What type of reaction is the reduction of camphor?
The process of replacing a double-bonded oxygen atom with a hydrogen atom and hydroxide ion is a type of reaction known as reduction. Chemically, a ketone (camphor) may be converted into one of its secondary alcohols (isoborneol) with a reducing agent (sodium borohydride).
What is the reaction of camphor?
In high doses, camphor produces symptoms of irritability, disorientation, lethargy, muscle spasms, vomiting, abdominal cramps, convulsions, and seizures. Lethal doses in adults are in the range 50–500 mg/kg (orally). Generally, two grams cause serious toxicity and four grams are potentially lethal.
What is reduced in the oxidation of isoborneol to camphor?
An alcohol (borneol) is being oxidized into a ketone (camphor). A subsequent reduction takes us back to another alcohol (isoborneol), which is an isomeric form of the original.
Why does camphor reduction favor isoborneol?
The reduction of camphor favored the production of isoborneol over borneol as opposed to an equal combination. This is because when the sodium borohydride attacks the camphor, it would attack in the endo-phase due to the steric strain caused by the two geminal methyl groups on one side of the cyclohexane ring.
Why is isoborneol more stable than borneol?
With more energy the molecules have more effective collisions on the opposite side. With the energy supplied in this reaction, there would be too much steric effect inhibiting the hydride ion from attacking the carbonyl carbon to make the more stable thermodynamic product borneol.
Is isoborneol the endo product?
During the reduction of camphor, the reducing agent can approach the carbonyl face with a one carbon bridge (termed exo attack) or the face with a two carbon bridge (termed endo). The two product stereoisomers are called borneol (from exo attack) and isoborneol (from endo attack).
Is isoborneol and camphor more polar?
The reduction of camphor favored the production of isoborneol over borneol as opposed to an equal combination. Additionally from this spectroscopy, it can be seen that borneol is slightly more polar than isoborneol since isoborneol comes off the GC column with a shorter retention time.
Why is reduction of camphor important?
In principle, the reduction of camphor can give two diastereomeric alcohols, corresponding to reaction of borohydride at the two faces of the C=O. bond. Reaction at the top (“exo”) face regenerates the original starting material, borneol.
Why the isoborneol is the major product in the reduction of camphor?
The Exo product is the major product because endo is favorable (less hindered). The driving force is the formation of very strong B-O-bond (ΔH=523 kJ/mol) in the tetraalkyl borate which are significantly stronger than π-bonds in the carbonyl (ΔH=380 kJ/mol).
What happens when you convert camphor to isoborneol?
chlorine gas will be emitted from the reaction mixture. The reduction of camphor to isoborneol involves diethyl ether, which is extremely flammable. Be certain that no open flames of any sort are in your vicinity when you are using ether.
How is camphor synthesized from α-pinene?
The “classical syntheses” of the camphor comprises several stages; the first of them is preparation of bornyl chloride (IV) by the action of dry hydrogen chloride on α-pinene (III). The first step of this reaction is electrophilic addition of hydrogen ion followed by Wagner-Meerwein rearrangement (Scheme 2) [3].
What is isobornyl acetate?
Synthesis of isobornyl acetate from camphene Isobornyl acetate (VII) is an important constituent of many essential oils, for example from needles of Siberian fir (40-45%), and its production seems more useful because isobornyl acetate possess a pleasant odor and could be used as a flavoring agent.
What are the properties of camphor?
One of the important properties of camphor is its ability to undergo steam distillation. Wood and foliage of camphor tree at first were chipped and then subjected to steam distillation. Crude camphor separated as a solid matter after cooling with the yield of about 1%.