Download Organic Chemistry II by Frank Pellegrini PDF

By Frank Pellegrini

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  • The reactions of fragrant compounds
  • Aldol, cross-aldol, and ketonic aldol condensation
  • Ester formation
  • Oxidation
  • Mass spectra

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Example text

The larger and bulkier the group(s), the greater the steric hindrance and the slower the rate of reaction. Table 3-2 shows the effect of steric hindrance on the rate of reaction for a specific, unspecified nucleophile and leaving group. Different nucleophiles and leaving groups would result in different numbers but similar patterns of results. 03 0 S 2 reactions give good yields on 1° (primary) alkyl halides, moderate yields on 2° (secondary) alkyl halides, and poor to no yields on 3° (tertiary) alkyl halides.

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. This polarization can lead to the formation of a partial or fully positive charge on the carbon atom. H H H δ H C C C δ H X H H H C C+ C H X− H + H or H H − H The full or partial positive charge on the carbon atom is delocalized (dispersed) down the carbon chain.

CH2CH2CH3 + CH3CH2CH2Cl AICl3 H3C — CH — CH3 + minor product major product The isopropyl benzene results from a rearrangement of the initially formed propyl carbocation to the more stable isopropyl carbocation. H H H H H H H—C—C—C—H + H H H—C—C—C—H + H H 1ϒ carbocation 2ϒ carbocation This rearrangement is called a 1,2-hydride ion shift. A hydride ion is H-. ORGANIC CHEMISTRY II 27 REACTIONS OF AROMATIC COMPOUNDS Friedel-Crafts Acylation Reaction The Friedel-Crafts acylation reaction, another example of an electrophilic aromatic substitution reaction, is similar to the FriedelCrafts alkylation reaction except that the substance that reacts with benzene is an acyl halide, O R—C—X instead of an alkyl halide, R — X .

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