Question: Nicotine can be made when the following salt is treated with Na2Co3 . Draw a stepwise mechanism for this reaction.

PROBLEM 7.69 - Organic Chemistry

PROBLEM 7.69

Question

Question: Nicotine can be made when the following salt is treated with Na₂Co₃ . Draw a stepwise mechanism for this reaction.

Step-by-Step Solution

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Answer

The stepwise mechanism for the formation of the nicotine molecule is given below:

Abstraction of H⁺ ion

Removal of bromide ion

Formation of nicotine

1Nicotine

It is an alkaloid compound that is used as a drug. It is produced naturally by the plant and can be used as a stimulant.

It is also used for the treatment of smoking addiction to help with withdrawal symptoms.

2The stepwise mechanism for making nicotine

The nicotine is produced by the intramolecular nucleophilic substitution reaction. The carbonate ion abstracts a proton from the amine group as shown in the following step:

Abstraction of H⁺ ion

The halide group, i.e., the bromide ion, then leaves as a leaving group, and the amine group attacks the resulting carbocation and forms a cyclic product as shown in the following step:

Removal of bromide ion

The removal of H⁺ ion by the carbonate ion results in the formation of the nicotine molecule.

Formation of nicotine

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