N-Bromosuccinimide (NBS) is an organic compound that can be used as a source of bromine in a variety of synthetic reactions. It acts as an electrophilic reagent and can react with both alkenes and aromatic compounds to form products through substitution, addition, or elimination reactions. In the case of aromatic compounds, NBS typically reacts at the least substituted carbon atom to give a brominated product.
Identify the product formed from the reaction of N bromosuccinimide with the following compounds. (a) p-tert Butyltoluene (b) 4-Methyl-3-nitroanisole
The reaction between NBS and p-tert butyltoluene will yield 1-bromo-4-(1,1 dimethyl ethyl) benzene. This reaction occurs when the nucleophilic Bromine from NBS attacks the electron rich ring of p-tert butyltoluene, displacing an equivalent amount of hydrogen atoms from their positions on the ring’s carbon atoms. As a result of this reaction, one new Br atom is attached to one of the tertiary carbons on the ring (the least substituted position), resulting in formation of 1-bromo-4-(1,1 dimethyl ethyl) benzene.
The second reaction which is between NBS and 4-methyl 3 nitroanisole yields 2 methyl 3 nitrobromobenzene as its final product. This happens when Bromine from NBS attacks the most electronegative group present in 4 -Methyl 3 Nitroanisole which are two nitro groups bonded to two adjacent carbons in ortho position relative to each other on benzene ring .Thus , one out of two electrons provided by Nitrogen atoms get displaced by electron rich Bromine from NBS resulting in displacement / replacement both Nitrogens simultaneously giving rise too 2 -Methyl 3 -Nitrobromobenzene as its final product .
In conclusion , it can be said that depending upon its ability to attack various functional groups present on molecule’s surface ,N – Bromosuccinimide offers toolbox for wide range transformations possible even with same starting materials by modifying just presence / absence & type/numberof functional groups present therein suitable for achieving desired end result !