Organic Chem Questions?
Write out a reaction that will produce butylbenzene from Benzene, be sure to pick a reaction that will aviod problems with rearrangements.
^ Do I need to use a reduction reaction for this? and I can't figure out if I should use Clemmensen or Wolff-Kishner
Also, if a cycloheptene ring with 3 double bonds and a pos charge on one carbon is planar with a p orbital on every carbon, is it aromatic, antiaromatic, or neither?
Thanks guys!
Answer:
Use the Friedel Crafts acylation reaction: react benzene with an acid chloride(butanoyl chloride) and an aluminum chloride catalyst, then reduce with hydrogen and palladium on carbon. The product is butylbenzene. This prevents rearrangments in carbocation intermediates.
The cycloheptatriene cation is aromatic because the positive charge means all carbons are sp^2 hybridized, and the ring of p-orbitals is thus unbroken.
the cycloheptene ring is aromatic.
React benzene with either butyl anhydride (CH3CH2CH2C(=O)OC(=O)CH2CH2CH3... or butyryl chloride (CH3CH2CH2COCl) using AlCl3 ie the Friedel-Craft reaction. The product of this will be 1-phenylbutan-1-one. Next reduce it using the Wolff-Kishner reaction. This is done under basic conditions and will not lead to acid catalyzed rearrangements. The Clemmensen reduction is run under acidic conditions and can lead to rearrangements. I believe the cycloheptatriene you describe is aromatic. I hope this helps
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