Synthons

Definition

Synthons are fundamental structural units that can be used as building blocks in organic synthesis. They represent reactive intermediates or functional groups that can be selectively transformed or coupled to construct more complex target molecules.

5 Must Know Facts For Your Next Test

1. Synthons are selected based on their ability to undergo predictable and reliable chemical transformations to construct the target molecule.
2. The choice of synthons in a retrosynthetic analysis is guided by the principles of atom economy, step economy, and redox economy to maximize efficiency.
3. Synthons can be classified as electrophilic, nucleophilic, or ambident based on their reactivity, which determines their compatibility in coupling reactions.
4. The disconnection approach in retrosynthetic analysis involves identifying key bond disconnections in the target molecule to reveal simpler synthons.
5. Functional group interconversion (FGI) is a critical tool for manipulating synthons to introduce the necessary functionality for the target molecule.

Review Questions

• Explain the role of synthons in the context of organic synthesis and retrosynthetic analysis.
  • Synthons are fundamental structural units that serve as building blocks in organic synthesis. They represent reactive intermediates or functional groups that can be selectively transformed or coupled to construct more complex target molecules. The choice of synthons is guided by the principles of atom economy, step economy, and redox economy to maximize the efficiency of the synthetic route. Retrosynthetic analysis involves identifying key disconnections in the target molecule to reveal simpler synthons, which can then be manipulated through functional group interconversions to build the desired product.
• Describe the different types of synthons based on their reactivity and how this influences their compatibility in coupling reactions.
  • Synthons can be classified as electrophilic, nucleophilic, or ambident based on their reactivity. Electrophilic synthons are attracted to electron-rich regions and typically participate in substitution or addition reactions. Nucleophilic synthons are electron-rich and react with electrophiles. Ambident synthons have multiple potential reaction sites and can exhibit both electrophilic and nucleophilic character, requiring careful consideration of their compatibility in coupling reactions. Understanding the reactivity of synthons is crucial for designing efficient synthetic routes that involve the selective transformation and coupling of these building blocks.
• Analyze the role of functional group interconversion (FGI) in the manipulation of synthons to construct the target molecule in organic synthesis.
  • Functional group interconversion (FGI) is a critical tool for manipulating synthons to introduce the necessary functionality for the target molecule. FGI involves converting one functional group into another, allowing for the selective transformation of synthons to access the desired reactivity and compatibility for subsequent coupling reactions. By strategically applying FGI, synthetic chemists can navigate the retrosynthetic analysis and efficiently construct the target molecule from simpler synthons. The ability to perform FGI on synthons is a key aspect of the disconnection approach in retrosynthetic analysis, as it enables the transformation of available starting materials into the required building blocks for the target compound.

Related terms

Retrosynthetic Analysis: A method of analysis used in organic synthesis to plan the most efficient synthetic route to a target molecule by working backwards from the desired product to the available starting materials.

Disconnection Approach: A strategy in retrosynthetic analysis that involves identifying key disconnections in a target molecule to reveal simpler precursor fragments or synthons.

Functional Group Interconversion (FGI): The process of converting one functional group into another, which is a crucial step in the manipulation of synthons to build more complex molecules.