Using cyclooctyne as your starting material, show how you would synthesize the following compounds. (Once you have shown how to synthesize a compound, you may use it as the starting material in any later parts of this problem.)
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Verified step by step guidance

1. Step 1: Begin with cyclooctyne as the starting material. Cyclooctyne is an eight-membered ring containing a triple bond. The goal is to break the ring and elongate the carbon chain while introducing functional groups.
2. Step 2: Perform oxidative cleavage of the alkyne bond in cyclooctyne using a reagent like ozone (O₃) followed by reductive workup (e.g., Zn/H₂O). This will yield two molecules of octanal (CH₃(CH₂)₆CHO).
3. Step 3: Convert octanal into octanoic acid (CH₃(CH₂)₆COOH) by oxidation. Use an oxidizing agent such as potassium permanganate (KMnO₄) or chromium-based reagents (e.g., Jones reagent).
4. Step 4: Perform a second oxidative cleavage on octanoic acid using a strong oxidizing agent like KMnO₄ under acidic conditions. This will break the carbon chain into smaller fragments, yielding the desired aldehyde and carboxylic acid functional groups.
5. Step 5: Adjust the reaction conditions to ensure the formation of the specific compound shown in the image, which contains both aldehyde and carboxylic acid groups at the ends of a linear chain. Purify the product using techniques like distillation or recrystallization.

Key Concepts

Cyclooctyne Structure and Reactivity

Cyclooctyne is a cyclic alkyne with a unique structure that influences its reactivity. Its strained ring system makes it more reactive than linear alkynes, allowing for various reactions such as cycloadditions and nucleophilic attacks. Understanding its geometry and electronic properties is crucial for predicting how it can be transformed into other compounds.

Synthetic Pathways in Organic Chemistry

Synthetic pathways refer to the series of chemical reactions used to convert one compound into another. In organic synthesis, it is essential to identify the most efficient route, considering factors like yield, selectivity, and the availability of reagents. Knowledge of functional group transformations and reaction mechanisms is vital for designing these pathways.

Functional Group Interconversion

Functional group interconversion involves transforming one functional group into another within a molecule. This concept is fundamental in organic synthesis, as it allows chemists to modify compounds to achieve desired properties or reactivity. Mastery of various reactions, such as oxidation, reduction, and substitution, is necessary for effective synthesis.