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19 Mar Reaction of phenol with chloroform and KOH to give salicylaldehyde is known as Reimer-Tiemann reaction. Mechanism:—- In this reaction,chloroform reacts first. The Reimer-Tiemann Reaction. Hans Wynberg. Chem. Rev., , 60 (2), pp – DOI: /cra Publication Date: April ACS Legacy . First of all, in the phenoxide ion, the lone pair on the oxygen atom doesn’t remain fully available, it remains in continuous conjugation with the double bond of the.

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After basic hydrolysis, the desired product 9 is formed.

Reimer–Tiemann reaction

The Reimer—Tiemann reaction can be altered to yield phenolic acids by substituting the chloroform with carbon tetrachloride. Reimer Tiemann reaction is one of the few reactions included reiner JEE syllabus which involves carbene mechanism. Hydroxides are generally not readily soluble in chloroform, thus the reaction is generally carried out in a deimer solvent system.

But, Carbon being less electronegative acts as a better nucleophile in this case rather than Oxygen. In the simplest sense this consists of an aqueous hydroxide solution and an organic phase containing the chloroform. Take learning on the go with our mobile app. You have selected the wrong answer!! Chloroform 1 tieemann deprotonated by a strong base normally hydroxide to form the chloroform carbanion 2 which will quickly alpha-eliminate to give dichlorocarbene 3 ; this is the principal reactive species.


Avnish Kabaj 3, 3 13 Practise s of questions mapped to your syllabus. In addition, many compounds can not withstand being heated in the presence of hydroxide.

The final product is not a major product I wasn’t even able to find it listed as a product after a cursory google searchso why does phenoxide attack the carbene from ortho position. Chemistry Stack Exchange works best with JavaScript enabled. From Wikipedia, the free encyclopedia.

Apart from this you can follow a reference book to understand the detailed mechanism of this reaction. This page was last edited on 31 Octoberat In Reimer-Tiemann reaction why does phenol attack the carbene from ortho position? Berichte der Deutschen Chemischen Gesellschaft. Views Read Edit View history. The Reimer—Tiemann reaction is a chemical reaction used for the ortho – formylation of phenols ; [1] [2] [3] [4] [5] with the simplest example being the conversion of phenol to salicylaldehyde.

This mechanism of the reaction can be explained in eight major steps:. Here is a picture of the intermidiate and a 3D view of it, This ordered transition state will not appear in case of attack by the Oxygen atom. Questions Tags Users Badges Unanswered.

By using this site, you agree to the Terms of Use and Privacy Policy. This interaction favors selective ortho-formylation. By using our site, you acknowledge that you have read and understand our Cookie PolicyPrivacy Policyand our Terms of Service.

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Reimer-Tiemann reaction ~

More over, attack from the ortho position, though creates a chance of Steric crowding, but the intermidiate generated from the attack by ortho-position creates an ordered transition state. The hydroxide will also deprotonate the phenol 4 to give a negatively charged phenoxide 5. When phenols are treated with chloroform in the presence of sodium hydroxide, an aldehyde group -CHO is introduced at the ortho position of benzene ring leading to the formation of o-hydroxybenzaldehyde.

First of all, in the phenoxide ion, the lone pair on the oxygen atom doesn’t remain fully available, it remains in continuous conjugation with the double bond of the benzene ring.

Substitution reactions Addition reactions Carbon-carbon bond forming reactions Name reactions Formylation reactions. The dichlorocarbene generated is a soft electrophilic species while the oxyanion form of the phenoxide is a hard nucleophilic species. As such the Reimer—Tiemann reaction may be unsuitable for substrates bearing these functional groups.

Berichte der Deutschen Chemischen Gesellschaft in German. Another way of rationalising is through the use of the Hard-Soft Acid-Base principle.