General Organic Chemistry (GOC)
General Organic Chemistry (GOC)
p a g e
i s t r y
1. IUPAC Nomenclature
/ c h e m /
m
2. Electronic Displacement in Covalent Bond
co g e . i n
3. Isomerism
u b e . t r y p a
. y o u t
4. Reactive Intermediate
e m i s
w w w w
5. Types of Reactions
. c h
: / / w w
s
6. Quantitative and Qualitative Analysis
ht t p
7. Purification of Organic Compounds
p a g e
i s t r y
/ c h e m /
co m
1. IUPAC Nomenclature
g e . i n
u b e . t r y p a
. y o u t e m i s
w w w w . c h
: / / w w
ht t p s
e
IUPAC Nomenclature
Seniority Table of Functional Groups
r y p a g
m i s t
/ c h e . i n /
e . co m p a g e
u t u b i s t r y
w . y o . c h e m
w w w w
p s : / / w
ht t
More Examples
p a g e
i s t r y
/ c h e m /
co m g e . i n
u b e . t r y p a
. y o u t e m i s
w w w w . c h
: / / w w
ht t p s
p a g e
i s t r y
/ c h e m /
co m g e . i n
u b e . t r y p a
. y o u t e m i s
w w w w . c h
: / / w w
ht t p s
p a g e
i s t r y
/ c h e m /
co m g e . i n
u b e . t r y p a
. y o u t e m i s
w w w w . c h
: / / w w
ht t p s
2. Electronic Displacement in Covalent Bond
p a g e
i s t r y
1. Inductive Effect
/ c h e m /
co m g e . i n
2. Resonance Effect
u b e . t r y p a
. y o u t
3. Hyper conjugation Effect
e m i s
w w w w .
4. Electromeric Effect
c h
: / / w w
ht t p s
p a g e
i s t r y
/ c h e m /
co m g e . i n
u b .
3. Isomerism
e t r y p a
. y o u t e m i s
w w w w . c h
: / / w w
ht t p s
4. Reactive Intermediate
p a g e
i s t r y
h e m
1. Carbocation, Carbenion and Free radicals
/ c /
2. Electrophiles
co m g e . i n
u b e . t r y p a
. y o u
3. Nucleophiles
t e m i s
w w w
4. Carbenes, Nitrenes
w . c h
: / / w w
ht t p s
Carbocation
p a g e
i s t r y
1. The have electron deficit carbon atom having 6 electrons in its valence shell
c h e m
2. Act as Lewis acid (electron pair acceptor)
/ /
o m g e . i n
3. They seek electron to complete its octet (electrophiles), hence unstable and very reactive
c
b e .
4. The hybridization of carbon is ۾܁
u t r y p a
. y o u t e m i s
5. The have trigonal planar geometry (bond angle 120)
w w w w . c h
: / / w w
ht t p s
p a g e
i s t r y
/ c h e m /
co m g e . i n
u b e . t r y p a
. y o u t e m i s
w w w w . c h
: / / w w
ht t p s
p a g e
i s t r y
/ c h e m /
co m g e . i n
u b e . t r y p a
. y o u t e m i s
w w w w . c h
: / / w w
ht t p s
Carbenion
p a g e
y
1. The have carbon atom having 8 electrons in its valence shell (nucleophiles)
2. Act as Lewis base (electron pair donor)
m i s t r
c
3. The hybridization of carbon is ۾܁
/ h e . i n /
e . co m
4. The have pyramidal geometry (3 bp and 1 lp)
p a g e
b r y
5. They are diamagnetic in nature
o u t u m i s t
w w . y . c h e
w / w w w
t p s : /
ht
Stability order of Carbenion
p a g e
i s t r y
/ c h e m /
co m g e . i n
u b e . t r y p a
. y o u t e m i s
w w w w . c h
: / / w w
ht t p s
p a g e
i s t r y
/ c h e m /
co m g e . i n
u b e . t r y p a
. y o u t e m i s
w w w w . c h
: / / w w
ht t p s
e
Free Radicals
r y p a g
s t
1. The are electron deficit, neutral molecule, highly unstable
e m i
2. They seek electron to complete its octet, hence very reactive
m /
3. They are paramagnetic in nature
c h e . i n /
e . co p a g
4. Free radicals combined to form neutral molecule
b y
u t u
5. The can be generated by
o m i s t r
. y h e
(HELPR) (H: Heat, E: Electricity, L: Light, P: Peroxide, R: Radicals)
w w . c
w / w w w
t p s : /
ht
Stability of Free Radicals
p a g e
i s t r y
/ c h e m /
co m g e . i n
u b e . t r y p a
. y o u t e m i s
w w w w . c h
w
A ܋ܑܔܡܔܔfree radicals
p s : / / w
ht t
p a g e
i s t r y
/ c h e m /
co m g e . i n
u b e . t r y p a
. y o u t e m i s
w w w w . c h
: / / w w
ht t p s
Electrophiles and Nucleophiles
p a g e
i s t r y
m
Rich species
e
deficit species
m / c h e . i n /
b e . co y p a g
o u t u m i s t r
w w . y . c h e
w / w w w
t p s : /
ht
Types of Nucleophiles
p a g e
i s t r y
/ c h e m /
co m g e . i n
u b e . t r y p a
. y o u t e m i s
w w w w . c h
: / / w w
ht t p s
Types of Electrophiles
p a g e
i s t r y
/ c h e m /
co m g e . i n
u b e . t r y p a
. y o u t e m i s
w w w w . c h
: / / w w
ht t p s
Carbenes
p a g e
i s t r y
/ c h e m /
co m g e . i n
u b e .
1. Neutral divalent carbon species
t r y p a
t i s
2. Carbon atom is bonded to two monovalent atom/groups
. y o u h e m
3. It contain two nonbonding electrons
w w w w . c
4. Central carbon atom has only six electrons in its valence shell
/ / w w
5. Its electron deficient species (Electrophiles)
:
ht t p s
Formation of Carbenes
p a g e
i s t r y
/ c h e m /
co m g e . i n
u b e . t r y p a
. y o u t e m i s
w w w w . c h
: / / w w
ht t p s
Orbital Structure of Carbenes
p a g e
i s t r y
/ c h e m /
co m g e . i n
u b e . t r y p a
. y o u t e m i s
w w w w . c h
/ w w
(H-C-H) Bond angle 103°
: /
(H-C-H) Bond angle 180°
ht t p s
Less stable, diamagnetic,
highly reactive
More stable, Paramagnetic,
Low reactive
Uses of Carbenes
p a g e
i s t r y
m
1. Reimer-Tiemann reaction
2. Carbylamine reaction
/ c h e . i n /
e . co m p a g e
y
3. Ring expension reaction
u t u b i s t r
o m
4. Addition reaction of alkene
w w . y . c h e
w / w w w
t t p s : /
h
Nitrene
p a g e
y
A nitrene is a species that has a formally neutral nitrogen atom bearing four nonbonded
valence electrons.
m i s t r
/ c h e . i n /
e . co m p a g e
u t u b i s t r y
w . y o h e m
1. Monovalent nitrogen species
. c
w w w w
2. Contain no charge
s : / / w
3. Electron deficient
p
ht t
4. Electrophile
5. Highly reactive
e
Uses of Nitrene
Types of Nitrene
r y p a g
t
1. Beckmann Rearrangement Reactions
e m i s
2. Hoffman Bromamide Reactions
m / c h . i n /
3. Curtius Rearrangement Reactions
e
b e . co p a g
4. Lossen Rearrangement Reactions
y
o u t u m i s t r
5. Schmidt Rearrangement Reactions
w w . y . c h e
w / w w w
t t p s : /
h
Types of Reactions
p a g e
i s t r y
/ c h e m /
1. Addition Reactions
co m g e . i n
u b e .
2. Substitution Reactions
t r y p a
o u t
3. Elimination Reactions
. y e m i s
w w w w . c h
4. Rearrangement Reactions
: / / w w
ht t p s
Addition Reactions
1.
a g e
Addition reactions are limited to chemical compounds that have multiple bonds
p
2.
s t r y
Molecules with carbon–carbon double bonds (alkenes), or with triple bonds (alkynes), and compounds that
i
e m
have rings
3.
m / c h e . i n /
Molecules containing carbon—hetero double bonds like carbonyl (C=O) groups, or imine (C=N) groups
4.
. co a g
Addition reactions are also encountered in polymerizations and called addition polymerization.
b e y p
o u t u m i s t r
w w . y . c h e
w / w w w
t p s : /
ht
Substitution Reaction
p a g e
i s t r y
/ c h e m /
co m g e . i n
A substitution reaction is an organic chemical
u b e . t r y p a
reaction during which a functional group replaces
u t i s
an atom or another functional group attached to a
w w w w
p s : / / w
ht t
e
Elimination Reactions
r y p a g
t
Chemical reactions in which a pair of atoms or groups of atoms are removed from a molecule, usually
m i s
through the action of acids, bases, or metals and, in some cases, by heating to a high temperature.
e
m / c h e . i n /
b e . co y p a g
o u t u m i s t r
w w . y . c h e
w / w w w
t t p s : /
h
Rearrangement Reactions
p a g e
i s t r y
/ c h e m /
co m g e . i n
u b e . t r y p a
. y o u t e m i s
w w w w . c h
: / / w w
ht t p s
Qualitative and Quantitative Analysis
p a g e
i s t r y
/ c h e m /
co m g e . i n
u b e . t r y p a
. y o u t e m i s
w w w w . c h
: / / w w
ht t p s
Detection of Carbon and Hydrogen
p a g e
i s t r y
/ c h e m /
co m g e . i n
u b e . t r y p a
. y o u t e m i s
w w w w . c h
: / / w w
ht t p s
Lassaigne’s test
a g e
1. Nitrogen, sulphur, halogens present in an organic compound are detected by ‘Lassaigne’s test’.
p
s t r y
2. Covalent compounds are converted into ionic form by fusing the compound with sodium metal.
i
/ c h e m /
co m g e . i n
u b e . t r y p a
. y o u t e m i s
w w w w . c h
: / / w w
ht t p s
Test for Nitrogen
p a g e
i s t r y
Sodium extract + Ferrous sulphate + Ferric chloride solution + dilute hydrochloric acid.
The appearance of a prussian blue colouration confirms the presence of nitrogen in the organic
compound.
/ c h e m /
co m g e . i n
u b e . t r y p a
. y o u t e m i s
w w w w . c h
: / / w w
ht t p s
Test for Sulphur
Sulphur, if present, in the given organic compound, upon fusion with sodium reacts to form sodium sulphide
p a g e
i s t r y
1. Lead acetate test
/ c h e m /
co m g e . i n
u b e . t r y p a
. y o u t
2. Sodium nitroprusside test
e m i s
w w w w . c h
: / / w w If nitrogen and sulphur both are present in
e
Upon fusion with sodium, the halogens in the organic compound are converted to sodium halides.
r y p a g
m i s t
/ c h e . i n /
e . co m p a g e
u t u b i s t r y
. y o e m
When nitrogen or sulphur is also present in the compound, the sodium extract before testing for
w . c h
w w
halogens is boiled with strong nitric acid to decompose the cyanide and the sulphite formed during
w w
/ w
the sodium fusion.
t t p s : /
h
Test for phosphorous
a g e
1. The compound is heated with an oxidising agent (sodium peroxide).
p
s t r y
2. The phosphorous present in the compound is oxidised to phosphate.
i
/ c h e m
3. The solution is boiled with ۶۽ۼ and treated with ammonium molybdate.
/
co m g e . i n
4. A yellow coloured ppt. indicates the presence of phosphorous.
u b e . t r y p a
. y o u t e m i s
w w w w . c h
: / / w w
s
Yellow coloured ppt.
ht t p
Quantitative Analysis
p a g e
i s t r y
m
1. Both carbon and hydrogen are estimated together in one operation.
2.
c h e /
A known weight of an organic compound is burnt in the presence of excess of oxygen and copper (II) oxide.
/ . i n
3.
o m g e
Carbon and hydrogen are oxidised to carbon dioxide and water respectively.
e . c p a
u t u b i s t r y
w . y o . c h e m
w w w w
p s : / / w
ht t
Estimation of Nitrogen
(i) Dumas method:
p a g e
i s t r y
This method is based on fact that the nitrogenous compounds when heated with copper oxide in an
c h e m
atmosphere of carbon dioxide yield free nitrogen,
/ /
co m g e . i n
u b e . t r y p a
. y o u t e m i s
w w w w . c h
: / / w w
ht t p s
e
(2) Kjeldahl method
Limitations:
r y p a g
m i s t
/ c h e n /
Kjeldahl method is not applicable to compounds containing nitrogen in nitro and azo
. i
. co m a g e
groups and nitrogen present in rings (e.g. pyridine, quinoline, isoquinoline) as nitrogen of
e p
t u b s t r y
these compounds does not convert to ammonium sulfate under the conditions of this method.
u i
w . y o . c h e m
w w w w
p s : / / w
ht t
e
(ii) Kjeldahl’s Methods
1.
r y p a g
Kjeldahl’s method is based on the fact that when an organic compound containing nitrogen is
m i s t
heated with con. H2S04 the nitrogen in it is converted to ammonium sulphate.
/ c h e n /
2. The resultant liquid is then treated with excess of alkali and the liberated ammonia gas absorbed in
. i
excess of standard acid.
e . co m p a g e
u b t r y
3. The amount of ammonia is determined by finding the amount of acid neutralised by back filtration
u t i s
y o m
with some std. alkali.
w w . . c h e
w / w w w
t p s : /
ht
Estimation of Halogen
p a g e
(Carius Method)
i s t r y
/ c h e m
In this method organic compound containing halogen is heated in a carius tube with fuming HNO3 in
/
presence of AgNO3, Silver halide (AgX) is precipitated.
co m g e . i n
e . a
By Knowing the wt. of silver halide & organic Compound percentage of halogens can be calculated
(x=-Cl, -Br,-I)
t u b i s t r y p
. y o u h e m
w w w w . c
: / / w w
ht t p s
Estimation of sulphur
Carius method
p a g e
i s t r y
/ c h e m
When an organic compound containing sulphur is heated with fuming nitric acid, sulphur is oxidised to sulphuric
/
. i n
acid. This is taken as barium sulphate by adding barium chloride solution. From the amount of barium sulphate,
. co m
percentage of sulphur can be calculated.
e p a g e
u t u b i s t r y
w . y o . c h e m
w w w w
p s : / / w
ht t
g e
Estimation of Phosphorus
Carius method
t r y p a
1.
i s
The organic compound containing phosphorus is heated with fuming nitric acid. Phosphorus is oxidised to
e m
c h /
phosphoric acid.
2.
o m / e . i n
It is precipitated as magnesium ammonium phosphate, MgNH4PO4, by the adding up of magnesia mixture
c g
u b e .
(MgSO4 + NH4OH + NH4Cl).
t r y p a
3.
u t i s
The magnesium ammonium phosphate is washed, dried and ignited when it is converted to magnesium
. y o e m
w h
pyrophosphate (Mg2P2O7).
w w w w . c
p s : / / w
ht t
Purification of Organic Compounds
p a g e
i s t r y
/ c h e m /
co m g e . i n
u b e . t r y p a
. y o u t e m i s
w w w w . c h
: / / w w
ht t p s
p a g e
Sublimation:
i s t r y
/ c h e m /
i n
1. This method is applicable for organic substance which has high vapour pressure at temperature
. co
below their melting point.
m a g e .
t u b e t r y p
2. Organic substances like benzoic acid, naphthalene and camphor when heated pass directly from
i s
. y o u e m
solid to vapor without melting into liquid. On cooling the vapours will give back solids.
h
w w w . c
3. It is a useful technique to separate volatile and non-volatile solid.
w / w w
4. It has limited application because only a few substance will sublime.
: /
ht t p s
Crystallization:
p a g e
y
1. Crystallization is defined as a process by which a chemical is converted from a liquid solution
into a solid crystalline state.
m i s t r
c h e /
2. An impure solid is completely dissolved in a minimal amount of hot, boiling solvent, and the hot
/ . i n
e . co m
solution is allowed to slowly cool.
p a g e
b r y
3. The developing crystals ideally form with high purity, while impurities remain in the saturated
o u t u m i s t
solution surrounding the solid (called the "mother liquor").
w w . y . c h e
4. The crystallized solid is then filtered away from the impurities.
w / w w w
t t p s : /
h
Distillation
p a g e
1.
t r y
This method is to purify liquids from non-volatile impurities, and used for separating the constituents of a
i s
e m
liquid mixture which differ in their boiling points.
2.
m / c h e . i n /
There are various methods of distillation depending upon the difference in the boiling points of the
co g
constituents.
3.
u b e . r y p a
The methods are (i) Simple distillation (ii) Fractional distillation (iii) Steam distillation (iv) Distillation
t
o u t
under reduced pressure
. y e m i s
w w w w . c h
: / / w w
ht t p s
e
Simple distillation
r y p a g
s t
Liquids with large difference in boiling point (about 40K) and do not decompose under ordinary pressure
can be purified by simply distillation
e m i
m / c h e . i n /
b e . co a g
Fractional distillation
y p
o u t u m i s t r
. y e
This is used to purify and separate liquids present in the mixture having their boiling point close to each other.
w w w . c h
In the fractional distillation, a fractionating column is fitted with distillation flask and a condenser. Petroleum, coal-
w
tar and crude oil.
: / / w w
ht t p s
Steam distillation:
p a g e
i s t r y
m
1. This method is applicable for solids and liquids. If the compound to be steam distilled the it
/ c h e . i n /
m
should not decompose at the steam temperature, should have a fairly high vapour pressure at
e . co p a g e
b y
373K, it should be insoluble in water and the impurities present should be non-volatile.
o u t u m i s t r
. y e
2. This method is used to recover essential oils from plants and flowers, also in the
w w w w . c h
manufacture of aniline and turpentine oil.
: / / w w
ht t p s
Distillation Under Reduced Pressure
p a g e
i s t r y
/ c h e m /
co m g e . i n
u b e . t r y p a
. y o u t e m i s
w w w w . c h
: / / w w
ttp s
Azeotropic Distillation
p a g e
y
1. These are the mixture of liquids that cannot be separated by fractional distillation.
m i s t r
2. The mixtures that can be purified only by azeotropic distillation are called as azeotropes.
/ c h e . i n /
m
3. These azeotropes are constant boiling mixtures, which distil as a single component at a fixed
e . co p a g e
b y
temperature. For example ethanol and water in the ratio (95:5)
o u t u m i s t r
. y e
4. In this method the presence of a third component like C6H6, CCl4, ether, glycerol, glycol which
w w w w . c h
act as a dehydrating agent depress the partial pressure of one component of azeotropic mixture and
: / / w w
s
raises the boiling point of that component and thus other component will distil over.
ht t p
Differential extraction:
p a g e
1. The process of removing a substance from its aqueous solution by shaking with a suitable organic
solvent is termed extraction.
i s t r y
/ c h e m /
2. When an organic substance present as solution in water can be recovered from the solution by
o m
means of a separating funnel.
c g e . i n
u b e . y p a
3. The aqueous solution is taken in a separating funnel with little quantity of ether or chloroform
t r
(CHCl3).
. y o u t e m i s
w c h
4. The organic solvent immiscible with water will form a separate layer and the contents are shaken
w wgently.
w w .
s : / / w
5. The solute being more soluble in the organic solvent is transfered to it.
p
ht t
6. The solvent layer is then separated by opening the tap of the separating funnel, and the substance
is recovered.
Chromatography:
1.
a g e
The principle behind chromatography is selective distribution of the mixture of organic substances between
p
i s t r y
two phases – a stationary phase and a moving phase.
2.
c h e m /
The stationary phase can be a solid or liquid, while the moving phase is a liquid or a gas.
/
co m g e . i n
. a
3. If the stationary phase is solid, the basis is adsorption, and when it is a liquid, the basis is partition.
4.
t u b e s t r y p
So the Chromatography is defined as a technique for the separation of a mixture brought about by differential
i
. y o u h e m
w
movement of the individual compound through porous medium under the influence of moving solvent.
w
5.
w w w . c
The various methods of chromatography are
p s : / / w
1. Column chromatography (CC)
a g e
The principle involved is different compounds are adsorbed on an adsorbent to different degree.
p
2.
i s t r y
Silica gel and alumina are the commonly used adsorbent.
3.
c h e m /
The components of the mixture move by varying distances over the stationary phase.
/
4.
co m g e . i n
Column chromatography and thin layer chromatography are the techniques based on the principle of
u b e .
differential adsorption.
t r y p a
. y o u t e m i s
w w w w . c h
: / / w w
ht t p s
e
Partition chromatography:
r y p a g
1. Paper chromatography (PC) is an example of partition chromatography.
m i s t
2. The same procedure is followed as in thin layer chromatography except that a strip of paper
acts as an adsorbent.
/ c h e . i n /
co m g e
3. This method involves continues differential portioning of components of a mixture between
e . p a
u b r y
stationary and mobile phase.
o u t m i s t
4. In paper chromatography, a special quality paper known as chromatography paper is used.
y
w w . . c h e
This paper act as a stationary phase.
w / w w w
t p s : /
ht