Course: CHM 1046 L Instructor: Manoharan

Mariappan, Ph.D.
Name: Madison Fuller Date: 2/1/2020

Reduction of Camphor to Isoborneol

Objectives:
In this experiment, I need to reduce Camphor to Isoborneol by using Sodium Borohydride.
Introduction:
Camphor and its reduction products, borneol and isoborneol, come from a bicyclic family called
terpenes.1 Terpenes are hydrocarbon terpenoids that contain double bonds. To further classify,
camphor is a monoterpene, a 10-carbon compound derived from two isoprene units.2 The
properties of camphor have been used in embalming fluid to preserve and prevent decomposition
of cadavers and for medicinal purposes such as relieving pain, itching or swelling caused by
irritations, treating fungal infection of the toenail, warts, hemorrhoids, minor burns etc. Other
uses would be used as an antimicrobial, essential oils, and insect repellents. 3 As for borneol, its
properties have been used to help the digestive system, improve circulation, treat bronchitis,
coughs and colds, reducing pain, swelling, and stress, etc. Also, has been used as an insect
repellent.

Oxidation-reduction reactions, also referred to as redox reactions, are important in organic

chemistry because the utility of the reaction occurs in everyday processes such as rust,
generating energy from natural resources, reactions occurring in living organisms, etc. Also, the
oxidation reaction of an alcohol to an aldehyde and ketone and the reduction of aldehyde and
ketone back to an alcohol is a very common reaction in organic chemistry.4 Alcohols are formed
from the reduction of carbonyl compounds. Popular reducing agents used in organic chemistry
are lithium aluminum hydride (LiAlH4), diisobutylaluminum hydride (DIBAL), and sodium
borohydride (NaBH4). Comparing lithium aluminum hydride and sodium borohydride, LiAlH4
is more reactive than NaBH4. LiAlH4 is able to reduce aldehydes, ketones, carboxylic acids and
its derivatives, and nitriles. NaBH4 is only capable of reducing aldehydes and ketones. In this
experiment, the reducing agent used is NaBH4.
I used Sodium Borohydride (NaBH4), like lithium aluminum hydride, LiAlH4, is a source
of hydride (H-). Hydride is a hydrogen atom with 2 electrons and thus it has a negative chare and
acts as a nucleophile. In this reaction the carbonyl carbon is the electrophile. Since NaBH4 has 4
hydrides, it can attack 4 carbonyl molecules, so the stoichiometry ratio is 1:4 (NaBH4: Ketone).
After all, 4 of the hydrides have been reacted, the tetraalkoxy boron intermediate is heated in
CH3OH solvent to give 4 alcohol product molecules.
Course: CHM 1046 L Instructor: Manoharan
Mariappan, Ph.D.
Name: Madison Fuller Date: 2/1/2020
The addition of the reducing agent NaBH4 is an interesting reaction to a carbonyl. Since
the carbonyl in this case the ketone is a sp2 hybridized and thus planar, the nucleophilic attack
will come from the front and back with equal probability. When the substituents on the ketone
are identical, a single products result which is achiral.

However, when the carbonyl substituents are different, a 50:50 mixture of chiral products above.
The above scenario results unless there is a reason for the nucleophile to preferentially attack one
face of the carbonyl carbon over the other. Such is the case with camphor.

Exo
attack

Nuc:

Endo

Attack

The methyl group on the bridge provide enough steric hindrance to force the nucleophile to
attack from the bottom (endo). In this experiment, I determined that the hydride attacks from the
bottom which forms isoborneol.
After you preform the reduction of camphor, the product will contain both isoborneol and
borneol. Determine the theoretical yield, actual yield, obtain the weight and figure out the
melting point.
Course: CHM 1046 L Instructor: Manoharan
Mariappan, Ph.D.
Name: Madison Fuller Date: 2/1/2020
Materials used:
5.2 grams Methanol Gloves 15 mL room temp H2O
0.650 grams of Camphor Pipette Distilled Water
25 mL round bottom flask 10 mL graduated cylinder Filtration Hose
Stir bar Weigh boat Buchner funnel
Hot stirring plate Spatula 500mL filtration flask
0.5 grams of NaBH4 Ring Stand Filter Paper
Condenser Ring Clamp Watch glass
Heating Mantle Ice Bath 10 mL room temp H2O

Procedure:
1. I placed 0.650 grams of Camphor into a 25 mL round bottom flask. Add 5.2 grams of
methanol due to the increase in the camphor compound so it would dissolve it better. I set the
mixture to stir at 8 on the hot stirring plate. The whole process should take 10 minutes.
Course: CHM 1046 L Instructor: Manoharan
Mariappan, Ph.D.
Name: Madison Fuller Date: 2/1/2020
2. Once all of the NaBH4 has been added, attach a condenser and heat the reaction for 5 minutes.

3. After heating, cool the flask in an ice bath add 10 mL room temp H2O. This should give a
white precipitate. Chop the solid with your spatula so that there are no chunks present.

4. Collect the solid product by vacuum filtration and rinse with 15 mL room temp H2O.
Course: CHM 1046 L Instructor: Manoharan
Mariappan, Ph.D.
Name: Madison Fuller Date: 2/1/2020

5. Transfer the product to a piece of watch glass to allow the product to air dry.
Course: CHM 1046 L Instructor: Manoharan
Mariappan, Ph.D.
Name: Madison Fuller Date: 2/1/2020
6. I obtained the weight (0.368 grams), melting point (202C) and the actual yield of the product
was 55%.

Results and Discussion:

Measurements:
0.650 grams of Camphor 5.2 grams of CH3OH 0.368 grams of Isoborneol
152.23 grams of Camphor 154.25 grams of Isoborneol 200C of Isoborneol
Course: CHM 1046 L Instructor: Manoharan
Mariappan, Ph.D.
Name: Madison Fuller Date: 2/1/2020
Calculations:

1. Explain how isoborneol and borneol are different from each other and how do they differ in
their physical property based on the melting point?
The camphor had an incense-like smell and the isoborneol–borneol mixture had a similar odor.
The reduction of camphor favored the production of isoborneol over borneol as opposed to an
equal combination. This difference in polarity is due to the location of the hydroxyl group in
borneol and isoborneol.
The melting point of Borneol is 213 C and the melting point for Isoborneol is 206C.
Course: CHM 1046 L Instructor: Manoharan
Mariappan, Ph.D.
Name: Madison Fuller Date: 2/1/2020
2. Write the mechanism for the reduction of camphor forming isoborneol.

Conclusions:
I obtained 55% of Isoborneol which is a 11% difference from the expected yield of 66%. Overall
this lab was a success in reducing Camphor to Isoborneol. But there might’ve been impurities in
this experiment which could account for such a small percentage yield.
Course: CHM 1046 L Instructor: Manoharan
Mariappan, Ph.D.
Name: Madison Fuller Date: 2/1/2020
Works Cited:
Reduction of Camphor to Borneol Using Sodium Borohydride. Web. Jan 9, 2020. Retrieved
from http://sites.psu.edu/jvh5562/wp-content/uploads/sites/25360/2015/04/Reduction-of-
Camphor-Synthesis.pdf
Preparation and Stereochemistry of Bicyclic Alcohols. Web. Jan 9 2020. Retrieved from
https://www.cerritos.edu/chemistry/chem_212/Documents/Lab/7_stereochem_camphor.pdf