• How easily can you understand the Witti...

How easily can you understand the Wittig Reaction in chemistry?

Learning about the Wittig reaction in your chemistry lessons? This post may be able to give you a helping hand!

Introducton to the Wittig Reaction

The Wittig reaction, also known as Wittig olefination, is a chemically active reaction in which an aldehyde carbonyl as well as the ketone carbonyl combines with a ylide (commonly triphenyl phosphonium) primarily referred to as a Wittig reagent, to produce a double bonded alkene and a salt of triphenylphosphine oxide. Georg Wittig, a chemist, established the subject reaction (Wittig) in 1954, which led to him being awarded the chemistry Nobel Prize in 1979. The reaction has found a wide application, notably in organic synthesis, for the preparation of alkenes attributable to its predictability.

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The reaction works for a broad array of alkyl/aryl (R) groups, as well as both the aldehydes and ketones. Whenever the simple alkyl or aryl groups are involved, it fundamentally generates/produces the Z-alkene product, however if the R groups are equivalent, E/Z mixes may result. The generation of a highly stable triphenylphosphine oxide (Ph3P=O) makes it possible for the reaction to take place. The reaction representation below illustrates how the reaction happens in general:

The functional groups targeted by the Wittig reaction 

The Wittig reaction takes place specifically at the carbonyl functional groups of aldehydes or ketones, but not esters or amides. Furthermore, a somewhat unusual-looking species is the ylide (a group having opposing formal charges on neighbouring atoms), specifically a "phosphonium ylide," since ylides of nitrogen and sulfur also exist.

The mechanism for occurrence of the Wittig reaction

Step 1:

The ylide's negatively charged carbon is nucleophilic. This carbon then performs a nucleophilic attack on the aldehyde or ketone's carbonyl carbon. As a result, a betaine, a charge-separated (as well as dipolar) intermediary, is formed.

Step 2:

The betaine intermediary obtained from stage 1 is then introduced/utilized for the production of a new O-P bonding, which results in the formation of another intermediary with a ring structure that is 4-membered.

Step 3: 

The C-O and C-P bonds are segregated/separated in a ring intermediary that is 4-membered. The oxygen accepts both the bonding electrons and establishes a new double bond with the phosphorus that releases the electrons pair that are ready to bond or attached with the C-atom. Having such pair of electrons, a new C=C double bond is generated, providing the needed alkene molecule.

 

 

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