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Synthesis of 1-bromobutane from 1-butanol? Pt. 1?
When 1-butanol, concentrated sufuric acid, sodium bromide, and water are mixed in this reaction, 1-bromobutane forms via an SN2 reaction. Under these reaction conditions a by product, dibutyl either (C4H9OC4H9, FW 130.23, MP -98 degrees C, BP 142-143 degrees C) is formed in the reaction.
What is a step by step mechanism for its formation? (remember the reaction conditions are acidic)
thanks buck... see if you can take a stab at part 2
1 Answer
- BuckLv 41 decade agoFavorite Answer
Protonation of the OH allows H2O to be the leaving group in the SN2 reaction.
C4H9OH + H+ <===> C4H9O^+H2 + HSO4-
C4H9O^+H2 + Br- ---> C4H9Br + H2O bromobutane product
C4H9O^+H2 + HOC4H9 ---> C4H9-O^+(H)-C4H9
C4H9-O^+(H)-C4H9 C4H9-O-C4H9 + H+ dibutyl ether product
