Number of isomeric aromatic amines with synthesized by Gabriel Phthalimide synthesis molecular formula C8H11N, which can be is ______. jee main 2023
Correct Answer: 6
Approach Solution - 1
Gabriel Phthalimide Synthesis Isomer Count
The Gabriel phthalimide synthesis is used to prepare primary amines (R-NH2). Since the question asks for aromatic amines with the formula C8H11N, we need to consider isomeric primary aromatic amines.
The degree of unsaturation (DU) for C8H11N is:
\( DU = C + 1 - \frac{H - N}{2} = 8 + 1 - \frac{11 - 1}{2} = 9 - 5 = 4 \)
A DU of 4 suggests the presence of a benzene ring (DU = 4). This leaves us with C2H5 to account for. Since the Gabriel synthesis produces primary amines, the nitrogen must be attached to one of these carbons.
The possible isomers are:
Other dimethylanilines (like 3,4-dimethylaniline) are identical to the ones listed above. 2,6-dimethylaniline is the same as 2,3-dimethylaniline.
Conclusion:
Therefore, there are 6 possible isomeric aromatic amines that can be synthesized by Gabriel phthalimide synthesis.
Approach Solution -2
Du = C + 1 - H - N/2, which equals 4, indicating the presence of a benzene ring. Thus, the number of isomeric aromatic amines that can be synthesized is 5.
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