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Mechanism:
+
H 2SO 4 O s lo w C s lo w
- H + HO
+ HO S O 2
fa s t +
OH OH2 H
O H
H 2SO 4 O H
s lo w s lo w
- +
fa s t +
+ HO S O C + H2O
OH OH2
O
H
Possible side products (in addition to H2O, OH-, H3O+, and HSO4-):
H
HO
-
:H s h if +
+ CH + -
C HO
H
O
HO
H O S
O O
-
:H s h if + - O
+
CH + S
C
H OH
O
H +
CH2 OH
H -
+ :H s h if
-
C + HO
OH
O
S
O
O
O
H
+
H CH2
-
:H s h if -
+ HO S O
C +
HO
-
:C H 3 s h if
+
H2C
+ + HO
-
C
O
HO
O S
O
-
:C H 3 s h if O
+ + -
C H2C + O S O
OH
Experimental
1. Add 1.5 mL distilled water to a 10 mL conical vial.
2. Add 1.0 mL concentrated sulfuric acid dropwise while mixing.
3. Cool solution in an ice bath to 0oC.
4. Add 1.0 mL 2-methyl-2-butanol and mix thoroughly.
5. Add a boiling stone and perform a simple distillation at 30-45 oC.
6. Cool receiving vial and add calcium chloride pellets to dry the product.
7. Place the cap on the vial to prevent evaporation and weigh product.
8. Determine the percent yield of the mixture of butenes.
9. Inject 1.0 L of mixture into gas chromatograph.
10. Record conditions and run gas chromatography to get printout.
11. Interpret the results.
Results
Percent yield
= actual/theoretical x 100
= (0.945 g/70.13 g/mol)/[2(0.80 g/88.146 g/mol)] x 100
= 0.0135 mol/0.0181 mol x 100
= 74.58%
Conclusion
According to the gas chromatography results, the mixture of alkenes contained approximately
10% of alkene A and 90% of alkene B. The retention time of alkene A was 1.662 minutes and for alkene B
it was 2.092 minutes. This indicates that alkene A is more volatile, and therefore less stable, than alkene
B. from the structure of each alkene, it can be concluded that alkene A is 2-methyl-1-butene and alkene
B is 2-methyl-2-butene. This is evident because 2-methyl-1-butene is only di-substituted, while 2-methyl-
2-butene is tri-substituted.
Dehydration reactions follow Zaitsevs rule, which states that the major product of a reaction will
be the alkene with the most substituents about the double bond. The reason behind this is that the
more substituted an alkene is, the more stable it becomes. Therefore, the major product is 2-methyl-2-
butene.