IUPAC

*
2 ORGANIC

ISOMERISM
* -
10:00 AM

SAT
* - GOC 10:00AM MON

THURS
NEXT
*

WEEK - HYDROCARBONS
SAT
-
-

t.me/neetpreparationadda247
ISOMERISM
chemical
same molecular
formula
but
different physical and

properties
STRUCTURAL ISOMERISM

CONFORMERS -> HYDROCARBONS

GEOMETRICAL
STEREO ISOMERISM
OPTICAL

t.me/neetpreparationadda247
A STRUCTURAL ISOMERISM

-
*
CHAIN ISOMERISM

*
POSITION ISOMERISM Y

FUNCTIONAL ISOMERISM
*
-

* METAMERISM -

RING
* CHAIN -

TAUTOMERISM
*
-

t.me/neetpreparationadda247
 CHAIN ISOMERISM
A
Number
*
-
of
carbon
=> atom
in
main chain different
* Word Root is
different. ↑

c -c C C C-c- C
↳
- -

42 But I 3
Prof.
4-i -

1
=

-
2
1
3 Pent
But

t.me/neetpreparationadda247
 *
POSITION ISOMERISM
*
Same Functional
group
*

Side Chain
same main carbon chain
*

M
>
-

FG/Substituent
Diffrent position
*

12
c -c C 2 "c-c-c
q
- -
-
c

on on
D 23 4 5 I 2345
*
c-c-c -c -
C C-2 -c -c -
c
&
! I
t.me/neetpreparationadda247
 *

* FUNCTIONAL ISOMERISM

Different
FG
*

x ALCOHOL and ETHER (R-O-R)

C5-M-M- 04 Mz-0-M,-M3

ALDEHYDE and KETONES

Cs-Ma-
e 15-M3

t.me/neetpreparationadda247
ACID
* and ESTER

R-c- R-c-
R

Crz-M2-Mz-o az-M--O-
CYANIDES
* and ISOCYANIDES
-

CN
-

NC

My-M
-
CN
Cz-My-NC

t.me/neetpreparationadda247
 AMINES R-NH2 CHz-M-M2-N42 10 Amine
-
-

↑"Amine R-NH2
⑪ 20 Amine
CHz-CH2-NH-M3 -
-

92" Amine R-NH

a Chy-N-Chs
34 Amine
e
>

⑦ 3"Amine R -
N-R M3
I Functional
R Homes
--

t.me/neetpreparationadda247
ALCOHOL
*
and PHENOL
of
I
---(H3
---M2-04
10 1 1O

--

DIENE
* and YNE
Bord
2- double -Triple
Band

CH CH
M2 HC c M Mb
My
= =
= -
- -

CyH6 Cuts

t.me/neetpreparationadda247
 * R-0- R R,-NH-R2
AMELAMERISM

Differentalkyl group
on either
side
of bridging
group.
functional 31
22

2 2

cuz-c-0-1
A

Ether Mz-M-0-1-M3
3 I 31 2 2 22

My-CHL-M-c-OS
Ester
M5C--O-C-
4 3 2
-'Amine as-M-c-c-NG-cy CG-C-Ma-NH-Warcs
41 32

t.me/neetpreparationadda247
t.me/neetpreparationadda247
A RING CHAIN ISOMERISM

CH2 CH M) CH3 M
= -
-

Cn48 Cyty
OPEN CHAIN RING

t.me/neetpreparationadda247
 ⑦ TAUTOMERISM E Isomwism
Functional
-
-

isomers exist
in
When I
functional dyname
*

with
each other
equilibrium
*
KETO-ENOL TAUTOMERISM
R
2
DYNAMIC
Ear
R

R- id
2
R
1,3
system
R-c-s
KETO
--

On
-
R
-- -
-
-

- -
ENOL
is --
3

① I2 Bhigho
Iga Hydrogen=>
is
&

D
②- Bhyho
Is a Band is

t.me/neetpreparationadda247
 2 CONDITIONS FOR TAUTOMERISM

It attlast
X-Hydrogen
on
1) must have one

sp" hybridisid carbon.

2) If regulowing
atom is
up, then it have
must

hydrogen If
atom in
--
of conjugation----
HYBRID IS A TIOM

c -
c -
sp3
=C =

sp
CC =
->
sp2
C= C ->
sp
t.me/neetpreparationadda247
 cugcms
Cry-c-e3 as
* -

5 304

Cuz-in--n
*

2x4
i i 3
-
eng-in-a
0
3

0 -

**
*
*

·
t.me/neetpreparationadda247
 ⑧
O HOGA
HOGA

So sor
-
- -

A
-

A *
-- X
Sp Spr
II
I1
II I
⑲so
·
O 8
"
A 2 -It
-
* sak,a
⑧
son of KETO-ENOh

I" equilibrium,
/

in
0x4

So I generally,
*

-
-

-
Nahi - sp
·x
KETO is
majorly present;
ga conditions, ENOL
But
few
in

&

is
dominating

t.me/neetpreparationadda247
 E
GEOMETRICAL ISOMERISM
A
E
I
*
about double bond

a CONDITIONS: -

I ~
a Eb
c C
=

/ I c E d - x

so
* GIX
D de

*
GI
* in
cyclo-alkans * sps
o GI HOGA
-
- -

Minimum 2
sf hybridised carbon atom
-
Sp
havingdifferent group.
on
A

t.me/neetpreparationadda247
SPY o a
t
 CIS-TRANS
**

E
a CH3 C43 HOGA C3
I ~ -
e
4
1 -
C C
=

C 2
=

I - d
b
I
H y /
GROUP
SAME I ⑳ .
M3
SAME SIDE

⑧
CIS F
↑
Br
HOGA
CH3
I ~Hy = C
--
-

HOGA
C C
=
->
C.
/
No is
17
↳ Cis
-
-
in trans

t.me/neetpreparationadda247
 E-2
system when
fou
*

all

(same Side) groups

are
different
-

↳ - Zussamen
-

(off side)
Es
Entgegon

t.me/neetpreparationadda247
CIP RULES
*

Higher
) the Number,
atomic
Higher
is
priority
F Be 40 C43
I /
I -
C C
=

C = C
/ I
/ I
E
HaN -
F
a Z I

t.me/neetpreparationadda247
 firstpointof difference
is same, then check next
If
*

pointof difference. F
11
c
CF3 4
-

F I -
3F
= C = C
-c c
=
I I
/ I E
C
2
CC3
=3
UN
-c

t.me/neetpreparationadda247
 more the atomic
mass, is
of Isotopes,
In case
* more

160
Priority H
It
C -
H
-
Cc =

/
D 2
Yo-4
0

t.me/neetpreparationadda247
If atoms
are
same, Triple-
Double 7
single
*

Bond Band
Bond

DB
↑ ↑ *
F
-CH M2
=

C C
=

/ I
2 C
C CH
TB

t.me/neetpreparationadda247
 A
* I" CH3
--
I
CH3 CH3
·

X CH3
n
-

CIS I en

4 4 CH3
TRANS
I

t.me/neetpreparationadda247
 SYN AND ANTA
A

OXIMES
*

H OH
H
--
-

CH3
I ⑯ I I
CN
=

C N
=

H
↓
or CH3 Anti loy
Y

syn
-

t.me/neetpreparationadda247
 ACO
*

-
GROUP
-
(N N)
=

·I
-
~of Ch3
I
N N
=

N N
=

-as
/
CH3 - -auz
syn Anti
--

t.me/neetpreparationadda247
 ⑰
A OPTICAL ISOMERISM

Solutionalactivity
is to be checked

= I - -> 444-
Plane Polarised
t
PRISM (PPL)
Light
Light POLARISER
electric
field ↑

Anti
&
944 Clockwise
Late
o
Clockwise
↑
deflinective
ection
-

No
denbro
rotatory
rolalary
- --

- (e) [7
Optically e (e) (+)
OPTICALLY ACTIVE

t.me/neetpreparationadda247
 CHIRAL ATOM
a
CONDITIONS: -

A
X i) a b c d

/I d
b
&
if Atom should be
sp" hybridised

t.me/neetpreparationadda247
 C -
2 sp3
e U ↳X X
I 2) 3) I

nu
I Sp
sp * C
C
a
/

-Ms "
/ -
↳
F
H

O
616

n) H- is-M3 5) (24g=
Al ↑
S =

M3 6) M calls
↓
↑
N

↓C2H5 I

30
12
+
018

30 + 12P

Sp

t.me/neetpreparationadda247
t.me/neetpreparationadda247
 #

BRIS CONFIGURATION

R -> Rectus -
a
a
S-> Sinister-
·

I
FISCHER C b
=>
⑧
d
- I
PROJECTION b I d
I
e

FISCHER
-
-

t.me/neetpreparationadda247
 *
CIP rules
Assign priority
* based on

HCS Houzontal Clockwise S

=>

VCR =>
Vatical R
Clockwise

you
prioritycrout
t.me/neetpreparationadda247
 3
HCS CH3
3
VCR
CH3
CLOCKWISE 2

s &
2 R A

↑
4 u Be
a H
CLOCKWISE

4x
N H
Be

*
D 4 F2
2 CLOCKWISE ANTI-C
3

- ·
4
F D u
R
CH3 a
Ch 1 3
CH3

VCR

t.me/neetpreparationadda247
 #
A ENANTIOMERS

Non
*
super-imposable
mirror
images
a then other l
one is is
*
If
opposite
and rotation
A
Equal

t.me/neetpreparationadda247
⑰ 3
CH3 ⑬ CH3
CLOCKWISE

&
2
S 4 R
C ⑳ H u ·
Be

Be H

+
200 - 20
OR
->

20 + 20°

t.me/neetpreparationadda247
 RACEMIC MIXTURE

5 50% of
A
N
ET ROTATION- ZERO

OPTICALLY INACTIVE
50% B
of -
--

Extunal
compensation
*

-
--

t.me/neetpreparationadda247
Relation
*

b/w 2 molecules when I Chiral atom

Molecule, Molecule-2 Retation

R R Identical
&

Idential
--

S S

R S Enantionier

S R Enartioner

TRICK 8 -
ODD EXCHANGES -> INVERT CONFIG.

EVEN EXCHANGES -> CONFIG.

SAME

t.me/neetpreparationadda247
 ⑬

zechs
⑪ doe

and
CH3
S AC - Identical
⑧
H ⑧
Br

~u
A
exchange u AB - Enauliomic

⑳
Be
·
exchange
- BC - Enantiomer
Re -
-
H ·
M3

t.me/neetpreparationadda247
 NOTWA *

chiral carbon is
present,
the
compound
If only
one
*

active
is
always
If
* 2 or more chiral carbon
present, for
then a
compound
should not have
active it pos or cos
to be
optically
POS:
of symmetry
- Plane

Center
COS:
of symmetry
-

t.me/neetpreparationadda247
 *

INACTIVECH3 CH3 ACTIVE

CH3 ACTIVE
-
-

H POSY
N2 X 40 4 H OH
POSX
POS
N2 4 X 4 Or
NU2
x 4

CH3
My CHz
-

D
4
I -
C. C
--
INACTIVE
-

/ COS I -

- C
H

t.me/neetpreparationadda247
OPTICALLY
*
OR NOT?
ACTIVE

I CH3 2) CH3 3) CH3

D H
↳ on H 04
D 4
I MR2 4 On

C3H7 C3
CH3

w COMMENT
-

t.me/neetpreparationadda247
 n) CH3 5) 0) U
U c
H
Ne
D 04
H H H a
N2 H

CHy

t.me/neetpreparationadda247
Relation
*

b/w 2 molecules Chiral atom

when I

Enantiomic
*
If opposite->
All Chiral

All Chiral same - Identical

*
If
Otherwise-> Diastereomer
*

t.me/neetpreparationadda247
 H
Ch U a -s
i
H U

Be
H Be Be 4

cate cass anti S

A B C

A $B- Enantiomer
I
BBC

ABC
-

->
Diastwomen

Diasteromes
-
-
⑯
VER

t.me/neetpreparationadda247
 COMPOUND
* MESO

Condition:- i) Two
-
or more chiral carbon.

is should have PIS or COS.

-

VE
Internal
*

compensation Y

t.me/neetpreparationadda247
 MESO OR NOT?
2) 3) CH3 4) CH3
1) CH3 ⑳n MESOL
F 4 N2 H Br
H
-

H ⑧ on
pos POSX POSI
POSV
-
4 NH2 D u
F
-

H &
04 4
MESOL H Be
MESO
MESO CH3
CH3 X
⑭ M3

t.me/neetpreparationadda247
ERYTHRO AND TUREO

CH3 CH3 T CH3 ↑

CH3
T
H on H OH H N2 ↳ NH2

H 04 40 4 H NH2 H
M2N

⑰ Cats Cats E cats Cats

same
group
Same Side

t.me/neetpreparationadda247
D and I
configuration
(No relation
with d and I)

and amino acids

applied
* on
carbohydrates
check lost
* chiral carbon

CHO
CHO D L

40 H
4 · O4

CHaOn CHON

t.me/neetpreparationadda247
 CHO

4 on

no H

M On
D
M ⑧
04

You

t.me/neetpreparationadda247
 AMINO ALIDS
COOn A L COOn

H Na *2N H

CH3 CH3

t.me/neetpreparationadda247
 ISOMERISM

Geometrical isomerism

1. Which can show the cis-trans isomerism :

(1) ClCH2CH2Cl (2) Cl2C=CH2 (3) Cl2C=CCl2 (4) ClCH =CHCl

2. Which of the following compounds will not show geometrical isomerism :

(1) Cyclooctene (2) 1-Bromo-2-chloroethene

(3) 1-Phenylpropene (4) 2-Methyl-2-butene

. Stereoisomers have different : .

(1) Molecular formula (2) Structural formula (3) Configuration (4) Molecular mass

4. Which of the following compound not show geometrical isomerism

(1) (2) CH3–CC–CH3 (3) (4) All of these

5. Which of the following will from geometrical isomers :

(1) (2) CH3CH=NOH (3) (4) All of these

6. Which of the following compound can show geometrical isomerism

(1) (2)

(3) (4)

7. The geometrical isomerism is shown by :-

CH2 CHCI
CHCI
CH 2
(1) (2) (3) (4)
8. Types of geometrical isomerism shown at point X, Y and Z of the following compound
respectively are

X Y Z

(1) cis cis trans

(2) cis trans trans

(3) trans cis cis

(4) cis trans cis

CIP Rules (E/Z Naming) & Physical Properties of G.I

9. Determine the double bond stereochemistry (E or Z) for the following molecules

(1) A : E ; B : E (2) A : Z ; B : Z (3) A : E ; B : Z (4) A : Z ; B : E

10. Identify (Z) - 2 - pentene :

(1) (2) (3) (4)

11. The correct stereochemical formula of Trans-3-chloro-1-phenylbut-1-ene is

(1) (2)

(3) (4)
12. The 'E'-isomer is/are :

(1) (2)

H C2H5
C
||
(3) HC C (4)
3 CH(CH3)2

13. Which of the following is correct set of physical properties of the geometrical isomers

&

Dipole
Boiling point Melting point Stability
moment
(1) I > II I > II II > I I > II
(2) II > I II > I II > I II > I
(3) I > II I > II I > II I > II
(4) II > I II > I I > II I > II

14. Which of the following is a synisomer :-

(1) (2) (3) (4)

15. The correct order/s for the given pair of isomers is

(1) > (Melting point)

(2) < (Dipole moment)

(3) > (Boiling point)

(4) > (Water solubility)

16. Out of the following compounds, which will have a zero dipole moment ?

(1) 1, 1 – Dichloro ethylene (2) cis 1, 2 – Dichloro ethylene

(3) trans 1, 2 – Dichloro ethylene (4) Trans 1, 2 – Dichloro propene

Chiral carbon and Projection Formula

17. The compound which has maximum number of chiral centres is

(1) (2) (3) (4)

18. Chiral molecules are :

(1) Superimposable on their mirror image

(2) Not superimposable on their mirror image

(3) unstable molecules

(4) capable of showing geometrical isomerism

19. Which of the following compounds possesses a chiral centre :

(1) (2) (3) (4)

20. Which of the following have chiral carbon ?

(1) 1–Butanol (2) 1–Propanol (3) 2–Chlorobutane (4) 4–

Hydroxyheptane
21. Number of chiral carbon persent in the following compound :

CH3 – CH – CH2 – CH – CH – CH3

| |
OH Br 52

(1) 2 (2)3 (3) 4 (4) 5

R/S & D/L Naming.

22. Which Fisher projection represents the given wedge dash structure :

(1) (2)

(3) (4)

23. Which of the following is not true for maleic acid and fumaric acid.

(1) Configurational isomers (2) Stereo isomers

(3) Z and E isomers (4) Optical isomers

24. represents the Fischer projection formula :

(1*) D (2) L (3) d (4) ℓ

25. Which of the following is the structure of (S)-Pentan-2-ol is ?

(1) (2) (3) (4)

26. Which of the following have same configuration.

F Br H
C H C Cl C Br
Cl Br H F F Cl

I II III

(1) I & II (2) II & III (3) I & III (4) All

27. Which has D configuration.

CH3 OH CH3 COOH

(1) HO H (2) H COOH (3) H OH (4) H2N H

COOH CH3 CHO CH3

28. The configuration of the given compound is :

(1) E (2) R (3) S (4) Z

29. D-Fructose (C6H12O6) has IUPAC name (3L,4D, 5D)1, 3, 4, 5, 6-Pentahydroxyhexan-2-one. Its
last asymmetric carbon atom (C*5) has D-configuration. The correct stereochemical formula
of D-Fructose is

(1) (2) (3) (4)

: Element of Symmetries (POS, COS)

30. Which of the following are chiral :

(1) (2) (3) (4)

(1) 1, 2, 3 (2) 1, 2, 4 (3) 2, 3, 4 (4) 1, 3, 4

31. Which statement is wrong about symmetry ?

(1) Plane of symmetry is an imaginary plane which bisects the molecule in two equal halves
in such a way that each half of the molecule is the mirror image of the other half.
(2) Centre of symmetry is the point in a molecule through which if the straight line is drawn
from any part of the molecule and if then this line encounters identical groups at equal
distances in opposite direction.
(3) A molecule which does not possess any element of symmetry is called asymmetric
molecule.
(4) A molecule which does not possess any element of symmetry is called symmetric
molecule.

32. Which of the following compound posses plane of symmetry ?

(1) (2) (3) (4)

Definition and Properties of Enantiomers, Diastereomers, Meso compounds

33. Which is not the pair of enantiomers ?

(1) (2)

(3) (4)
34. Which of the following pairs of compounds are enantiomers :

CH3 CH3 CH3 CH3

H OH HO H H OH HO H
(1) OH H and H OH (2) HO H and HO H

CH3 CH3 CH3 CH3

CH3 CH3 CH3

H OH HO H HO H
(3) and (4) and
H OH H OH HO H

CH3 CH3 CH3

35. Which of the following statements is not correct :

(1) Enantiomers are Eessentially chiral and optically active

(2) Diastereomers are not neccesarily chiral and optically active

(3) All geometrical isomers are diastereomers

(4) All diastereomers are chiral and optically active

36. What is the relationship between (I) & (II)

(1) Enantiomer (2) Diastereomers

(3) Constitutional isomer (4) Identical molecules

37. Stereoisomers which are not mirror image of each other, are called :

(1) Enantiomers (2) Tautomers (3) Meso (4) Diastereomers

38. Which one among the following is not diastereomeric pair.

(1) I and III (2) I and II (3) II and III (4) I and IV

specific rotation, observed rotation, optical purity and enantiomeric excess Racemic
mixture, Optical Resolution

39. Meso form of tartaric acid is

(1) Dextorotatory

(2) laevorotatory

(3) neither Laevo not dextro rotatory due to internal compensation

(4) A mixture of equal quantities of dextro and leavorotatory forms

40. The instrument which can be used to measure optical activity, i.e., specific rotation:

(1) Refractometer (2) Photometer (3) Voltmeter (4) Polarimeter

41. If optical rotation produced by is + 36º then that produced by

is

(1) –36º (2) 0º (3) +36º (4) unpredictable

42. The racemic mixture of Alanine can be resolved by using,

(1) (+)-2-Butanol (2) (ℓ)-2-Chlorobutanoic acid

(3) (±) -2-Butanol (4) (dℓ mix)-2-Chlorobutanoic acid

(1) 1 & 2 only (2) 1 & 3 only (3) 2 & 4 only (4) 3 & 4 only

43. Which of the following pair of isomers can not be separated by fractional crystallisation or
fractional distillation:

(1) Maleic acid and Fumaric acid (2) (+)-Tartaric acid and meso-tartaric acid

(3) CH3 CH COOH and H N–CH –CH –COOH (4) (+)-lactic acid and (–)-lactic acid
2 2 2
|
NH2

Conformations, strains and stability

44. The eclipsed and staggered conformation of ethane is due to –

(1) Free rotation about C–C single bond (2) Restricted rotation about C–C single bond

(3) Absence of rotation about C–C bond (4) None of the above

45. The minimum torsional strain developed in butane is at dihedral angle(s)

(1) 0º, 108º (2) 120°, 240º (3) 60°, 180°, 300° (4) 60°, 120°, 180°

46. Which statement is FALSE :

(1) When value of dihedral angle is 180º then this conformation is called anti conformation.

(2) When  = 60º then this conformation is called gauche.

(3) When  = 0º then this conformation is called eclipsed conformation.

(4) Other than staggered and eclipsed conformation are called gauche conformations.
47. The Baeyer’s angle strain is expected to be maximum in

(1) Cyclodecane (2) Cyclopentane (3) Cyclobutane (4*) Cyclopropane

Conformational analysis of Ethane, Propane, Butane and Substituted butane

48. Which of the following is an achiral molecule?

(1) (2) (3) (4)

49. Which of the following is correct P.E. diagram for propane and butane respectively ?

(I) P.E. (II) P.E.

Dihedral angle Dihedral angle

(III) P.E. (IV) P.E.

Dihedral angle Dihedral angle

(1) I & II (2*) I & III (3) II & IV (4) IV & II

50. In the following the most stable conformation of n-butane is :

(1) (2) (3) (4)

51. Newman projection of Butane is given,C-2 is rotated by 120º along C2-C3 bond in
anticlockwise direction the conformation formed is :
 (1) anti (2) fully eclipsed (3) gauche (4) partially
eclipsed

52. The dipole moment of 1, 2-Dichloroethane is 1.12 D. Which statement is correct about this
compound.

(1) It exists mainly in fully eclipsed conformation.

(2) It exists only in anti conformation.

(3) The polarity is due to gauche (skew) conformation.

(4) The anti conformation has highest dipole moment.

53. The newman projection formula of 2,3-dimethylbutane is given as

X,Y respectively can be :

(1) –CH(CH3)2 and H (2) –CH3 and –C2H5 (3) –C2H5 and –CH3 (4*) H and –
CH(CH3)2
Conformational analysis of compound having intramolecular H-bonding.

54. In 2-Fluoroethanol which conformer will be most stable ?

(1) Eclipsed (2) Skew (3*) Gauche (4) Staggered

55. Incorrect about the compounds I, II, III is :

, ,

(1) I & II are diastereomers (2) I & III are identical

(3) I| & III are diastereomers (4) I & II are optically active

56. The true statement about the following corformation is :

(1) It has maximum angle strain.

(2) It does not have eclipsing strain (tortional strain).

(3) It does not have any intramolecular hydrogen bonding.

(4) It has maximum vander waal strain.

57. The structures I and II are

COOH COOH

H OH H COOH

H OH H OH
COOH OH
I II

(1) Diastereomers (2) Enantiomers

(3) Meso (4) Identical

Cyclohexane

58. The least stable conformation of cyclohexane is

(1) Boat (2) Chair (3) Twist boat (4) Half chair

59. Flagpole interaction is present in :

(1) Boat form of cyclohexane (2) Chair form of cyclohexane

(3) Anti form of n-butane (4) Fully eclipsed form of n-butane

60. Chair form of cyclohexane is more stable than boat form because :

(1) In chair form carbons are in staggered form and in boat form carbons are in eclipsed
form
(2) In chair form carbons are in eclipsed form and in boat form all the carbons are in
staggered form
(3) Bond angle in chair form is 111° and bond angle in boat form is 109.5°
(4) Bond angle in chair form is 109.5° and in boat form 111°

Counting of stereoisomers

61. Total number of geometrical isomers in the given compound is :

(1) 3 (2)6 (3) 8 (4) 16

62. How many geometrical isomers are possible for the given compound ?

Ph – CH = CH – CH = CH – COOH

(1) 3 (2)4 (3) 2 (4) 1

63. How many geometrical isomers are possible for the given compound ?

CH3 – CH = CH – CH = CH – CH = CH2

(1) 2 (2)4 (3) 6 (4) 8

64. No. of Geometrical isomers for following compound is :

(1) 8 (2) 16 (3) 32 (4) 10

65. Total number of geometrical isomers in the given compound is :

C = CH – DC = CD – HC = C

(1) 2 (2)4 (3) 6 (4) 8

66. Select the correct options for molecular formula C2H2Cl2 :

(1) The total number of isomers is 4.

(2) All the structures show geometrical isomerism.

(3) All isomers have 5 bonds and one  bond. (4) Its has linear shape.

67. CH3 – CH – CH – CH – CH3

|
Br Br Br

Total number of stereoisomers in above compound is :

(1) 6 (2)4 (3) 8 (4) 16

68. The total number of isomers for C4H8 is

(1) 5 (2*) 6 (3) 7 (4) 8

69. CH3 – CH – CH – CH – CH3

|
Cl Br OH

Total number of stereoisomers in above compound is :

(1) 6 (2) 4 (3)8 (4) 16

70. Total number of stereoisomers of compound is :

CH3 CH CH CH3
|
OH Br

(1) 2 (2)4 (3) 6 (4) 8

71. The total number of isomers for C4H8 is

(1) 5 (2) 6 (3) 7 (4) 8

72. How many meso steroisomers are possible for 2, 3, 4–pentanetriol :

(1) 1 (2)2 (3) 3 (4) None

SOLUTIONS

1. Sol. Follow conditions of geometrical isomerism.

2. ol. Follow conditions of geometrical isomerism.

3. Sol. Stereoisomers have same connectivity of atoms but different orientations (configurations) in
space.

4.(d)

5. (d)

6. Sol. (3) is non planner molecule

7.

Sol. Follow conditions of geometrical isomerism.

8. sol(A)

9. sol(d)

10.

Sol. (Z) -2-pentene

[Senior groups at same side of restricted rotation]

11.

Sol. trans-3-chloro-1-phenyl but-1-ene.

12.

Sol. E-isomers have senior groups on anti-orientation.

13.

Ans. 3

14. (C)

15. sol(D)

16.

Sol. (1) 1, 1-dichloro ethylene

(2) cis-1, 2-dichloro ethylene

(3) Trans-1, 2-dichloro ethylene

(4) Trans-1, 2-dichloro propene

17.

Sol. Four chiral carbon atoms

18. sol(B)

19. sol(a)

20. sol(c)

21.

* * *
Sol. CH3 – CH – CH2 – CH – CH – CH3 has three chiral carbons.
| | |
OH Br C2H5

22.

Sol. First decide the (R/S) configuration in wedge-dash and then draw fischer projection for same
configuration.

23. sol(d)

24.

Sol. R and D

25.

Sol. the arrow is clockwise but least priority group is on horizontal line of fischer

projection.

26. sol(a)

27. sol(a)

28.

Sol. R.
29.

Sol.

30. sol(a)

31. sol(d)

32. sol(C)

33. sol(D)

34.

Sol.

non-super imposible mirror image stereoisomers.

35. sol(d)

36. sol(b)

37. sol(d)

38. sol(a)

39. sol(c)

40. sol(d)

41.

Sol. Compound is a meso compound hence it has zero optical rotation.

42.

Sol. + two diastereomeric esters

+ two diastereomeric amides

(–) –2–chlorobutanoicacid

Racemic mixture can be resolved by using optically active compounds.

43.

Sol. Enatiomers have same physical properties so they can not be separated by any physical
method which diastereomers have different physical properties.

44.

Sol. The eclipsed and staggered conformation of ethane is due to free rotation about C — C
single bond.

45. sol(c)

46.

Sol.

47.

Sol. Deviation in normal bond angles increases the angle strain. In cyclopropane deviation in
bond angle is maximum.
 48.

Sol. (1) is meso form so it is achiral molecule





Meso form

49. Which of the following is correct P.E. diagram for propane and butane respectively ?

(I) P.E. (II) P.E.

Dihedral angle Dihedral angle

(III) P.E. (IV) P.E.

Dihedral angle Dihedral angle

(1) I & II (2*) I & III (3) II & IV (4) IV & II

50.

Sol. Anti form of butane is more stable because of less strains.

51. sol(c)

52. sol(c)

Hint : Cl – CH2 – CH2 – Cl has two staggered conformations.

Only Gauche form is polar. Anti form is nonpolar.

53.

Sol. X = Hydrogen Y = –CH(CH3)2

54.

Sol.

Although steric repulsion exist but hydrogen bonding as shown above, gives stability to the
gauche form.

55. sol(D)

56. sol(b)

57. sol(1)

58. sol(d)

59. sol(a)

60. sol(a)

61.

n1
2
Sol. Geometrical isomers for symmetrical compounds = 2n – 1 + 2

n = 3, total G.I. = 6

62.

Sol. Unsymmetrical compound with 2 stereocentres has 4 geometrical isomers (22 = 4).

63.

Sol. Unsymmetrical compound with 2 stereocentres has 4 geometrical isomers.

64.

Sol. Number of geometical centres (n) = 4. So, total G.I. = 24 = 16

65.

Sol. Unsymmetrical compound with 2 stereocentres has 4 geometrical isomers.

66.

Sol. ,

 Total no. isomers are 3.

 C is sp2 hybridised in each isomer, therefore geometry is trigonal planar.

67.

Sol. Symmetrical compound with three chiral centres has 2n – 1 = 23 – 1 = 4 stereoisomers.

68.

Sol. C4H8 (D.U. = 1) ; Total isomers = 6

H3C–H2C–CH=CH2 ; CH3–CH=CH–CH3 (cis/trans.) ; ; ;

69.

Sol. Unsymmetrical compound with three chiral centres has 2n = 23 = 8 stereoisomers.

70.

Sol. Unsymmetrical compound with 2 chiral centres has 22 = 4 stereoisomers.

71.

Sol. C4H8 (D.U. = 1) ; Total isomers = 6

H3C–H2C–CH=CH2 ; CH3–CH=CH–CH3 (cis/trans.) ; ; ;

72.

Sol. 2,3,4 -pentanetriol