Ch_322b_12.02

Ch_322b_12.02 - Oxidation-Reduction Reactions in Organic...

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Oxidation-Reduction Reactions in Organic Chemistry An oxidation reaction often can be recognized by either an increase in oxygen content or a decrease in hydrogen content. Similarly, a reduction reaction usually involves the opposite changes. RCOH O = carboxylic acid reduction oxidation RC-H H OH alcohol [H] [O] The symbol [H] means reduction and the symbol [O] means oxidation.
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Formal Oxidation States A formal oxidation state may be assigned to a carbon as follows: C C C • A bond to another carbon is 0 (zero). • A bond to H (or anything less electronegative) is -1. • A bond to a more electronegative atom (O, N, halogen) is +1. Example: For the sequence R-C-H H H R-C-OH H H [H] [O] [H] [O] [H] [O] R-C-H O = R-C-OH O The formal oxidation states at C are: (-3) (-1) (+1) (+3)
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Alcohols by Reduction of Carbonyl Compounds Primary and secondary alcohols may be prepared by the reduction of several carbonyl functional groups: R-C-H O = aldehyde [H] R-C-H H OH primary alcohol R-C-R' O [H] ketone R-C-R' H OH secondary alcohol R-C-OH O [H] carboxylic acid R-C-H H OH primary alcohol R-C-OR' O [H] ester R-C-H H OH primary alcohol (+ R'OH)
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Ch_322b_12.02 - Oxidation-Reduction Reactions in Organic...

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