Reactions of Ketones and Aldehydes Susan F. Hornbuckle Associate Professor of Chemistry Clayton...

Reactions of Reactions of Ketones and AldehydesKetones and Aldehydes

Susan F. Hornbuckle

Associate Professor of Chemistry

Clayton State University

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.

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

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

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

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

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

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

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

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

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

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

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

CH3

CH2

C

O

H

H

O CH3 CH3

CH2

C

O

H

OCH3

H

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

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

CH2

C

O

H

O

CH3

H H

OCH3 CH3

CH2C

O

H

O

CH3

CH3

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

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

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

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

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

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

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

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

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

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

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

O

CH2

CH2CH2

C

O

H

H

O

H

CH2

CH3

O

CH2

CH2CH2

C

O

H

CH2CH3

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