ISOMERISM

PART - I : ONLY ONE OPTION CORRECT TYPE

1. Which of the following molecule is chiral.

Cl
Cl H H

Cl Cl Cl Cl
H H
(A) (B) H (C) (D)
Br
H H Cl Cl Cl
Br

2. Which one of the following compounds will show enantiomerism ?

(A) CH3 –– –– CH3 (B) H3C – – CH3

O O
(C) –– OH (D) –– OH
O
––

HO – H2C

3. Number of conformational isomers of ethane

(A) 7 (B) 3 (C) 4 (D) Infinite
4. Which of the following statement regarding the projections shown below is true ?

(A) ‘a’ and ‘b’ both represent the same configuration (B) Both ‘a’ and ‘b’ are optically active
(C) ‘b’ alone is optically active (D) ‘a’ alone is optically active
5. The structures represent

&

(A) geometrical isomers (B) positional isomers

(C) conformational isomers (D) configurational isomers

6. The given compound (X) has :

(A) chirality (B) superimposability on its mirror image isomer

(C) plane of symmetry (D) C2 axis of symmetry
7. The compounds X and Y in below reaction can be
 Ph – NH . NH2 + (X) + (Y)

(A) CH3  CH2  C  CH3 + CH3  C  Ph (B) Ph  C  CH3 + CH3CHO

|| || ||
O O O

(C) CH2 = O + CH3CHO (D) CH2 = O + CH3  C  CH3

||
O

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

(A) 8 (B) 16 (C) 32 (D) 10

9. How many stereoisomers are possible for ?

(A) 128 (B) 64 (C) 32 (D) 16

10. How many spatial orientations are possible in the following compound ?

(A) 2 (B) 8 (C) 6 (D) 4

PART - II : SINGLE AND DOUBLE VALUE INTEGER TYPE

1. How many cyclic and acyclic structural isomers of C5H10 can show geometrical isomerism?
2. In given compounds how many can show geometrical isomerism-

(i) (ii) (iii) (iv)

3. In given compounds how many have Z configuration along double bond ?

(i) (ii)

(iii) (iv)
4. Sum of C2 & C3 axis of symmetry is

5. Optical rotaion data are expressed in standard way (specific rotation []D).
If magnituted of specific rotation of isomer d-lactic acid is 3.82. What will be the magnitude of specific
rotation of acetic acid in degree.

6. How many of the following are cis dichlorocyclohexane.

(i) (ii) (iii) (iv)

(v) (vi) (vii) (viii)

7. How many of the following are (configurational) enantionmers of (A) ?

(A) =

(p) (q) (r) (s) (t)

8. Pure cholesterol has a specific rotation of –32. A sample of cholesterol prepared in the lab has a specific
rotation of –8. The enatiomeric excess of the sample of chloresterol is x%. x is :

9. Pure (R) Mandelic acid has specific rotation of –150. If a smaple contains 60% of the R

and 40% of its enantiomer, then [] of this solution is.

10. Total number of geometrical isomers in the given compound are

C = CH – DC = CD – HC = C
11. Total number of geometrical isomers in the given compound are :

12. Total number of stereoisomers of compound CH3  CH  CH  CH  CH  CH  CH3 are :

|
Cl

13. Total number of optically active stereoisomers of CH3 – CH – CH  CH – CH – CH3 are :

| |
Cl Cl

14. For the compound A–CH2–CH27–A draw the newmann projection formula of all the stable conformational
isomers if obs = 2D and Xanti = 0.75 then find gauche.(If A = NO2)

15. Total number of stereoisomers possible for the given structure excluding the configuration mentioned is :

16. Observe the com pound 'M'

M=

If in this compound
X = Total number of asymmetric C* atoms
Y = Number of similar asymmetric C* atoms
Z = Number of optically active stereoisomers
W = Number of opticaly inactive isomers
R = Number of geometrical orientations in space
Report your answer as :
X+Y+Z+W+R

PART - III : ONE OR MORE THAN ONE OPTIONS CORRECT TYPE

1. What should be the minimum conditions to show geometrical isomerism ?
(A) Restricted rotation about double bond or ring.
(B) Groups which are responsible to show geometrical isomerism differ in their relative distance.
(C) Free rotation about single bond.
(D) Two different groups at both restricted atoms.
2. Which of the following compounds has cis configuration at each double bond ?
(A) (B)

(C) (D)

3. Which of the following carbonyl compounds can give two oximes on reaction with hydroxyl amine ?
(A) HCHO (B) CH3CHO (C) PhCHO (D) CH3COPh
4. Which of the following is true for maleic acid and fumaric acid.
(A) Configurational isomers (B) Stereo isomers
(C) Z and E isomers (D) Constitutional isomers
5. Which of the following is correct statement :
(A) Geometrical isomers are not mirror image isomer.
(B) A compound having double bond (restricted bond) always show geometrical isomerism.
(C) Acyclic compoubd having single bond does not show geometrical isomerism.
(D) Cyclodecene can show cis & trans form.
6. Which of the following statement(s) is/are correct for given compound :

(A) It is a optically active compound

(B) It can show geometrical isomerism
(C) It posses centre of symmetry but not plane of symmetry.
(D) It is a meso compound
7. Find out correct statement/s.
(A) All chiral centers are stereogenic centers.
(B) All stereogenic centers are not chiral center.
(C) A compound may be chiral without chiral center.
(D) A compound will be chiral only if it has at least one chiral center.

8. Which is/are not the structure of 3-Methyl butan-2-ol.

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

H
OH
C2H5 C
9. H C
OH
CH3
Fischer projection formula of this compound can be represented as :

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

10. Which of the following compounds will have C2 axis of symmetry ?

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

11. is :

(A) optically active molecule. (B) having plane of symmetry.

(C) having axis of symmetry. (D) having centre of symmetry
12. The correct relation between compound(s) I and II is/are

(I) (II)

(A) identical. (B) diastereomers. (C) enantiomers. (D) configurational isomers

13. Enantiomers have
(A) Similar physical properties (generally).
(B) Similar chemical properties with optical active compounds.
(C) Same absolute value of specific rotation.
(D) Different configurations.
14. Which of the following will show geometrical isomerism?

(A) CH3–CH=C=C=CH–CH3 (B)

(C) (D)

PART - IV : COMPREHENSION
Read the following passage carefully and answer the questions.
Comprehension # 1
Different arrangements of atoms that can be converted into one another by rotation about single bonds are
called conformations. The energy required to rotate the molecule about carbon-carbon bond is called torsional
energy. When size and number of groups increases torsional energy also increases. In staggered conformation
Van der Waal's and torsional strains are less so these conformations are relatively more stable.

1. Which conformation has maximum energy.

OH OH
OH OH
H NO2 H H
NO2 H

(A) CH H (B) Me H (C) H (D) H

3
Me H Me H
NO2 H O2N
H
2. In which conformation torsional strain (rotational barrier) is minimum.

CH3 H
CH3 CH3 CH3 CH3

(A) CH3 CH3 (B) H H

CH3 CH3

H H CH3
H H H H

(C) H H (D) H H

H H H

Comprehension # 2
Tartaric acid [HO2CCH(OH)CH(OH)CO2H] was an important compound in history of stereochemistry. Two
naturally occuring forms of tartaric acid are optically inactive. One optically inactive form (P) has a melting
point of 210-212°C and can be separated into two optically acitve forms, whereas other optically inactive form
(Q) cannot be resolved further.
3. Optically inactive form Q is

(A) (B)

(C) (D) none of these

4. A optically inactive form P is :

(A) Optically inactive due to internal compensation.
(B) Optically inactive due to presence of plane of symmetry.
(C) Optically inactive due to external compensation.
(D) Optically inactive due to intramoleuclar hydrogen bonding.