By Frank Pellegrini
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Additional resources for Organic Chemistry II
H O O C — CH3 C — CH3 + H + − 5. The proton reacts with the AlCl4 to regenerate the AlCl3 catalyst and form the product HCl. + − H + AICl4 HCl + AICl3 Directing Group Influence Substituents already attached to benzene exert an influence on additional atoms or groups attempting to bond to the benzene ring via electrophilic aromatic substitution reactions. An atom or group already attached to a benzene ring may direct an incoming electrophile to either the ortho-para positions or the meta position.
The major product is predicted by Zaitsev’s Rule, which states that the more highly branched alkene will be the major product. For example, in the dehydrohalogenation reaction between 2-chlorobutane and sodium methoxide, the major product is 2-butene. H H H Cl H C C C C H H H H − + H + CH3O Na ORGANIC CHEMISTRY II H H H H H C C C C H H 1-butene H + H H H H H C C C C H H H 2-butene 49 ALKYL HALIDES Mechanism of Elimination Reactions As noted earlier, the halogen-carbon bond in an alkyl halide is polarized due to the electronegativity difference between the atoms.
Nature of the carbon skeleton Only those molecules that form extremely stable cations undergo S 1 mechanisms. Normally, only compounds that yield 3° (tertiary) carbonications (or resonance-stabilized carbocations) undergo S 1 mechanisms rather than S 2 mechanisms. Carbocations of tertiary alkyl halides not only exhibit stability due to the inductive effect, but the original molecules exhibit steric hindrance of the rear lobe of the bonding orbital, which inhibits S 2 mechanisms from occurring. Primary alkyl halides, which have little inductive stability of their cations and exhibit no steric hindrance of the rear lobe of the bonding orbital, generally undergo S 2 mechanisms.