Reactions
Reactants Reagents Products Help
c1ccc(cc1)CO Magnify
c1ccc(cc1)C(=O)O Magnify

Note: Strong oxidizing reagents will oxidize benzylic alcohols and carbonyls to carboxylic acids



Cc1ccccc1 Magnify
c1ccc(cc1)C(=O)O Magnify

Caution: Strong oxidizing reagents will oxidize benzylic alkyl groups even if no initial C-O bond exists



c1ccc2c(c1)CCC2 Magnify
c1ccc(c(c1)C(=O)O)C(=O)O Magnify

Caution: Even with extended alkyl chains, the strong oxidizing agent will wipe out all of the substituent chains down to benzylic carboxylic acids



c1ccc2c(c1)CCC2 Magnify
c1ccc(c(c1)C(=O)O)C(=O)O Magnify

Caution: Cr(IV) derived oxidizing reagents work to generate benzylic carboxylic acids as well. The difference is these are run under acidic conditions instead of basic



CC(C)(C)c1ccccc1 Magnify
Magnify

Note: Benzylic oxidation requires the presence of at least one benzylic hydrogen, so tert-butyl benzene is resistant to oxidation.



c1ccc(cc1)CO Magnify
c1ccc(cc1)C=O Magnify

Note: Milder oxidant to oxidize benzylic alcohols to carbonyls



C[C@@H](c1ccccc1)O Magnify
CC(=O)c1ccccc1 Magnify

Note: Milder oxidant to oxidize benzylic alcohols to carbonyls



CC(C)(c1ccccc1)O Magnify
Magnify

Note: Benzylic oxidation requires the presence of a benzylic hydrogen, so no reaction occurs here



CCO Magnify
Magnify

Note: This reagent only works on benzylic alcohols, not 'regular' alkyl alcohols



CC(=O)c1ccccc1 Magnify
CCc1ccccc1 Magnify

Note: Clemmenen reduction converts aldehydes and ketones into alkanes under acidic conditions



CC(=O)c1ccccc1 Magnify NN.[Na]O
heat
CCc1ccccc1 Magnify

Note: Wolff-Kishner reduction converts aldehydes and ketones into alkanes under basic conditions



c1ccc(cc1)[N+](=O)[O-] Magnify
c1ccc(cc1)N Magnify

Note: Nitro groups can be reduced to amino groups with H2 and a metal catalyst



Cc1ccccc1 Magnify N1(Br)C(=O)CCC1=O
Light, Peroxide
c1ccc(cc1)CBr Magnify

Note: Benzylic carbons can be brominated with NBS and peroxide, or Br2 and light



(0.105 sec) Link