2-phenylethanol

Definition

2-phenylethanol is an organic compound with the chemical formula C$_{6}$H$_{5}$CH$_{2}$CH$_{2}$OH. It is a colorless, viscous liquid with a rose-like odor and is used in the production of perfumes, flavorings, and pharmaceuticals.

5 Must Know Facts For Your Next Test

1. 2-phenylethanol can be synthesized through the nucleophilic addition of a Grignard reagent, such as phenylmagnesium bromide, to acetaldehyde.
2. The reaction involves the addition of the Grignard reagent to the carbonyl carbon of acetaldehyde, followed by the protonation of the alkoxide intermediate to form the final alcohol product.
3. This reaction is an example of the broader class of reactions known as nucleophilic addition of hydride and Grignard reagents to form alcohols.
4. 2-phenylethanol is a valuable compound used in the production of rose-scented perfumes, as well as in certain pharmaceutical and flavor applications.
5. The presence of both the phenyl ring and the hydroxyl group in 2-phenylethanol gives it unique physical and chemical properties that make it useful in a variety of industrial and commercial applications.

Review Questions

• Explain the mechanism of the reaction between a Grignard reagent and acetaldehyde to form 2-phenylethanol.
  • The mechanism for the formation of 2-phenylethanol from a Grignard reagent and acetaldehyde involves several steps. First, the nucleophilic Grignard reagent, such as phenylmagnesium bromide, attacks the electrophilic carbonyl carbon of acetaldehyde. This forms a tetrahedral alkoxide intermediate. Next, the alkoxide is protonated, typically by water, to displace the magnesium-containing group and generate the final alcohol product, 2-phenylethanol. This reaction is an example of the broader class of nucleophilic addition reactions used to synthesize alcohols.
• Describe the key properties of 2-phenylethanol that make it a useful compound in various applications.
  • 2-phenylethanol possesses several properties that contribute to its utility in various applications. The presence of both the phenyl ring and the hydroxyl group gives 2-phenylethanol a unique fragrance profile, with a pleasant rose-like odor. This makes it a valuable ingredient in the production of rose-scented perfumes and fragrances. Additionally, the combination of the aromatic ring and the alcohol functionality allows 2-phenylethanol to be used in certain pharmaceutical and flavor formulations, where its specific chemical characteristics are advantageous. The viscous, liquid nature of 2-phenylethanol also facilitates its incorporation into various products and applications.
• Analyze the role of nucleophilic addition reactions, such as the addition of Grignard reagents to aldehydes, in the broader context of organic synthesis and the formation of alcohols.
  • Nucleophilic addition reactions, including the addition of Grignard reagents to aldehydes, are fundamental transformations in organic chemistry that are widely used for the synthesis of alcohols and other important organic compounds. These reactions allow for the formation of carbon-carbon bonds through the addition of a nucleophile, such as a Grignard reagent, to an electrophilic carbonyl carbon. The resulting alkoxide intermediate can then be protonated to yield the desired alcohol product. This class of reactions is highly versatile and enables the construction of more complex organic molecules from simpler starting materials. The ability to form alcohols, like 2-phenylethanol, through nucleophilic addition is a powerful tool in the arsenal of organic synthesis, with applications in the production of pharmaceuticals, fragrances, and other valuable chemicals.

Related terms

Grignard Reagent: A Grignard reagent is an organometallic compound with the general formula R-Mg-X, where R is an organic group and X is a halogen. Grignard reagents are powerful nucleophiles and are used in organic synthesis to form carbon-carbon bonds.

Nucleophilic Addition: Nucleophilic addition is a type of organic reaction where a nucleophile (an electron-rich species) attacks an electrophilic carbon, forming a new bond and adding the nucleophile to the molecule.

Alcohol Formation: Alcohol formation is the process of creating an alcohol (a compound containing a hydroxyl group, -OH) from other organic precursors, such as through the addition of a hydride or Grignard reagent to a carbonyl group.