ELECTROPHILIC ADDITION REACTION (EAR)
ELECTROPHILIC ADDITION REACTION (EAR)
EAR is characteristic reaction of alkene and alkyne. SHORT
NOTES
Important Points:
1. 1st step is the rate determining step (rds) of this reaction.
2. Carbocation intermediate is formed. Rerrangement may be possible.
3. Rate of EAR Nucleophilicity of alkene
(More electron density)
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ELECTROPHILIC ADDITION REACTION (EAR)
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NOTES
[Link]'s reagent
(cold dilute alkaline KMnO4
Syn
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2.(i)OsO4 (ii) NaHSO3/H2O NOTES
Hydroxylation
Anti
Reductive
Ozonolysis
Oxidative
1. Reaction with CONC. H-X ( HALOGEN ACID )
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If a new chiral centre is generated in EAR by attack on SP2 Classical cation then that carbon has
50 % and 50% R configuration on that carbon in product
If EAR is performed on conjugated diene then there may be 2 types of products
1, TCP(Thermodynamically Controlled Product) ….more Stable product
2. KCP (Kinetically controlled Product)……..formed by more stable cation
In this case at room temp/ High Temp. TCP will be major product But Extremely low temp. KCP
becomes major product
IF DB & TB are isolated then Addition take place on DB
IF DB & TB are conjugated then Addition take place on TB
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2. REACTION WITH CONC. H2SO4
Alkyl hydrogen
sulphate SHORT
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Points-
1. Follow Markovnikov’s rule.
2. Intermediate is Carbocation which may rearrange as per condition.
[Link] reaction is used to separate alkene from alkane as alkenes react with
conc. H2SO4 at room temperature whereas alkanes do not react because it
doesn’t have pi bond.
3. REACTION WITH DILUTE H2SO4 /
Acidic hydration of alkyne ( KUCHEROV’S REACTION )
Enol intermediate Final Product
• Rate of reaction is slow. Hence to increase the rate of reaction
ions are used as catalyst to increase the rate of reaction.
• Follow Markovnikov’s rule & Enol intermediate is formed. SHORT
• No rearrangement because +ve is on atom. NOTES
• H2O attacks at stable carbocation.
Note: During acidic hydration acetylene forms aldehyde except all alkyne. All
other alkynes will form ketone.
4. ADDITION OF HALOGEN IN NON POLAR SOLVENT
Cyclic bromonium ion
or
NCC (non classical
carbocation)
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NOTES
1.. Fluorination is uncontrolled and explosive reaction
2..product of iodination is unstable so only chlorination and bromination take place
or is called as Test of unsaturation .After Test Reddish Brown Colour of
Bromine gets Disappear
5. Addition of Halogen in polar solvent
6. Reaction with NOCl (Tilden’s reagent) :
+ NOCl
7. Addition of I-Cl
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I-Cl
8. OXYMERCURATION DEMERCURATION (OMDM)
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NOTES Alcohol
9. HYDROBORATION (HBO/ HBR ) SHORT
NOTES
Alcohol
Electrophile
Dil.H2SO4 OXYMERCURATION HYDROBORATION
DEMERCURATION OXIDATION (HBO)
SHORT (OMDM)
NOTES
50%R + 50%S
10. HYDROXYLATION
ANTI HYDROXYLATION
SYN HYDROXYLATION
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Reagents
[Link]'s reagent
(cold dilute alkaline KMnO4)
2.(i)OsO4 (ii) NaHSO3/H2O
NOTE
1. Baeyer's reagent is also used as test of unsaturation.
[Link]’s reagent is purple in colour. As the reaction proceeds, NOTE: IF WATER NOT PRESENT THEN EPOXIDE
the purple colour RING WILL BE FINAL PRODUCT.
disappears and brown precipitate of MnO2 is observed. .
11. OZONOLYSIS
Reductive ozonolysis
Ozonide Reductive ozonolysis
Molozonide
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Oxidative ozonolysis Trick
At first perform Reductive ozonlysis then make following changes in formed products of reductive ozonolysis
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