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

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

• Oxidation and Reduction

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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

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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

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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

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Oxidation

• Is a gain of oxygen (O)
• or
• A loss of hydrogen (H)

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Alcohols

• 1alcohols are oxidized to aldehydes and 2
  alcohols are oxidized to ketones
• Alcohols
• 1 2
• aldehydes ketones

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Oxidation of Alcohols

• O
• Primary alcohol aldehyde
• OH O
• O ?
• CH3-C-H CH3-C-H
• H
• Ethanol Ethanal
• (ethyl alcohol) (acetaldehyde)

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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)

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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

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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

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Learning Check Ox-Red 3

• Select the product for the reaction of
  CH3CH2CH2OH in the following conditions
• O ?
• 1) CH3CHCH2 2) CO2 H2O 3) CH3CH2CH
• A. H, heat _________
• B. O _________
• C. O2, heat _________

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Solution Ox-Red 3

• Select the product for the reaction of
  CH3CH2CH2OH in the following conditions
• A. H, heat 1) CH3CHCH2
• O
• ?
• B. O 3) CH3CH2CH
• C. O2, heat 2) CO2 H2O

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Learning Check Ox-Red 4

• Write the structure of the following
• A. 3-pentanol
• B. Dimethyl ether
• C. 3-methylcyclobutanol

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Solution Ox-Red 4

• Write the structure of the following
• OH
• A. 3-pentanol CH3CH2CHCH2CH3
• B. Dimethyl ether CH3-O-CH3
• C. 3-methylcyclobutanol

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Reduction

• Is a loss of oxygen (O)
• or
• gain of hydrogen (H)

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Reduction

• Aldehydes are reduced to 1 alcohols and ketones
  are reduced to 2 alcohols
• Alcohols
• 1 2
• aldehydes ketones