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