May 14, 2021

ALDEHYDE

- General Formula RCHO

- Functional group is -CHO carbonyl (the aliphatic alkyl group, R, is attached to a -CHO group at
the end of the molecule
- Formed by the oxidation of a primary alcohol

H H

R – C – OH + [O] → R – C = O + H2O

primary alcohol aldehyde

The oxidation of an alcohol requires the use of some oxidizing agent such as KMnO4, K2Cr2O7, or
CuO. In the above equation, the [O] represents an oxidizing agent, which represents any substance that
will yield the oxygen needed for the reaction.

Example:

The reaction below represents the oxidation of methyl alcohol (CH3OH), a primary alcohol.

H H

H – C – OH + [O] → H – C = O + H2O

methyl alcohol formaldehyde

During the oxidation, one H was removed from the -OH group and another H from the carbon to
which the -OH group was attached (the only carbon in the compound). Water is one of the products of
this reaction; the other product is a new kind of compound called an aldehyde. In the example above, it
is formaldehyde. Formaldehyde can also be written as HCHO.

- IUPAC name of aldehyde: alkane name with the e replaced with -al. (alkanal)
o Take the longest chain containing the aldehyde group, drop the -e and replace it with
the ending -al.
o Or alkane name with the e replaced with -al. (alkanal)
- Common name: special name of prefix + aldehyde

Molecular Formula IUPAC Name Special Prefix Common Name

HCHO methanal form- formaldehyde
CH3CHO ethanal acet- acetaldehyde
C2H5CHO propanal propion- propionaldehyde
C3H7CHO butanal butyr- butyraldehyde
C4H9CHO pentanal valer- valeraldehyde
C5H11CHO hexanal capro- caproaldehyde
C6H13CHO heptanal enanth- Enanthaldehyde or
enanthal
C7H15CHO octanal capryl- caprylic aldehyde
C8H17CHO nonanal pelargon- pelargonaldehyde
C9H19CHO decanal Capr- capraldehyde

# of C IUPAC Name Common Name Special Prefix

11 Undecanal Undecylaldehyde Undecyl-

12 Dodecanal Laurylaldehyde Lauryl-

13 Tridecanal Tridecylaldehyde Tridecyl-

14 Tetradecanal Myristylaldehyde Myristyl-

15 Pentadecanal Pentadecylaldehyde Pentadecyl-

16 Hexadecanal Palmitaldehyde Cetyl- (Palmityl-)

17 Heptadecanal Heptadecylaldehyde Heptadecyl-

18 Octadecanal StearylaldehydeStearyl-

19 Nonadecanal Nonadecylaldehyde Nonadecyl-

20 Eicosanal Arachidylaldehyde Arachidyl-

Note that in the common name, the term aldehyde comes from the words alcohol and
dehydrogenation.

Exercises:

1. Name the following compound (IUPAC):

Br

CH3 – CH – CH – CH – CH2 – CH2 – CH2 – CHO

CH3 CH3

The largest chain containing the aldehyde group contains eight carbon atoms, so it is an octanal.
Carbon no. 1 is the CHO group. There is a bromine in carbon no. 6, and methyl group in carbons no. 5
and 7. Naming the groups in alphabetic order, we have 6-bromo-5,7-dimethyloctanal.

2. Draw the structure of 4,4-dichloro-2,3-dimethylpentanal.

For performance task (do not submit yet)

1. Draw 2,3-dichloropropanal
2. Draw 3,5-dimethyloctanal

Aromatic Aldehydes

- The general formula is ArCHO, where Ar stands for an aromatic ring.

- The simplest aromatic aldehyde is benzaldehyde, which consists of an aldehyde group attached
to a benzene ring.
- The mild oxidation of toluene prepares Benzaldehyde.

CeO2 – Ceric oxide or Cerium (IV) oxide, cerium atomic number is 58

H+ - hydrogen ion, a proton, usually present in acidic solutions

This formula appears in redox (reduction-oxidation) reactions, especially in analytical

chemistry. CeO₂ can be reduced in an acidic solution:

Example redox reaction:

CeO2 + 4H+ + e− → Ce3+ + 2H2O

This shows Ce⁴⁺ in CeO₂ being reduced to Ce³⁺, while H⁺ participates by balancing the charge and
forming water.

A redox reaction (short for reduction-oxidation reaction) is a chemical reaction in which

there is a transfer of electrons between substances. It involves two key processes:

🔴 Oxidation

– Loss of electrons
– Increase in oxidation number
– Often involves gaining oxygen or losing hydrogen

🔵 Reduction
– Gain of electrons
– Decrease in oxidation number
– Often involves losing oxygen or gaining hydrogen

🔄 Redox = Oxidation + Reduction

These two processes always occur simultaneously—when one substance is oxidized, another is
reduced.

Benzaldehyde – colorless, oily liquid with a cherry-almond-like odor

- Used in the preparation of flavoring agents, perfumes, drugs, and dyes

- Bitter almonds and cherries are natural sources of benzaldehyde

Vanillin – occurs in vanilla beans and gives the particular taste and odor to vanilla extract

- Has an aldehyde structure

- 4-hydroxy-3-methoxybenzaldehyde

Cinnamic aldehyde (cinnamaldehyde) – present in oil of cinnamon, an oil found in cinnamon bark
Both vanillin and cinnamic aldehyde can be prepared synthetically, and both are used as
flavoring agents.

Uses of aldehydes

1. Formaldehyde, a colorless gas with a very sharp odor, is used in the laboratory as a water
solution containing about 40 percent formaldehyde, commonly known as formalin, an effective
germicide for the disinfection of rooms and clothing, and is also used in embalming fluids and
preservatives for biologic specimens.

Pure
Formaldehyde Gas Industrial chemical, polymer precursor
CH₂O
Liquid ~37% formaldehyde in water + Preservation, disinfection,
Formalin
solution methanol embalming

2. Formaldehyde and its oxidation product, formic acid, are primarily responsible for the systemic
toxicity of methyl alcohol.
3. Glutaraldehyde is superior to formaldehyde as a sterilizing agent.
4. Paraldehyde is formed by the polymerization (joining) of three molecules of acetaldehyde and
depresses the central nervous system. It is used as a hypnotic, a sleep producer.

5. Acetaldehyde (ethanal) is responsible for many of the unpleasant side effects of ethyl alcohol
consumption.

6. Glyceraldehyde is an important component in the metabolism of carbohydrates.

Tests for Aldehydes

1. With Benedict’s or Fehling’s reagent, heated, will form a red precipitate of copper oxide (Cu2O).
This is the test for glucose (sugar) in urine.
2. Tollen’s reagent (which contains Ag+ complex ion) will form a bright, shiny mirror on the inside
of the test tube (silver mirror test).

Reactions of Aldehydes

1. Oxidation. Aldehydes can be oxidized to form acids.

RCHO + [O] → RCOOH

Aldehyde carboxylic acid

2. Reduction. Aldehydes can be reduced to the corresponding primary alcohols.

RCHO + [H] → RCH2OH

Aldehyde primary alcohol

CH3CHO + [H] → CH3CH2OH

+ [H] →