methyl cyclopentane is formed. Reaction involves tertiary proton abstraction.

Second step : When it is treated with small but strong base NaOEt in EtOH medium then 1-Methyl-1-cyclopentene is formed. As base is smaller secondary proton abstraction leads to the formation of more stable tri-substituted alkene.