Question

Which of the following products is obtained when 2-methyl-2-nitropropane is treated with NaOCl solution?
A.1-chloro-2-methyl-2-nitropropane
B.A mixture of 1-chloro-2-methyl-2-nitropropane and 1,3-dichloro-2-methyl-2-nitropropane
C.1,3-dichloro-2-(chloromethyl)-2-nitropropane
D.None of the above

Answer 1

Hint:For nitro alkanes, one must recall primary nitro alkanes, secondary nitroalkanes and tertiary nitroalkanes. The difference between the primary, secondary and tertiary nitroalkanes is done, based on the carbon to which the nitro group is attached and not on the basis of nitrogen atom. NaOCl is used for halogenation of nitro alkanes.

Complete answer:
Nitro alkanes are organic compounds that contain alkane and nitro functional groups which is \( - N{O_2}\). Nitro group is a group that generally makes a compound explosive. The structure of nitro alkane is given by:

Nitro alkanes are considered to form highly substituted alkanes, alkenes, amines, carboxylic acids, aldehydes, ketones etc.
Primary nitro alkanes are compounds in which the nitro group which is \( - N{O_2}\) is attached to the primary carbon. For example,

that is 1-nitromethane.
Secondary nitro alkanes are compounds in which the nitro group is attached to the secondary carbon. For example,

that is 2-nitropropane.
Tertiary nitro alkanes are compounds in which the nitro group is attached to the tertiary carbon. For example,

that is 2-methyl-2-nitropropane.
NaOCl solution is used for halogenation of nitro alkanes.
We have understood that 2-methyl-2-nitropropane is a tertiary nitroalkane from the above-mentioned example. Tertiary nitro alkanes do not readily react with NaOCl solutions. Hence no product can be formed when 2-methyl-2-nitropropane is treated with NaOCl solution.

Therefore, the correct option is D.
Note:
Usually, nitro alkanes combine with solid catalysts and they offer the opportunity to perform reactions more efficiently.
Also remember that primary carbons are bonded with only one other carbon, secondary carbons are bonded with two other carbons, tertiary carbons are bonded with three other carbons and quaternary carbons are bonded with four other carbons.