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REACTION MECHANISM
Reaction Mechanism :
Substrate (Alkyl Halides) CH3 X 1 R X Reagent Dominating Mechanism SN2 SN2 Major
Any nucleophile Any nucleophile (except hindered base) *Hindered base give E-2 reaction.
2 R X
! !
2 R X 2 R X 3 R X
Strong base ( NH2 , Alc.KOH,MeO, EtO, tBuO, Et3N) Weak nucleophile + Polar Protic solvent (H2O, ROH, RCOOH) Strong nucleophile ( SH , RS I , Br , Cl , OAc )
! ! !
3 R X 3 R X Substrate (Alcohol) ROH (3 2 &1 with " -branch) ROH (1 without "-branch) ROH (1>2>3) ROH (1>2>3) ROH (3>2>1) ROH ROH
Strong base ( NH2 , alc. KOH, MeO, EtO, t-BuO, Et3N,OH) Weak nucleophile or weak base (H2O, ROH, RCOOH) Reagent
SN2
PX3, PX5, P4+ X2, SOCl2/Base SOCl2 without base Conc.H2SO4,H3PO4,HClO4, KHSO4/# Al2O3/#, P2O5/# (Saytzeff elimination without rearrangement) dehydration reaction ThO2/#, WO3/# (Hoffmann elimination without rearrangement) dehydration reaction
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Important feature of reaction mechanism SN1 SN2 Two steps process/Intermediate C+/Rearrangement/Weak Nu./PPS/Racemisation/ Rate : 3 > 2 > 1 or (Stability of C+),Ag+ $ One step process/No intermediate/No rearrangement/Strong Nu/PAS/Inversion at %-carbon/ Rate : CH3 X > 1RX > 2 R X/Stereospecific reaction. E1 Two step process/Intermediate C+/Rearrangement/Weak base/#/Regioselective reaction saytzeff alkene (more branched) major. Rate : 3 > 2 > 1 or (Stability of C+) E2 One step process/No rearr./Strong base, #/Regioselective, Regiospecific, stereoselective, stereospecific, antielimination reaction. ! Kinetic primary isotopic effect is observed. ! Rate of E-2 : 3 > 2 > 1 ! Smaller base & Saytzeff alkene ! Big base & Hofmann alkene. E1 cB Two step/Intermediate C!/Hofmann elimination product. ! Regioselective, stereospecific, anti elimination reaction. ! Dexchange at "-carbon.
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! Condition : More acidic " -H or e.g. (F, NR 3 , SR 2 ) or EWG at " position. Condition for Hofmann elimination : (1) Hindered strong base (2) Poor leaving group.
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(3) When Strong I groups behave as leaving group. (F, NR 3 SR 2 ) (4) When()-carbon is quaternary.
RESONANCE
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RESONANCE
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