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TITLE

Synthesis of Camphor from Camphene.

AIM

To prepare synthetic camphor from camphene by a multistep analysis.

THEORY

Camphor is a waxy, white or transparent solid with a strong, aromatic odor. It is a terpenoid with the
chemical formula C10H16O. It is found in wood of the camphor laurel, a large evergreen tree found in
Asia. It can also be synthetically produced from oil of turpentine. It is used for its scent, as an ingredient
in cooking, as an embalming fluid, in religious ceremonies, as a plasticizer for nitrocellulose, as a moth
repellent, as an antimicrobial substance for embalming purposes and medical uses. It has a melting point
of 1800C and is optically active.

Figure 1
Camphor
Synthetic Camphor can be prepared by the oxidation of isoboneol, but this is a three step reaction with
camphene being the starting compound. Camphene is a bicyclic monoterpene with a chemical formula
C10H16, which is insoluble in water however very soluble in most organic solvents. It is produced
industrially by catalytic isomerization of alpha pipene. Camphene is a minor constituent in camphor oil,
and is used in the preparation of fragrances and as a food additive for flavoring.

Figure 2

Camphene

Camphor can also be prepared using the Gustav Komppa’s mechanism with the starting compound being
the camphoric acid. In this experiment a three step reaction for the synthesis of camphor was used. The
reaction scheme is shown on figure 3 below.
CHEMICAL EQUATION AND MECHANISM FOR THE SYNTHESIS OF CAMPHOR

Figure 3

Gustav Komppa’s Total Synthesis of Camphor:

PRECAUTIONS

Some of the materials used in this synthetic procedure are potentially dangerous. Acetic acid for instance
is capable of producing serious burns without inflicting much, if any, initial pain. In addition, the fumes
are harmful to the mucous membranes and eyes. Alcoholic potassium hydroxide is strongly caustic. Even
camphor and the other substances used as the major reactants are toxic and may cause problems if the
proper safety equipment, including the fume hood is not used.
Reagents used

Reagent Mass Used Molar Mass No. of moles Safety Hazards


Camphene 13,624g 136,24g/mol 0.1 mol Toxic
Glacial Acetic 31.685ml 60g/mol - Irritant, Corrosive
acid

Sulphuric acid 1,5ml 98g/mol - Corrosive, Toxic

Sodium carbonate 30ml 106g/mol - Toxic

Potassium 24ml 56.1g/mol - Corrosive


hydroxide

Jones’ reagent 20.15ml - - Corrosive

RESULTS:

Prelab Exercise

Calculated mass of camphene

Masscamphene= n/mol × Mr/g.mol-1

= 0.1 mol × 136.24 g.mol-1


= 13.624 g

Weighed mass=13.6241g camphene

Calculation for the volume of glacial acetic acid to be used

Molar massglacial acetic acid= 60.0 g × 0.5 mol


= 30.0 g

𝜌 = 𝑚𝑎𝑠𝑠⁄𝑣𝑜𝑙.

𝑣𝑜𝑙. = 𝑚𝑎𝑠𝑠⁄𝜌

30.0𝑔
= ⁄1.05𝑔/𝑚𝑙

= 29 ml
The masses obtained during the experiment

Compounds produced Molar mass in g/mol Actual mass yield in g

Isoborneol 154.25 11.514

Camphor 152.23 1.757

Isobonyl acetate = 17 ml 196.29 g.mol-1

Camphor was purified by evaporating in a closed beaker using a watch glass to trap the pure camphor.

Calculating the limiting reagent


Mass isobornyl aceate = vol × density
= 17 ml ×0.983 g.ml-1
= 16.711g
Moles Isoborneol Acetate = 16.711 g / 137g.mol-1
= 0.122 mol
Mass Isoborneol = 0.122 mol × 154.25 g.mol-1
= 18.8185 g
% yield = (Actual Yield/Theoretical yield) x 100
= (11.514/18.8185) x 100%
= 61 %
Moles Isoborneol = 11.514 g / 154 g.mol-1
= 0.07477 mol
Therefore Isoborneol is the limiting reactant since it has the least number of moles

Mole ratio  Isoborneol: Camphor = 1:1

Therefore moles Camphor = 0.07477 mol

Mass camphor = Moles x Molar mass


= 0.07477 mol x 152.23 g.mol-1
= 11.38 g
% yield = (Actual Yield/Theoretical yield) x 100
= (1.757/11.38) x 100%
= 15.44%
The melting point for the purified camphor sample that was measured in this experiment = 1730C

DISCUSSION

Camphor is very compact and its molecular structure is symmetrical which gives it the property to change
directly from a solid to a vapour when heated. Therefore, camphor can easily be purified by sublimation
technique. Sublimation is a phase change in which a solid phase passes directly into the vapor without
going through an intermediate liquid phase. Solids which have vapour pressure below melting points can
be purified by 1) heating the solid to sublime it 2) condensing the vapor on a cold surface 3) scraping off
the condensed solid. Sublimation was not a very accurate method as recrystallization or chromatography.
The advantages of sublimation technique is that solvent is not required and not too much transferring was
involved, so losses in transfer can be kept low, (John W. Lehman, pg 653).

The calculated percentage yield for Isoborneol was 61%. Camphor is known to sublimate from solid to
vapour at high temperature. While going under sublimation, camphor was condensed and collected and
appears as a white-flaky solid. Once collected the product was weighed to be 1.717g. The calculated
percent yield is 15.4%, therefore, the reaction never reached completion this may be due to not enough
kinetic energy being supplied to the solution, the rate at which reactants collide is increased and failure to
do so leaves the reactants stationary. A consequence of this is a very slow reaction. Also, since the
reaction is kept at low temperature there is less free energy available in order to reach the transition state.
Since the mixture did not reach completion, during sublimation, large amounts of isoborneol is found in
the final product.

The measured melting point of camphor was 173oC; this value is low but close compared to the
theoretical melting point of pure camphor which is 1740C-1770C. The lower melting point could be an
indication that the camphor sample was contaminated with trace amounts of impurities.

CONCLUSION

The order of carbocation stability obeys the following trend: next to O or N >tertiary, allylic, or
benzylic>secondary>primary>methyl. It is very difficult to form a primary carbocation and virtually
impossible to form a methyl carbocation in solution. If a secondary carbocation can rearrange to form a
tertiary carbocation by shifting an alkyl, arly, or hydride group from a neighbouring carbon, it is likely to
do so. The major step in this experiment was to ensure that the reaction goes into completion, and the
correct parameters were followed which in turn gave a good yield of camphor in its purest form.
REFERENCES

John W. Lehman, pg 653

https://www.wou.edu/.../...

Courses.chem.psu.edu/…/Exp125Syn06.pdf

Experiments in Organic Chemistry: From Microscale to Macroscale by Jonathon S. Nimitz, Prentice-Hall,


1991.

Introduction to Organic Laboratory Techniques: A Small Scale Approach, edited by Donald Pivia,
Cengage Learning, 2005. Pp 155-157.