Nuceophiles vs Electrophiles

Recognizing Nucleophiles
1. Inductive effect – a polar bond between a Metal and a Nonmetal
ie. LiAlH4
2. Lone Pairs – a pair of electron at a nucleophilic atom
ie. H20 or Cl-
3. Pi bond – a pair of electrons in a pi bond (double/triple bonds)
ie. C=C
Recognizing Electrophiles
1. Inductive effects
ie. a C and Cl bonded together, Cl pulls electrons away from C, putting a partial positive on C (C is electrophile)
2. Empty P orbital – electrophiles lacking a complete octet
ie. a carbocation (+) or BF3 (no charge but still missing a complete octet)
3. Pi bonds – where C=X and X is an electronegative atom
ie. ketone (C is electrophile)
Factors Affecting Nucleophilicity
1. Electron density – charge:
+ is electrophilic, – is nucleophilic
2. Polarizability – down the periodic table = more polar = more nucleophilic
3. Steric Bulk – more steric bulk = less nucleophilic
4. Solvent – polar protic (N-H or O-H) = less nucleophilic
polar aprotic = more nucleophilic
ie. DMSO
Common Acids
HCl, H2SO4 (TsOH), H3O+, HBr, H3PO4, HI, HNO3,
Common Bases
-OH (ie. NaOH or LiOH), RO-+M (ie. EtOH or tBuO-K+),
M+-NH2 (ie. LDA), NH3 (ie. Et3N), alkane bonded to a metal
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