BIOCHEMISTRY LECTURE

MODULE # 6
HYDROCARBON DERIVATIVES II
ALDEHYDES, KETONES, AND
CARBOXYLIC ACIDS
ESTERS, AMINES, AND AMIDES
 V. THE ALDEHYDES

Aldehydes all have the -CHO (called a carbonyl group) at

the end of the chain. The general formula for an aldehyde is
RCHO where R is an alkyl radical and -CHO as the
functional group.
Aldehydes are prepared by the mild oxidation of primary
alcohols
oxidation
Primary alcohol aldehyde
Example: CH3OH + HCHO +
(O) H 2O
Methanol methanal
The IUPAC names for all aldehydes end in - al. To name an aldehyde
according to the IUPAC system, take the name of the longest chain
containing the functional group -CHO, drop the ending - e of the
alkane, and replace it with the ending - al. That is, from alkane to
alkanal.
The common names of aldehydes start with the following
prefixes which correspond to the number of carbon atoms in the
chain followed by the word aldehyde:

form - for 1
carbon Acet - for 2
carbons Propion - for
3 carbons Butyr -
for 4 “
Valer - for 5 “
Examples:Give the IUPAC and common names of the
following compounds
Molecular IUPAC name Common name
formula HCHO methanal formaldehyde
CH3CHO ethanal acetaldehyde
CH3CH2CHO or propanal propionaldehyde
C
CH2H 5CHO
3CH 2CH2CHO or butanal butyraldehyde
C3H7CHO CH3(CH2)3CHO or pentanal valeraldehyde
C4H9CHO
Some aldehydes and their
uses:
1.Formaldehyde - is a colorless gas with a very sharp odor. It
is used in the laboratory as a water solution containing about
40% formaldehyde called formalin. Formalin is an effective
germicide for the disinfection of excreta, rooms, and clothing. It
is used in embalming fluids and also a preservative for biologic
specimens.

2.Glutaraldehyde - ie superior to formaldehyde as a

sterilizing agent and therefore is replacing it in use.
Glutaraldehyde is microcidal against all microorganisms,
including spores and many viruses. It does not have the
disagreeable odor that formaldehyde does, and it is less irritating
3. Paraldehyde - is formed by
polymerization
the of three molecules
of acetaldehyde. It used as a hypnotic, a
sleep producer. It is also used in the
treatment of alcoholism.
4. Acetaldehyde - is responsible for many
of the unpleasant side effects of
alcohol consumption. The drug antabuse, is
used to treat alcoholics, functions by
increasing the concentration of acetaldehye
 5.Benzaldehyde - is an aromatic
aldehyde prepared by the mild oxidation of
phenol, an aromatic alcohol. Benzaldehyde
is a colorless, oily liquid with an almond-
cherrylike odor. It Is used in the preparation
of flavoring agents, perfumes, drugs, and
dyes.
6.Cinnamic aldehyde - is present in oil
of cinnamon, an oil found in cinnamon
Tests for Aldehydes:
In general, aldehydes are good reducing agents.
Laboratory tests for the presence of aldehydes are based on
their ability to reduce copper(II) cupric ions to form copper (I)
cuprous oxide.
1.Benedict’s or Fehling’s solution or clini-test tablet (all
of which contain Copper2+ complex ion - when aldehydes
are heated with these reagents, a red precipitate of
copper (I) oxide or Cu2O is formed. This is actually the test
for glucose (sugar) in urine, since glucose is an aldehyde.
2.Tollen’s Reagent or Silver mirror test - this test contains
silver ion (Ag1+). In this test, the presence of an aldehyde
causes the formation of a bright, shiny mirror on the inside of
Reactions of Aldehydes
1. Oxidation - aldehydes can be oxidized to form organic acids. Note that this type of
oxidation involves the addition of an oxygen atom.
RCHO + [O] RCOOH
Aldehyde organic acid
Example: HCHO + HCOOH
[O] nethanoic acid or formic
Methanal acid
2. Reduction - is the reverse process whereby a primary alcohol was oxidized to yield
an
aldehyde.
CH3OH + [H] HCHO
Methanol methanal

+ [H]
 VI.
KETONES
The general formula of ketones is RCOR
RCOOR’where
or R and R’ are alkyl radicals. As before,
the oxygen atom from the oxidizing agent reacts with
the hydrogen (H) from the -OH group and with the H
attached to the same carbon as the -OH group, forming
water and a new class of compound called KETONES.
The oxidation of a secondary alcohol yields a
ketone,RCOR, That is, a ketone has two alkyl
groups attached to the carbonyl group -C=O which is
present to both ketones and aldehydes. However, the
carbonyl group is at the end of the chain in an aldehyde
and not at the end in a ketone.
The general equation for the preparation of a ketone is given
by

R - C - R + [O] R- C- R +

H2O OH O
Secondary alcohol ketone
Example: CH3 - C - + [O] CH3 - C - CH3
CH3 + H2O
OH O
2 propanol 2-propanone or(acetone)
dimethyl ketone
The most common ketone is the acetone, commercial name of 2-propanone
(IUPAC name) or dimethyl ketone (traditional or common name). Acetone is a
good solvent for fats and oils. It is also frequently used fingernail polish. Acetone is
present in small amount in the urine and blood. In diabetes mellitus it is present
in larger amounts in the blood and urine and even in the expired air
The test for acetone and ketone bodies makes use of the reaction between
sodium nitroprusside and ketone and ketone bodies to produce a lavender color.
The reaction between an aldehyde and an alcohol yields a hemiacetal and the
reaction between a ketone and an alcohol yields a hemiketal.
 VII. ORGANIC ACIDS OR CARBOXYLIC
ACIDS
The general formula for organic acids is RCOOH, where -COOH is
called the carboxyl functional group of organic acids. Organic acids is
prepared by the partial oxidation of an aldehyde as shown by the general
equation,
RCHO + [O] RCOOH +
Aldehyde H2O
organic acid
Example: CH3OH + HCOOH +
[O] H2O
Methanol formic acid
The IUPAC name for organic acids end in - oic. To name an
acid according to the IUPAC system take the longest carbon chain
containing the acid functional group, -COOH, drop the ending - e of the
alkane and add - oic acid.
The common names of acids are derived from the
names of the aldehyde from which they maybe
prepared. Thus, the acidderived from
acetaldehyde or ethanal, CH3CHO, is acetic acid
or ethanoic acid, CH3COOH. Some examples of organic
Formula
acids: IUPAC Name Common
name
CHHCOOH
3COO
Methanoic
Ethanoic acid
acid Formicacid
acetic acid
CH3CH2COO
H Propanoic propionic
H 3CH2CH2COOH acid
CH Butanoic acid acid butyric
CH3(CH2)3COOH Pentanoic acid valeric
acid
Some organic acids and their use/s or importance
1.Formic acid - is a colorless liquid with a
sharp, irritating odor. It is found in the sting of
bees and ants and causes the characteristic
pain and swelling when injected into the tissues
2.Acetic acid - is one of the components
of vinegar, where it is usually found as a 4
to 5 percent solution
3.Citric acid - is found in citrus fruits. It is both
an alcohol and an acid. It is an example
o a tricarboxylic acid.
 4.Lactic acid - is found in sour milk. It is formed in
the fermentation of milk sugar, lactose. It is also both an
alcohol and an acid. It is formed whenever the body
produces energy anaerobically.
5.Oxalic acid - is used to remove stains, particularly rust
and KMnO4 stains from clothing.
6.Benzoic acid - is a white crystalline compound that is
slightly soluble in water and more soluble in hot water. It
is used medicinally as an antifungal agent.
7.Salicylic acid - is both an alcohol and an acid. It has
similar properties with that of benzoic acid. It is used in the
treatment of fungal infections and also for the removal of
warts and corns.
8. Acetyl-salicylic acid is commonly called
Aspirin
aspirin. is used as an analgesic and as an antipyretic;
for the treatment of colds, headaches, minor aches,
and pains and as a mild blood thinner, especially
for individuals who have had a coronary artery by-
pass. Use of aspirin is contraindicated after surgery
because it interferes with normal blood clotting and
can induce hemorrhaging.
9. Acetaminophen or commonly called as tylenol -
has
been used as a substitute for aspirin because it does
not cause gastrointestinal bleeding and does not affect
blood clotting.
 VIII.
ESTERS
Esters are produced by the reaction of an alcohol with an organic
acid and have the formula, RCOOR’ where R and R’ are alkyl
radicals. The general reaction of an alcohol with an acid is illustrated
by the following equation:

RCOOH + RCOOR’ +
R’OH H2O
WhenAcid
a carboxylic
alcohol acid reactsester
with an alcohol to form an ester, water
(HOH) is also produced. Esters have a carboxylic acid part, and
alcohol part. The acid part is easily identified since it contains the
carbonyl group (C=O).
Rewriting the general formula of esters above in terms of
structural formulas
 O
R O - R’
- C - alcohol part
If the formula
Aciof an ester is written with the formula of water, HOH, placed below so that the OH
part of the
d part
water molecule is below the carbonyl group and the H part of the water molecule is
below the alcohol part, then the name of the ester can be easily determined by reading downward
on each side of the vertical line
O
R - C - O - R’
HO H
Acid alcohol part
part

Systems of naming the esters:

Example: Give the IUPAC and common names of the ff.
Ester Solution:
O
H - C - O -
HO CH2CH3 H
Acid alcohol part
part
1. IUPAC
system
Step 1. The alcohol on the right side above, is a two-carbon
alcohol or ethanol
Step 2. The acid part of the ester contains one carbon atom so,
it Is methanoic acid.
Step 3. Dropping the ending “ic” from the acid and adding the
ending “ate” we have the name of the ester as ethyl methanoate.
2. COMMON name
Step 1. The name of the alcohol, as indicated above, is ethyl
alcohol. Step 2. The common name of the acid with one carbon
atom is formic acid.
Step 3. Dropping the ending “ic” and adding the ending “ate”,
we have the common name of the ester as “ethyl formate”.
 IX. ALIPHATIC
AMINES
Amines are organic compounds derived from ammonis, NH3.
There are three classes of amines namely: primary, secondary and
tertiary amines.
1.Primary Amines - are those in which one of the hydrogen
atoms of ammonia, NH3, has been replaced by an alkyl group.
Primary amines have the general formula RNH2.
2.Secondary Amines - are those in which two of the
hydrogen atoms of thw ammonia have been replaced by
alkyl groups. Secondary amines have the general formula R2NH.
3.Tertiary Amines - are those in which all the hydrogen atoms
of ammonia have been replaced by alkyl groups. The general
formula of tertiary amines is R3N.
Naming Aliphatic Amines
1.IUPAC - The -NH group is called the amino group and
is indicated numerically according to its position on
the carbon chain. If there is more than carbon carbon
chain attached to the nitrogen, then the longest chain is
the one used as the parent name. The other or others are
indicated by the letter “N” to indicate that they are
attached to the nitrogen.
2.In the common system, the word amine is added after
the name of the alkyl group. The common system is
used primarily for simple compounds. For more
complex compounds, the IUPAC system is used. With this
system the prefix “amino” is used to denote the
presence of a -NH2 group.
For example, give the IUPAC and common names of the ff.
Compounds:
1. Primary amine, RNH2
H H Molecular formula IUPAC Name Common Name
a.) H - C - CH3NH2 aminomethane methylamine
NH H
H H H
b.) H - C - C - 2-aminopropane isopropylamine
C -H H NH2 H

2. Secondary amine,
R2NH H H H
a.) H - C - N - C - H dimethylamine
(CH H3)2NH2H H

3. Tertiary amine, R3N

H
H N - C - H or (CH3)3N trimethylamine
HH H - C -H
a.) H - C - H
H
Preparation of Amines - Amines are prepared by the
reaction of an ammonia with alkyl halides or with another
amine.
Example: CH3Cl + NH3 CH3NH2 +
Methyl methylamine
HCl
Chloride (primary amine)
CH3NH2 + (CH3)2N +
CH3Cl HCl
Amines are generally
Methyla basic compounds.
dimethyl When
amine they react with
HCl acid ammonium
mine salts are formed. These ammonium
salts are named by placing the word “hydrochloride” after the
name of he amine. Examples are; thiamine hydrochloride (Vit.
B1) and procaine hydrochloride (novocaine, a local anesthetic).
AROMATIC AMINES - The simplest aromatic
amine consists of an amino acid attached to a
benzene ring. Its IUPAC name is aniline. Aniline
is prepared by the reduction of nitrobenzene.

Aniline is used commercially in the preparation

of many dyes and drugs. When aniline is
reacted with acetic acid acetanilide is formed
Acetanilide has been used as an
antipyretic and as an analgesic.
ALKALOIDS - are nitrogen-containing compounds
produced by plants. The term alkaloids (alkali-like)
comes from the basic properties of amines.
The following are examples of alkaloids:
1.Caffeine - occurs in coffee and tea. It stimulates
the central nervous system and also acts as a
“diuretic”. Caffeine is used in various headache
remedies in conjunction with analgesic drugs.
2.Cocaine - obtained from the leaves of coca shrubs, it
is administered medicinally in the form of hydrochloride
to enhance its solubility. Cocaine is widely used as a
local analgesic because it blocks nerve conduction.
 3.Nicotine - found in tobacco leaves is one of
the few water soluble alkaloid.s. It has no
therapeutic use but is used as an insecticide.
Nicotine is found in the body after cigarette
smoking. It increases the blood pressure and
pulse rate and constricts the blood vessels,
4.Ephedrine - is used to elevate blood
pressure during spinal anesthesia. It is also
used to treat asthma, coughs, and colds and
as a nasal decongestant.
 X. AMIDES

Amides are formed by the reaction of organic acids with ammonia as shown
by the following equation:

RCOOH + NH3 RCONH2 +

Acid
H2O
Amides are names
amide as follows:

1.IUPAC System - Drop ending - oic and

the word acid from the name of the acid and then add
the word amide.
2.Common Name - Drop the ending - ic and the word acid from the name of the
acid then add the word amide.
 For
example:
CH3COOH + NH3 CH3CONH2 + H2O
Ethanoic acid ethanamide ( IUPAC name )
or propionic acid propionamide( common name )
CH3OH + NH3 CH3CONH2 + H2O
Methanoic acid methanamide (IUPAC name)
Formic acid formamide (common name)

Properties of amides - amides are neutral compoundscompared to amines which are

basic compounds

1.Acid hydrolysis of simple amides yields an organic acid.

HCl
For example: CH3CONH2 CH3COOH
H2O
2. Base hydrolysis of simple amides yields the salt
of an organic acid
NaOH
For example: HCONH2
HCOONa H2O