2-methyl-2-phenylpropanol

Definition

2-methyl-2-phenylpropanol is an organic compound with the molecular formula C₁₀H₁₄O. It consists of a benzene ring (phenyl group) attached to a 2-methylpropanol group, forming a tertiary alcohol. This compound is relevant in the context of nucleophilic addition reactions and the formation of alcohols using hydride and Grignard reagents.

5 Must Know Facts For Your Next Test

1. The addition of a Grignard reagent, such as phenylmagnesium bromide, to acetone can form 2-methyl-2-phenylpropanol as the product.
2. Nucleophilic addition of a hydride (H⁻) to the carbonyl carbon of acetone, followed by protonation, can also yield 2-methyl-2-phenylpropanol.
3. The presence of the phenyl group and the tertiary alcohol functionality in 2-methyl-2-phenylpropanol can affect its physical and chemical properties, such as boiling point and reactivity.
4. 2-Methyl-2-phenylpropanol is a useful intermediate in the synthesis of various organic compounds, including pharmaceuticals and fragrances.
5. The steric hindrance around the tertiary alcohol group in 2-methyl-2-phenylpropanol can impact its reactivity and selectivity in certain organic reactions.

Review Questions

• Explain the mechanism for the formation of 2-methyl-2-phenylpropanol using a Grignard reagent.
  • The formation of 2-methyl-2-phenylpropanol using a Grignard reagent, such as phenylmagnesium bromide, involves a nucleophilic addition reaction. First, the Grignard reagent acts as a nucleophile, attacking the carbonyl carbon of acetone. This is followed by the addition of a proton, which results in the formation of the tertiary alcohol, 2-methyl-2-phenylpropanol. The presence of the phenyl group and the tertiary alcohol functionality can influence the physical and chemical properties of the final product.
• Describe the role of the hydride nucleophile in the synthesis of 2-methyl-2-phenylpropanol.
  • The addition of a hydride (H⁻) nucleophile to the carbonyl carbon of acetone is another method for the synthesis of 2-methyl-2-phenylpropanol. In this reaction, the hydride acts as a reducing agent, attacking the carbonyl carbon and forming an alkoxide intermediate. Subsequent protonation of the alkoxide yields the final tertiary alcohol product, 2-methyl-2-phenylpropanol. The steric hindrance around the tertiary alcohol group can impact the reactivity and selectivity of this compound in further organic transformations.
• Evaluate the significance of 2-methyl-2-phenylpropanol as an intermediate in organic synthesis, considering its structural features and reactivity.
  • 2-Methyl-2-phenylpropanol is an important intermediate in organic synthesis due to its unique structural features and the reactivity of the tertiary alcohol group. The presence of the phenyl group and the tertiary alcohol functionality can influence the physical and chemical properties of the compound, making it a valuable precursor for the synthesis of various organic compounds, including pharmaceuticals and fragrances. The steric hindrance around the tertiary alcohol group can also impact the selectivity and reactivity of 2-methyl-2-phenylpropanol in subsequent organic reactions, making it a versatile building block in the field of organic chemistry.

Related terms

Nucleophilic Addition: A type of organic reaction where a nucleophile adds to an electrophilic carbon, forming a new covalent bond and often resulting in the formation of an alcohol or other functional group.

Grignard Reagent: An organometallic compound with the general formula RMgX, where R is an alkyl or aryl group and X is a halogen. Grignard reagents are strong nucleophiles used in the synthesis of alcohols and other organic compounds.

Tertiary Alcohol: An alcohol where the hydroxyl group (-OH) is attached to a carbon atom that is bonded to three other carbon atoms, resulting in a characteristic tetrahedral structure.