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tert-Butyl alcohol

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tert-Butyl alcohol

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Sample of partially crystalised tert-butanol colspan=2 style="background:#f8eaba; border-top:2px solid transparent; border-bottom:2px solid transparent; text-align:center;" #REDIRECTmw:Help:Magic words#Other
This page is a soft redirect. Names

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IUPAC name
2-Methylpropan-2-ol[1]
Other names
tert-Butanol[1]
Trimethyl carbinol[2]
2-Methyl-2-propanol[1]
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906698 75-65-0 7pxY ChEBI CHEBI:45895 7pxY ChEMBL ChEMBL16502 7pxY ChemSpider 6146 7pxY DrugBank DB03900 7pxY EC number 200-889-7 1833 Jmol-3D images Image MeSH tert-Butyl+Alcohol PubChem Template:Chembox PubChem/format RTECS number EO1925000 Template:Chembox UNII UN number 1120 colspan=2 style="background:#f8eaba; border-top:2px solid transparent; border-bottom:2px solid transparent; text-align:center;" #REDIRECTmw:Help:Magic words#Other
This page is a soft redirect. Properties

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C4H10O Molar mass Lua error in Module:Math at line 495: attempt to index field 'ParserFunctions' (a nil value). g·mol−1 Appearance Colorless liquid Odor Camphorous Density 0.775 g/mL Melting point Script error: No such module "convert". Boiling point Script error: No such module "convert". miscible[3] log P 0.584 Vapor pressure 4.1 kPa (at 20 °C) Acidity (pKa) 16.54 [4] 1.387 colspan=2 style="background:#f8eaba; border-top:2px solid transparent; border-bottom:2px solid transparent; text-align:center;" #REDIRECTmw:Help:Magic words#Other
This page is a soft redirect. Thermochemistry

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215.37 J K−1 mol−1 189.5 J K−1 mol−1 −360.04–−358.36 kJ mol−1 −2.64479–−2.64321 MJ mol−1 colspan=2 style="background:#f8eaba; border-top:2px solid transparent; border-bottom:2px solid transparent; text-align:center;" #REDIRECTmw:Help:Magic words#Other
This page is a soft redirect. Hazards

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SDS inchem.org GHS pictograms The flame pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS) The exclamation-mark pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS) GHS signal word DANGER H225, H319, H332, H335 P210, P261, P305+351+338 EU Index 603-005-00-1 EU classification Highly Flammable F Harmful Xn R-phrases R11, R20, R36/37 S-phrases (S2), S9, S16, S46 NFPA 704

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Flash point Script error: No such module "convert". Script error: No such module "convert". Explosive limits 2.4–8.0% US health exposure limits (NIOSH):

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This page is a soft redirect. TWA 100 ppm (300 mg/m3)[2] #REDIRECTmw:Help:Magic words#Other
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This page is a soft redirect. Related compounds

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Related butanols
2-Butanol

n-Butanol
Isobutanol

Related compounds
2-Methyl-2-butanol
Trimethylsilanol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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tert-Butyl alcohol (TBA), or 2-methyl-2-propanol (2M2P), is the simplest tertiary alcohol. It is one of the four isomers of butanol. tert-Butyl alcohol is a clear liquid (or a colorless solid, depending on the ambient temperature) with a camphor-like odor. It is very 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.

Natural occurrence

t-Butyl alcohol has been identified in beer and chickpeas.[5] It is also found in cassava[6] which is used as fermentation ingredient in certain alcoholic beverages.

Preparation

tert-Butyl alcohol is derived commercially from isobutane as a co-product of propylene oxide production. It can also be produced by the catalytic hydration of isobutylene, or by a Grignard reaction between acetone and methylmagnesium chloride.

Applications

tert-Butyl alcohol is used as a solvent, ethanol denaturant, paint remover ingredient, and gasoline octane booster and oxygenate. It is a chemical intermediate used to produce MTBE and ETBE by reaction with methanol and ethanol, and TBHP by reaction with hydrogen peroxide.

Chemistry

As a tertiary alcohol, tert-butyl alcohol is more stable to oxidation and less reactive than the other isomers of butanol.

When tert-butyl alcohol 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.[7]

K + tBuOH → tBuOK+ + 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 substitution, such as in a Williamson ether synthesis or an SN2 reaction.

Conversion to alkyl halide

tert-Butyl alcohol reacts with hydrogen chloride to form tert-butyl chloride and water via an SN1 mechanism.

The overall reaction, therefore, is:

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Because tert-butyl alcohol 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 undergo an SN2 mechanism because the relative stability of a primary carbocation intermediate is very low. The tertiary carbocation in this case is stabilized through hyperconjugation where the neighboring C–H sigma bonds donate electrons into the empty p-orbital of the carbocation.

References

  1. ^ a b c "tert-Butyl Alcohol - Compound Summary". PubChem Compound. National Center for Biotechnology Information. 2005-03-26. Retrieved 2012-05-19. 
  2. ^ a b c d "NIOSH Pocket Guide to Chemical Hazards #0078". National Institute for Occupational Safety and Health (NIOSH). 
  3. ^ http://www.inchem.org/documents/icsc/icsc/eics0114.htm
  4. ^ Reeve, W.; Erikson, C.M.; Aluotto, P.F. Can. J. Chem, 1979, 57, 2747.
  5. ^ http://toxnet.nlm.nih.gov/cgi-bin/sis/search/a?dbs+hsdb:@term+@DOCNO+50
  6. ^ http://www.sc.mahidol.ac.th/scbc/bc_internet/publication/696.pdf
  7. ^ Johnson, W. S.; Schneider, W. P. (1950). "β-Carbethoxy-γ,γ-diphenylvinylacetic acid". Org. Synth. 30: 18. ; Coll. Vol. 4, p. 132 

External links


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