key term - Tert-Butanol

Definition

tert-Butanol, also known as tertiary butyl alcohol, is an organic compound with the chemical formula (CH3)3COH. It is a colorless, flammable liquid with a characteristic alcoholic odor, and is an important intermediate in organic synthesis as well as a widely used industrial solvent.

5 Must Know Facts For Your Next Test

1. tert-Butanol is a tertiary alcohol, meaning the hydroxyl group is attached to a carbon atom that is bonded to three other carbon atoms.
2. The presence of the tertiary carbon atom in tert-Butanol gives it unique physical and chemical properties, such as increased stability and a higher boiling point compared to primary and secondary alcohols.
3. In the context of 17.11 Spectroscopy of Alcohols and Phenols, the infrared (IR) spectrum of tert-Butanol exhibits a characteristic strong and broad absorption band around 3400-3600 cm^(-1) due to the stretching vibration of the hydroxyl (-OH) group.
4. The carbon-oxygen (C-O) stretching vibration of the hydroxyl group in tert-Butanol appears as a strong absorption band in the range of 1000-1100 cm^(-1) in the IR spectrum.
5. The presence of the three methyl (CH3) groups in tert-Butanol leads to distinctive signals in the ^1H NMR spectrum, with a singlet peak at around 1.2 ppm corresponding to the nine protons of the three methyl groups.

Review Questions

• Explain the significance of the tertiary carbon atom in the structure of tert-Butanol and how it influences the compound's physical and chemical properties.
  • The presence of the tertiary carbon atom in the structure of tert-Butanol is crucial in determining its unique properties. The tertiary carbon atom is bonded to three other carbon atoms, which provides increased stability to the molecule compared to primary and secondary alcohols. This stability is reflected in the higher boiling point of tert-Butanol, as well as its increased resistance to oxidation and other chemical reactions. The tertiary carbon configuration also affects the reactivity of the hydroxyl group, making tert-Butanol less nucleophilic and more stable compared to other alcohols. These structural features contribute to the distinct physical and chemical properties of tert-Butanol, making it an important intermediate in organic synthesis and a widely used industrial solvent.
• Describe the characteristic infrared (IR) spectroscopic features of tert-Butanol and explain how they can be used to identify and characterize the compound.
  • The infrared (IR) spectrum of tert-Butanol exhibits several distinctive features that can be used to identify and characterize the compound. The most prominent absorption band in the IR spectrum of tert-Butanol is a strong and broad peak around 3400-3600 cm^(-1), which corresponds to the stretching vibration of the hydroxyl (-OH) group. This absorption band is characteristic of alcohols and provides valuable information about the presence and nature of the hydroxyl functional group. Additionally, the carbon-oxygen (C-O) stretching vibration of the hydroxyl group in tert-Butanol appears as a strong absorption band in the range of 1000-1100 cm^(-1). These IR spectroscopic features, along with the overall pattern of absorption bands, can be used to distinguish tert-Butanol from other alcohols and confirm its identity in organic analysis and characterization.
• Analyze the ^1H NMR spectrum of tert-Butanol and explain how the signals observed can be used to elucidate the structure and purity of the compound.
  • The ^1H NMR spectrum of tert-Butanol provides valuable information about the structure and purity of the compound. The most prominent signal in the ^1H NMR spectrum of tert-Butanol is a singlet peak at around 1.2 ppm, which corresponds to the nine protons of the three equivalent methyl (CH3) groups. This distinctive singlet signal is a result of the high degree of symmetry in the tert-Butanol molecule, where the three methyl groups are magnetically equivalent. Additionally, the hydroxyl (-OH) proton in tert-Butanol typically appears as a broad singlet signal in the range of 2-4 ppm, depending on factors such as solvent and concentration. The presence of these characteristic signals, along with the absence of any additional peaks, can be used to confirm the purity and structural integrity of tert-Butanol samples in organic analysis and characterization.

Related terms

Isomers:

Isomers are molecules with the same molecular formula but different structural arrangements of atoms, leading to distinct physical and chemical properties.

Alcohols:

Alcohols are organic compounds containing a hydroxyl (-OH) functional group attached to a saturated carbon atom.

Infrared Spectroscopy:

Infrared spectroscopy is a technique used to identify and characterize organic compounds by analyzing the absorption of infrared radiation, which corresponds to the vibrational modes of molecular bonds.