Transcript Reactions of Aldehydes and Ketones Flow Chart and Examples

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