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Aldehydes
Carbonyl Group
- is a carbon atom double-
bonded to an oxygen atom.
Aldehydes
-is a carbonyl-containing organic
compound in which the carbonyl
carbon atom has at least one hydrogen
atom directly attached to it.
- Linear notations: -CHO and -RCHO
•An aldehyde functional group can be bonded
to only one carbon atom because three of the
four bonds from an aldehyde carbonyl carbon
must go to oxygen and hydrogen.
•Always found at the end
•Cyclic aldehydes are not possible
Nomenclature for Aldehydes
Aldehydes are named using the suffix –al. The
suffix –al denotes an aldehyde.
The IUPAC rules are:
Rule 1: Select as the parent carbon chain the
longest chain that includes the carbon atom of
the carbonyl group
•Rule 2: Name the parent chain by changing the
–e ending of the corresponding alkane name to
–al.
•Rule 3: Number the parent chain by assigning
the number 1 to the carbonyl carbon atom of
the aldehyde group. The number 1, however,
does not become part of the name.
•Rule 4: Determine the identity and
location of any substituents, and append
this information to the front of the parent
chain name.
•Rule 5: When an aldehyde functional
group is attached to a carbon ring, name
the ring and add the suffix –carbaldehyde.
•The common name for aldehydes are one
word.
•The aldehyde common names illustrate a
second method for counting from one to
four in organic chemistry language: form-
, acet- , propion- , butyr- , benz- ,
ISOMERISM FOR ALDEHYDES
Constitutional isomers exist for aldehydes.
Ex:
Aldehyde
Skeletal isomers: CH3 ─ CH2 ─ CH2 ─ C ─ H
═
O
CH3 ─ CH ─ C ─ H
CH3
═
O
═
SELECTED COMMON ALDEHYDES
Formaldehyde
-an irritating gas when in room
temperature and pressure
-bubbling through water produces formalin
-reacts with water, producing methylene
glycol
CH3─OH ───── H─C─H + H2
═
O
Ag Catalyst
600°C ─ 700°C
Formaldehyde is manufactured on a
large scale by oxidation of methanol
Formalin
• Used for preserving biological specimens
• Has pungent odor
• Most widely used preservative chemical in
embalming fluids
• Reacts with protein molecules that leads to
“hardening” of the protein.
H ─ C ─ H + H ─ O ─ H ───── HO ─ CH2 ─ OH
═
O
ACETALDEHYDE
• widespread, naturally occurring, colorless
and flammable liquid with a suffocating smell
• Used for acetic acids, perfumes, dyes and
drugs, as a flavoring agent and as an
intermediate in the metabolism of alcohol
• reasonably anticipated to be a human
carcinogen
• Somewhat more toxic than ethanol
CHEMICAL FORMULA OF ACETALDEHYDE
VANILLIN
• Primary component of vanilla
bean
• used as a flavoring agent in
foods, beverages, and
pharmaceuticals
• First commercial synthesis of
vanillin began with eugenol
STRUCTURAL FORMULA OF VANILLIN
(Methoxybenzaldehyde)
PHYSICAL PROPERTIES OF ALDEHYDE
•Straight-chain saturated aldehydes are liquids,
and the higher aldehydes are solid
•Higher boiling point than alkanes
•Has lower boiling point than alcohols
•Soluble in both organic solvents and water if it has
less than 6 carbon atoms
•Having 6 or more carbon atoms, compounds
are soluble in organic solvents and not in
water
•Low-molecular-mass have pungent,
penetrating, unpleasant odors
•Higher-molecular-mass (above C8) are more
fragrant
Type of
Compound
Compound Structure Molecular
Mass
Boiling
Point
(8°C)
Alkane
Aldehyde
Alcohol
Ethane
Methanal
Methanol
CH3─CH3
H─CHO
CH3─OH
30
30
32
─ 89
─ 21
65
Alkane
Aldehyde
Alcohol
Propane
Ethanal
Ethanol
CH3─CH2─CH3
CH3─CHO
CH3─CH2─OH
44
44
46
─ 42
20
78
Alkane
Aldehyde
Alcohol
Butane
Propanal
1-propanol
CH3─CH2─CH2─CH3
CH3─CH2─CHO
CH3─CH3─CH2─OH
58
58
60
─ 1
49
97
Water Solubility
Number of
Carbon Atoms
Aldehyde Water Solubility
of Aldehyde
1 Methanal Infinite
2 Ethanal Infinite
3 Propanal 16
4 Butanal 7
5 Pentanal 4
6 Hexanal 1
7 Heptanal 0.1
8 octanal insoluble
Oxidation of Aldehydes
Oxidation is an increase in the number of C-O
bonds
•The aldehyde gains an oxygen atom
•Aldehydes must be protected from air
•When prepared from oxidation of primary alcohol, it
is usually removed from the reaction mixture
immediately to prevent it from being further oxidized
to carboxylic acid
•Oxidizing agent potassium dichromate (K2Cr2O7) is
often used for aldehyde oxidation reactions
•Oxidation of an aldehyde involves breaking a
carbon-hydrogen bond
•The Tollens Test or silver mirror test, involves
a solution that contains silver nitrate (AgNO3)
and ammonia (NH3) in water
•When added to an aldehyde, Ag+ ion is
reduced to silver metal, forming a silver
mirror.
R ─ C ─ H + Ag+ ─────── R ─ C ─ OH + Ag
NH3, H2O
heat
═
O
═
Aldehyde Carboxylic
Acid
O
Silver
metal
Reduction of Aldehyde
• Aldehydes are easily reduced by hydrogen gas
(H2) in the presence of a catalyst (Ni, Pt, or Cr)
to form alcohols.
• Produces primary alcohols
Aldehyde ──────── primary alcohol
Reduction
Aldehyde reduction to produce alcohols is the “opposite”
of the oxidation of alcohols to produce aldehydes.
Primary
Alcohol
Aldehyde
Oxidation
Reduction
REACTION OF ALDEHYDES
Aldehyde reacts with alcohols to form hemiacetals and
acetals. Reaction with one molecule of alcohol produces a
hemiacetal, which is then converted to an acetal by reaction
with a second alcohol molecule.
Aldehyde + Alcohol ─────── hemiacetal
Acid
Catalyst
Hemiacetal + Alcohol ─────── acetal
Acid
Catalyst
H. Stephen Stoker. (2011). Aldehydes and Ketones. General,
Organic and Biological Chemistry Sixth Edition. (pp. 469-487).
BROOKS/COLE CENGAGE Learning.
THANK
YOU! 😃

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ALDEHYDES

  • 2. Carbonyl Group - is a carbon atom double- bonded to an oxygen atom.
  • 3. Aldehydes -is a carbonyl-containing organic compound in which the carbonyl carbon atom has at least one hydrogen atom directly attached to it. - Linear notations: -CHO and -RCHO
  • 4. •An aldehyde functional group can be bonded to only one carbon atom because three of the four bonds from an aldehyde carbonyl carbon must go to oxygen and hydrogen. •Always found at the end •Cyclic aldehydes are not possible
  • 5. Nomenclature for Aldehydes Aldehydes are named using the suffix –al. The suffix –al denotes an aldehyde. The IUPAC rules are: Rule 1: Select as the parent carbon chain the longest chain that includes the carbon atom of the carbonyl group
  • 6. •Rule 2: Name the parent chain by changing the –e ending of the corresponding alkane name to –al. •Rule 3: Number the parent chain by assigning the number 1 to the carbonyl carbon atom of the aldehyde group. The number 1, however, does not become part of the name.
  • 7. •Rule 4: Determine the identity and location of any substituents, and append this information to the front of the parent chain name. •Rule 5: When an aldehyde functional group is attached to a carbon ring, name the ring and add the suffix –carbaldehyde.
  • 8. •The common name for aldehydes are one word. •The aldehyde common names illustrate a second method for counting from one to four in organic chemistry language: form- , acet- , propion- , butyr- , benz- ,
  • 9. ISOMERISM FOR ALDEHYDES Constitutional isomers exist for aldehydes. Ex: Aldehyde Skeletal isomers: CH3 ─ CH2 ─ CH2 ─ C ─ H ═ O CH3 ─ CH ─ C ─ H CH3 ═ O ═
  • 10. SELECTED COMMON ALDEHYDES Formaldehyde -an irritating gas when in room temperature and pressure -bubbling through water produces formalin -reacts with water, producing methylene glycol
  • 11. CH3─OH ───── H─C─H + H2 ═ O Ag Catalyst 600°C ─ 700°C Formaldehyde is manufactured on a large scale by oxidation of methanol
  • 12. Formalin • Used for preserving biological specimens • Has pungent odor • Most widely used preservative chemical in embalming fluids • Reacts with protein molecules that leads to “hardening” of the protein. H ─ C ─ H + H ─ O ─ H ───── HO ─ CH2 ─ OH ═ O
  • 13. ACETALDEHYDE • widespread, naturally occurring, colorless and flammable liquid with a suffocating smell • Used for acetic acids, perfumes, dyes and drugs, as a flavoring agent and as an intermediate in the metabolism of alcohol • reasonably anticipated to be a human carcinogen • Somewhat more toxic than ethanol
  • 14. CHEMICAL FORMULA OF ACETALDEHYDE
  • 15. VANILLIN • Primary component of vanilla bean • used as a flavoring agent in foods, beverages, and pharmaceuticals • First commercial synthesis of vanillin began with eugenol
  • 16. STRUCTURAL FORMULA OF VANILLIN (Methoxybenzaldehyde)
  • 17. PHYSICAL PROPERTIES OF ALDEHYDE •Straight-chain saturated aldehydes are liquids, and the higher aldehydes are solid •Higher boiling point than alkanes •Has lower boiling point than alcohols •Soluble in both organic solvents and water if it has less than 6 carbon atoms
  • 18. •Having 6 or more carbon atoms, compounds are soluble in organic solvents and not in water •Low-molecular-mass have pungent, penetrating, unpleasant odors •Higher-molecular-mass (above C8) are more fragrant
  • 19. Type of Compound Compound Structure Molecular Mass Boiling Point (8°C) Alkane Aldehyde Alcohol Ethane Methanal Methanol CH3─CH3 H─CHO CH3─OH 30 30 32 ─ 89 ─ 21 65 Alkane Aldehyde Alcohol Propane Ethanal Ethanol CH3─CH2─CH3 CH3─CHO CH3─CH2─OH 44 44 46 ─ 42 20 78 Alkane Aldehyde Alcohol Butane Propanal 1-propanol CH3─CH2─CH2─CH3 CH3─CH2─CHO CH3─CH3─CH2─OH 58 58 60 ─ 1 49 97
  • 20. Water Solubility Number of Carbon Atoms Aldehyde Water Solubility of Aldehyde 1 Methanal Infinite 2 Ethanal Infinite 3 Propanal 16 4 Butanal 7 5 Pentanal 4 6 Hexanal 1 7 Heptanal 0.1 8 octanal insoluble
  • 21. Oxidation of Aldehydes Oxidation is an increase in the number of C-O bonds
  • 22. •The aldehyde gains an oxygen atom •Aldehydes must be protected from air •When prepared from oxidation of primary alcohol, it is usually removed from the reaction mixture immediately to prevent it from being further oxidized to carboxylic acid •Oxidizing agent potassium dichromate (K2Cr2O7) is often used for aldehyde oxidation reactions
  • 23. •Oxidation of an aldehyde involves breaking a carbon-hydrogen bond •The Tollens Test or silver mirror test, involves a solution that contains silver nitrate (AgNO3) and ammonia (NH3) in water •When added to an aldehyde, Ag+ ion is reduced to silver metal, forming a silver mirror.
  • 24. R ─ C ─ H + Ag+ ─────── R ─ C ─ OH + Ag NH3, H2O heat ═ O ═ Aldehyde Carboxylic Acid O Silver metal
  • 25. Reduction of Aldehyde • Aldehydes are easily reduced by hydrogen gas (H2) in the presence of a catalyst (Ni, Pt, or Cr) to form alcohols. • Produces primary alcohols Aldehyde ──────── primary alcohol Reduction
  • 26. Aldehyde reduction to produce alcohols is the “opposite” of the oxidation of alcohols to produce aldehydes. Primary Alcohol Aldehyde Oxidation Reduction
  • 27. REACTION OF ALDEHYDES Aldehyde reacts with alcohols to form hemiacetals and acetals. Reaction with one molecule of alcohol produces a hemiacetal, which is then converted to an acetal by reaction with a second alcohol molecule. Aldehyde + Alcohol ─────── hemiacetal Acid Catalyst Hemiacetal + Alcohol ─────── acetal Acid Catalyst
  • 28. H. Stephen Stoker. (2011). Aldehydes and Ketones. General, Organic and Biological Chemistry Sixth Edition. (pp. 469-487). BROOKS/COLE CENGAGE Learning.