November 23, 2024, 11:15:45 PM
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Topic: Electrophilic Aromatic Substitution(addition order for three substituents)  (Read 2293 times)

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Offline WILBERTHNARVAEZ

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I have attached photographs of a synthesis problem that consists of adding three different substituents to benzene: The handwritten method was the one I came up with, while the other is the answer found in the solutions manual. Is my method correct? If not, why does it fail to produce the correct product?

Offline salteen

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When using EAS to add multiple substituents to an aromatic ring, the order of addition can sometimes be important.  The major difference between your answer and the solution key is the order in which the nitro group and chlorine are added.

Based on what you know about the directing preferences of the functional groups, try thinking about which regioisomers will form if the order of addition is changed.

Offline Dan

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In addition to salteen's comments, you need to consider the reactivity of alkenes when choosing the sequence order.
My research: Google Scholar and Researchgate

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