tert-butyl chloride (2-chloro-2-methylpropane) from tert- butyl alcohol (tert-butanol) using an acid catalyzed dehydration reaction
Physical Constants
|
Compound |
Mol. Wt (g/mol) |
Density (g/mL) |
b.p. (°C) |
m.p. (°C) |
|
2-Methyl-2-propanol |
74.12 |
0.786 |
82 |
25 |
|
2-Chloro-2- methylpropane |
92.57 |
0.851 |
51 |
-25 |
|
Hydrochloric acid |
37% soln in H2O |
1.18 |
-85 |
-26 |
12.0ml of t-butyl alcohol, with 25.0ml 12.0M HCl, 12ml of water, 12ml of saturated aqueous sodium bicarbonate, 12ml of saturated aqueous sodium chloride, magnesium sulfate
1 (CH3)COH + 1 H3O^+ Cl^- -> 1 (CH3)3CCl + 2 H2O
Typically yield 6.34g
Why is the percent yield be lower than expected? 53.9% .. Is it due to evaporation? What is the major product of this reaction? isobutene or t-butylchloride?
If this reaction was with 2-butanol/HCl instead of tert butanol, how would I obtain the products/mechanism (SN2?), and determine major products? If sn2, why?
Thank you!!
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