I've been studying organic chemistry and came across this example :

CH3-CH2-CH(+)-CH3 ---> CH3-CH=CH-CH3, the explanation the textbook gave was related to deprotonation. I've tried drawing lewis structures to understand this. But it looks incomplete.

My work :

From my basic understanding of deprotonation, it'll be

CH3-CH(-)-CH(+)-CH3, but how does a double bond form in between these 2 atoms? This is the part I'm getting confused with.

Any suggestions to point in the right direction? I'm pretty sure I'm missing something.

P.S. I came across this issue while dealing with a reaction of butan-1-ol heated with concentrated H2S04.

  • 4
    $\begingroup$ $\ce{C^--C^+}$ and $\ce{C=C}$ are resonance structures of the same thing. By the way, "deprotonation" doesn't necessarily imply just breaking a C–H bond; it really only says that "a proton is lost". In this case, the proton is lost, and a double bond is formed; it's still a deprotonation. $\endgroup$
    – orthocresol
    Nov 29, 2021 at 16:34
  • $\begingroup$ @orthocresol Thanks a lot! Everything makes sense now :) $\endgroup$
    – Fr0zen
    Nov 29, 2021 at 16:37
  • $\begingroup$ If you got your answer, feel free to self answer it. Self answer are always appreciated and it also help future readers. $\endgroup$ Nov 30, 2021 at 2:09


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