ORGANIC CHEMISTRY

ORGANIC CHEMISTRY IS THE STUDY OF CARBON COMPOUNDS.

CHEMISTS TREAT ORGANIC CHEMISTRY AS A SEPERATE BRANCH OF
SCIENCE BECAUSE CARBON ATOM CAN BOUND TOGETHER TO FORM
LONG CHAINS OR RINGS. UP TO NOW, MORE THAN 17 MILLION OF
ORGANIC COMPOUNDS HAVE BEEN KNOWN.
CARBON MAKES COVALENT, SINGLE, DOUBLE OR TRIPLE BOND
USING HYBRID ORBITALS sp3. sp2. OR sp.

TETRAHEDRAL, 109O TRIGONAL, 120O LINEAR, 180O

SINGLE BOND DOUBLE BOND TRIPLE BOND
SATURATED COMPOUNDS UNSATURATED COMPOUNDS
ALKANES AND THEIR ISOMERSS
ALKANES ARE HYDROCARBON WITH MOLECULAR FORMULA : CnH2n+2

THE OLNY WAY FOR CARBON AND HYDROGEN TO COMBINE IN THESE

THREE MOLECULES OF HYDROCARBONS ARE AS SHOWN ABOVE
 BUTANE, C4 H10

CH3-CH2-CH2-CH3 (CH3 )2-CH-CH3

BUT FOR BUTANE, THERE ARE TWO WAYS HOW CARBON AND HYDROGEN
COMBINED, STRAIGHT OR BRANCH CHAIN. THESE TWO STRUCTURES ARE
CALLED ISOMERS, THEY HAVE THE SAME MOLECULAR FORMULA, BUT
DIFFERENT STRUCTURES.
 PENTANE, C5 H12

CH3 CH2 CH2 CH2 CH3 (CH3)2 CH CH2 CH3 (CH3 )2 C (CH3 )2

PENTANE WITH MOLECULAR FORMULA C5H12 HAS 3 ISOMERS SUCH AS SHOWN

 NAMING ALKANES
IN EARLY TIME, NEW COMPOUNDS WERE NAMED AT THE WHIM OF THEIR
DISCOVERER. UREA IS A CRYSTALLINE SUBSTANCE FIRST ISOLATED FROM
URINE, AND BARBITURATES ARE NEMED BY THEIR DISCOVERER IN HONOR
OF HIS FRIEND BARBARA. AS MORE AND MORE COMPOUNDS BECOME
KNOWN, THE NEEDED FOR A SYSTIMATIC METHOD OF NAMING
COMPOUNDS BECAME APPEARENT.
THE SYSTEM OF NAMING THE CHEMICAL COMPOUNDS WAS DEVISED BY
INTERNATIONAL UNION OF PURE AND APPLIED CHEMISTRY (IUPAC). IN
THIS SYSTEM, A CHEMICAL NAME HAS THREE PARTS : PREFIX, PARENT AND
SUFIX.

WITH THE EXCEPTION OF THE FIRST 4 COMPOUNDS, METHANE,

ETHANE, PROPANE AND BUTANE, THE ALKANES ARE NAMED FROM
GREEK NUMBERS ACCORDING TO THE NUMBER OF CARBONS PRESENT.
THUS, PENTANE IS A FIVE-CARBON ALKANE, HEXANE IS THE SIX-CARBON
ALKANE AND SO ON.
 IF 1 H ATOM IS REMOVED FROM
BRANCHED ALKANE (EXAMPLES)
ALKANE, ALKYL GROUP IS FORMED
IF 1 H ATOM IS REMOVED FROM AN ALKANE, AN ALKYL GROUP
IS FORMED
Eg. METHANE BECOME METHYL
ETHANE BECOME ETHYL, ETC.
CYCLOALKANES
CYCLOALKANE CONTAINS RINGS OF CARBON ATOMS. CYCLOALKANES
ARE WELL KNOWN AND ARE WIDESPREAD THROUGHOUT NATURE .
COMPOUNDS OF ALL RING SIZES ARE FROM 3 THROUGH 30 CARBONS
AND BEYOND HAVE BEEN PREPARED. FOUR THE SIMPLEST
CYCLOALKANES ARE:
REACTIONS OF ALKANES
ALKANES HAVE LOW CHEMICAL REACTIVITY, INERT TO ACIDS AND
BASES AND TO MOST OTHER COMMON LABORATORY REAGENTS, BUT
CAN REACTS WITH OXYGEN AND HALOGENS UNDER APPROPRIATE
CONDITIONS.
CH4(g) + 2 O2(g) CO2(g) + 2H2O DHo = -890 kJ.

ALKANES ARE EASILY BURNT. C1 -C2 (LNG), C3 -C4 (LPG), C5 -C11

(GASOLINE), C11 -C14 (KEROSINE).

REACTIONS OF ALKANE WITH HALOGENS (Cl OR Br) OCCURS WHEN A

MIXTURE OF THE TWO REACTANTS ARE IRRADIATED WITH
ULTRAVIOLET (hn).
FAMILIES OF ORGANIC MOLECULES:
FUNCTIONAL GROUPS.
ORGANIC COMPOUNDS CAN BE CLASSIFIED INTO FAMILIES ACCORDING
TO THEIR STRUCTURAL FEATURES, SO THAT THE CHEMICAL BEHAVIOR
CAN BE PREDICTED. THE STRUCTURAL FEATURES THAT MAKE IT
POSSIBLE TO CLASS COMPOUNDS TOGETHER ARE CALLED FUNCTIONAL
GROUPS.
A FUNCTIONAL GROUP IS COMPOSED OF AN ATOM OR GROUP OF
ATOMS WITHIN A MOLECULE AND HAS A CHARACTERISTIC CHEMICAL
BEHAVIOR. FOR EXAMPLE THE ETHYLENE AND a-PINENE REACT WITH
H2 IN THE SAME WAY, ADDED TO THE DOUBLE BONDS.
TABLE 23.3 CONTINUED
SOLVE THESE PROBLEMS
ALKENES AND ALKYNES
ALKENES AND ALKYNES ARE UNSATURATED COMPOUNDS, BOTH
ALKENES AND ALKYNES HAVE MULTIPLE BONDS. ALKENES CONTAIN,
C=C, DOUBLE BONDS AND ALKYNES CONTAIN , C=C , RIPLE BONDS.
THE UNSATURATED BONDS HAVE FEWER H-ATOMS PER CARBON
THAN THE RELATED ALKANES.
H2C=CH2
Ethene
(Ethylene
)
ISOMERS ARE ALSO POSSIBLE FOR BUTENE AND HIGHER ALKENES.
CIS – TRANS ISOMERS
REACTIONS OF ALKENES AND ALKYNES
ADDITION REACTIONS ( WITH H2 , Cl2 OR Br2 , HCl AND H2O).
 AROMATIC COMPOUNDS AND THEIR REACTIONS

AROMATIC : THE CLASS OF COMPOUNDS THAT CAN BE REPRESENTED

AS HAVING A SIX-MEMBERED RING WITH THREE DOUBLE BONDS.

ALTHOUGH AROMATIC COMPOUNDS HAVE 3 DOUBLE BONDS, THEY ARE

MUCH LESS REACTIVE THAN ALKENES, AND THEY NORMALLY DO NOT
UNDERGO ADDITION REACTIONS.
DIFFERENT FROM ALKENES, AROMATIC COMPOUNDS USUALLY
UNDERGO SUBSTITUTION REACTIONS.

NITRATION
HALOGENATION (CHLORINATION)

SULFONATION
ALCOHOLS, ETHERS AND AMINES
ALCOHOLS.
ALCOHOLS CAN BE THOUGHT AS DERIVATIVES OF WATER, IN WHICH
ONE OF THE HYDROGEN ATOMS IS REPLACED BY AN ORGANIC
SUBSTITUENT, OR AS A DERIVATIVES OF ALKANES IN WHICH ONE OF
THE HYDROGENS IS REPLACED BY A HYDROXYL GROUP (-OH).
ALCOHOLS FORM HYDROGEN BOND SAME AS IN WATER, THESE
BONDS AFFECT THEIR CHEMICAL AND PHYSICAL PROPERTIES
ALCOHOLS ARE GENERALLY HAVE HIGHER BOILING POINT THAN
ALKANES OF SIMILAR SIZE, AND SIMPLE ALCOHOLS ARE SOLUBLE
IN WATER.

ALCOHOLS ARE NAMED BY SPECIFYING THE POINT OF ATTACHMENT

OF THE –OH GROUP TO THE HYDROCARBON CHAIN AND USING THE
FAMILY SUFFIX –OL TO REPLACE THE TERMINAL -e IN ALKANES.
NUMBERING OF THE CHAIN BEGINS AT THE END NEARER THE –OH
GROUP. FOR EXAMPLE. OH
METHANOL , (CH3OH), IS THE SIMPLEST MEMBER OF THE ALCOHOLS
FAMILY, IS PREPARED BY CATALYTIC REDUCTION OF CARBON
MONOXIDE.

METHANOL IS DANGEROUS TO HUMAN, IN LOW DOSES (15 mL)

CAUSING BLIND, AND IN LARGER AMOUNT (100 – 200 ) CAUSING
DEATH.
METHANOL IS USED AS A STARTING MATERIAL IN INDUSTRY FOR
MAKING FORMALDEHYDE (CH2O), AND ACETIC ACID (CH3COOH) AND
ETHANOL,
OTHER CH3CH2OH), IS PRODUCED INDUSTRIALLY BY
CHEMICALS.
FERMENTATION OF GRAINS AND SUGARS, AND ITS SUBSEQUENCE
PURIFICATION BY DISTILLATION.
ETHANOL, SOMETIMES CALLED GRAIN ALCOHOL, IS THE ALCOHOL
PRESENT IN WINES (10-13%), BEERS (3-5%), AND DISTILLED LIQUORS (35-
90%).
MOST OF ETHANOL IS OBTAINED FROM ACID CATALYTIC ADDITION OF
WATER TO ETHYLENE AND ONLY 5% COME FROM FERMENTATION.

2-PROPANOL, [(CH ) CHOH], IS USED PRIMARILY AS A SOLVENT, AND

PREPARED INDUSTRIALLY BY ADD ITION OF WATER TO PROPANE.
OTHER ALCOHOLS SUCH AS:
- 1,2-ETHANEDIOL (ETHYLENE
GLYCOL) IS THE PRINCIPAL
CONSTITUENT OF AOTOMOBILE
ANTIFREEZE;

- 1,2,3-PROPANE TRIOL (GLYCEROL)

IS USED AS MOISTURIZING AGENT
IN MANY FOOD AND COSMETICS,
AND

- THE AROMATIC ALCOHOL

(PHENOL) IS USED FOR
PREPARING NYLON, EPOXY
ADHESIVES AND HEAT-SETTING
RESIN.
ETHERS
ETHERS ARE COMPOUNDS THAT HAVE TWO ORGANIC GROUPS
BONDED TO THE SAME OXYGEN ATOM. CHEMICALLY, THEY ARE FAIRLY
INERT, AND ALWAYS USED AS A SOLVENT IN CHEMICAL REACTIONS.
DIETHYL ETHER IS THE MOST COMMON MEMBER OF THE ETHERS WAS
USED FOR MANY YEARS AS A SURGICAL ANESTETIC AGENT, BUT HAS
NOW BEEN RELACED BY SAFER NONFLAMMABLE ALTERNATIVES.

AMINES
AMINES ARE ORGANIC DERIVATIVES OF AMMONIA, THAT IS ONE OR
MORE OF THE AMMONIA HYDROGENS IS REPLACED BY AN ORGANIC
SUBSTITUENT. THE SUFFIX AMINE IS USED IN NAMING THESE
COMPOUNDS.
H

H
AMINES ARE BASES
BECAUSE THEY HAVE
LONE PAIR ON NITROGEN
ATOM TO ACCEPT
PROTON FROM AN ACID
TO GIVE AMMONIUM
SALTS. THE SALTS ARE
MORE SOLUBLE IN WATER
THAN TEIR
CORRESPONDING
AMINES.
An electron pair on N-atom
 ALDEHYDES AND KETONES

CARBOHYDRATES, FATS, PROTEINS SND NUCLEIC ACIDS ALL CONTAIN

CARBONYL GROUPS, ( C=O), IN THEIR MOLECULES. THE ( C=O) BOND
IN CARBONYL COMPOUNDS IS POLAR. BUT SOME OF CARBONYL
COMPOUNDS ARE MORE POLAR THAN THE OTHERS BECAUSE OF
WHAT ELSE IS BONDED TO THE CARBONYL CARBON ATOM.

CARBONYL COMPOUNDS ARE CLASSIFIED INTI TWO CATEGORIES BASED

ON THE NATURE OF THE GROUPS BONDED TO THE C=O AND ON
CHEMICAL PROPERTIES THAT RESULT.
IN ONE CATEGORY ARE ALDEHYDES AND KETONES ; AND THE OTHER
ARE CARBOXYLIC ACIDS, ESTERS AND AMIDES.
 ALDEHYDES AND KETONES.
CARBONYL CARBON IS
BONDED TO ATOMS (H AND C)
THAT ARE NOT STRONGLY
ELECTRONEGATIVE AND THUS
CONTRIBUTES NO
ADDITIONAL POLARITY TO
THE MOLECULE.

IN CARBOXYLICACIDS,
ASTERS AND AMIDES, THE
CARBONYL GROUP
CARBON IS BONDED T O
AN ATOM (O OR N) THAT
IS STRONGLY
ELECTRONEGATIVE,
GIVING THESE
COMPOUNDS GREATER
A SOLUTION OF FORMALDEHYDE (METHANAL OR FORMALIN) IS USED
AS A BIOLOGICAL STERILANT OR PRESERVATIVE. IN CHEMICAL
INDUSTRY, IT IS USED AS :
- A STARTING MATERIAL FOR MANUFACTURING OF THE PLASTICS
BAKELITE AND MELAMINE,
- A COMPONENT OF ADHESIVES USED TO BIND PLYWOOD,
- A PART OF THE FOAM INSULATION USED IN HOUSES.
ACETONE (PROPANONE) IS THE MOST WIDELY USED OF ALL ORGANIC
SOLVENTS. IN PAINT STORE, ACETONE IS SOLD FOR GENERAL PURPOSE
CLEAN-UP WORK.
WHEN NAMING THESE GROUPS OF COMPOUNDS, ALDEHYDES TAKE
SUFFIX –AL, AND KETONES TAKE SUFFIX –ONE, AS SHOWN BELOW.
 GLUCOSE AND OTHER SUGARS CONTAIN ALDEHYDE GROUPS,
TESTOSTERONE AND MANY OTHER STEROID HORMONES CONTAIN
KETONE GROUPS.

THE INDUSTRIAL PREPARATION OF SIMPLE ALDEHYDES AND KETONES

USUALLY INVOLVES AN OXIDATION REACTION OF RELATED ALCOHOL.
CARBOXYLIC ACIDS, ESTERS AND AMIDES
CARBOXYLIC ACIDS, ESTERS AND AMIDES HAVE THEIR CARBONYL GROUPS
BONDED TO AN ATOM (O OR N), THAT STRONGLY ATT ACTS ELECTRONS.
ALL THREE FAMILIES UNDERGO CARBONYL-GROUP SUBSTITUTION REACT
IONS, IN WHICH A GROUP WE CAN REPRESENT AS –Y SUBSTITUTES FOR
THE –OH, -OC, OR –N GROUP OF THE CARBONYLREACTANT.
CARBOXYLIC ACIDS.
CONTAIN THE –COOH FUNCTIONAL GROUP, OCCUR WIDELY IN THE
PLANT AND ANIMAL KINGDOMS. ACETIC ACID IS THE PRINCIPAL
ORGANIC CONSTITUENT OF VINEGAR, AND BUTANOIC ACID IS
RESPONSIBLE FOR THE ODOR OF RANCID BUTTER. LONG CHAIN
CARBOXYLIC ACID SUCH AS STEARIC ACID ARE COMPONENTS OF ALL
ANIMAL FATS AND VEGETABLE OILS. SYSTEMATIC NAMES ARE DERIVED
BY REPLACING THE FINAL –E FOR THE CORRESPONDING ALKANE WITH –
OIC ACID.
ACETIC ACID IS ACIDIC WITH A pKa VALUE OF 4.75 , (OR ONLY ~ 1% OF
ACETIC ACID MOLECULES DISSOCIATE IN 0.1 M AQUEOUS SOLUTION)

ONE OF THE MOST IMPORTANT TRANSFORMATION OF CARBOXYLIC

ACIDS IS THEIR CAT ALYZED REACTION WITH AN ALCOHOL TO YIELD
AN ESTER. FOR EXAMPLE: REACTION OF ACETIC ACID WITH
ETHANOLCATALYZED BY ACID TO FORM ETHYLACETATE.
ESTERS.
CONTAIN –COOC FUNCTIONAL GROUP, AND HAVE MANY USES IN
MEDICINE, SUCH AS ASPIRIN, BENZOCAINE (LOCAL ANESTETIC), IN
INDUSTRY KNOWN AS POLYESTERS SUCH AS DACRON AND MYLAR, WHICH
ARE USED TO MAKE SYNTHETIC FIBRES AND FILMS, AND IN NATURE,
SIMPLE ESTERS ARE RESPONSIBLE FOR THE FRAGRANT ODORS OF FRUITS
AND FLOWERS. FOR EXAMPLE : PENTYLACETATE IS FOUND IN BANANAS
AND OCTYLACETATE IN ORANGES.

BANANA GIVES
NICE ODOR DUE
TO PENTYL
ACETATE.
 SOME SIMPLE ESTERS FOUND IN NATURE

ESTERS UNDERGO A REACTION, (A HYDROLYSIS) WITH WATER, THAT

SPLITS THE ESTER MOLECULE INTO CARBOXYLIC ACID AND AN
ALCOHOL. THE REACTION IS CATALYSE BOTH BY ACID OR BASE. BASE
CATALYZED ESTER IS OFTEN CALLED SAPONIFICATION (SAPO = SOAP).
SOAP IS A MIXTURE OF SODIUM SALTS OF LONG CHAIN CARBOXYLIC
ACIDS AND IS PRODUCED BY HYDROLYSIS WITH AQUEOUS NaOH.
AMIDES
COMPOUNDS WITH THE –CON FUNCTIONAL GROUP. THE AMIDE
BOND BETWEEN NITROGEN AND A CARBONYL GROUP CARBON IS THE
FUNDAMENTAL LINK USED BY ORGANISMS TO FORM PROTEINS, AND
PERHAPS THERE WOULD BE NO LIFE WITHOUT AMIDES
SOME SYNTHETIC POLYMERS SUCH AS NYLON, ALSO CONTAIN AMIDE
GROUPS.
IN PHARMACEUTICAL AGENTS, ACETAMINOPHEN, TYLENOL AND
EXCEDRIN ARE ALSO AMIDES.

DIFFERENT FROM AMINES, AMIDES ARE NEUTRAL RATHER THAN BASIC,

THEY DO NOT ACCEPT PROTON AND DO NOT FORM AMMONIUM SALTS.
THE NEIGBOURING CARBONYL GROUP CAUSES THE UNSHARED PAIR OF
ELECTRONS ON NITROGEN TO BE HELD TIGHLY, PREVENTING
ELECTRONS FROM BONDING TO H+ .
AMIDES ARE PREPARED BY REACTION OF A CARBOXYLIC ACID WITH
AMMONIA OR AN AMINE.

AMIDES UNDERGO AN ACID OR BASE CATALYZED HYDROLYSIS REACTION

WITH WATER