This MedLibrary.org supplementary page on Tert-Butanol is provided directly from the open source Wikipedia as a service to our readers. Please see the note below on authorship of this content, as well as the Wikipedia usage guidelines. To search for other content from our encyclopedia supplement, please use the form below:
Related Sponsors
| tert-Butanol[1] | |
|---|---|
 |
 |
| IUPAC name | 2-Methyl-2-propanol |
| Other names | t-Butanol tert-Butanol t-Butyl alcohol tert-Butyl alcohol tertiary-Butyl alcohol |
| Identifiers | |
| CAS number | [75-65-0] |
| SMILES |
|
| Properties | |
| Molecular formula | C4H10O |
| Molar mass | 74.1216(42) g/mol |
| Density | 0.78086 g/cm³ |
| Melting point |
25.69 °C, 299 K, 78 °F |
| Boiling point |
82.4 °C, 356 K, 180 °F |
| Hazards | |
| MSDS | Oxford MSDS |
| NFPA 704 |
 3
1
0
|
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox references |
|
tert-Butanol, or 2-methyl-2-propanol, is the simplest tertiary alcohol. It is one of the four isomers of butanol. tert-Butanol is a clear liquid with a camphor-like odor. It is well soluble in water and miscible with ethanol and diethyl ether. It is unique among the isomers of butanol because it tends to be a solid at room temperature, with a melting point slightly above 25 °C.
Contents |
Preparation
tert-Butyl alcohol can be manufactured industrially by the catalytic hydration of isobutylene.
Applications
tert-Butyl alcohol is used as a solvent, as a denaturant for ethanol, as an ingredient in paint removers, as an octane booster for gasoline, as an oxygenate gasoline additive, and as an intermediate in the synthesis of other chemical commodities such as flavors and perfumes.
Chemistry
As a tertiary alcohol, tert-butanol is more stable to oxidation and less reactive than the other isomers of butanol.
When tert-butanol is deprotonated with a strong base, the product is an alkoxide anion. In this case, it is tert-butoxide. For example, the commonly used organic reagent potassium tert-butoxide is prepared by refluxing dry tert-butanol with potassium metal.[2]
- K + tBuOH → tBuO−K+ + 1/2 H2
The tert-butoxide species is itself useful as a strong, non-nucleophilic base in organic chemistry. It is able to abstract acidic protons from the substrate molecule readily, but its steric bulk inhibits the group from participating in nucleophilic addition, such as in a Williamson ether synthesis or an SN2 reaction.
Conversion to alkyl halide
tert-Butanol (also tert-butyl alcohol) reacts with hydrogen chloride to form tert-butyl chloride and water via an SN1 mechanism.
|
|
|
|
 |
 |
 |
The overall reaction, therefore, is:
Because tert-butanol is a tertiary alcohol, the relative stability of the tert-butyl carbocation in the Step 2 allows the SN1 mechanism to be followed. Primary alcohols generally require an SN2 mechanism because the energy barrier to produce a primary carbocation is so high that it will not reasonably happen. The SN2 mechanism allows the carbocation intermediate to be avoided.
References
- ^ Merck Index, 11th Edition, 1542
- ^ William S. Johnson and William P. Schneider (1963). "β-Carbethoxy-γ,γ-diphenylvinylacetic acid". Org. Synth.; Coll. Vol. 4: 132.
|
||||||||||||||
Wikipedia content modification information:
- This page was last modified on 13 August 2008, at 20:53.
Wikipedia Authorship and Review
Wikipedia content provided here is not reviewed directly by MedLibrary.org. Wikipedia content is authored by an open community of volunteers and is not produced by or in any way affiliated with MedLibrary.org.
Wikipedia Usage Guidelines
This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article on "Tert-Butanol".
The URL for this specific entry is:
All Wikipedia text is available under the terms of the GNU Free Documentation License. (See Copyrights for details). Wikipedia® is a registered trademark of the Wikimedia Foundation, Inc.