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)

2008-12-03T18:26:46Z

thanks buck... see if you can take a stab at part 2

http://answers.yahoo.com/question/index;_ylt=Ap4U2_3SbBeR1sqQOASZJyTsy6IX;_ylv=3?qid=20081203180224AA3VCuH

Buck2008-12-03T18:18:29Z

Favorite 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

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