tert-Butanol
You don't need to be Editor-In-Chief to add or edit content to WikiDoc. You can begin to add to or edit text on this WikiDoc page by clicking on the edit button at the top of this page. Next enter or edit the information that you would like to appear here. Once you are done editing, scroll down and click the Save page button at the bottom of the page.
| tert-Butanol[1] | |
|---|---|
| Image:T-Butanol.png Image:T-butanol-3D-vdW.png | |
| Chemical name | 2-Methyl-2-propanol |
| Other names | t-Butanol tert-Butanol t-Butyl alcohol tert-Butyl alcohol tertiary-Butyl alcohol |
| Chemical formula | C4H10O |
| Molecular mass | 74.1216(42) g/mol |
| CAS number | [75-65-0] |
| Density | 0.78086 g/cm³ |
| Melting point | 25.69 °C |
| Boiling point | 82.4 °C |
| SMILES | C(C)(C)(C)O |
| NFPA 704 |
 3
1
0
|
| Disclaimer and references | |
Please Take Over This Page and Apply to be Editor-In-Chief for this topic: There can be one or more than one Editor-In-Chief. You may also apply to be an Associate Editor-In-Chief of one of the subtopics below. Please mail us [1] to indicate your interest in serving either as an Editor-In-Chief of the entire topic or as an Associate Editor-In-Chief for a subtopic. Please be sure to attach your CV and or biographical sketch.
Overview
tert-Butanol, or 2-methyl-2-propanol, is a 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 degrees Celsius.
Applications
tert-Butanol 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.
Preparation
tert-Butanol can be manufactured industrially by the catalytic hydration of isobutylene.
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, when tert-butanol is deprotonated with sodium hydride, the resultant is sodium tert-butoxide.
- NaH + tBuOH → tBuO−Na+ + 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.
Step 1 :
Step 2 :
(rate determining)
Step 3 :
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
External links
Alcohols | |
|---|---|
| Primary alcohols | Methanol • Ethanol • Propan-1-ol • Butanol • Isobutanol • 1-Pentanol • 1-Hexanol • 1-Heptanol • Octanol • Nonanol • Decanol • Dodecanol • 1-Tetradecanol • Cetyl alcohol • Stearyl alcohol |
| Secondary alcohols | Isopropyl alcohol • 2-Butanol • 2-Hexanol |
| Tertiary alcohols | tert-Butanol |
fr:Méthylpropan-2-olfi:Tert-butanoli it:2-metil-2-propanolo nl:2-methyl-2-propanol
Acknowledgement and Attribution Regarding Sources of Content
Some of the initial content on this page may be incorporated in part from copyleft sources in the public domain including wikis such as Wikipedia and AskDrWiki. Drug information for patients came from the The National Library of Medicine. Infectious disease information may have come from the Centers for Disease Control (CDC). Differential Diagnoses are drawn from clinicians as well as an amalgamation of 3 sources: 1.The Disease Database; 2. Kahan, Scott, Smith, Ellen G. In A Page: Signs and Symptoms. Malden, Massachusetts: Blackwell Publishing, 2004:3; 3. Sailer, Christian, Wasner, Susanne. Differential Diagnosis Pocket. Hermosa Beach, CA: Borm Bruckmeir Publishing LLC, 2002:7 .
