3
$\begingroup$

During aldol condensation reaction the aldol formed reacts further to give alkene (which is probably called enone)

an enone is an alkene and aldol is an alcohol that is what i understand

I am really struggling with this part of the reaction as my textbook says nothing about the mechanism of this particular step the medium during aldol condensation reaction is alkaline but the end product is a dehydrated product and the conversion of alcohol into alkene is dehydration. Do we need to make the medium acidic at later stage of reaction, or does some mechanism causes dehydration in alkaline medium?

Also please suggest if there is some other reaction, or examples depicting similar phenomenon that I could go through for better understanding

(I am really new to chemistry as well as to asking questions. thank you)

$\endgroup$
  • 1
    $\begingroup$ Google “e1cb mechanism”. $\endgroup$ – orthocresol Mar 27 at 10:34
2
$\begingroup$

The commonly accepted mechanism for the base-catalysed aldol example here is that the alpha hydrogen (shown in blue on your scheme) is removed by OH- present in the reaction medium, and the negative charge on the enolate then forms the alkene by loss of OH-. This mechanism falls under the general heading of E1cB, further information on this mechanism may be found here and here 3.

Thanks to @orthocresol for the note about this

$\endgroup$
2
$\begingroup$

Usually aldol products are dehydrated under acidic conditions or at elevated temperatures . But it can also be done employing strong bases like alkoxide or hydroxide ion , and it follows E1CB mechanism . The mechanism involves the formation of an enolate ion which subsequently eliminated the hydroxide ion

enter image description here

Here is the mechanism of Aldol . Next is the Dehydration Step , shown as below

enter image description here

More Detailed Base Catalysed Dehydration :

enter image description here

$\endgroup$

Your Answer

By clicking “Post Your Answer”, you agree to our terms of service, privacy policy and cookie policy

Not the answer you're looking for? Browse other questions tagged or ask your own question.