Following is the structural formula of the tranquilizer meparfynol (Oblivon). Propose a synthesis for this compound starting with acetylene and a ketone. (Notice the \(-y n\) - and \(-o l\) in the chemical name of this compound, indicating that it contains alkyne and hydroxyl functional groups.)

Acetylene is a crucial molecule in the field of organic chemistry, particularly for its application in creating complex molecules. It is a hydrocarbon with the formula \( C_2H_2 \) and is the simplest alkyne—a hydrocarbon with at least one carbon-carbon triple bond. This triple bond is highly reactive due to the presence of \r \r two \r \r electrons and makes acetylene an excellent starting material for various chemical reactions, including organic synthesis.

In synthesizing meparfynol, acetylene is utilized to add a carbon-carbon triple bond to a ketone, which significantly alters the molecule's structure and reactivity. By building on acetylene's reactive alkyne group, chemists can introduce complexity into otherwise simple organic molecules and pave the way for creating specialized compounds such as pharmaceuticals.

Ketones are organic compounds characterized by a carbonyl group \((C=O)\) flanked by two carbon atoms. They are polar molecules due to the carbonyl group, which makes them reactive towards nucleophiles.

In the context of meparfynol synthesis, selecting a proper ketone, such as acetophenone, is vital. Acetophenone comprises a benzene ring connected to a carbonyl group and serves as a precursor to the tranquilizer's phenyl core.

Linking acetylene to acetophenone under basic conditions introduces an alkyne group to the ketone, transforming it into an intermediate compound that is crucial for the final synthesis steps. Ketones like acetophenone are fundamental in organic chemistry, as they are prevalent and can be modified in numerous ways to create new compounds.

An alkyne functional group contains one of the most reactive bonds in organic chemistry: the carbon-carbon triple bond. Alkynes, like acetylene, are known for their versatility in forming carbon-carbon bonds, which is a critical aspect of synthesizing complex molecules.

In the creation of meparfynol, the alkyne group from acetylene is used to introduce a specific structural element into the molecule. This incorporation is part of a broader strategy called functional group interconversion (FGI), where one functional group is converted into another to achieve a desired chemical structure.

The alkyne functionality not only provides a site for further chemical modification but also lays the groundwork for the formation of the tranquilizer's unique molecular architecture.

Tautomerization is a chemical reaction where a compound, known as a tautomer, isomerizes within itself, usually by the shifting a hydrogen atom and forming a double bond. This process is reversible and can significantly change the compound's chemical properties. One of the most common forms of tautomerism involves keto-enol tautomerization, where a ketone is in equilibrium with its corresponding enol (a compound with a hydroxyl group attached to a double-bonded carbon).

In the synthesis of meparfynol, tautomerization plays a crucial role in converting the ynol intermediate into a stable phenol. This crucial step is not just an incidental occurrence but an integral part of the synthetic route, ensuring the transfer of the -OH group to the correct position in the final molecule. Understanding tautomerization is essential for chemists because it often influences the stability and reactivity of compounds in both laboratory syntheses and biological systems.

Organic synthesis is the process by which organic chemists construct complex molecules from simpler ones. It requires a thorough understanding of chemical reactivity and mechanism.

Building a compound like meparfynol from acetylene and a ketone involves several steps, each of which needs careful planning and execution. The process starts with the selection of suitable starting materials and encompasses a series of reactions that involve bond formation, functional group manipulations, and protection-deprotection strategies.

The goal of organic synthesis is not only to create a target molecule but to do so in an efficient and selective manner. The art and science of this process have vast applications, from creating pharmaceuticals to developing new materials, making it a cornerstone of modern chemistry and industry.