Dehydration of Pentan-2-ol

Lawrence Dhaniel L. De Jesus

Department of Chemistry, University of Southern Mindanao, Kabacan, North Cotabato
Date Performed: October 19, 2017
Date Submitted: October 19, 2017

I. Introduction
hot conc. H2SO4

→
pentan-2-ol pent-2-ene pent-1-ene
+ + water
(2-pentanol) (2-pentene) (1-pentene)

The sulfuric acid catalyzed dehydration of pentan-2-ol proceeds readily to give a mixture of alkenes that can be analyzed
by fourier-transform infrared spectroscopy. The mechanism of this reaction involves the intermediate formation of the
relatively stable tertiary carbocation followed by loss of a proton either from a primary carbon atom to give the terminal
olefin, pent-1-ene, or from a secondary carbon to give pent-2-ene. Each step of this E1 elimination is reversible and thus
the reaction is driven to completion by removing one of its products, the alkene. In these reaction, several alkene isomers
can be produced. The Saytzeff rule states that the more substituted alkene is the more stable and therefore the one
formed in larger amount. And the trans (E) isomer is more stable than the cis (Z) isomer. 1

II. Materials & Reagents

Materials

 Simple Distillation Apparatus

 Beakers
 Vial
 Water Bath
 Thermometer
 Iron Stand w/ Clamp
 Ice packs
 Distilled H2O (s), (l)

Reagents

 Pentan-2-ol
 H2SO4
 3M NaOH

III. Methodology

On the long neck flask, add 1.00ml of H2O then proceed to add 0.5mL of concentrated H2SO4 drop-wise and then cool the
flask in an ice-bath. Add 1.00ml of pentan-2-ol and mix the solution.

Setup the Simple Distillation Apparatus, clamp a beaker under the condenser, and place a vial in beaker and pack ice
around the vial. Warm the beaker under uniform heat and distil the product over 30-45 degrees Celsius of temperature.
Transfer the contents of the vial over into the reaction tube and add 0.1 mL of cold 3M NaOH solution unto the tube, mix.

Use a Pasteur pipette to extract the aqueous layer off the solution and then discard.

Collect the distillate, and prepare for FTIR analysis.

IV. Results & Discussion

As stated in the The Saytzeff rule, the more substituted isomer, Trans, is highly favoured than compared to the less-
substituted isomer, Cis. This is due to the Trans being more stable in its structure. However, the reaction yielded uncanny
results. The following data was acquired from the distillation:

Reactants Temperature (First-Last pH Level Observation

Drop)

Pentan-2-ol 95°C — 80°C 2 A colourless liquid with an

organic layer

The sample was then analysed in the FTIR instrument. The following data was acquired:

 A broad peak at 3200-3400cm-1 which indicates the presence of –OH bonds

 A weak peak at 1600-1700cm-1 which indicates the presence of C=C bonds

Unfortunately, the broad peak interprets the presence of water, which deems this experiment failure.

V. Conclusion

Based on the results of the FTIR, we failed to synthesize alkenes as the broad peaks indicated the presence of
water which was not complete eliminated during the dehydration process. This result may have been due to the system
having leaks or not maintaining the cold temperature through the distillation.

VI. References

1. K. L. Williamson, Macroscale and Microscale Organic Experiments, 2nd Ed. 1994, Houghton Mifflin, Boston. p268;
revise 10/9/00