Sage-Tips

Why is isoborneol favored over borneol?

The peak differences show that isoborneol was preferred over borneol, due to the steric strain caused by the two geminal methyl groups on one side of the cyclohexane. Since there is still a camphor peak on the gas chromatography spectra, the reduction reaction did not go to completion.

Is isoborneol endothermic or exothermic?

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 borneol or isoborneol more stable?

Though borneol is the more stable product, the energy requirements to form isoborneol are lower because the borohydride is adding to the less sterically hindered point on the carbonyl carbon.

Why is methanol used in reduction of camphor?

Methanol is used as solvent in Chem 30BL, which is a compromise in terms of polarity to dissolve both compounds. The initial dissolution of camphor favors the reduction of the carbonyl group over the reaction of the sodium borohydride with the the protic solvent, methanol.

How does sodium borohydride reduce camphor?

Sodium borohydride is a much milder reducing agent, working effectively only with aldehydes and ketones. 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.

What is the relationship between isoborneol and borneol?

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 is the reduction of camphor stereoselective?

In principle, the reduction of camphor can give two diastereomeric alcohols, corresponding to reaction of borohydride at the two faces of the C=O. Since “endo-attack” of borohydride avoids this steric interaction, we might predict that it should proceed faster than exo-attack, leading to stereoselective reduction.

How will you distinguish borneol isoborneol and camphor by NMR?

In NMR, the CH(OH) peak differed by 0.5 ppm for borneol and isoborneol. Camphor and the remaining borneol/isoborneol peaks couldn’t be distinguished by NMR. TLC is not an ideal technique to monitor the borneol oxidation. Only the reactant borneol can be seen on the TLC, not the product camphor.

What is the major product of the reduction of camphor?

borneol
Camphor and its reduction products, borneol and isoborneol, come from a bicyclic family called terpenes.

What is the difference of isoborneol and camphor?

Camphor and Isoborneol differ only by the bonds of a single carbon atom. Chemically, a ketone (camphor) may be converted into one of its secondary alcohols (isoborneol) with a reducing agent (sodium borohydride).

Why is reduction of camphor stereoselective?

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 happens when sodium borohydride is used to reduce camphor?

The reduction of camphor using the reducing agent sodium borohydride resulted in the formation of two isomers, borneol and isoborneol, as shown in Scheme 1: Reduction of Camphor. In a methanol solvent, the sodium borohyride attacks the bottom side, the less sterically hindered side, of the camphor.

Can NABH be used to reduce camphor?

is only capable of reducing aldehydes and ketones. In this experiment, the reducing agent used is NaBH. 4. . The reduction of camphor using the reducing agent sodium borohydride resulted in the formation of two isomers, borneol and isoborneol, as shown in Scheme 1: Reduction of Camphor.

Which reducing agent is used in the reduction of camphor?

the reducing agent used is NaBH4. The reduction of camphor using the reducing agent sodium borohydride resulted in the formation of two isomers, borneol and isoborneol, as shown in Scheme 1: Reduction of Camphor. In a methanol

What is the difference between camphor and isoborneol?

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.