what is SN1(lim)and SN2(lim)reactions....and its associative and dissociative,interchange mechanism.....plz plz answer mi in details...plz help mi
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( for mechanism of sn2 see attached file 1)
♦♦♦• Reaction is:
Stereospecific (Walden Inversion of configuration)
Concerted - all bonds form and break at same time
Bimolecular - rate depends on concentration of both nucleophile and substrate
♦♦♦• Substrate:
Best if primary (one substituent on carbon bearing leaving group)
works if secondary, fails if tertiary
♦♦♦• Nucleophile:
Best if more reactive (i.e. more anionic or more basic)
♦♦♦• Leaving Group: Best if more stable (i.e. can support negative charge well):
TsO- (very good) > I- > Br- > Cl- > F- (poor)
RF , ROH , ROR , RNH2
♦♦♦• Solvent:
Polar Aprotic (i.e. no OH) is best.
For example dimethylsulfoxide ( CH3 ( HCON(CH3)2 ), acetonitrile ( CH3
Protic solvents (e.g. H2 but can be used in some case are NEVER Substrates for SN2 reactions
Leaving Groups on double-bonded carbons are never replaced by SN2 reactions SOCH3 ), dimethylformamide CN ). O or ROH) deactivate nucleophile by hydrogen bonding
( for mechanism of sn1 see attached file 2)
♦♦♦• Reaction is:
Non-stereospecific (attack by nucleophile occurs from both sides)
Non-concerted - has carbocation intermediate
Unimolecular - rate depends on concentration of only the substrate
♦♦♦• Substrate:
Best if tertiary or conjugated (benzylic or allylic) carbocation can be formed as leaving group departs
never primary
♦♦♦• Nucleophile:
Best if more reactive (i.e. more anionic or more basic)
♦♦♦• Leaving Group: Same as SN2
best if more stable (i.e. can support negative charge well)
Examples: TsO- (very good) > I- > Br- > Cl- > F- (poor)
However, tertiary or allylic ROH or ROR' can be reactive under strongly acidic conditions to replace OH or OR
♦♦♦• Solvent:
Same as SN2
Polar Aprotic (i.e. no OH) is best
Examples: dimethylsulfoxide ( CH3 ( HCON(CH3)2 ), acetonitrile ( CH3
Protic solvents (e.g. H2
SOCH3 ), dimethylformamide CN ).
O or ROH) deactivate but can be used in some cases
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hope that helps you..............
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