Alkylation of benzonitrile

[MarcL]

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 :/

 

[Lamebert]

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.