Orgo question

[mag7ical]

Q. How would you convert a benzyl alcohol into an aniline?

A. PhCH2OH -> KMnO4 -> NH3 -> OBr- -> PhNH2

Can someone walk me through each step? I'm unable to follow.

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[RCT PC CRN]

Q. How would you convert a benzyl alcohol into an aniline?

A. PhCH2OH -> KMnO4 -> NH3 -> OBr- -> PhNH2

Can someone walk me through each step? I'm unable to follow.

Step 1. Oxidation to -COOH using KMnO4
Step 2. Nu substitution using NH3 to yield Amide
Step 3. Hoffman rearrangement using Br2/OH - gives you Aniline and CO2

Hope this help

 

[UndergradGuy7]

Q. How would you convert a benzyl alcohol into an aniline?

A. PhCH2OH -> KMnO4 -> NH3 -> OBr- -> PhNH2

Can someone walk me through each step? I'm unable to follow.

KMnO4 makes CH2OH into a carboxylic acid.

NH3 + carboxylic acid makes C=O(OH) into C=O(NH2) an amide.

OBr- is the Hoffman rearrangement I think. It makes you lose the C=O group. So its just phenyl-NH2