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  • Chapter

    • Alcohol Synthesis

      • I. From Alkanes

        • 1. Hydration REVIEW*

          • a. Acid catalyzed

          • b. Oxymercuration-demurcuration

          • c. Hydrobromination-oxidation

        • 2. Hydroxylation: forms vicinal diols (glycols)*

          • a. Syn hydroxylation

          • b. Anti hydroxylation

      • II. From alkyl halides: Nucleophilic Substitution

        • 1. Nucleophilic Substitution*

          • a. Sn1

          • b. Sn2

      • III. From carbonyl compounds: Nucleophilic Addition to the carbonyl group

        • 1. Addition of a Grignard or organolithium reagent*

          • a. Addition to formaldehyde gives 1° alcohol

          • b. Addition to an aldehyde gives 2° alcohol

          • c. Addition to a ketone gives 3° alcohol

          • d. Addition to an acid halide or and ester gives 3° alcohol

          • e. Addition to ethylene oxide gives a primary alcohol and 2 carbon atoms added

        • 2.  Reduction of carbonyl compounds*

          • a.  Catalytic hydrogenation of aldehydes and ketones

          • b.  Use of hydride reagents*

            • 1.  Reduction of and aldehyde gives 1° alcohol

            • 2.  Reduction of a ketone gives 2° alcohol

            • 3.  Reduction of an acid or ester gives 1° alcohol