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Synthesis of 1-bromobutane from 1-butanol. Pt. 2?
This question is an add on to this:
http://answers.yahoo.com/question/index;_ylt=Ap4U2...
Another by-product, 1-butene (C4H8, FW 56.22, MP -185 degrees C, BP -6.3 degrees C) is formed under the same reaction conditions specified in the above question.
What is a step by step mechanism for its formation?
(hint: E2, reaction conditions are acidic, not basic)
1 Answer
- BuckLv 41 decade agoFavorite Answer
Based on the way the question is asked, I would say that the mechanism begins the same way as the substitutions to give
CH3CH2CH-CH2-O^+H2 where one of the CH2 H's on carbon 2
.............| .........................is emphasized.
.............H
Some base in the system (and they are all weak bases under these strongly acidic conditions), perhaps another molecule of butanol, then removes the H and the electron pair holding it on the C falls between carbons 1 and 2 with simultaneous loss of H2O to give
CH3CH2CH=CH2 + CH3CH2CH2CH2-O^+H2
