For each of the following target molecules, design a multistep synthesis to show how it can be prepared from the given starting material:
c.
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Identify the functional groups in the starting material and the target molecule. The starting material is a cyclopentyl ethene, and the target molecule is a cyclopentyl propanal.
Recognize that the transformation involves converting an alkene to an aldehyde. This suggests an oxidation reaction.
Consider using hydroboration-oxidation to convert the alkene to an alcohol, which can then be oxidized to an aldehyde.
Perform hydroboration of the alkene using BH3 to form the corresponding alcohol.
Oxidize the alcohol to an aldehyde using PCC (Pyridinium chlorochromate) or a similar mild oxidizing agent.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Alkynes and Alkylation
Alkynes are hydrocarbons containing at least one carbon-carbon triple bond. In organic synthesis, alkylation refers to the process of adding an alkyl group to a molecule, often using alkyl halides. This is crucial for constructing complex molecules, as it allows for the introduction of functional groups and the formation of new carbon-carbon bonds.
Stereochemistry is the study of the spatial arrangement of atoms in molecules and how this affects their chemical behavior. Understanding stereochemistry is essential in synthesis, as the configuration of chiral centers can influence the reactivity and properties of the target molecules. This is particularly important when designing multistep syntheses that involve stereospecific reactions.
Functional group transformations involve converting one functional group into another through various chemical reactions. This concept is fundamental in organic synthesis, as it allows chemists to modify the reactivity and properties of molecules. Recognizing how to strategically change functional groups is key to achieving the desired target molecule from a given starting material.