reactions of ketones and aldehydes susan f. hornbuckle associate professor of chemistry clayton...
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![Page 1: Reactions of Ketones and Aldehydes Susan F. Hornbuckle Associate Professor of Chemistry Clayton State University](https://reader035.vdocuments.mx/reader035/viewer/2022062511/551444f25503462d4e8b4b25/html5/thumbnails/1.jpg)
Reactions of Reactions of Ketones and AldehydesKetones and Aldehydes
Susan F. Hornbuckle
Associate Professor of Chemistry
Clayton State University
![Page 2: Reactions of Ketones and Aldehydes Susan F. Hornbuckle Associate Professor of Chemistry Clayton State University](https://reader035.vdocuments.mx/reader035/viewer/2022062511/551444f25503462d4e8b4b25/html5/thumbnails/2.jpg)
Reactions Flow ChartWhat are the
reaction conditions?
H2/ Pt, Pd, or Ni
“Reduction Conditions”
H2SO4 + 2 alcohols
“Acetal Formation”
K2Cr2O7 / H2SO4
“Oxidation Conditions”
Is the starting an aldehyde or ketone?
Aldehyde
Insert an oxygen atom in the C-H
bond of the carbonylto form a
CARBOXYLIC ACID.
Ketone
NO RXN.
Break the H-H bond.Break one of the C=O bonds. Form a bond
between the alpha-carbonand one H. Form a bond
between the O and the other H to
form an ALCOHOL.
Break the O-H bond of one alcohol. Break one of the C=O bonds. Form a bond between the carbonyl carbon and the O of
the alcohol. Form a bond between the H and the O of the carbonyl to form a HEMIACETAL.
Break the O-H bond of the other alcohol. Break the C-O bond between the alpha-carbon and the O of the O-H of the hemiacetal.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.
![Page 3: Reactions of Ketones and Aldehydes Susan F. Hornbuckle Associate Professor of Chemistry Clayton State University](https://reader035.vdocuments.mx/reader035/viewer/2022062511/551444f25503462d4e8b4b25/html5/thumbnails/3.jpg)
Reactions Flow ChartWhat are the
reaction conditions?
H2/ Pt, Pd, or Ni
“Reduction Conditions”
H2SO4 + 2 alcohols
“Acetal Formation”
K2Cr2O7 / H2SO4
“Oxidation Conditions”
Is the starting an aldehyde or ketone?
Aldehyde
Insert an oxygen atom in the C-H
bond of the carbonylto form a
CARBOXYLIC ACID.
Ketone
NO RXN.
Break the H-H bond.Break one of the C=O bonds. Form a bond
between the alpha-carbonand one H. Form a bond
between the O and the other H to
form an ALCOHOL.
Break the O-H bond of one alcohol. Break one of the C=O bonds. Form a bond between the carbonyl carbon and the O of
the alcohol. Form a bond between the H and the O of the carbonyl to form a HEMIACETAL.
Break the O-H bond of the other alcohol. Break the C-O bond between the alpha-carbon and the O of the O-H of the hemiacetal.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.
CH3
CH2
CH2
C
O
H
K2Cr2O7
H2SO4
Example 1
![Page 4: Reactions of Ketones and Aldehydes Susan F. Hornbuckle Associate Professor of Chemistry Clayton State University](https://reader035.vdocuments.mx/reader035/viewer/2022062511/551444f25503462d4e8b4b25/html5/thumbnails/4.jpg)
Reactions Flow ChartWhat are the
reaction conditions?
H2/ Pt, Pd, or Ni
“Reduction Conditions”
H2SO4 + 2 alcohols
“Acetal Formation”
K2Cr2O7 / H2SO4
“Oxidation Conditions”
Is the starting an aldehyde or ketone?
Aldehyde
Insert an oxygen atom in the C-H
bond of the carbonylto form a
CARBOXYLIC ACID.
Ketone
NO RXN.
Break the H-H bond.Break one of the C=O bonds. Form a bond
between the alpha-carbonand one H. Form a bond
between the O and the other H to
form an ALCOHOL.
Break the O-H bond of one alcohol. Break one of the C=O bonds. Form a bond between the carbonyl carbon and the O of
the alcohol. Form a bond between the H and the O of the carbonyl to form a HEMIACETAL.
Break the O-H bond of the other alcohol. Break the C-O bond between the alpha-carbon and the O of the O-H of the hemiacetal.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.
CH3
CH2
CH2
C
O
H
K2Cr2O7
H2SO4
Example 1
![Page 5: Reactions of Ketones and Aldehydes Susan F. Hornbuckle Associate Professor of Chemistry Clayton State University](https://reader035.vdocuments.mx/reader035/viewer/2022062511/551444f25503462d4e8b4b25/html5/thumbnails/5.jpg)
Reactions Flow ChartWhat are the
reaction conditions?
H2/ Pt, Pd, or Ni
“Reduction Conditions”
H2SO4 + 2 alcohols
“Acetal Formation”
K2Cr2O7 / H2SO4
“Oxidation Conditions”
Is the starting an aldehyde or ketone?
Aldehyde
Insert an oxygen atom in the C-H
bond of the carbonylto form a
CARBOXYLIC ACID.
Ketone
NO RXN.
Break the H-H bond.Break one of the C=O bonds. Form a bond
between the alpha-carbonand one H. Form a bond
between the O and the other H to
form an ALCOHOL.
Break the O-H bond of one alcohol. Break one of the C=O bonds. Form a bond between the carbonyl carbon and the O of
the alcohol. Form a bond between the H and the O of the carbonyl to form a HEMIACETAL.
Break the O-H bond of the other alcohol. Break the C-O bond between the alpha-carbon and the O of the O-H of the hemiacetal.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.
CH3
CH2
CH2
C
O
H
K2Cr2O7
H2SO4
Example 1
![Page 6: Reactions of Ketones and Aldehydes Susan F. Hornbuckle Associate Professor of Chemistry Clayton State University](https://reader035.vdocuments.mx/reader035/viewer/2022062511/551444f25503462d4e8b4b25/html5/thumbnails/6.jpg)
Reactions Flow ChartWhat are the
reaction conditions?
H2/ Pt, Pd, or Ni
“Reduction Conditions”
H2SO4 + 2 alcohols
“Acetal Formation”
K2Cr2O7 / H2SO4
“Oxidation Conditions”
Is the starting an aldehyde or ketone?
Aldehyde
Insert an oxygen atom in the C-H
bond of the carbonylto form a
CARBOXYLIC ACID.
Ketone
NO RXN.
Break the H-H bond.Break one of the C=O bonds. Form a bond
between the alpha-carbonand one H. Form a bond
between the O and the other H to
form an ALCOHOL.
Break the O-H bond of one alcohol. Break one of the C=O bonds. Form a bond between the carbonyl carbon and the O of
the alcohol. Form a bond between the H and the O of the carbonyl to form a HEMIACETAL.
Break the O-H bond of the other alcohol. Break the C-O bond between the alpha-carbon and the O of the O-H of the hemiacetal.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.
CH3
CH2
CH2
C
O
H
K2Cr2O7
H2SO4
O
CH3
CH2
CH2
C
O
OH
Example 1
![Page 7: Reactions of Ketones and Aldehydes Susan F. Hornbuckle Associate Professor of Chemistry Clayton State University](https://reader035.vdocuments.mx/reader035/viewer/2022062511/551444f25503462d4e8b4b25/html5/thumbnails/7.jpg)
Reactions Flow ChartWhat are the
reaction conditions?
H2/ Pt, Pd, or Ni
“Reduction Conditions”
H2SO4 + 2 alcohols
“Acetal Formation”
K2Cr2O7 / H2SO4
“Oxidation Conditions”
Is the starting an aldehyde or ketone?
Aldehyde
Insert an oxygen atom in the C-H
bond of the carbonylto form a
CARBOXYLIC ACID.
Ketone
NO RXN.
Break the H-H bond.Break one of the C=O bonds. Form a bond
between the alpha-carbonand one H. Form a bond
between the O and the other H to
form an ALCOHOL.
Break the O-H bond of one alcohol. Break one of the C=O bonds. Form a bond between the carbonyl carbon and the O of
the alcohol. Form a bond between the H and the O of the carbonyl to form a HEMIACETAL.
Break the O-H bond of the other alcohol. Break the C-O bond between the alpha-carbon and the O of the O-H of the hemiacetal.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.
Example 2
CH3
CH2
CH2
C
O
CH3
+ H2Pd
![Page 8: Reactions of Ketones and Aldehydes Susan F. Hornbuckle Associate Professor of Chemistry Clayton State University](https://reader035.vdocuments.mx/reader035/viewer/2022062511/551444f25503462d4e8b4b25/html5/thumbnails/8.jpg)
Reactions Flow ChartWhat are the
reaction conditions?
H2/ Pt, Pd, or Ni
“Reduction Conditions”
H2SO4 + 2 alcohols
“Acetal Formation”
K2Cr2O7 / H2SO4
“Oxidation Conditions”
Is the starting an aldehyde or ketone?
Aldehyde
Insert an oxygen atom in the C-H
bond of the carbonylto form a
CARBOXYLIC ACID.
Ketone
NO RXN.
Break the H-H bond.Break one of the C=O bonds. Form a bond
between the alpha-carbonand one H. Form a bond
between the O and the other H to
form an ALCOHOL.
Break the O-H bond of one alcohol. Break one of the C=O bonds. Form a bond between the carbonyl carbon and the O of
the alcohol. Form a bond between the H and the O of the carbonyl to form a HEMIACETAL.
Break the O-H bond of the other alcohol. Break the C-O bond between the alpha-carbon and the O of the O-H of the hemiacetal.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.
Example 2
CH3
CH2
CH2
C
O
CH3
+ H2Pd
![Page 9: Reactions of Ketones and Aldehydes Susan F. Hornbuckle Associate Professor of Chemistry Clayton State University](https://reader035.vdocuments.mx/reader035/viewer/2022062511/551444f25503462d4e8b4b25/html5/thumbnails/9.jpg)
Reactions Flow ChartWhat are the
reaction conditions?
H2/ Pt, Pd, or Ni
“Reduction Conditions”
H2SO4 + 2 alcohols
“Acetal Formation”
K2Cr2O7 / H2SO4
“Oxidation Conditions”
Is the starting an aldehyde or ketone?
Aldehyde
Insert an oxygen atom in the C-H
bond of the carbonylto form a
CARBOXYLIC ACID.
Ketone
NO RXN.
Break the H-H bond.Break one of the C=O bonds. Form a bond
between the alpha-carbonand one H. Form a bond
between the O and the other H to
form an ALCOHOL.
Break the O-H bond of one alcohol. Break one of the C=O bonds. Form a bond between the carbonyl carbon and the O of
the alcohol. Form a bond between the H and the O of the carbonyl to form a HEMIACETAL.
Break the O-H bond of the other alcohol. Break the C-O bond between the alpha-carbon and the O of the O-H of the hemiacetal.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.
Example 2
CH3
CH2
CH2
C
O
CH3
+ H2Pd
![Page 10: Reactions of Ketones and Aldehydes Susan F. Hornbuckle Associate Professor of Chemistry Clayton State University](https://reader035.vdocuments.mx/reader035/viewer/2022062511/551444f25503462d4e8b4b25/html5/thumbnails/10.jpg)
CH3
CH2
CH2
C
O
CH3
H
H
![Page 11: Reactions of Ketones and Aldehydes Susan F. Hornbuckle Associate Professor of Chemistry Clayton State University](https://reader035.vdocuments.mx/reader035/viewer/2022062511/551444f25503462d4e8b4b25/html5/thumbnails/11.jpg)
Reactions Flow ChartWhat are the
reaction conditions?
H2/ Pt, Pd, or Ni
“Reduction Conditions”
H2SO4 + 2 alcohols
“Acetal Formation”
K2Cr2O7 / H2SO4
“Oxidation Conditions”
Is the starting an aldehyde or ketone?
Aldehyde
Insert an oxygen atom in the C-H
bond of the carbonylto form a
CARBOXYLIC ACID.
Ketone
NO RXN.
Break the H-H bond.Break one of the C=O bonds. Form a bond
between the alpha-carbonand one H. Form a bond
between the O and the other H to
form an ALCOHOL.
Break the O-H bond of one alcohol. Break one of the C=O bonds. Form a bond between the carbonyl carbon and the O of
the alcohol. Form a bond between the H and the O of the carbonyl to form a HEMIACETAL.
Break the O-H bond of the other alcohol. Break the C-O bond between the alpha-carbon and the O of the O-H of the hemiacetal.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.
Example 2
CH3
CH2
CH2
C
O
CH3
+ H2Pd
CH3
CH2
CH2
C
O
CH3
H
H
![Page 12: Reactions of Ketones and Aldehydes Susan F. Hornbuckle Associate Professor of Chemistry Clayton State University](https://reader035.vdocuments.mx/reader035/viewer/2022062511/551444f25503462d4e8b4b25/html5/thumbnails/12.jpg)
Reactions Flow ChartWhat are the
reaction conditions?
H2/ Pt, Pd, or Ni
“Reduction Conditions”
H2SO4 + 2 alcohols
“Acetal Formation”
K2Cr2O7 / H2SO4
“Oxidation Conditions”
Is the starting an aldehyde or ketone?
Aldehyde
Insert an oxygen atom in the C-H
bond of the carbonylto form a
CARBOXYLIC ACID.
Ketone
NO RXN.
Break the H-H bond.Break one of the C=O bonds. Form a bond
between the alpha-carbonand one H. Form a bond
between the O and the other H to
form an ALCOHOL.
Break the O-H bond of one alcohol. Break one of the C=O bonds. Form a bond between the carbonyl carbon and the O of
the alcohol. Form a bond between the H and the O of the carbonyl to form a HEMIACETAL.
Break the O-H bond of the other alcohol. Break the C-O bond between the alpha-carbon and the O of the O-H of the hemiacetal.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.
Example 3
CH3
CH2
C
O
H
H2SO4+ 2 CH3-OH
![Page 13: Reactions of Ketones and Aldehydes Susan F. Hornbuckle Associate Professor of Chemistry Clayton State University](https://reader035.vdocuments.mx/reader035/viewer/2022062511/551444f25503462d4e8b4b25/html5/thumbnails/13.jpg)
Reactions Flow ChartWhat are the
reaction conditions?
H2/ Pt, Pd, or Ni
“Reduction Conditions”
H2SO4 + 2 alcohols
“Acetal Formation”
K2Cr2O7 / H2SO4
“Oxidation Conditions”
Is the starting an aldehyde or ketone?
Aldehyde
Insert an oxygen atom in the C-H
bond of the carbonylto form a
CARBOXYLIC ACID.
Ketone
NO RXN.
Break the H-H bond.Break one of the C=O bonds. Form a bond
between the alpha-carbonand one H. Form a bond
between the O and the other H to
form an ALCOHOL.
Break the O-H bond of one alcohol. Break one of the C=O bonds. Form a bond between the carbonyl carbon and the O of
the alcohol. Form a bond between the H and the O of the carbonyl to form a HEMIACETAL.
Break the O-H bond of the other alcohol. Break the C-O bond between the alpha-carbon and the O of the O-H of the hemiacetal.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.
Example 3
CH3
CH2
C
O
H
H2SO4+ 2 CH3-OH
![Page 14: Reactions of Ketones and Aldehydes Susan F. Hornbuckle Associate Professor of Chemistry Clayton State University](https://reader035.vdocuments.mx/reader035/viewer/2022062511/551444f25503462d4e8b4b25/html5/thumbnails/14.jpg)
Reactions Flow ChartWhat are the
reaction conditions?
H2/ Pt, Pd, or Ni
“Reduction Conditions”
H2SO4 + 2 alcohols
“Acetal Formation”
K2Cr2O7 / H2SO4
“Oxidation Conditions”
Is the starting an aldehyde or ketone?
Aldehyde
Insert an oxygen atom in the C-H
bond of the carbonylto form a
CARBOXYLIC ACID.
Ketone
NO RXN.
Break the H-H bond.Break one of the C=O bonds. Form a bond
between the alpha-carbonand one H. Form a bond
between the O and the other H to
form an ALCOHOL.
Break the O-H bond of one alcohol. Break one of the C=O bonds. Form a bond between the carbonyl carbon and the O of
the alcohol. Form a bond between the H and the O of the carbonyl to form a HEMIACETAL.
Break the O-H bond of the other alcohol. Break the C-O bond between the alpha-carbon and the O of the O-H of the hemiacetal.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.
Example 3
CH3
CH2
C
O
H
H2SO4+ 2 CH3-OH
![Page 15: Reactions of Ketones and Aldehydes Susan F. Hornbuckle Associate Professor of Chemistry Clayton State University](https://reader035.vdocuments.mx/reader035/viewer/2022062511/551444f25503462d4e8b4b25/html5/thumbnails/15.jpg)
CH3
CH2
C
O
H
H
O CH3 CH3
CH2
C
O
H
OCH3
H
![Page 16: Reactions of Ketones and Aldehydes Susan F. Hornbuckle Associate Professor of Chemistry Clayton State University](https://reader035.vdocuments.mx/reader035/viewer/2022062511/551444f25503462d4e8b4b25/html5/thumbnails/16.jpg)
Reactions Flow ChartWhat are the
reaction conditions?
H2/ Pt, Pd, or Ni
“Reduction Conditions”
H2SO4 + 2 alcohols
“Acetal Formation”
K2Cr2O7 / H2SO4
“Oxidation Conditions”
Is the starting an aldehyde or ketone?
Aldehyde
Insert an oxygen atom in the C-H
bond of the carbonylto form a
CARBOXYLIC ACID.
Ketone
NO RXN.
Break the H-H bond.Break one of the C=O bonds. Form a bond
between the alpha-carbonand one H. Form a bond
between the O and the other H to
form an ALCOHOL.
Break the O-H bond of one alcohol. Break one of the C=O bonds. Form a bond between the carbonyl carbon and the O of
the alcohol. Form a bond between the H and the O of the carbonyl to form a HEMIACETAL.
Break the O-H bond of the other alcohol. Break the C-O bond between the alpha-carbon and the O of the O-H of the hemiacetal.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.
Example 3
CH3
CH2
C
O
H
H2SO4+ 2 CH3-OHCH3
CH2
C
O
H
O
CH3
H
![Page 17: Reactions of Ketones and Aldehydes Susan F. Hornbuckle Associate Professor of Chemistry Clayton State University](https://reader035.vdocuments.mx/reader035/viewer/2022062511/551444f25503462d4e8b4b25/html5/thumbnails/17.jpg)
Reactions Flow ChartWhat are the
reaction conditions?
H2/ Pt, Pd, or Ni
“Reduction Conditions”
H2SO4 + 2 alcohols
“Acetal Formation”
K2Cr2O7 / H2SO4
“Oxidation Conditions”
Is the starting an aldehyde or ketone?
Aldehyde
Insert an oxygen atom in the C-H
bond of the carbonylto form a
CARBOXYLIC ACID.
Ketone
NO RXN.
Break the H-H bond.Break one of the C=O bonds. Form a bond
between the alpha-carbonand one H. Form a bond
between the O and the other H to
form an ALCOHOL.
Break the O-H bond of one alcohol. Break one of the C=O bonds. Form a bond between the carbonyl carbon and the O of
the alcohol. Form a bond between the H and the O of the carbonyl to form a HEMIACETAL.
Break the O-H bond of the other alcohol. Break the C-O bond between the alpha-carbon and the O of the O-H of the hemiacetal.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.
Example 3
CH3
CH2
C
O
H
H2SO4+ 2 CH3-OHCH3
CH2
C
O
H
O
CH3
H
![Page 18: Reactions of Ketones and Aldehydes Susan F. Hornbuckle Associate Professor of Chemistry Clayton State University](https://reader035.vdocuments.mx/reader035/viewer/2022062511/551444f25503462d4e8b4b25/html5/thumbnails/18.jpg)
CH3
CH2
C
O
H
O
CH3
H H
OCH3 CH3
CH2C
O
H
O
CH3
CH3
![Page 19: Reactions of Ketones and Aldehydes Susan F. Hornbuckle Associate Professor of Chemistry Clayton State University](https://reader035.vdocuments.mx/reader035/viewer/2022062511/551444f25503462d4e8b4b25/html5/thumbnails/19.jpg)
Reactions Flow ChartWhat are the
reaction conditions?
H2/ Pt, Pd, or Ni
“Reduction Conditions”
H2SO4 + 2 alcohols
“Acetal Formation”
K2Cr2O7 / H2SO4
“Oxidation Conditions”
Is the starting an aldehyde or ketone?
Aldehyde
Insert an oxygen atom in the C-H
bond of the carbonylto form a
CARBOXYLIC ACID.
Ketone
NO RXN.
Break the H-H bond.Break one of the C=O bonds. Form a bond
between the alpha-carbonand one H. Form a bond
between the O and the other H to
form an ALCOHOL.
Break the O-H bond of one alcohol. Break one of the C=O bonds. Form a bond between the carbonyl carbon and the O of
the alcohol. Form a bond between the H and the O of the carbonyl to form a HEMIACETAL.
Break the O-H bond of the other alcohol. Break the C-O bond between the alpha-carbon and the O of the O-H of the hemiacetal.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.
Example 3
CH3
CH2
C
O
H
H2SO4+ 2 CH3-OHCH3
CH2
C
O
H
O
CH3
H
CH3
CH2C
O
H
O
CH3
CH3
![Page 20: Reactions of Ketones and Aldehydes Susan F. Hornbuckle Associate Professor of Chemistry Clayton State University](https://reader035.vdocuments.mx/reader035/viewer/2022062511/551444f25503462d4e8b4b25/html5/thumbnails/20.jpg)
Reactions Flow ChartWhat are the
reaction conditions?
H2/ Pt, Pd, or Ni
“Reduction Conditions”
H2SO4 + 2 alcohols
“Acetal Formation”
K2Cr2O7 / H2SO4
“Oxidation Conditions”
Is the starting an aldehyde or ketone?
Aldehyde
Insert an oxygen atom in the C-H
bond of the carbonylto form a
CARBOXYLIC ACID.
Ketone
NO RXN.
Break the H-H bond.Break one of the C=O bonds. Form a bond
between the alpha-carbonand one H. Form a bond
between the O and the other H to
form an ALCOHOL.
Break the O-H bond of one alcohol. Break one of the C=O bonds. Form a bond between the carbonyl carbon and the O of
the alcohol. Form a bond between the H and the O of the carbonyl to form a HEMIACETAL.
Break the O-H bond of the other alcohol. Break the C-O bond between the alpha-carbon and the O of the O-H of the hemiacetal.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.
CH3
CH2
CH2
C
O
CH3
K2Cr2O7
H2SO4
Example 4
![Page 21: Reactions of Ketones and Aldehydes Susan F. Hornbuckle Associate Professor of Chemistry Clayton State University](https://reader035.vdocuments.mx/reader035/viewer/2022062511/551444f25503462d4e8b4b25/html5/thumbnails/21.jpg)
Reactions Flow ChartWhat are the
reaction conditions?
H2/ Pt, Pd, or Ni
“Reduction Conditions”
H2SO4 + 2 alcohols
“Acetal Formation”
K2Cr2O7 / H2SO4
“Oxidation Conditions”
Is the starting an aldehyde or ketone?
Aldehyde
Insert an oxygen atom in the C-H
bond of the carbonylto form a
CARBOXYLIC ACID.
Ketone
NO RXN.
Break the H-H bond.Break one of the C=O bonds. Form a bond
between the alpha-carbonand one H. Form a bond
between the O and the other H to
form an ALCOHOL.
Break the O-H bond of one alcohol. Break one of the C=O bonds. Form a bond between the carbonyl carbon and the O of
the alcohol. Form a bond between the H and the O of the carbonyl to form a HEMIACETAL.
Break the O-H bond of the other alcohol. Break the C-O bond between the alpha-carbon and the O of the O-H of the hemiacetal.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.
CH3
CH2
CH2
C
O
CH3
K2Cr2O7
H2SO4
Example 4
![Page 22: Reactions of Ketones and Aldehydes Susan F. Hornbuckle Associate Professor of Chemistry Clayton State University](https://reader035.vdocuments.mx/reader035/viewer/2022062511/551444f25503462d4e8b4b25/html5/thumbnails/22.jpg)
Reactions Flow ChartWhat are the
reaction conditions?
H2/ Pt, Pd, or Ni
“Reduction Conditions”
H2SO4 + 2 alcohols
“Acetal Formation”
K2Cr2O7 / H2SO4
“Oxidation Conditions”
Is the starting an aldehyde or ketone?
Aldehyde
Insert an oxygen atom in the C-H
bond of the carbonylto form a
CARBOXYLIC ACID.
Ketone
NO RXN.
Break the H-H bond.Break one of the C=O bonds. Form a bond
between the alpha-carbonand one H. Form a bond
between the O and the other H to
form an ALCOHOL.
Break the O-H bond of one alcohol. Break one of the C=O bonds. Form a bond between the carbonyl carbon and the O of
the alcohol. Form a bond between the H and the O of the carbonyl to form a HEMIACETAL.
Break the O-H bond of the other alcohol. Break the C-O bond between the alpha-carbon and the O of the O-H of the hemiacetal.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.
CH3
CH2
CH2
C
O
CH3
K2Cr2O7
H2SO4
Example 4
![Page 23: Reactions of Ketones and Aldehydes Susan F. Hornbuckle Associate Professor of Chemistry Clayton State University](https://reader035.vdocuments.mx/reader035/viewer/2022062511/551444f25503462d4e8b4b25/html5/thumbnails/23.jpg)
Reactions Flow ChartWhat are the
reaction conditions?
H2/ Pt, Pd, or Ni
“Reduction Conditions”
H2SO4 + 2 alcohols
“Acetal Formation”
K2Cr2O7 / H2SO4
“Oxidation Conditions”
Is the starting an aldehyde or ketone?
Aldehyde
Insert an oxygen atom in the C-H
bond of the carbonylto form a
CARBOXYLIC ACID.
Ketone
NO RXN.
Break the H-H bond.Break one of the C=O bonds. Form a bond
between the alpha-carbonand one H. Form a bond
between the O and the other H to
form an ALCOHOL.
Break the O-H bond of one alcohol. Break one of the C=O bonds. Form a bond between the carbonyl carbon and the O of
the alcohol. Form a bond between the H and the O of the carbonyl to form a HEMIACETAL.
Break the O-H bond of the other alcohol. Break the C-O bond between the alpha-carbon and the O of the O-H of the hemiacetal.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.
Example 4
CH3
CH2
CH2
C
O
CH3
K2Cr2O7
H2SO4
No Reaction
![Page 24: Reactions of Ketones and Aldehydes Susan F. Hornbuckle Associate Professor of Chemistry Clayton State University](https://reader035.vdocuments.mx/reader035/viewer/2022062511/551444f25503462d4e8b4b25/html5/thumbnails/24.jpg)
Reactions Flow ChartWhat are the
reaction conditions?
H2/ Pt, Pd, or Ni
“Reduction Conditions”
H2SO4 + 2 alcohols
“Acetal Formation”
K2Cr2O7 / H2SO4
“Oxidation Conditions”
Is the starting an aldehyde or ketone?
Aldehyde
Insert an oxygen atom in the C-H
bond of the carbonylto form a
CARBOXYLIC ACID.
Ketone
NO RXN.
Break the H-H bond.Break one of the C=O bonds. Form a bond
between the alpha-carbonand one H. Form a bond
between the O and the other H to
form an ALCOHOL.
Break the O-H bond of one alcohol. Break one of the C=O bonds. Form a bond between the carbonyl carbon and the O of
the alcohol. Form a bond between the H and the O of the carbonyl to form a HEMIACETAL.
Break the O-H bond of the other alcohol. Break the C-O bond between the alpha-carbon and the O of the O-H of the hemiacetal.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.
Example 5
CH2
CH2
C
O
H
H2SO4+ CH3-CH2-OH
CH2
HO
![Page 25: Reactions of Ketones and Aldehydes Susan F. Hornbuckle Associate Professor of Chemistry Clayton State University](https://reader035.vdocuments.mx/reader035/viewer/2022062511/551444f25503462d4e8b4b25/html5/thumbnails/25.jpg)
Reactions Flow ChartWhat are the
reaction conditions?
H2/ Pt, Pd, or Ni
“Reduction Conditions”
H2SO4 + 2 alcohols
“Acetal Formation”
K2Cr2O7 / H2SO4
“Oxidation Conditions”
Is the starting an aldehyde or ketone?
Aldehyde
Insert an oxygen atom in the C-H
bond of the carbonylto form a
CARBOXYLIC ACID.
Ketone
NO RXN.
Break the H-H bond.Break one of the C=O bonds. Form a bond
between the alpha-carbonand one H. Form a bond
between the O and the other H to
form an ALCOHOL.
Break the O-H bond of one alcohol. Break one of the C=O bonds. Form a bond between the carbonyl carbon and the O of
the alcohol. Form a bond between the H and the O of the carbonyl to form a HEMIACETAL.
Break the O-H bond of the other alcohol. Break the C-O bond between the alpha-carbon and the O of the O-H of the hemiacetal.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.
Example 5
CH2
CH2
C
O
H
H2SO4+ CH3-CH2-OH
CH2
HO
![Page 26: Reactions of Ketones and Aldehydes Susan F. Hornbuckle Associate Professor of Chemistry Clayton State University](https://reader035.vdocuments.mx/reader035/viewer/2022062511/551444f25503462d4e8b4b25/html5/thumbnails/26.jpg)
Reactions Flow ChartWhat are the
reaction conditions?
H2/ Pt, Pd, or Ni
“Reduction Conditions”
H2SO4 + 2 alcohols
“Acetal Formation”
K2Cr2O7 / H2SO4
“Oxidation Conditions”
Is the starting an aldehyde or ketone?
Aldehyde
Insert an oxygen atom in the C-H
bond of the carbonylto form a
CARBOXYLIC ACID.
Ketone
NO RXN.
Break the H-H bond.Break one of the C=O bonds. Form a bond
between the alpha-carbonand one H. Form a bond
between the O and the other H to
form an ALCOHOL.
Break the O-H bond of one alcohol. Break one of the C=O bonds. Form a bond between the carbonyl carbon and the O of
the alcohol. Form a bond between the H and the O of the carbonyl to form a HEMIACETAL.
Break the O-H bond of the other alcohol. Break the C-O bond between the alpha-carbon and the O of the O-H of the hemiacetal.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.
Example 5
CH2
CH2
C
O
H
H2SO4+ CH3-CH2-OH
CH2
HO
![Page 27: Reactions of Ketones and Aldehydes Susan F. Hornbuckle Associate Professor of Chemistry Clayton State University](https://reader035.vdocuments.mx/reader035/viewer/2022062511/551444f25503462d4e8b4b25/html5/thumbnails/27.jpg)
CH2
CH2
C
O
H
CH2
O
H
CH2
CH2
C
O
HCH2
HO
CH2
CH2
C
O
H
CH2
O
H
O
CH2
CH2CH2
C
O
H
H
![Page 28: Reactions of Ketones and Aldehydes Susan F. Hornbuckle Associate Professor of Chemistry Clayton State University](https://reader035.vdocuments.mx/reader035/viewer/2022062511/551444f25503462d4e8b4b25/html5/thumbnails/28.jpg)
Reactions Flow ChartWhat are the
reaction conditions?
H2/ Pt, Pd, or Ni
“Reduction Conditions”
H2SO4 + 2 alcohols
“Acetal Formation”
K2Cr2O7 / H2SO4
“Oxidation Conditions”
Is the starting an aldehyde or ketone?
Aldehyde
Insert an oxygen atom in the C-H
bond of the carbonylto form a
CARBOXYLIC ACID.
Ketone
NO RXN.
Break the H-H bond.Break one of the C=O bonds. Form a bond
between the alpha-carbonand one H. Form a bond
between the O and the other H to
form an ALCOHOL.
Break the O-H bond of one alcohol. Break one of the C=O bonds. Form a bond between the carbonyl carbon and the O of
the alcohol. Form a bond between the H and the O of the carbonyl to form a HEMIACETAL.
Break the O-H bond of the other alcohol. Break the C-O bond between the alpha-carbon and the O of the O-H of the hemiacetal.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.
Example 5
CH2
CH2
C
O
H
H2SO4+ CH3-CH2-OH
CH2
HO
O
CH2
CH2CH2
C
O
H
H
![Page 29: Reactions of Ketones and Aldehydes Susan F. Hornbuckle Associate Professor of Chemistry Clayton State University](https://reader035.vdocuments.mx/reader035/viewer/2022062511/551444f25503462d4e8b4b25/html5/thumbnails/29.jpg)
Reactions Flow ChartWhat are the
reaction conditions?
H2/ Pt, Pd, or Ni
“Reduction Conditions”
H2SO4 + 2 alcohols
“Acetal Formation”
K2Cr2O7 / H2SO4
“Oxidation Conditions”
Is the starting an aldehyde or ketone?
Aldehyde
Insert an oxygen atom in the C-H
bond of the carbonylto form a
CARBOXYLIC ACID.
Ketone
NO RXN.
Break the H-H bond.Break one of the C=O bonds. Form a bond
between the alpha-carbonand one H. Form a bond
between the O and the other H to
form an ALCOHOL.
Break the O-H bond of one alcohol. Break one of the C=O bonds. Form a bond between the carbonyl carbon and the O of
the alcohol. Form a bond between the H and the O of the carbonyl to form a HEMIACETAL.
Break the O-H bond of the other alcohol. Break the C-O bond between the alpha-carbon and the O of the O-H of the hemiacetal.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.
Example 5
CH2
CH2
C
O
H
H2SO4+ CH3-CH2-OH
CH2
HO
O
CH2
CH2CH2
C
O
H
H
![Page 30: Reactions of Ketones and Aldehydes Susan F. Hornbuckle Associate Professor of Chemistry Clayton State University](https://reader035.vdocuments.mx/reader035/viewer/2022062511/551444f25503462d4e8b4b25/html5/thumbnails/30.jpg)
O
CH2
CH2CH2
C
O
H
H
O
H
CH2
CH3
O
CH2
CH2CH2
C
O
H
CH2CH3
![Page 31: Reactions of Ketones and Aldehydes Susan F. Hornbuckle Associate Professor of Chemistry Clayton State University](https://reader035.vdocuments.mx/reader035/viewer/2022062511/551444f25503462d4e8b4b25/html5/thumbnails/31.jpg)
Reactions Flow ChartWhat are the
reaction conditions?
H2/ Pt, Pd, or Ni
“Reduction Conditions”
H2SO4 + 2 alcohols
“Acetal Formation”
K2Cr2O7 / H2SO4
“Oxidation Conditions”
Is the starting an aldehyde or ketone?
Aldehyde
Insert an oxygen atom in the C-H
bond of the carbonylto form a
CARBOXYLIC ACID.
Ketone
NO RXN.
Break the H-H bond.Break one of the C=O bonds. Form a bond
between the alpha-carbonand one H. Form a bond
between the O and the other H to
form an ALCOHOL.
Break the O-H bond of one alcohol. Break one of the C=O bonds. Form a bond between the carbonyl carbon and the O of
the alcohol. Form a bond between the H and the O of the carbonyl to form a HEMIACETAL.
Break the O-H bond of the other alcohol. Break the C-O bond between the alpha-carbon and the O of the O-H of the hemiacetal.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.
Example 5
CH2
CH2
C
O
H
H2SO4+ CH3-CH2-OHCH2
HO
O
CH2
CH2CH2
C
O
H
H
O
CH2
CH2CH2
C
O
H
CH2CH3