Inductive effect

Displacement of an electron (shared) pair along the

carbon chain due to the difference in electronegativity
of the groups present along with carbon chain

Example :

Halogen atom present at the end of a carbon chain

𝛿𝛿𝛿⊕ 𝛿𝛿⊕ 𝛿⊕ 𝛿⊝
C4 >C3 >> C>>>
2 C1
X
Inductive effect
Inductive effect
Mesomeric effect

When a group releases or withdraw orbital electron in

any conjugated system then it is called M effect group
and effect is known as mesomeric effect or resonance
effect

+M/+R group -M/-R group

Electron releasing group Electron withdrawing group

Mesomeric effect

Order of +M group :
Mesomeric effect

Order of -M group :
Mesomeric effect
Mesomeric effect
Mesomeric effect
Mesomeric effect
Mesomeric effect
Mesomeric effect
Resonance

Resonating
Resonance hybrid
Structures
 Pi alternate pi

Example :

:
:
Benzene
Pi alternate positive charge

Example :
Pi alternate negative charge

Example :
Pi alternate odd electron

Example :
Lone pair alternate positive charge

Example :
 I Cl
II Cl

III Cl IV Cl
Among these compounds, which one has shortest C - Cl bond?

A I

B II

C III

D IV
 I Cl
II Cl

III Cl IV Cl
Among these compounds, which one has shortest C - Cl bond?

A I

B II

C III

D IV
Solution:

In, I resonance can occur so partial double bond character

will be there, Hence, it will have shortest C - Cl bond length.

Cl ⊝ ⊕
Cl
Give the order of stability of following resonating structures:

A I > II > III > IV > V

B I > III > II > IV > V

C III > II > I >IV > V

D I > II > V > IV > III

Give the order of stability of following resonating structures:

A I > II > III > IV > V

B I > III > II > IV > V

C III > II > I >IV > V

D I > II > V > IV > III

Solution:

In (I), there are maximum number of Pi bonds. Therefore, it is most stable, in

(II) and (V), the number of pi bonds is equal but charge separation is greater
in (V). Therefore, (II) is more stable than (V). In (III) and (IV), there is
maximum charge separation but (III) is highly unstable due to electrostatic
repulsion. order of stability is I > II > V > IV > III
Q: The correct stability order for the following species is

A (II) > (IV) > (I) > (III)

B (I) > (II) > (III) > (IV)

C (II) > (I) > (IV) > (III)

D (I) > (III) > (II) > (IV)

Q: The correct stability order for the following species is

A (II) > (IV) > (I) > (III)

B (I) > (II) > (III) > (IV)

C (II) > (I) > (IV) > (III)

D (I) > (III) > (II) > (IV)

Solution :
Hyperconjugation

Delocalization of conjugated (C–H) sigma electrons with

-bond or positive charge or free radical is called
hyperconjugation or H-effect.
Hyperconjugation
Hyperconjugation
Find the order of stability of following alkenes:

A II > III > I

B I > II > III

C III > II > I

D I > III > II

Find the order of stability of following alkenes:

A II > III > I

B I > II > III

C III > II > I

D I > III > II

Solution :

4α-H′S
7α-H′S
3α-H′S
Thus the order of stability = II > III > I
In which of the following alkenes hyperconjugation is
not possible?

A B

C H2C = CH2 D
In which of the following alkenes hyperconjugation is
not possible?

A B

C H2C = CH2 D
Aromatic compounds

Huckel’s rule

Characteristics for ring being aromatic-

❖ Planarity (2-D) [sp2 carbon]
❖ Conjugated system (de-localisation of 𝜋 e-in ring)
❖ Cyclic
❖ Presence of (4n + 2)𝜋 e- in the ring. Where,
n = 0, 1, 2, 3...
Aromatic compounds
Anti-aromatic compounds

❖ Cyclic
❖ Planar
❖ Conjugated System
❖ 4n𝜋 e- should present in the ring where
(n = 1 2,3,...)

Cyclobutadiene
(n = 1 ⇒ 4𝜋e-)
(Highly Unstable)
Non-aromatic compounds

Compounds which are neither aromatic non-antiaromatic

Stability order of compounds :

Aromatic > non aromatic > Anti - Aromatic

Which of the following is least stable?

A B
N

C D
O
Which of the following is least stable?

A B
N

C D
O
Solution:

● Cyclic

● Non-conjugated

● Non-aromatic
Which compound (s) out of the following is/are not aromatic?

⊕ ⊕
(I) (II) (III) (IV)

A (II), (III) and (IV)

B (III) and (IV)

C (II)

D (I) and (III)

Which compound (s) out of the following is/are not aromatic?

⊕ ⊕
(I) (II) (III) (IV)

A (II), (III) and (IV)

B (III) and (IV)

C (II)

D (I) and (III)

Solution:

is aromatic; (4 ⨉ 0 + 2) = 2 𝜋e- in conjugation

⊕

and are antiaromatic

⊕
4𝜋e- 8𝜋e-

Is non aromatic due to the presence of sp3 carbon.

Acidity

For an acid HA(aq) ⇌ H+(aq) + A–(aq)

From law of mass action, Ka = [H+(aq)][A–(aq)]

[HA]
Where, Ka ⟶ Acidity constant, or dissociation constant
of acid

Ka ⟶ Explain the strength of acid

pKa = –log Ka, Ka ∝ Acidic strength ∝ 1/pKa

pH = –log [H+]

Acidic strength ∝ stability of conjugate base ∝ –M effect

∝ 1/+M ∝ –I ∝ 1/+I
Acidity
Acidity
Acidity
The correct order of acid character of the following compounds is

A IV > III > II > I

B II > III > IV > I

C I > II > III > IV

D III > II > I > IV

The correct order of acid character of the following compounds is

A IV > III > II > I

B II > III > IV > I

C I > II > III > IV

D III > II > I > IV

Solution :
Acidic strength

Since carboxylic acids are more acidic than phenols.

–I and – R effect increase the acidic strength where as +I and +R
effect decrease the acidic strength of carboxylic acids.
The increasing order of the acidity of the α-hydrogen of the
following compounds is :

A (C) < (A) < (B) < (D)

B (B) < (C) < (A) < (D)

C (A) < (C) < (D) < (B)

D (D) < (C) < (A) < (B)

The increasing order of the acidity of the α-hydrogen of the
following compounds is :

A (C) < (A) < (B) < (D)

B (B) < (C) < (A) < (D)

C (A) < (C) < (D) < (B)

D (D) < (C) < (A) < (B)

Solution :
Acidity ∝ stability of conjugate base

(Stability of conjugate bases)

Basicity
For an base, BOH(aq) ⇌ B+(aq) + OH–(aq)

From law of mass action, Kb = [B+(aq)][OH–(aq]

[BOH]
Where, Kb ⟶ Basicity constant, or dissociation constant
of base

Kb ⟶ Explains the strength of base

Kb ∝ Basic strength ∝ 1/pKb

pKb = –log Kb

pOH = –log [OH–]

basic strength ∝ +M ∝ 1/–M ∝ + I ∝ 1/–I

Basicity
Basicity
Basicity
Consider the basicity of the following aromatic amines:
(i) aniline (ii) p-nitroaniline
(iii) p-methoxyaniline (iv) p-methylaniline
The correct order of decreasing basicity is:

A III > IV > I > II

B III > IV > II > I

C I > II > III > IV

D IV > III > II > I

Consider the basicity of the following aromatic amines:
(i) aniline (ii) p-nitroaniline
(iii) p-methoxyaniline (iv) p-methylaniline
The correct order of decreasing basicity is:

A III > IV > I > II

B III > IV > II > I

C I > II > III > IV

D IV > III > II > I

Solution:

I II III IV
NH2 NH2 NH2 NH2

NO2 OCH3 CH3

-M +M +I
Order : III > IV > I > II
Which of the following is least basic?

D
Which of the following is least basic?

D
Solution :
Basic strength ∝ availability of lone pair.

..
In this case lone pair of N is highly participating in resonance.
LEVEL-1
In the following structure, the double bonds are marked as I, II,
III and IV
Geometrical isomerism is not possible at site (s):

II A III

III
B I
I IV

C I and III

D III and IV
In the following structure, the double bonds are marked as I, II,
III and IV
Geometrical isomerism is not possible at site (s):

II A III

III
B I
I IV

C I and III

D III and IV
Solution :

a H
Hb
I
a a
Both are same
(Isomer not possible)
The correct order of acid strength of
compounds
CH☰CH, CH3–C☰CH and CH2=CH2 is as
follows

A CH3–C☰CH > CH☰CH > CH2=CH2

B CH3–C☰CH, CH2=CH2 > HC☰CH

C HC☰CH > CH3–C☰CH > CH2=CH2

D CH☰ CH > CH2=CH2 > CH3–C☰CH

The correct order of acid strength of
compounds
CH☰CH, CH3–C☰CH and CH2=CH2 is as
follows

A CH3–C☰CH > CH☰CH > CH2=CH2

B CH3–C☰CH, CH2=CH2 > HC☰CH

C HC☰CH > CH3–C☰CH > CH2=CH2

D CH☰ CH > CH2=CH2 > CH3–C☰CH

Solution : (C)
Acidic strength ∝ Stability of conjugate base
E.N. → sp carbon > sp2 carbon > sp3 carbon
Q- The compound most likely to lose water on protonation is

A B

C D
The compound most likely to lose water on protonation is

A B

C D
Solution :
Q: Arrange the following compounds in order of decreasing acidity :

A II > IV > I > III

B I > II > III > IV

C III > I > II > IV

D IV > III > I > II

Arrange the following compounds in order of decreasing acidity :

A II > IV > I > III

B I > II > III > IV

C III > I > II > IV

D IV > III > I > II

Solution:

Electron releasing group decreases and electron withdrawing

group increases acidic strength.
Arrange the following amines in
the decreasing order of basicity :

A I > III > II

B III > I > II

C III > II >I

D I > II > III

Arrange the following amines in
the decreasing order of basicity :

A I > III > II

B III > I > II

C III > II >I

D I > II > III

Solution : (B)
Which of the following orders is correct for the stability of
these carbocations ?

A I > II > III

B III > II > I

C II > III > I

D III > I > II

Which of the following orders is correct for the stability of
these carbocations ?

A I > II > III

B III > II > I

C II > III > I

D III > I > II

Solution :
Correct order is

Hence, option (a) is correct.

Which of the following is least stable?

A I

B II

C III

D None
Which of the following is least stable?

A I

B II

C III

D None
Solution :
In I and III, Nitrogen holds negative charge in its resonance structures.
Negative charge on most electronegative atom is more stable. But in II
it is not possible.Hence, II is least stable. Option b is correct.
Q: Among

the compound which is not aromatic is

A i

B ii

C iii

D iv
Among

the compound which is not aromatic is

A i

B ii

C iii

D iv
Solution :
Q- Which of the following is the strongest base?

A B

C D
Which of the following is the strongest base?

A B

C D
Solution:

Lone pairs of Nitrogen are not taking part in conjugation

whereas in other options lone pairs are taking part in
conjugation.
LEVEL-2
Q- The correct order of acidity for the following compounds is

A I > II > III > IV

B III > I > II > IV

C III > IV > II > I

D I > III > IV > II

The correct order of acidity for the following compounds is

A I > II > III > IV

B III > I > II > IV

C III > IV > II > I

D I > III > IV > II

Solution:

Due to ortho effect, ortho substituted benzoic acid is more

acidic than meta & para isomers.
In the following carbocation; H/CH3 that is most likely to
migrate to the positively charged carbon is

A CH3 at C-4

B H at C-4

C CH3 at C-2

D H at C-2
In the following carbocation; H/CH3 that is most likely to
migrate to the positively charged carbon is

A CH3 at C-4

B H at C-4

C CH3 at C-2

D H at C-2
Solution :
Which of the following orders is correct for the stability
of these carbocations ?

A I > II > III

B III > II > I

C II > I > III

D II > III > I

Which of the following orders is correct for the stability
of these carbocations ?

A I > II > III

B III > II > I

C II > I > III

D II > III > I

Solution :
Positive charge on bridged carbon is unstable. Thus,the order of stability
is II > III > I. Hence, option (d) is correct.
With respect to the compounds I-V, choose the incorrect
statement(s).

A The acidity of compound I is due to delocalization in the conjugate

base.

B The conjugate base of compound IV is aromatic.

C Compound II becomes more acidic, when it has a -NO2

substituent.

D The acidity of compounds follows the order I > IV > V > II > III.
With respect to the compounds I-V, choose the incorrect
statement(s).

A The acidity of compound I is due to delocalization in the conjugate

base.

B The conjugate base of compound IV is aromatic.

C Compound II becomes more acidic, when it has a -NO2

substituent.

D The acidity of compounds follows the order I > IV > V > II > III.
Solution :
Select the basic strength order of following molecules ?

A (IV) > (I) > (III) > (IV)

B (III) > (I) > (IV) > (II)

C (II) > (I) > (III) > (IV)

D (I) > (III) > (II) > (IV)

Select the basic strength order of following molecules ?

A (IV) > (I) > (III) > (IV)

B (III) > (I) > (IV) > (II)

C (II) > (I) > (III) > (IV)

D (I) > (III) > (II) > (IV)

Solution :
(I) sp3 'N', (III) sp3 'N' and – I effect, (II) sp2 'N' , (IV) Aromaticity (lp
delocalised)
Q-The most acidic hydrogen in the following molecule is

A I

B II

C III

D IV
The most acidic hydrogen in the following molecule is

A I

B II

C III

D IV
The most acidic hydrogen in the following molecule is

Solution :
The conjugate base of II OH is resonance stabilized.
Correct order of basicity of various nitrogen in

A 1>2>3

B 2>1>3

C 2>3>1

D 3>2>1
Correct order of basicity of various nitrogen in

A 1>2>3

B 2>1>3

C 2>3>1

D 3>2>1
Solution :

N (1) will be least basic because its L.P. will participate

in resonance on both sides. In N(2) no, resonance is present so it will be
most basic. In N (3) resonance is present but two ethyl groups will
provide electrons through +I effect. So, option c is correct.
Write the correct order of basic strength ?

1 2 3 4

A 3>4>1>2 B 2>4>3>2

C 3>1>4>2 D 2>4>1>3
Write the correct order of basic strength ?

1 2 3 4

A 3>4>1>2 B 2>4>3>2

C 3>1>4>2 D 2>4>1>3
Solution:
Isomerism
Isomerism
Structural Isomers

❏ Chain isomerism :

It arises due to difference in the arrangement of the carbon atoms

constituting the chain.

For example: Butane and 2-methylpropane are chain isomers.

C C C C C C C
C
butane 4C 2 – methyl propane 3C
 Unsaturation Number

The presence of rings or double bonds within a molecule is

indicated by a quantity called the unsaturation number of a
hydrocarbon.

Where: C → Total number of tetravalent atoms

H → Total number of monovalent atoms
N → Total number of trivalent atoms
Calculate the unsaturation number of the following
compound C5H6Br2

A 1

B 2

C 3

D 4
 Calculate the unsaturation number of the following
compound C5H6Br2

A 1

B 2

Solution : C 3

D 4
U=2
 Position Isomers

Compounds having the same molecular formula but

different in position substituents, C = C, C ≡ C or
functional group are called position isomers.

Example:
 Functional isomers

It is observed due to the presence of different

functional groups in a molecule
 Metamerism

The Compounds having same molecular formula but different

structural formulae due to different nature of alkyl groups
present on either side of the polyvalent functional group are
called Metamers and the phenomenon is known as
Metamerism.

Polyvalent functional groups which shows metamerism

are – O –, – S –, – NH –, – N – , and – CO – etc.
 Metamerism

Examples:
The number of structural isomers for C6H14 is:

A 4

B 3

C 6

D 5
The number of structural isomers for C6H14 is:

A 4

B 3

C 6

D 5
Solution :
 Tautomerism

The type of functional isomerism in which a substance exists

in two readily interconvertible different structures leading to
dynamic equilibrium is known as Tautomerism and the
different forms are called Tautomers.
 Tautomerism

Example:
Keto-enol Tautomerism.

Acid-Base Theory: W.A. S.A.

Thermodynamics: More stable Less stable
 Tautomerism

The interconversion of the tautomers can be catalyzed by either by acid or base.

❖ Base-catalyzed keto-enol interconversion.

(Keto) (Enolate ion) (Enol)

 Tautomerism

❖ Acid-catalyzed keto-enol interconversion.

(Keto (Enol)
)
 Tautomerism

Keto-enol tautomerization :

Keto Enol The energy released during formation of

bonds of keto form is much higher than
enol, thus in general thermodynamically
(W.A) (S.A)
keto form is more stable than enol
form.
Conditions for Tautomerism

❏ Compound should have at least one α H, that is H attached to α – C

❏ 𝛼H should be present on a sp3 hybridised atom.

KETO ENOL

C−H O−H

C＝O C＝C

C−C C−O

❏ Compound should have electron withdrawing

 Conditions for Tautomerism

❏ Compound should have electron withdrawing

Which of the following compounds will show the maximum
‘enol’ content?

A CH3COCH2COOC2H5

B CH3COCH2COCH3

C CH3COCH3

D CH3COCH2CONH2
Which of the following compounds will show the maximum
‘enol’ content?

A CH3COCH2COOC2H5

B CH3COCH2COCH3

C CH3COCH3

D CH3COCH2CONH2
Solution :

Enol content ∝ Acidity of active methylene hydrogens.

O O
|| ||
CH3 ー C ー CH ー C ー CH3
|
H} (Most acidic hydrogen)
Maximum enol content
 Stereoisomerism

Compounds having same molecular formula, same connectivity and

structural formula but differ due to spatial arrangement of group or atom are
said to be stereo isomers and phenomenon is termed as stereoisomerism.
Geometrical Isomerism

The different arrangement of

atoms in a space remains fixed due to
restricted rotation of double bond
Geometrical Isomerism

cis-1,2-dibromocyclopentane

trans-1,2-dibromocyclopentane
How many cyclic isomers exists(structural and geometrical only) for
C3H3Cl3?

A 2

B 4

C 3

D 5
How many cyclic isomers exists(structural and geometrical only) for
C3H3Cl3?

A 2

B 4

C 3

D 5
Solution:
 CIP Rule

Rule -1:

Atom of first point of attachment having higher atomic number is

given highest priority

Example: I > Br > Cl > S > F > O > N > C > H

Rule -2:

If two isotopic atoms are present then the isotope

of higher mass number is priorities over other

Example: –T > –D > – H.

Rule -3:

If the atom of the first point of attachment is same go to

the next atom to find the difference and so on…

Example: –CH2Cl > –CH2OH > –CH2NH2 > –CH2CH3 > –CH3
 CIP Rule

Rule -4:

The doubly bonded atom is considered to be duplicated and

triply bonded atom is considered to be triplicated
 E/Z Nomenclature

● To Assign an E, Z configuration, first assign a priority to the

substituents on each carbon of the double bond.

● If the groups of higher priority are on the same side of the

double bond, the configuration is Z (German: zusammen,
together).

● If the groups of higher priority are on opposite sides of the

double bond, the configuration is E (German: entgegen,
opposite).
E/Z Nomenclature
 E/Z Nomenclature

Priority groups on opposite Priority groups on same

sides E configuration side Z configuration
Identify the following molecules as E or Z isomers.

A I= E, II=Z

B I= Z, II=E

C I= Z, II=Z

D I= E, II=E
Identify the following molecules as E or Z isomers.

A I= E, II=Z

B I= Z, II=E

C I= Z, II=Z

D I= E, II=E
Number of Geometric Isomers
LEVEL-1
Which of the following compound will not undergo tautomerism?

A B

C D
Which of the following compound will not undergo tautomerism?

A B

C D
Solution:
How many cycloalkene isomers exist for C5H8 which contain at
least one methyl locant directly present on the ring?

A 2

B 4

C 5

D 6
How many cycloalkene isomers exist for C5H8 which contain at
least one methyl locant directly present on the ring?

A 2

B 4

C 5

D 6
Solution:
How many minimum no. of C-atoms are required for position &
geometrical isomerism in alkene?

A 4,3

B 4,4

C 3,4

D 3,3
How many minimum no. of C-atoms are required for position &
geometrical isomerism in alkene?

A 4,3

B 4,4

C 3,4

D 3,3
Solution :
The E-isomer among the following is

A B

C D
The E-isomer among the following is

A B

C D
Solution:
Which is the metamer of the compound P?

A B

C D
Which is the metamer of the compound P?

A B

C D
Geometrical isomerism is possible in :

A B

C D
Geometrical isomerism is possible in :

A B

C D
Geometrical isomerism is possible in :

Solution :
Which of the following compounds is isomeric with methyl
vinyl ether?

A Propanal

B 1-propanol

C Ethyl methyl ether

D Ether
Which of the following compounds is isomeric with methyl
vinyl ether?

A Propanal

B 1-propanol

C Ethyl methyl ether

D Ether
Which of the following compounds is isomeric with methyl
vinyl ether?

Solution :
Tautomerism is not exhibited by :

A B

C D
Tautomerism is not exhibited by :

A B

C D
Tautomerism is not exhibited by :
LEVEL-2
Which of the following will form geometrical isomers?

A B

C D
Which of the following will form geometrical isomers?

A B

C D
 Which of the following will form geometrical isomers?

Solution:
Number of structural isomers of compound having molecular
formula C4H7Cl is:

A 4

B 8

C 12

D 16
Number of structural isomers of compound having molecular
formula C4H7Cl is:

A 4

B 8

C 12

D 16
Solution:
Solution:
The most stable enolic form of 2, 4-pentanedione is

A B

C D
The most stable enolic form of 2, 4-pentanedione is

A B

C D
The most stable enolic form of 2, 4-pentanedione is

Solution:
The number of isomers for the compound with
molecular formula C2BrClFl is

A 6

B 5

C 4

D 3
The number of isomers for the compound with
molecular formula C2BrClFl is

A 6

B 5

C 4

D 3
Solution
Number of geometrical isomers in the following compound
CH3 – CH = CH – CH = CH – C2H5 is

A 4

B 3

C 2

D 5
Number of geometrical isomers in the following compound
CH3 – CH = CH – CH = CH – C2H5 is

A 4

B 3

C 2

D 5
Solution :

H H H CH = CH − C2H5
C=C C=C
CH3 CH = CH − C2H5 CH3 H

CH3− CH = CH H H H
C=C C=C
H C2H5 CH3− CH = CH C2H5

Since the number of double bonds in the given compound is 2 and the ends
are different (i.e., CH3 and C2H5), therefore the total number of geometrical
isomers are 22 = 4.
HYDROCARBON
Methods of preparation of alkane
Methods of preparation of alkane
CHEMICAL PROPERTIES OF ALKANES

Substitution Reaction:

Halogenation- The characteristics reaction of alkanes are

free radical substitution reaction (F.R.S.R)
CHEMICAL PROPERTIES OF ALKANES

Isomerisation:
Normal alkane when heated (200°C) in the presence of AlCl3
and HCl gives branched alkanes
CHEMICAL PROPERTIES OF ALKANES

Aromatisation or Reforming or Hydroformation:

n-Hexane and onwards on aromatisation in the presence of
Cr2O3 or Al2O3 or MoO3 at 500°C and 15 atm gives benzene and
its derivatives.
CHEMICAL PROPERTIES OF ALKANES

Carbene Insertion:
• The lower alkanes are converted into higher homologues.
• Reagent: diazomethane or ketene acts as insertion reagent.
CHEMICAL PROPERTIES OF ALKANES

Oxidation
CHEMICAL PROPERTIES OF ALKANES

Pyrolysis or Cracking: The decomposition of a compound by heat

is called pyrolysis. When pyrolysis occurs in alkanes,the process
is termed cracking.
1-Bromo-3-chloro cyclobutane on reaction with
2-equivalent of sodium in ether gives

D
1-Bromo-3-chloro cyclobutane on reaction with
2-equivalent of sodium in ether gives

D
1-Bromo-3-chloro cyclobutane on reaction with
2-equivalent of sodium in ether gives

Solution :
Methods of preparation of alkene
CHEMICAL PROPERTIES OF ALKENES

HBr/peroxide
CHEMICAL PROPERTIES OF ALKENES
CHEMICAL PROPERTIES OF ALKENES

O3/H2O2
The major product formed in the following reaction is :

A B

C D
The major product formed in the following reaction is :

A B

C D
Solution:
For the given reaction :

What is 'A'?

A B

C
D CH3CH2CH2NH2
For the given reaction :

What is 'A'?

A B

C
D CH3CH2CH2NH2
Solution :
Methods of preparation of alkyne
Methods of preparation of alkyne
CHEMICAL PROPERTIES OF ALKYNES
CHEMICAL PROPERTIES OF ALKYNES
The major product in the following reaction is –

A B

C D
The major product in the following reaction is –

A B

C D
Solution :
Methods of preparation of Benzene
Methods of preparation of Benzene
 Substitution Reactions

❖ Halogenation :

Cold, dark FeCl3

Cl+ Cl + HCl
+

FeCl3 + Cl2 ⟶ FeCl4- + Cl+

 Nitration

❖ Nitration :

● HNO3 alone is a weak nitrating agent whereas the mixture of

concentrated HNO3 and concentrated H2SO4 is strong nitrating
mixture.
● In this mixture HNO3 acts as base
 Substitution Reactions
❖ Sulphonation :

Δ
+ H2SO4
SO3H + H2O
 Substitution Reactions

❖ Introduction of alkyl and acyl groups in presence of Catalysts :

AlCl3 FeCl3 SbCl3 (acting as Lewis acids) or protonating agents
like HF,
H2SO4, H3PO4 etc. These are known as Friedel Craft reactions.
❖ Alkylation :
 Substitution Reactions

❖ Acylation :

+ R-COCl ⟶
COR + HCl
Acyl chloride

RCOCl + AlCl3 ⟶ R AlCl4-

+ +
C
Acylium ion is Electrophile
In the following reactions, X,Y and Z are

A X = CH3Cl;Y = anhydrous AlCl3; Z = HNO3 + H2SO4

B X = CH3COCl;Y = anhydrous AlCl3; Z = HNO3 + H2SO4

C X = CH3Cl;Y = conc. H2SO4; Z = HNO3 + H2SO4

D X = CH3Cl; Y = dil. H2SO4; Z = HNO3

In the following reactions, X,Y and Z are

A X = CH3Cl;Y = anhydrous AlCl3; Z = HNO3 + H2SO4

B X = CH3COCl;Y = anhydrous AlCl3; Z = HNO3 + H2SO4

C X = CH3Cl;Y = conc. H2SO4; Z = HNO3 + H2SO4

D X = CH3Cl; Y = dil. H2SO4; Z = HNO3

Solution :
LEVEL-1
The trans-alkenes are formed by the reduction of alkynes with

A H2-Pd/C, BaSO4

B NaBH4

C Na/liq. NH3

D Sn-HCl
The trans-alkenes are formed by the reduction of alkynes with

A H2-Pd/C, BaSO4

B NaBH4

C Na/liq. NH3

D Sn-HCl
Solution:

Sodium metal in liquid ammonia reduces alkynes with anti

stereochemistry to give trans alkenes. The reduction is
selectively anti since the vinyl radical formed during reduction
is more stable in trans configuration.
The reagent(s) for the following conversion,

is are

A alcoholic KOH

B alcoholic KOH followed by NaNH2

C aqueous KOH followed by NaNH2

D Zn/CH3OH
The reagent(s) for the following conversion,

is are

A alcoholic KOH

B alcoholic KOH followed by NaNH2

C aqueous KOH followed by NaNH2

D Zn/CH3OH
Solution:
2,3-Dimethylbut-2-ene when reacted with bromine
forms a compound which upon heating with alcoholic
KOH produce the following major product.

A B

C D
2, 3-Dimethylbut-2-ene when reacted with bromine
forms a compound which upon heating with alcoholic
KOH produce the following major product.

A B

C D
Solution :
An organic compound A(C4H9Cl) on reaction with Na/ether gives a
hydrocarbon which on monochlorination gives only one chloro
derivative then A is

A t-butyl chloride

B sec-butyl chloride

C isobutyl chloride

D n-butyl chloride
An organic compound A(C4H9Cl) on reaction with Na/ether gives a
hydrocarbon which on monochlorination gives only one chloro
derivative then A is

A t-butyl chloride

B sec-butyl chloride

C isobutyl chloride

D n-butyl chloride
Solution:
CH3Cl → CH4
Above conversion can be achieved by :

A Zn / H+ B LiAlH4

C Mg / (ether) then H2O D all of these

CH3Cl → CH4
Above conversion can be achieved by :

A Zn / H+ B LiAlH4

C Mg / (ether) then H2O D all of these

Solution:
Major product (A) is :

A B

C D
Major product (A) is :

A B

C D
Solution:
Anti-Markovnikoff’s rule
Identify A in the given chemical reaction :

A B

C D
Identify A in the given chemical reaction :

A B

C D
Solution:

n–Alkanes having six or more carbon atoms on heating

to 773 K at 10–20 atmospheric pressure in the presence
of oxides of vanadium, molybdenum or chromium
supported over alumina get dehydrogenated and
cyclised to benzene and its homologues.
The major product formed in the oxidation of acetylene
by alkaline KMnO4 is

A ethanol

B acetic acid

C formic acid

D oxalic acid
The major product formed in the oxidation of acetylene
by alkaline KMnO4 is

A ethanol

B acetic acid

C formic acid

D oxalic acid
Solution :
Q-16: Which compound would give 5-keto-2-methyl hexanal upon
ozonolysis?

A B

C D
Which compound would give 5-keto-2-methyl hexanal upon
ozonolysis?

A B

C D
Solution:
Q- In the reaction of 1-bromo-3-Chlorocyclobutane with
two equivalents of sodium in ether, the major product is

A B

C D
In the reaction of 1-bromo-3-Chlorocyclobutane with
two equivalents of sodium in ether, the major product is

A B

C D
Solution :
A compound X formed after heating coke with lime
reacts with water to give Y which on passing over
red-hot iron at 873 K produces Z. The compound Z is :

A B

C D
A compound X formed after heating coke with lime
reacts with water to give Y which on passing over
red-hot iron at 873 K produces Z. The compound Z is :

A B

C D
Solution :
LEVEL-2
Q-The increasing order of the boiling point of the major
products A, B and C of the following reactions will be:

(A) (B)

(C)
The increasing order of the boiling point of the major
products A, B and C of the following reactions will be:

(A) (B)

(C)

A B<C<A

B C<A<B

C A<B<C

D A<C<B
Solution :

The boiling points of isomeric haloalkanes decreases with

increase in branching.
So order of B.P. is A > C > B.
Q- The major product [B] in the following sequence of
reactions is:

A B

C D
The major product [B] in the following sequence of reactions
is:

A B

C D
Solution :
In which of the following reactions, alkanes containing the same number
of carbons as the substrate are obtained?

Codes is:

A b, c, d

B c, d, e

C a, d, e

D a, e, c
In which of the following reactions, alkanes containing the same number
of carbons as the substrate are obtained?

Codes is:

A b, c, d

B c, d, e

C a, d, e

D a, e, c
Solution:
Product (C) of the reaction is :

A B

C D
Product (C) of the reaction is :

A B

C D
Solution:
Relation between A and B, C and D are :

A Position, chain B Position, Functional

C Chain, Identical D Metamer, Functional

Relation between A and B, C and D are :

A Position, chain B Position, Functional

C Chain, Identical D Metamer, Functional

Solution:
IUPAC Nomenclature
 ORGANIC COMPOUND

Open chain/ Acyclic/ Aliphatic Closed chain/ Ring chain/Cyclic

Straight Branched
Alicyclic Aromatic
chain chain

Hetero Alicyclic Homoaromatic Heteroaromatic

n - Pentane isopentane

Homoalicyclic
Tetrahydro
Benzene Pyridine
Furan

Cyclohexane
International Union of Pure and Applied Chemistry
 IUPAC

Secondary prefix + Primary prefix + Word root + Primary suffix + Secondary suffix
 IUPAC : Straight Chain Hydrocarbons
The names of straight chain hydrocarbons consist of word root and primary suffix.

Number of Carbon Number of Carbon

Word root Word root
Atoms Atoms
C1 Meth C7 Hept
C2 Eth C8 Oct
C3 Prop C9 Non
C4 But C10 Dec
C5 Pent C11 Undec
C6 Hex C12 Dodec
 Nomenclature of Branched Chain Alkanes:

Certain rules the branched chain hydrocarbons can be named without any difficulty.

❏ Longest Chain Rule

❏ Lowest Number Rule

❏ Alphabetical Order of the Side Chain

❏ Numbering of Different Alkyl Groups at Equivalent Positions

❏ Naming the Hydrocarbon with Complex Substituent

❏ First point of difference Rule
 Rules for naming the compound :

Rule 1 : Select the longest continuous (need not be straight) chain of carbon
Atoms, such that it include the functional group (if contain) i.e. 20 suffix
Example :
C C C

C C C C C C C C C C C C C C C C C C

C C C
Longest chain ⇒ 8 C
Longest chain ⇒ 9 C
 Rules for naming the compound :

Rule 2 : Assign the number to the carbon atoms of the longest chain such that
the substituent receives the lowest possible number irrespective of their
nature.
Example 1 :
 Rules for naming the compound :

If two different substituents (let’s say methyl and ethyl) are at the equivalent
position, then numbering should be done in such a way that alphabetically
preferred substituent should receive the lowest number
Example :

1 2 3 4 5 6 7 8 9
C C C C C C C C C
9 8 7 6 5 4 3 2 1

C C C
m e
L – R : 3 – Methyl, 7 - ethyl

R – L : 3 – Ethyl, 7 - methyl

IUPAC name : 3 - Ethyl - 7 - methylnonane

 Rules for naming the compound :

Rule 4:

When a molecule contain two or more identical substituents, use numerical prefix such
as di, tri, tetra etc. for two, three, four substituents respectively, however their initial
alphabet shouldn't be considered for ordering the substituents in the final naming
m C
1 2 3 4 5 6 7 8 9
C C C C C C C C C
9 8 7 6 5 4 3 2 1

C C C
e m

L–R:377 R–L:337
7 – Ethyl – 3, 3 - dimethylnonane
Identify an alkane among the following

A C3H6

B C8H14

C C7H16

D C4H6
Identify an alkane among the following

A C3H6

B C8H14 Solution:

C C7H16 C3H6 - alkene

C8H14 - alkyne
D C4H6
C7H16 - alkane
C4H6 - alkyne
Assign IUPAC name to the following compound

A 2,4 - diethyl – 2– methyl hexane

B 4 - Ethyl – 3, 3– dimethyl nonane

C 4 - Ethyl – 5, 5 – dimethyl heptane

D 4 - Ethyl – 3, 3 – dimethyl heptane

Assign IUPAC name to the following compound

A 2,4 - diethyl – 2– methyl hexane

B 4 - Ethyl – 3, 3– dimethyl nonane

C 4 - Ethyl – 5, 5 – dimethyl heptane

D 4 - Ethyl – 3, 3 – dimethyl heptane

Assign IUPAC name to the following compound

Solution :
e

6 2
4 3
7 5 1
m m

4 - Ethyl – 3, 3 – dimethylheptane
Naming of compound containing one or more
functional groups

👉A longest continuous chain of C – atom is to be selected in such a way that

it contains / includes as many functional group and the numbering of C-
atoms is to be done in such a way that functional group receives lowest
possible no.

👉In case of polyfunctional compound one of the functional group is chosen

as a principle functional group (based on their priority order) which is to be
treated as a suffix and rest all are to be treated as a prefix.
👉If the organic compound contains a functional group , multiple bond , side
chain or substituent , the following order of preference must be followed:

Functional groups > Double Bond > Triple Bond > Side chain
 Prefix and suffix names of various functional groups
Functional Formula Prefix Suffix
groups

Acid halide Halo carbonyl carbonyl halide

–– oyl halide

Alcohols ––OH Hydroxy ol

Aldehydes Formyl carbaldehyde

oxo al
Functional Formula Prefix Suffix
groups

Amides Carbamoyl carboxamide

– amide

Amines –NH2 Amino amine

Carboxylic Carboxy carboxylic acid
acid

oic acid
–
 Functional Formula Prefix Suffix
groups

Ethers Alkoxy ––

Ester Alkoxy carbonyl Alkyl ..carboxylate

– Alkyl …alkanoate

Ketone oxo one

Cyano
carbonitrile
cyanides/ Nitrile –
nitrile
 Functional Formula Prefix Suffix
groups

Sulphonic acid –SO3H Sulpho Sulphonic acid

Thiol –SH Sulfamyl thiol

Order of priority of various functional groups
 Exercise

1. ⇒ Pent + ane + oic acid

5 4 3 2 1 Pentanoic acid
2.

3.

4.
 m
2. = 2 –Methylbutanoic acid

4 3 2 1

6
3. 5 7 1
6 2 1 = Cyclohexane carboxylic acid
5 3 2
4 4
3

4. = But – 2 – enal
1 4
2 3
 5.

6.

7.
5. = Pent an – 3 – one
1 2 3 4 5

6. = Pent – 2 – one
5 4 3 2 1

2 1
5 4 3
7. = Pent – 3 – yn – 1 – ol
8.

9.
 4 1
5 3 2
8. = 4 – Bromo pent – 2 – en – 1 – ol

2
4 3 1
9. = 3 – Oxobutanoic acid
 Alkene and alkyne & their relative priorities and as a substituents :

2 4
4 3 5 L – R : 1, 5 Hex – 1 – en – 5 – yne
5
1 3 2
6 6
R – L : 1, 5
1

Chain selection rule :

1. Select a chain which contain maximum number of double bonds or triple
bonds
2. If two chains are competing for selection with equal no. of multiple bonds
then choice goes to
a. The chain with greater no. of c-atoms
b. If the no. of c – atoms in the chain are equal then the chain with more
no. of double bond is priorities
 Alkene and alkyne & their relative priorities and as a substituents :

Example 1

Example 2
 Alkene and alkyne & their relative priorities and as a substituents :

Example 1
e

8 6 1
5 3 – Ethyl – 4 – propylocta – 1 – 3 – dien – 7 – yne
3
7 4 2

Example 2

6 5
9 7 1
4 3
2 4 – vinylnon – 1 – en – 6 - yne
8
Ethenyl /
vinyl 4 – Ethenylnon – 1 – en – 6 - yne
Assign IUPAC name to the following compound

A 5-Methylhex-2-yne

B 2-Methylhex-4-yne

C 5-Methylhex-3-yne

D 2-Methylhex-3-yne
Assign IUPAC name to the following compound

A 5-Methylhex-2-yne

B 2-Methylhex-4-yne

C 5-Methylhex-3-yne

D 2-Methylhex-3-yne
Assign IUPAC name to the following compound

Solution :

1 2 3 4 5 6
H3C C C CH2 CH CH3

CH3 m

5-Methylhex-2-yne
 Naming of Cyclic Compounds :

⇒ Alphabetical order of Numbering:

 Naming of Cyclic Compounds :

⇒ More branched carbon gets lower number

 Nomenclature of Substituted Benzene Compounds

Monosubstituted Benzene Compounds:

Naming the substituted benzene compounds, the prefix used for the substituent is
prefixed to the word ‘benzene’ simply.
 Ortho / Meta / Para positions in monosubstituted benzene

X / FG
ortho ortho
Note : ortho, meta, para naming is used
meta only for disubstituted benzene
meta
Examples : para
Br
Br
Br
Br

Br
Br
1,2-dibromobenzene 1,3-dibromobenzene 1,3-dibromobenzene

OR OR OR

o-Dibromobenzene m-Dibromobenzene p-Dibromobenzene

Write bond line formulas for: Isopropyl alcohol.

A B

C D
Write bond line formulas for: Isopropyl alcohol.

A B

C D
Write bond line formulas for: Isopropyl alcohol.

Solution :

Name Bond line formula

Isopropyl alcohol
PRACTICE
Q- The IUPAC name of the following compound is :

A 2,5,6-trimethylheptane

1,3-isopropyl-3-methylpropane
B

C 2,6,3-trimethylheptane

D 2,3,6-trimethylheptane
Q- The IUPAC name of the following compound is :

A 2,5,6-trimethylheptane

1,3-isopropyl-3-methylpropane
B

C 2,6,3-trimethylheptane

D 2,3,6-trimethylheptane
Solution:

Name the longest C chain using the Lowest Locant Rule.

So, according to IUPAC Nomenclature the compound is named as 2,3,6-

trimethylheptane.
Q- The IUPAC name of

A 4-Bromo-3-chloro-6-nitro heptane

B 6-Bromo-5-chloro-3-nitro heptane

C 4-Bromo-3-chloro-6-nitro octane

D 5-chloro-6-Bromo-3-nitro heptane
Q- The IUPAC name of

A 4-Bromo-3-chloro-6-nitro heptane

B 6-Bromo-5-chloro-3-nitro heptane

C 4-Bromo-3-chloro-6-nitro octane

D 5-chloro-6-Bromo-3-nitro heptane
Solution:
Q- The correct IUPAC name of the following compound is:

A 5-chloro-4-methyl-1-nitrobenzene

B 2-chloro-1-methyl-4-nitrobenzene

C 3-chloro-4-methyl-1-nitrobenzene

D 2-methyl-5-nitro-1-chlorobenzene
Q- The correct IUPAC name of the following compound is:

A 5-chloro-4-methyl-1-nitrobenzene

B 2-chloro-1-methyl-4-nitrobenzene

C 3-chloro-4-methyl-1-nitrobenzene

D 2-methyl-5-nitro-1-chlorobenzene
Solution:

The numbering is done keeping lowest sum rule in mind.

Q- The IUPAC name of the following compound is :

A 3-ethyl-4-methylhex-4-ene

B 4,4-diethyl-3-methylbut-2-ene

C 4-methyl-3-ethylhex-4-ene

D 4-ethyl-3-methylhex-2-ene
Q- The IUPAC name of the following compound is :

A 3-ethyl-4-methylhex-4-ene

B 4,4-diethyl-3-methylbut-2-ene

C 4-methyl-3-ethylhex-4-ene

D 4-ethyl-3-methylhex-2-ene
Q- The IUPAC name for the following compound is :

A 3-methyl-4-(3-methylprop-1-enyl)-1-heptyne

B 3,5-dimethyl-4-propylhept-1-en-6-yne

C 3,5-dimethyl-4-propylhept-6-en-1-yne

D 3-methyl-4-(1-methylprop-2-ynyl)-1-heptene
Q- The IUPAC name for the following compound is :

A 3-methyl-4-(3-methylprop-1-enyl)-1-heptyne

B 3,5-dimethyl-4-propylhept-1-en-6-yne

C 3,5-dimethyl-4-propylhept-6-en-1-yne

D 3-methyl-4-(1-methylprop-2-ynyl)-1-heptene
Solution:
Qualitative Analysis of Organic Compounds
Detection of Carbon and Hydrogen

Liebig’s Test
Test For Nitrogen
Q:- Which of the following compounds does not show
Lassaigne’s test for nitrogen?

A urea

B azobenzene

C hydrazine

D Phenyl hydrazine
Q:- Which of the following compounds does not show
Lassaigne’s test for nitrogen?

A urea

B azobenzene

C hydrazine

D Phenyl hydrazine
Solution:
Q:- The compound formed in the positive test for nitrogen with
the Lassaigne solution of an organic compound is

A Fe(CN)3

B Fe4[Fe(CN)6]3

C Na4[Fe(CN)5NOS]

D Na3[Fe(CN)6]
Q:- The compound formed in the positive test for nitrogen with
the Lassaigne solution of an organic compound is

A Fe(CN)3

B Fe4[Fe(CN)6]3

C Na4[Fe(CN)5NOS]

D Na3[Fe(CN)6]
Solution:
Test For Sulphur

Sodium nitroprusside test:

The one portion of the extract, a few drops sodium
nitroprusside are added. The appearance of violet colouration
indicates sulphur.
Test For Halogens
Test for phosphorus
Q:- Match List - I with List - II.
List - I List - II
(Test/Reagents/Observations) (Species detected)

A. Lassaigne’s test (i) Carbon

B. Cu(II) oxide (ii) Sulphur

C. Silver nitrate (iii) N, S, P, and halogen

D. The sodium fusion extract (iv) Halogen

gives black precipitate with specifically
acetic acid and lead acetate

The correct match is

A A - (iii), B - (i), C - (ii), D - (iv)

B A - (i), B - (iv), C - (iii), D - (ii)

C A - (iii), B - (i), C - (iv), D - (ii)

D A - (i), B - (ii), C - (iv), D - (iii)

Q:- Match List - I with List - II.
List - I List - II
(Test/Reagents/Observations) (Species detected)

A. Lassaigne’s test (i) Carbon

B. Cu(II) oxide (ii) Sulphur

C. Silver nitrate (iii) N, S, P, and halogen

D. The sodium fusion extract (iv) Halogen

gives black precipitate with specifically
acetic acid and lead acetate

The correct match is

A A - (iii), B - (i), C - (ii), D - (iv)

B A - (i), B - (iv), C - (iii), D - (ii)

C A - (iii), B - (i), C - (iv), D - (ii)

D A - (i), B - (ii), C - (iv), D - (iii)

Solution:
Quantitative analysis
Estimation of Carbon and Hydrogen:
On complete combustion, 0.246 g of an organic compound
gave 0.198g of carbon dioxide and 0.1014g of water.
Determine the percentage composition of carbon and
hydrogen in the compound.
On complete combustion, 0.246 g of an organic compound
gave 0.198g of carbon dioxide and 0.1014g of water.
Determine the percentage composition of carbon and
hydrogen in the compound.

Solution :
Estimation of Nitrogen
Estimation of Nitrogen
Estimation of Halogens
In Carius method of estimation of halogen, 0.15 g of an
organic compound gave 0.12 g of AgBr. Find out the
percentage of bromine in the compound.
Solution :
Molar mass of AgBr = 108 + 80 = 188 g mol-1
188 g AgBr contains 80 g bromine
0.12 g AgBr contains g bromine

Percentage of bromine
Estimation of Sulphur and Phosphorus
In sulphur estimation, 0.157 g of an organic compound gave
0.4813g of barium sulphate. What is the percentage of
sulphur in the compound?
Solution :

Molecular mass of BaSO4 = 137 + 32 + 64 = 233 g

233 g BaSO4 contains 32 g sulphur 0.4813 g BaSO4 contains

Percentage of sulphur
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