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Chapter 12 Alcohols, Phenols, Ethers, Aldehydes, and Ketones

Chapter 12 Alcohols, Phenols, Ethers, Aldehydes, and Ketones. Oxidation and Reduction. Classification of Alcohols. Primary (1º) Secondary (2º ) Tertiary (3º) H CH 3 CH 3 CH 3 -C-OH CH 3 -C-OH CH 3 -C-OH

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Chapter 12 Alcohols, Phenols, Ethers, Aldehydes, and Ketones

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  1. Chapter 12Alcohols, Phenols, Ethers, Aldehydes, and Ketones Oxidation and Reduction Timberlake LesturePLUS 1999

  2. Classification of Alcohols Primary (1º) Secondary (2º ) Tertiary (3º) H CH3 CH3 CH3-C-OH CH3-C-OH CH3-C-OH H H CH3 1 CH3 2 CH3 3 CH3 attached attached attached to C-OH to C-OH to C-OH Timberlake LesturePLUS 1999

  3. Learning Check Ox-Red 1 Classify the following as 1º, 2º, or 3º alcohols: OH A. CH3CH2CH2OH B. CH3-CH-CH2CH3 C. D. OH CH3-C-CH2CH3 CH3 Timberlake LesturePLUS 1999

  4. Solution Ox-Red 1 Classify the following as 1º, 2º, or 3º alcohols: OH A. CH3CH3CH2OH 1º B. CH3-CH-CH2CH3 2º C. 2º D. OH 3º CH3-C-CH2CH3 CH3 Timberlake LesturePLUS 1999

  5. Oxidation • Is a gain of oxygen (O) or • A loss of hydrogen (H) Timberlake LesturePLUS 1999

  6. Alcohols 1°alcohols are oxidized to aldehydes and 2° alcohols are oxidized to ketones Alcohols 1° 2° aldehydes ketones Timberlake LesturePLUS 1999

  7. Oxidation of Alcohols [O] Primary alcohol aldehyde OH O [O]  CH3-C-H CH3-C-H H Ethanol Ethanal (ethyl alcohol) (acetaldehyde) Timberlake LesturePLUS 1999

  8. Oxidation of Alcohols [O] Secondary alcohol ketone OH O [O]  CH3-C-CH3 CH3-C-CH3 2-Propanol 2-propanone (isopropyl alcohol) (dimethyl ketone, “acetone”) Timberlake LesturePLUS 1999

  9. Oxidation of Alcohols [O] Tertiary alcohols no reaction OH [O] CH3-C-CH3 no product CH3 no H on the C-OH to oxidize 2-Methyl-2-propanol Timberlake LesturePLUS 1999

  10. Oxidation of Ethanol in the Body • Enzymes in the liver oxidize ethanol • Aldehyde product impairs coordination • Blood alcohol over 0.4% can be fatal. O O  CH3CH2OH CH3CH CH3COH 2CO2 + H2O ethyl alcohol acetaldhyde acetic acid Timberlake LesturePLUS 1999

  11. Learning Check Ox-Red 3 Select the product for the reaction of CH3CH2CH2OH in the following conditions: O  1) CH3CH=CH2 2) CO2 + H2O3) CH3CH2CH A. H+, heat _________ B. [O] _________ C. O2, heat _________ Timberlake LesturePLUS 1999

  12. Solution Ox-Red 3 Select the product for the reaction of CH3CH2CH2OH in the following conditions: A. H+, heat 1) CH3CH=CH2 O  B. [O] 3) CH3CH2CH C. O2, heat 2) CO2 + H2O Timberlake LesturePLUS 1999

  13. Learning Check Ox-Red 4 Write the structure of the following: A. 3-pentanol B. Dimethyl ether C. 3-methylcyclobutanol Timberlake LesturePLUS 1999

  14. Solution Ox-Red 4 Write the structure of the following: OH | A. 3-pentanol CH3CH2CHCH2CH3 B. Dimethyl ether CH3-O-CH3 C. 3-methylcyclobutanol Timberlake LesturePLUS 1999

  15. Reduction • Is a loss of oxygen (O) or • gain of hydrogen (H) Timberlake LesturePLUS 1999

  16. Reduction Aldehydes are reduced to 1° alcohols and ketones are reduced to 2° alcohols Alcohols 1° 2° aldehydes ketones Timberlake LesturePLUS 1999

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