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ABSTRACT
Tert-butyl alcohol was reacted with a hydrogen halide (hydrochloric acid) to produce tert-butyl chloride. The reaction was carried out
via nucleophilic substition (specifically, an SN1 mechanism). Cold concentrated HCl was added in excess to tert-butyl alcohol.
Afterwards, solid NaHCO3 and anhydrous CaCl2 were added to purify the compound and to maintain the product as an alkyl halide.
Finally, the crude tert-butyl chloride was distilled to obtain pure tert-butyl chloride. 2.93 g of tert-butyl chloride was obtained after
distillation. With a theoretical yield of 9.812 g, the % yield was 29.86%. While crude tert-butyl chloride was successfully synthesized
from tert-butyl alcohol, the experimenters failed to obtain a significant amount of pure product, with a percent yield of <30%.
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1. Introduction
Alcohols are an organic compound wherein a hydroxyl
group (-OH) is bonded to a sp3 hybridized carbon. When
reacted with hydrogen halides (such as HCl), alcohols can
undergo a nucleophilic substitution reaction to form an
alkyl halide.
In this experiment, tert-butyl alcohol is reacted with
concentrated hydrochloric acid to form tert-butyl
chloride. This reaction occurs via an S N1 mechanism. SN1
reactions are nucleophilic reactions where the ratedetermining step is unimolecular (McMurry, 2015).
Alkyl halides are simply alkanes containing one or
more halogens. While normal alkanes are non-polar, alkyl
halides are polar compounds. This is due to the
electronegative nature of halogens. In the C-X bond, the
carbon exhibits a partial positive charge while the
halogen exhibits a partial negative charge.
Alkyl halides can be classified into 3 types: primary,
secondary, and tertiary. Primary alkyl halides are
compounds wherein the carbon that is bonded to the
halogen is bonded to only 1 other carbon. Likewise, the
carbon with the halogen attached in secondary alkyl
halides are bonded to 2 other carbons while in tertiary
alkyl halides the carbon is attached to 3 other carbons.
An example of a tertiary alkyl halide is tert-butyl chloride,
the final product of this experiment.
As far as physical properties go, alkyl halides have
higher boiling points compared to alkanes. This is due to
the increase in size of the molecule by replacing a
hydrogen with a halogen. Alkyl halides are also soluble
in organic solvents but are only slightly soluble in water.
In the experiment, tert-butyl alcohol is reacted with
concentrated hydrochloric acid to synthesize tert-butyl
chloride. Afterwards, tert-butyl chloride is purified via
distillation.
(Source: http://academic.keystone.edu/JFalcone/tBuClPrepv2_files/image004.gif)
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chloride.
Table 2
Physical Properties of tert-Butyl Alcohol and tert-Butyl
Chloride
Properties
tert-Butyl Alcohol
tert-Butyl
Chloride
Color
colorless
colorless
Solubility in water
soluble
insoluble
Boiling point
82.41C
51C
It was observed that the tert-butyl chloride is less
soluble in water than the original alcohol and also has a
lower boiling temperature.
4. Conclusion and Recommendations
Crude tert-butyl chloride was successfully
synthesized from tert-butyl alcohol and concentrated
hydrochloric acid. However, in terms of the amount of
tert-butyl chloride produced, the experiment was a
failure because of the low percent yield. The
methodology can be improved by storing the crude tertbutyl chloride when not in use to prevent evaporation of
the product.
References
Pavia, D.
McMurry, J. Organic Chemistry, 7th ed.; Thomson: California,
2008; pp 372-380.
Rapra Technology. Rigid PVC Foams: A New Twist to an Old
Technology. Cellular Polymers III. 1995, 134.
UC Davis ChemWiki. http://chemwiki.ucdavis.edu/ (accessed
March 2, 2016).
Appendices
(See attached data sheet)