Elimination reactions, Chemistry Assignment Help

Assignment Help: >> Chemical Properties of Alkyl Halides >> Elimination reactions, Chemistry

Elimination reactions : The positive charge on carbon is propagated to the neighbouring carbon atoms by inductive effect. When moved toward by a strongest base (B), it leads to lose a proton generally from the b-carbon atom. Such reactions are named as elimination reactions. They are also E1 and E2 reactions.

         E1 reaction: 110_elimination reaction.png

         E2 Reaction: 905_elimination reaction1.png

         As the above reactions involve leaving of X- the reactivity of alkyl halides (Same alkyl group, different halogens) should be limited with C-X bond strength.

         Kind of bond                       C - I         C - Br          C - Cl

         Bond strength (kcal/mol)        45.5            54              66.5

         The dividing of the bond becomes more and more difficult and thus, the reactivity decrease.

         The sequence of reactivity (Tertiary > Secondary > Primary) is due to +I effect of the alkyl groups which increases the polarity of C -X bond.

2167_elimination reaction2.png

         The primary alkyl halides undergo reactions either by S N2 or E2 mechanisms which involve the formation of transition position. The bulky sets reason of steric hinderance in the formation of transition position. Therefore, higher homologues are not reactive than lower homologues. CH3X > C2H5X > C3H7X, etc

         Example of elimination reaction

         (a) Dehydrohalogenation :

            380_elimination reaction3.png

In that reaction, ether is a by-product as potassium ethoxide is always present in small quantity.

            1670_elimination reaction4.png

         (b) Action of heat :

            1621_elimination reaction5.png

         The decomposition chases the given sequence,

         Iodide > Bromide > Chloride      (When similar alkyl set is present) and

         Tertiary > Secondary > Primary (When similar halogen is present).

 

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