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CHEM2213 Topic 4: Haloalkanes - Sn2 Mechanisms.docx

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Western University
Chemistry 1027A/B
Mark Workentin

Topic 4 Haloalkanes  Alkyl Halide: compound containing a halogen atom covalently bonded to an sp hybridized C atom, given symbol RX How Are Haloalkanes Named?  Haloalkanes are named alkyl halides, where the name is derived by naming alkyl group followed by name of the halide as a separate word  Haloforms: compounds of the type CHX 3 What Are The Characteristic Reactions Of Haloalkanes?  Nucleophile: atom / group that donates pair of electrons to another atom / group to form a new covalent bond  Nucleophilic Substitution: reaction in which one nucleophile is substituted for another o Halide ions are among best and most important leaving groups  β-Elimination: removal of atoms / groups from 2 adjacent C atoms  Substitution reactions always result in the replacement of atom / group in a reactant with another atom / group  β-Elimination reactions always result in removal of a H and an atom / group on adjacent C atoms and in the formation of a C-C double bond What Are The Products Of Nucleophilic Aliphatic Substitution Reactions?  If the nucleophile is negatively charged, then the atom donating the pair of electrons in the substitution reaction becomes neutral in the product  If the nucleophile is uncharged, then the atom donating the pair of electrons in the substitution reaction becomes positively charged in the product (often undergo second step involving proton
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