What Are the Products of Benzonitrile with CH3CH2CH2Cl and CH3COCl Using AlCl3?

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Benzonitrile reacts with CH3CH2CH2Cl and AlCl3 to form a product via Friedel-Crafts alkylation, but this reaction is limited due to the deactivation of the aromatic ring and the length of the alkyl chain. The meta-directing nature of the cyano group leads to a more stable resonance structure when the electrophile attacks at the meta position. In contrast, the reaction with CH3COCl and AlCl3 does not occur because Friedel-Crafts acylations are ineffective on deactivated benzenes. Overall, the discussion highlights the limitations of Friedel-Crafts reactions with certain substrates. Understanding these reactivity patterns is crucial for predicting product formation in organic chemistry.
MarcL
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Homework Statement


Draw the products formed when benzonitrile ( C6H5CN) is treated with each reagent
D. CH3CH2CH2Cl, AlCl3
E. CH3COCl, AlCl3

Homework Equations



CN is meta director because N pulls the electron density, leaving the carbon atom more positively charged, therefore leading to resonance structure that isn't stabled if ortho / para.

The Attempt at a Solution



Well I thought we could do the reaction for D if we rearranged the alkyl halide to put the carbocation on a ( at least) 2ndare carbon.

for E I am not too sure why the reaction doesn't occur :/
 
You're correct for the first one, although I was taught that Friedel-Crafts alkylations are unreactive to deactivated benzenes, as well as poorly reactive to an alkyl chain longer than 2 carbons.

For the second one, Friedel-Crafts acylations are nonreactive to deactivated benzenes.
 

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