Experiment 7

Esterification: Banana Oil

Discussion

Esters have low molecular weight that makes them have characteristic flavours and
pleasant odours associated with essential oils. They occur prevalently in nature and often have
fruity taste or odour. Ester functional group can be synthesized by many different methods.
Simplest of these methods is the Fisher esterification done by reacting a carboxylic acid and an
alcohol in the presence of a concentrated acid catalyst.

Isopentyl acetate, known as banana oil, is an example of an ester. In this experiment,

banana oil is synthesized by direct esterification of acetic acid with isopentyl alcohol in the
presence of sulfuric acid as catalyst. General reaction occurs as below.

Mechanism of the reaction above involves initial protonation of the carbonyl group in acetic acid
by H2SO4 . The hydroxyl group of the alcohol adds to the carbonyl carbon via nucleophilic
attack. A proton tranfer and loss of water followed by the loss of acid catalyst are the remaining
steps before isopentyl acetate is formed.

The reaction stated is a slow and so reflux of reactants is needed to aid completion. This
is done in order to prevent loss of reactants. Heat was employed to thermodynamically control
the reflux process and form the most stable ester. The boiling chips added played a significant
role in the process. It allowed smooth heating of the process preventing violet heating from
occuring.

To furthermore push reaction equilibrium to product formation, Le chatelier's principle is

exploited by adding excess of any of the two reactants. Acetic acid was added in excess and not
isopentyl alcohol to favor product formation. The reason for this is that it is hard to separate
residual isopentyl alcohol from banana oil because they have comparable solubility. Bothare
soluble in organic media. Meanwhile, acetic has poor solubility of organic solvents making it
easier to separate from banana oil. Excess acetic acid is removed by adding sodium bicarbonate.
Na2CO3 converts acetic acid to its conjugate base forming sodium acetate. Sodium acetate is
easily removed from the organic layer because it is not soluble on organic compounds but
soluble in water. Continues acidity measurement of the mixture determines whether all of the
acetic acid is removed. Basic solution indicates that all of the acetic acid is removed and
converted to sodium acetate.

Addition of saturated NaCl enables separation of water from the organic layer. Because
of strong intermolecular attractive between water molecules and NaCl ions, water is pulled from
the synthesized banana oil and thus, can be discarded. Also, unreacted salts present can be
carried by water reducing impurities from the crude sample. Addition of anhydrous magnesium
sulfate furthemore removes remaining water in the sample during drying. Charged Mg 2+ and
SO42- ions have high affinity to water molecules and therefore effective in removing residual
water from the sample. Purification of banana oil was carried through distillation.

Figure 1 shows the FTIR analysis of the synthesized isopentyl acetatem as compared to
literature data.

Prominent peak at around 3000 cm-1 corresponds to C-H bond functionality while
peak at 1700 cm-1 corresponds to the carbonyl functionality. This two results coincide with the
structural functional groups present in isopentyl acetate. Moreover, it is seen that experimental
IR analysis (left figure) has comparable results with the literature data (right figure)

Conclusion

Banana oil or isopentyl acetate is synthesized from esterification of acetic acid with
isopentyl alcohol. Crude sample was isolated by extraction method using sodium bicarbonate
solution while purification was carried through distillation. Because esterification process is
slow, reflux of reactants is needed as the reaction is thermodynamically controlled. Synthesized
banana oil has comparable IR-spectrum with literature data, having peaks at 3000 cm -1 and at
1700 cm-1 depicting C-H and carbonyl functionalities respectively.

References

Smith, J. Organic Chemistry; McGraw-hill: New York, 2011; p. 847-848.

Solomons, G.; Fryhle, C.; Synder, S.Organic Chemistry, 11th edition; John Wiley &
Sons,Inc.: United States of America, 2014; p. 850

Antic, D., Ph.D., The Fisher) Esterfication Reaction Synthesis of Isopentyl Acetate (Banana Oil).
Thermo Fisher Scientific [Online] https://static.fishersci.eu/...II.../pS45-Fisher-Isoamyl-
Acetate.pdf (accessed 22 November 2016