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Reactions of Ketones and Aldehydes Susan F. Hornbuckle Associate Professor of Chemistry Clayton State University Reactions Flow Chart What are the reaction conditions? H2/ Pt, Pd, or Ni H2SO4 + 2 alcohols “Reduction Conditions” “Acetal Formation” Break the O-H bond of one alcohol. Break one of the C=O Break the H-H bond. bonds. Form a bond between the carbonyl carbon and the O of Break one of the C=O the alcohol. Form a bond between the H and the O of the bonds. Form a bond carbonyl to form a HEMIACETAL. between the alpha-carbon and one H. Form a bond between the O and Break the O-H bond of the other alcohol. Break the C-O bond the other H to between the alpha-carbon and the O of the O-H of the hemiacetal. form an ALCOHOL. Form a bond between the H (from the alcohol) and the O-H (from the hemiacetal) to form H2O. Form a bond between the O (from the alcohol) and the alpha-carbon to form an ACETAL. K2Cr2O7 / H2SO4 “Oxidation Conditions” Is the starting an aldehyde or ketone? Aldehyde Ketone Insert an oxygen atom in the C-H bond of the carbonyl to form a CARBOXYLIC ACID. NO RXN. Reactions Flow Chart Example 1 What are the reaction conditions? H2/ Pt, Pd, or Ni H2SO4 + 2 alcohols “Reduction Conditions” “Acetal Formation” Break the O-H bond of one alcohol. Break one of the C=O Break the H-H bond. bonds. Form a bond between the carbonyl carbon and the O of Break one of the C=O the alcohol. Form a bond between the H and the O of the bonds. Form a bond carbonyl to form a HEMIACETAL. between the alpha-carbon and one H. Form a bond between the O and Break the O-H bond of the other alcohol. Break the C-O bond the other H to between the alpha-carbon and the O of the O-H of the hemiacetal. form an ALCOHOL. Form a bond between the H (from the alcohol) and the O-H (from the hemiacetal) to form H2O. Form a bond between the O (from the alcohol) and the alpha-carbon to form an ACETAL. O CH2 CH3 K2Cr2O7 C CH2 H H2SO4 K2Cr2O7 / H2SO4 “Oxidation Conditions” Is the starting an aldehyde or ketone? Aldehyde Ketone Insert an oxygen atom in the C-H bond of the carbonyl to form a CARBOXYLIC ACID. NO RXN. Reactions Flow Chart Example 1 What are the reaction conditions? H2/ Pt, Pd, or Ni H2SO4 + 2 alcohols “Reduction Conditions” “Acetal Formation” Break the O-H bond of one alcohol. Break one of the C=O Break the H-H bond. bonds. Form a bond between the carbonyl carbon and the O of Break one of the C=O the alcohol. Form a bond between the H and the O of the bonds. Form a bond carbonyl to form a HEMIACETAL. between the alpha-carbon and one H. Form a bond between the O and Break the O-H bond of the other alcohol. Break the C-O bond the other H to between the alpha-carbon and the O of the O-H of the hemiacetal. form an ALCOHOL. Form a bond between the H (from the alcohol) and the O-H (from the hemiacetal) to form H2O. Form a bond between the O (from the alcohol) and the alpha-carbon to form an ACETAL. O CH2 CH3 K2Cr2O7 C CH2 H H2SO4 K2Cr2O7 / H2SO4 “Oxidation Conditions” Is the starting an aldehyde or ketone? Aldehyde Ketone Insert an oxygen atom in the C-H bond of the carbonyl to form a CARBOXYLIC ACID. NO RXN. Reactions Flow Chart Example 1 What are the reaction conditions? H2/ Pt, Pd, or Ni H2SO4 + 2 alcohols “Reduction Conditions” “Acetal Formation” Break the O-H bond of one alcohol. Break one of the C=O Break the H-H bond. bonds. Form a bond between the carbonyl carbon and the O of Break one of the C=O the alcohol. Form a bond between the H and the O of the bonds. Form a bond carbonyl to form a HEMIACETAL. between the alpha-carbon and one H. Form a bond between the O and Break the O-H bond of the other alcohol. Break the C-O bond the other H to between the alpha-carbon and the O of the O-H of the hemiacetal. form an ALCOHOL. Form a bond between the H (from the alcohol) and the O-H (from the hemiacetal) to form H2O. Form a bond between the O (from the alcohol) and the alpha-carbon to form an ACETAL. O CH2 CH3 K2Cr2O7 C CH2 H H2SO4 K2Cr2O7 / H2SO4 “Oxidation Conditions” Is the starting an aldehyde or ketone? Aldehyde Ketone Insert an oxygen atom in the C-H bond of the carbonyl to form a CARBOXYLIC ACID. NO RXN. Reactions Flow Chart Example 1 What are the reaction conditions? H2/ Pt, Pd, or Ni H2SO4 + 2 alcohols “Reduction Conditions” “Acetal Formation” K2Cr2O7 / H2SO4 “Oxidation Conditions” Break the O-H bond of one alcohol. Break one of the C=O Break the H-H bond. bonds. Form a bond between the carbonyl carbon and the O of Break one of the C=O the alcohol. Form a bond between the H and the O of the bonds. Form a bond carbonyl to form a HEMIACETAL. between the alpha-carbon and one H. Form a bond between the O and Break the O-H bond of the other alcohol. Break the C-O bond the other H to between the alpha-carbon and the O of the O-H of the hemiacetal. form an ALCOHOL. Form a bond between the H (from the alcohol) and the O-H (from the hemiacetal) to form H2O. Form a bond between the O (from the alcohol) and the alpha-carbon to form an ACETAL. Is the starting an aldehyde or ketone? Aldehyde Ketone Insert an oxygen atom in the C-H bond of the carbonyl to form a CARBOXYLIC ACID. NO RXN. O O O K2Cr2O7 CH2 CH3 C CH2 H H2SO4 CH2 CH3 C CH2 OH Reactions Flow Chart Example 2 What are the reaction conditions? H2/ Pt, Pd, or Ni H2SO4 + 2 alcohols “Reduction Conditions” “Acetal Formation” Break the O-H bond of one alcohol. Break one of the C=O Break the H-H bond. bonds. Form a bond between the carbonyl carbon and the O of Break one of the C=O the alcohol. Form a bond between the H and the O of the bonds. Form a bond carbonyl to form a HEMIACETAL. between the alpha-carbon and one H. Form a bond between the O and Break the O-H bond of the other alcohol. Break the C-O bond the other H to between the alpha-carbon and the O of the O-H of the hemiacetal. form an ALCOHOL. Form a bond between the H (from the alcohol) and the O-H (from the hemiacetal) to form H2O. Form a bond between the O (from the alcohol) and the alpha-carbon to form an ACETAL. O CH2 CH3 C CH2 + H2 CH3 Pd K2Cr2O7 / H2SO4 “Oxidation Conditions” Is the starting an aldehyde or ketone? Aldehyde Ketone Insert an oxygen atom in the C-H bond of the carbonyl to form a CARBOXYLIC ACID. NO RXN. Reactions Flow Chart Example 2 What are the reaction conditions? H2/ Pt, Pd, or Ni H2SO4 + 2 alcohols “Reduction Conditions” “Acetal Formation” Break the O-H bond of one alcohol. Break one of the C=O Break the H-H bond. bonds. Form a bond between the carbonyl carbon and the O of Break one of the C=O the alcohol. Form a bond between the H and the O of the bonds. Form a bond carbonyl to form a HEMIACETAL. between the alpha-carbon and one H. Form a bond between the O and Break the O-H bond of the other alcohol. Break the C-O bond the other H to between the alpha-carbon and the O of the O-H of the hemiacetal. form an ALCOHOL. Form a bond between the H (from the alcohol) and the O-H (from the hemiacetal) to form H2O. Form a bond between the O (from the alcohol) and the alpha-carbon to form an ACETAL. O CH2 CH3 C CH2 + H2 CH3 Pd K2Cr2O7 / H2SO4 “Oxidation Conditions” Is the starting an aldehyde or ketone? Aldehyde Ketone Insert an oxygen atom in the C-H bond of the carbonyl to form a CARBOXYLIC ACID. NO RXN. Reactions Flow Chart Example 2 What are the reaction conditions? H2/ Pt, Pd, or Ni H2SO4 + 2 alcohols “Reduction Conditions” “Acetal Formation” Break the O-H bond of one alcohol. Break one of the C=O Break the H-H bond. bonds. Form a bond between the carbonyl carbon and the O of Break one of the C=O the alcohol. Form a bond between the H and the O of the bonds. Form a bond carbonyl to form a HEMIACETAL. between the alpha-carbon and one H. Form a bond between the O and Break the O-H bond of the other alcohol. Break the C-O bond the other H to between the alpha-carbon and the O of the O-H of the hemiacetal. form an ALCOHOL. Form a bond between the H (from the alcohol) and the O-H (from the hemiacetal) to form H2O. Form a bond between the O (from the alcohol) and the alpha-carbon to form an ACETAL. O CH2 CH3 C CH2 + H2 CH3 Pd K2Cr2O7 / H2SO4 “Oxidation Conditions” Is the starting an aldehyde or ketone? Aldehyde Ketone Insert an oxygen atom in the C-H bond of the carbonyl to form a CARBOXYLIC ACID. NO RXN. H O H CH2 CH3 C CH2 CH3 Reactions Flow Chart Example 2 What are the reaction conditions? H2/ Pt, Pd, or Ni H2SO4 + 2 alcohols “Reduction Conditions” “Acetal Formation” K2Cr2O7 / H2SO4 “Oxidation Conditions” Break the O-H bond of one alcohol. Break one of the C=O Break the H-H bond. bonds. Form a bond between the carbonyl carbon and the O of Break one of the C=O the alcohol. Form a bond between the H and the O of the bonds. Form a bond carbonyl to form a HEMIACETAL. between the alpha-carbon and one H. Form a bond between the O and Break the O-H bond of the other alcohol. Break the C-O bond the other H to between the alpha-carbon and the O of the O-H of the hemiacetal. form an ALCOHOL. Form a bond between the H (from the alcohol) and the O-H (from the hemiacetal) to form H2O. Form a bond between the O (from the alcohol) and the alpha-carbon to form an ACETAL. Is the starting an aldehyde or ketone? Aldehyde Ketone Insert an oxygen atom in the C-H bond of the carbonyl to form a CARBOXYLIC ACID. NO RXN. H O CH2 CH3 C CH2 O + H2 CH3 Pd H CH2 CH3 C CH2 CH3 Reactions Flow Chart Example 3 What are the reaction conditions? H2/ Pt, Pd, or Ni H2SO4 + 2 alcohols “Reduction Conditions” “Acetal Formation” Break the O-H bond of one alcohol. Break one of the C=O Break the H-H bond. bonds. Form a bond between the carbonyl carbon and the O of Break one of the C=O the alcohol. Form a bond between the H and the O of the bonds. Form a bond carbonyl to form a HEMIACETAL. between the alpha-carbon and one H. Form a bond between the O and Break the O-H bond of the other alcohol. Break the C-O bond the other H to between the alpha-carbon and the O of the O-H of the hemiacetal. form an ALCOHOL. Form a bond between the H (from the alcohol) and the O-H (from the hemiacetal) to form H2O. Form a bond between the O (from the alcohol) and the alpha-carbon to form an ACETAL. O CH3 + 2 CH3-OH C CH2 H H2SO4 K2Cr2O7 / H2SO4 “Oxidation Conditions” Is the starting an aldehyde or ketone? Aldehyde Ketone Insert an oxygen atom in the C-H bond of the carbonyl to form a CARBOXYLIC ACID. NO RXN. Reactions Flow Chart Example 3 What are the reaction conditions? H2/ Pt, Pd, or Ni H2SO4 + 2 alcohols “Reduction Conditions” “Acetal Formation” Break the O-H bond of one alcohol. Break one of the C=O Break the H-H bond. bonds. Form a bond between the carbonyl carbon and the O of Break one of the C=O the alcohol. Form a bond between the H and the O of the bonds. Form a bond carbonyl to form a HEMIACETAL. between the alpha-carbon and one H. Form a bond between the O and Break the O-H bond of the other alcohol. Break the C-O bond the other H to between the alpha-carbon and the O of the O-H of the hemiacetal. form an ALCOHOL. Form a bond between the H (from the alcohol) and the O-H (from the hemiacetal) to form H2O. Form a bond between the O (from the alcohol) and the alpha-carbon to form an ACETAL. O CH3 + 2 CH3-OH C CH2 H H2SO4 K2Cr2O7 / H2SO4 “Oxidation Conditions” Is the starting an aldehyde or ketone? Aldehyde Ketone Insert an oxygen atom in the C-H bond of the carbonyl to form a CARBOXYLIC ACID. NO RXN. Reactions Flow Chart Example 3 What are the reaction conditions? H2/ Pt, Pd, or Ni H2SO4 + 2 alcohols “Reduction Conditions” “Acetal Formation” Break the O-H bond of one alcohol. Break one of the C=O Break the H-H bond. bonds. Form a bond between the carbonyl carbon and the O of Break one of the C=O the alcohol. Form a bond between the H and the O of the bonds. Form a bond carbonyl to form a HEMIACETAL. between the alpha-carbon and one H. Form a bond between the O and Break the O-H bond of the other alcohol. Break the C-O bond the other H to between the alpha-carbon and the O of the O-H of the hemiacetal. form an ALCOHOL. Form a bond between the H (from the alcohol) and the O-H (from the hemiacetal) to form H2O. Form a bond between the O (from the alcohol) and the alpha-carbon to form an ACETAL. O CH3 + 2 CH3-OH C CH2 H H2SO4 K2Cr2O7 / H2SO4 “Oxidation Conditions” Is the starting an aldehyde or ketone? Aldehyde Ketone Insert an oxygen atom in the C-H bond of the carbonyl to form a CARBOXYLIC ACID. NO RXN. H O CH3 O C CH2 CH3 CH3 CH2 H O H C O H CH3 Reactions Flow Chart Example 3 What are the reaction conditions? H2/ Pt, Pd, or Ni H2SO4 + 2 alcohols “Reduction Conditions” “Acetal Formation” K2Cr2O7 / H2SO4 “Oxidation Conditions” Break the O-H bond of one alcohol. Break one of the C=O Break the H-H bond. bonds. Form a bond between the carbonyl carbon and the O of Break one of the C=O the alcohol. Form a bond between the H and the O of the bonds. Form a bond carbonyl to form a HEMIACETAL. between the alpha-carbon and one H. Form a bond between the O and Break the O-H bond of the other alcohol. Break the C-O bond the other H to between the alpha-carbon and the O of the O-H of the hemiacetal. form an ALCOHOL. Form a bond between the H (from the alcohol) and the O-H (from the hemiacetal) to form H2O. Form a bond between the O (from the alcohol) and the alpha-carbon to form an ACETAL. H O CH3 O + 2 CH3-OH C CH2 H H2SO4 CH3 C CH2 O H CH3 Is the starting an aldehyde or ketone? Aldehyde Ketone Insert an oxygen atom in the C-H bond of the carbonyl to form a CARBOXYLIC ACID. NO RXN. Reactions Flow Chart Example 3 What are the reaction conditions? H2/ Pt, Pd, or Ni H2SO4 + 2 alcohols “Reduction Conditions” “Acetal Formation” K2Cr2O7 / H2SO4 “Oxidation Conditions” Break the O-H bond of one alcohol. Break one of the C=O Break the H-H bond. bonds. Form a bond between the carbonyl carbon and the O of Break one of the C=O the alcohol. Form a bond between the H and the O of the bonds. Form a bond carbonyl to form a HEMIACETAL. between the alpha-carbon and one H. Form a bond between the O and Break the O-H bond of the other alcohol. Break the C-O bond the other H to between the alpha-carbon and the O of the O-H of the hemiacetal. form an ALCOHOL. Form a bond between the H (from the alcohol) and the O-H (from the hemiacetal) to form H2O. Form a bond between the O (from the alcohol) and the alpha-carbon to form an ACETAL. H O CH3 O + 2 CH3-OH C CH2 H H2SO4 CH3 C CH2 O H CH3 Is the starting an aldehyde or ketone? Aldehyde Ketone Insert an oxygen atom in the C-H bond of the carbonyl to form a CARBOXYLIC ACID. NO RXN. H H CH3 O O CH3 C CH2 O H O CH3 CH3 CH2 CH3 O C CH3 H Reactions Flow Chart Example 3 What are the reaction conditions? H2/ Pt, Pd, or Ni H2SO4 + 2 alcohols “Reduction Conditions” “Acetal Formation” K2Cr2O7 / H2SO4 “Oxidation Conditions” Break the O-H bond of one alcohol. Break one of the C=O Break the H-H bond. bonds. Form a bond between the carbonyl carbon and the O of Break one of the C=O the alcohol. Form a bond between the H and the O of the bonds. Form a bond carbonyl to form a HEMIACETAL. between the alpha-carbon and one H. Form a bond between the O and Break the O-H bond of the other alcohol. Break the C-O bond the other H to between the alpha-carbon and the O of the O-H of the hemiacetal. form an ALCOHOL. Form a bond between the H (from the alcohol) and the O-H (from the hemiacetal) to form H2O. Form a bond between the O (from the alcohol) and the alpha-carbon to form an ACETAL. Ketone Insert an oxygen atom in the C-H bond of the carbonyl to form a CARBOXYLIC ACID. NO RXN. CH3 O + 2 CH3-OH C CH2 Aldehyde H O CH3 Is the starting an aldehyde or ketone? H O H2SO4 CH3 CH3 C CH2 O H CH2 CH3 O C CH3 H Reactions Flow Chart Example 4 What are the reaction conditions? H2/ Pt, Pd, or Ni H2SO4 + 2 alcohols “Reduction Conditions” “Acetal Formation” Break the O-H bond of one alcohol. Break one of the C=O Break the H-H bond. bonds. Form a bond between the carbonyl carbon and the O of Break one of the C=O the alcohol. Form a bond between the H and the O of the bonds. Form a bond carbonyl to form a HEMIACETAL. between the alpha-carbon and one H. Form a bond between the O and Break the O-H bond of the other alcohol. Break the C-O bond the other H to between the alpha-carbon and the O of the O-H of the hemiacetal. form an ALCOHOL. Form a bond between the H (from the alcohol) and the O-H (from the hemiacetal) to form H2O. Form a bond between the O (from the alcohol) and the alpha-carbon to form an ACETAL. O K2Cr2O7 CH2 CH3 C CH2 CH3 H2SO4 K2Cr2O7 / H2SO4 “Oxidation Conditions” Is the starting an aldehyde or ketone? Aldehyde Ketone Insert an oxygen atom in the C-H bond of the carbonyl to form a CARBOXYLIC ACID. NO RXN. Reactions Flow Chart Example 4 What are the reaction conditions? H2/ Pt, Pd, or Ni H2SO4 + 2 alcohols “Reduction Conditions” “Acetal Formation” Break the O-H bond of one alcohol. Break one of the C=O Break the H-H bond. bonds. Form a bond between the carbonyl carbon and the O of Break one of the C=O the alcohol. Form a bond between the H and the O of the bonds. Form a bond carbonyl to form a HEMIACETAL. between the alpha-carbon and one H. Form a bond between the O and Break the O-H bond of the other alcohol. Break the C-O bond the other H to between the alpha-carbon and the O of the O-H of the hemiacetal. form an ALCOHOL. Form a bond between the H (from the alcohol) and the O-H (from the hemiacetal) to form H2O. Form a bond between the O (from the alcohol) and the alpha-carbon to form an ACETAL. O K2Cr2O7 CH2 CH3 C CH2 CH3 H2SO4 K2Cr2O7 / H2SO4 “Oxidation Conditions” Is the starting an aldehyde or ketone? Aldehyde Ketone Insert an oxygen atom in the C-H bond of the carbonyl to form a CARBOXYLIC ACID. NO RXN. Reactions Flow Chart Example 4 What are the reaction conditions? H2/ Pt, Pd, or Ni H2SO4 + 2 alcohols “Reduction Conditions” “Acetal Formation” Break the O-H bond of one alcohol. Break one of the C=O Break the H-H bond. bonds. Form a bond between the carbonyl carbon and the O of Break one of the C=O the alcohol. Form a bond between the H and the O of the bonds. Form a bond carbonyl to form a HEMIACETAL. between the alpha-carbon and one H. Form a bond between the O and Break the O-H bond of the other alcohol. Break the C-O bond the other H to between the alpha-carbon and the O of the O-H of the hemiacetal. form an ALCOHOL. Form a bond between the H (from the alcohol) and the O-H (from the hemiacetal) to form H2O. Form a bond between the O (from the alcohol) and the alpha-carbon to form an ACETAL. O K2Cr2O7 CH2 CH3 C CH2 CH3 H2SO4 K2Cr2O7 / H2SO4 “Oxidation Conditions” Is the starting an aldehyde or ketone? Aldehyde Ketone Insert an oxygen atom in the C-H bond of the carbonyl to form a CARBOXYLIC ACID. NO RXN. Reactions Flow Chart Example 4 What are the reaction conditions? H2/ Pt, Pd, or Ni H2SO4 + 2 alcohols “Reduction Conditions” “Acetal Formation” Break the O-H bond of one alcohol. Break one of the C=O Break the H-H bond. bonds. Form a bond between the carbonyl carbon and the O of Break one of the C=O the alcohol. Form a bond between the H and the O of the bonds. Form a bond carbonyl to form a HEMIACETAL. between the alpha-carbon and one H. Form a bond between the O and Break the O-H bond of the other alcohol. Break the C-O bond the other H to between the alpha-carbon and the O of the O-H of the hemiacetal. form an ALCOHOL. Form a bond between the H (from the alcohol) and the O-H (from the hemiacetal) to form H2O. Form a bond between the O (from the alcohol) and the alpha-carbon to form an ACETAL. K2Cr2O7 / H2SO4 “Oxidation Conditions” Is the starting an aldehyde or ketone? Aldehyde Ketone Insert an oxygen atom in the C-H bond of the carbonyl to form a CARBOXYLIC ACID. NO RXN. O K2Cr2O7 CH2 CH3 C CH2 CH3 H2SO4 No Reaction Reactions Flow Chart Example 5 What are the reaction conditions? H2/ Pt, Pd, or Ni H2SO4 + 2 alcohols “Reduction Conditions” “Acetal Formation” Break the O-H bond of one alcohol. Break one of the C=O Break the H-H bond. bonds. Form a bond between the carbonyl carbon and the O of Break one of the C=O the alcohol. Form a bond between the H and the O of the bonds. Form a bond carbonyl to form a HEMIACETAL. between the alpha-carbon and one H. Form a bond between the O and Break the O-H bond of the other alcohol. Break the C-O bond the other H to between the alpha-carbon and the O of the O-H of the hemiacetal. form an ALCOHOL. Form a bond between the H (from the alcohol) and the O-H (from the hemiacetal) to form H2O. Form a bond between the O (from the alcohol) and the alpha-carbon to form an ACETAL. O CH2 HO CH2 C CH2 + CH3-CH2-OH H H2SO4 K2Cr2O7 / H2SO4 “Oxidation Conditions” Is the starting an aldehyde or ketone? Aldehyde Ketone Insert an oxygen atom in the C-H bond of the carbonyl to form a CARBOXYLIC ACID. NO RXN. Reactions Flow Chart Example 5 What are the reaction conditions? H2/ Pt, Pd, or Ni H2SO4 + 2 alcohols “Reduction Conditions” “Acetal Formation” Break the O-H bond of one alcohol. Break one of the C=O Break the H-H bond. bonds. Form a bond between the carbonyl carbon and the O of Break one of the C=O the alcohol. Form a bond between the H and the O of the bonds. Form a bond carbonyl to form a HEMIACETAL. between the alpha-carbon and one H. Form a bond between the O and Break the O-H bond of the other alcohol. Break the C-O bond the other H to between the alpha-carbon and the O of the O-H of the hemiacetal. form an ALCOHOL. Form a bond between the H (from the alcohol) and the O-H (from the hemiacetal) to form H2O. Form a bond between the O (from the alcohol) and the alpha-carbon to form an ACETAL. O CH2 HO CH2 C CH2 + CH3-CH2-OH H H2SO4 K2Cr2O7 / H2SO4 “Oxidation Conditions” Is the starting an aldehyde or ketone? Aldehyde Ketone Insert an oxygen atom in the C-H bond of the carbonyl to form a CARBOXYLIC ACID. NO RXN. Reactions Flow Chart Example 5 What are the reaction conditions? H2/ Pt, Pd, or Ni H2SO4 + 2 alcohols “Reduction Conditions” “Acetal Formation” Break the O-H bond of one alcohol. Break one of the C=O Break the H-H bond. bonds. Form a bond between the carbonyl carbon and the O of Break one of the C=O the alcohol. Form a bond between the H and the O of the bonds. Form a bond carbonyl to form a HEMIACETAL. between the alpha-carbon and one H. Form a bond between the O and Break the O-H bond of the other alcohol. Break the C-O bond the other H to between the alpha-carbon and the O of the O-H of the hemiacetal. form an ALCOHOL. Form a bond between the H (from the alcohol) and the O-H (from the hemiacetal) to form H2O. Form a bond between the O (from the alcohol) and the alpha-carbon to form an ACETAL. O CH2 HO CH2 C CH2 + CH3-CH2-OH H H2SO4 K2Cr2O7 / H2SO4 “Oxidation Conditions” Is the starting an aldehyde or ketone? Aldehyde Ketone Insert an oxygen atom in the C-H bond of the carbonyl to form a CARBOXYLIC ACID. NO RXN. H O O CH2 HO CH2 C CH2 CH2 O H C CH2 CH2 H H O CH2 CH2 C CH2 O O O CH2 H H CH2 C H CH2 Reactions Flow Chart Example 5 What are the reaction conditions? H2/ Pt, Pd, or Ni H2SO4 + 2 alcohols “Reduction Conditions” “Acetal Formation” K2Cr2O7 / H2SO4 “Oxidation Conditions” Break the O-H bond of one alcohol. Break one of the C=O Break the H-H bond. bonds. Form a bond between the carbonyl carbon and the O of Break one of the C=O the alcohol. Form a bond between the H and the O of the bonds. Form a bond carbonyl to form a HEMIACETAL. between the alpha-carbon and one H. Form a bond between the O and Break the O-H bond of the other alcohol. Break the C-O bond the other H to between the alpha-carbon and the O of the O-H of the hemiacetal. form an ALCOHOL. Form a bond between the H (from the alcohol) and the O-H (from the hemiacetal) to form H2O. Form a bond between the O (from the alcohol) and the alpha-carbon to form an ACETAL. H O CH2 HO CH2 C CH2 O O + CH3-CH2-OH H H2SO4 CH2 CH2 C H CH2 Is the starting an aldehyde or ketone? Aldehyde Ketone Insert an oxygen atom in the C-H bond of the carbonyl to form a CARBOXYLIC ACID. NO RXN. Reactions Flow Chart Example 5 What are the reaction conditions? H2/ Pt, Pd, or Ni H2SO4 + 2 alcohols “Reduction Conditions” “Acetal Formation” K2Cr2O7 / H2SO4 “Oxidation Conditions” Break the O-H bond of one alcohol. Break one of the C=O Break the H-H bond. bonds. Form a bond between the carbonyl carbon and the O of Break one of the C=O the alcohol. Form a bond between the H and the O of the bonds. Form a bond carbonyl to form a HEMIACETAL. between the alpha-carbon and one H. Form a bond between the O and Break the O-H bond of the other alcohol. Break the C-O bond the other H to between the alpha-carbon and the O of the O-H of the hemiacetal. form an ALCOHOL. Form a bond between the H (from the alcohol) and the O-H (from the hemiacetal) to form H2O. Form a bond between the O (from the alcohol) and the alpha-carbon to form an ACETAL. H O CH2 HO CH2 C CH2 O O + CH3-CH2-OH H H2SO4 CH2 CH2 C H CH2 Is the starting an aldehyde or ketone? Aldehyde Ketone Insert an oxygen atom in the C-H bond of the carbonyl to form a CARBOXYLIC ACID. NO RXN. H H O O CH2 CH2 O C CH2 H CH2 O O CH3 CH2 CH2 CH2 C H CH2 CH3 Reactions Flow Chart Example 5 What are the reaction conditions? H2/ Pt, Pd, or Ni H2SO4 + 2 alcohols “Reduction Conditions” “Acetal Formation” K2Cr2O7 / H2SO4 “Oxidation Conditions” Break the O-H bond of one alcohol. Break one of the C=O Break the H-H bond. bonds. Form a bond between the carbonyl carbon and the O of Break one of the C=O the alcohol. Form a bond between the H and the O of the bonds. Form a bond carbonyl to form a HEMIACETAL. between the alpha-carbon and one H. Form a bond between the O and Break the O-H bond of the other alcohol. Break the C-O bond the other H to between the alpha-carbon and the O of the O-H of the hemiacetal. form an ALCOHOL. Form a bond between the H (from the alcohol) and the O-H (from the hemiacetal) to form H2O. Form a bond between the O (from the alcohol) and the alpha-carbon to form an ACETAL. Is the starting an aldehyde or ketone? Aldehyde Ketone Insert an oxygen atom in the C-H bond of the carbonyl to form a CARBOXYLIC ACID. NO RXN. CH2 H O CH2 HO CH2 C CH2 + CH3-CH2-OH H O O H2SO4 CH2 CH2 C CH2 H CH2 O O CH2 C H CH2 CH3
