Day -6 Isomerism

Objective
1. The decreasing order of stability of the following compounds is

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

(a) (iv) > (iii) > (i) > (ii) (b) (i) > (iii) > (ii) > (iv)
(c) (ii) > (iii) > (i) > (iv) (d) (iv) > (i) > (iii) > (ii)

2. The most stable configuration of ethylene glycol is

(a) Anti (b) Gauche
(c) Partially eclipsed (d) fully eclipsed

3. Which of the following compounds will show optical isomerism?

(a) Butanal (b) 2Chlorobutanol
(c) 2Propanol (d) 1Butene

4. Fischer projection indicates

(a) Horizontal substituents above the plane.
(b) Vertical substituents above the plane.
(c) Both horizontal and vertical substituents below the plane.
(d) Both horizontal and vertical substituents above the plane.

5. The compound given below are

HO COOH and HO COOH

(a) Enantiomers (b) Identical

(c) Regiomers (d) Diastereomers

6. In the boat conformation of cyclohexane, the most destabilizing interaction is

(a) Eclipsing (b) 1,3diaxial
(c) 1,3Diequatorial (d) Flagpole  Flagpole

7. The Bayer’s angle strain is expected to be maximum in

(a) cyclodecane (b) cyclopentane
(c) cyclohexane (d) cyclo octane

8. (+) Mandelic acid has a specific rotation of +158°. What would be the observed specific rotation of the
mixture of 25% () mandelic acid and 75% (+) mandelic acid?
(a) +118.5° (b) 118.5°
(c) 79° (d) +79°

9. The total number of optically active and meso forms possible for the compound [HOOC(CH(OH))3 
COOH] respectively are
(a) 4, 4 (b) 2, 2
(c) 3, 2 (d) 2, 3
10. Certain ester of tartaric acid is optically active but on hydrolysis yields an optically inactive acid. The
dibasic acid is
(a) (+)Tartaric acid (b) ()Tartaric acid
(c) mesoTartaric acid (d) ()Tartaric acid
11. The most stable conformation of chlorohydrin at room temperature is
(a) fully eclipsed (b) partially eclipsed
(c) gauche (d) staggered

12. cis2butene and trans2butene can be distinguished on the basis of

(a) their optical properties (b) their reduction properties
(c) the products on ozonolysis (d) the products on addition of Br2

13. The dihedral angles between the two CBr bonds in gauche, partially eclipsed, staggered and fully
eclipsed conformations of 1,2dibromoethane respectively are:
(a) 60°, 120°, 180°, 0° (b) 0°, 60°, 120°, 180°
(c) 120°, 60°, 180°, 0° (d) 0°, 120°, 60°, 180°

14. Which of the following statement is false about cyclopropane1,2dicarboxylic acid?

(a) It has two geometric isomers.
(b) It has three stereoisomers.
(c) All the stereoisomers are optically active.
(d) Only transisomer shows enantiomorphism.

15. The total number of isomers possible for trisubstituted C6H3Br2Cl is

(a) Six (b) Four
(c) Three (d) Two

16. Chirality is lost when

(a) CH3CH(OH)COOH is heated (b) O is heated
CH3
COOH
(c) CH3CH(OH)CH2COOH is heated (d) CH3CHCOOH is heated.
CH2COOH

17. Which of the following compounds cannot show tautomerism?

O

O
(a) HOCH=CH2 (b)

O O

O NH
(c) (d)

O O
D
CH3CCH2COC2H5
+
18. A
(D+ is catalyst), compound A is
OH O O OH
(a) CH3C=CHCOC2H5 (b) CH3CCH=COC2H5

OD O OH O
(c) CH3C=CHCOC2H5 (d) CH3C=CHCOC2H5

19. The compound

 CH3 H
C=C
Cl [CH2]4CHOHCH3
will give
(a) 4 geometrical and 4 optical isomers (b) 2 geometrical and 2 optical isomers
(c) 2 geometrical and 4 optical isomers (d) 2 geometrical isomers only

20. Which of the following does not show stereo isomerism.

CH3 CH3 CH3 H
CONH COHN
(a) (b)
NHCO HNCO
H H H CH3
CO2H
H C OH
(c) CH3CH2CO2H (d)
H C OH
CO2H

21. Which of the following statement is wrong?

(a) Enantiomers are similar chemically, but their rates of reaction with other optically active substances
are usually different.
(b) A sample of secbutyl chloride is optically inactive due to the absence of chiral carbon atom.
(c) Diastereomers are optical isomers but not mirror images.
(d) Diastereomers differ in their physical properties.

22. Each of the following statements is correct except

(a) Both cis and transisomers of HO2CCH=CHCO2H on catalytic reduction give succinic acid.
(b) Both cis and transisomers of HO2CCH=CHCO2H are planar molecules.
(c) Both cis and transisomers of HO2CCH=CHCO2H are optically active.
(d) Out of cis and transisomers of HO2CCH=CHCO2H only the cisisomer forms anhydride when
heated.
23. Which of the Newmann projections shown below represents the most stable conformation about the
C1–C2 bond of 1-iodo-2-methylpropane?
H3C I CH3
H I
(a) (b)
H H CH3
H H CH3 H
CH3 H3C H
I H
(c) (d)
H CH3 I
H
H H CH3

24. How many asymmetric carbon atoms are present in the following compound coccinellin?

H O
H
N

CH3
H
Coccinellin
(a) 2 (b) 3
(c) 4 (d) 6

O O
O O
25.

(I) (II)
Enol percentage will be more for
(a) (I) (b) (II)
(c) equal in both (d) none of these

Subjective
1. Find out the total geometrical isomers of and name them.

2. Find out the total stereoisomers for the following compound,

3. Which of the following compound will cyclise on treatment with a base?

..
OH N
N
.. ,
O
H
CH2 CH2
Cl Cl
(I) (II)
 CH3 CH3 CH3
4. Are the following isomers, and CH3 , optically active or not?
H H H
(I) H
(II)
Cl Cl

5. Is the given isomer, Cl , optically active or not?

Cl

6. How many optical isomers are possible for the compound,

F
C Cl ?
Br

CO2C2H5 CH3
H CH3 EtCO2 H
7. H CO2C2H5 CH3 CO2C2H5

CH3 H
(I) (II)

What is the relation between the structures (I) and (II)?

H
OH OH
8. Is the given isomer, OH
HO
, optically active or not?
H H
(I)
H

NH2
9. The compound, O cyclises to form one amide linkage. How many optical isomers will be there
Cl
for the cyclic product?

10. How many stereoisomers can be obtained for the following structure?

11. One or more of the following compound are in their most stable tautomeric forms. Which are they?
OH O
C C
(a) H3C C OCH2CH3 (b)
H N O
H
 O
H CH
(d) CH3C
CCH3
(c) H
OH O

12. Draw the corresponding tautomer of the following compounds (if possible).
O O
CH3 H3C CH3
H3C C
(a) (b)
CH3 CH3
O
H3C H3C CH3
(c) C=O (d) H3C CH3
H3C

13. Draw sawhorse and Newman projection diagrams of the following structures, which are shown as
Fischer projections. Which compound is optically inactive?
CH3 OH
H OH H3C H
(a) HO H (b) H OH
CH3 CH3
H CHO
H3C OH HO H
(c) H OH (d) H OH
CH3 CH2OH
CH3 CO2H
H Br H OH
(e) H Br (f) H OH
CH3 CO2H

14. Write the structure of a proton tautomer of each of the following compounds.
O
N CH3
(a) OH (b) Ph (c)
O OH
O
O O
(d) HO N=O (e) (f)

O O
H
(g) N (h) CH3NO2 (i) H3C NO2

O
CH3
(j) CN (k) Ph N
H

15. In what stereoisomeric forms would you except the following compounds to exist?
 (a) EtCH(CO2H)Me (b)
O

(c) (d) Et(Me)C=C=C(Me)Et

Ph CO2H I

(e) (f)
Ph CO2H
Br

Objective

1. (a) 2. (b) 3. (b) 4. (a) 5. (b)

6. (d) 7. (a) 8. (d) 9. (b) 10. (c)

11. (c) 12. (d) 13. (a) 14. (c) 15. (a)

16. (c) 17. (c) 18. (c) 19. (b) 20. (c)

21. (b) 22. (c) 23. (c) 24. (a) 25. (a)

Subjective
1. 4 geometrical isomers namely: (cis, cis), (cis, trans), (trans, cis) and (trans, trans).

2. 4 geometrical isomers which are (E, E), (E, Z), (Z, Z), (Z, E) and each geometrical isomers will have 2
optical isomers. So, a total of 8 stereoisomers will be obtained.

3. (II) will cyclise because of favoured orientation.

.. ..
N N N:
B Cl
OH BH O O
CH2 CH2 CH2
Cl Cl

CH3 CH3 CH3

CH3
4. and are optically inactive as both of them posses
H H H
H
plane of symmetry.

5. No, because it has a plane of symmetry.

6. 2

7. Diastereomers

8. Optically active

*
* NH ,
9. 4 optical isomers
O

10. Zero
CH CH
11. CH3C COEt CH3C CCH3
O O O O
H H
(Crossconjugation and intramolecular hydrogen bonding)

OH OH
CH3 H3C CH3
H3C C
12. (a) (b)
CH3 CH3
H2C
(c) COH
H3C
O
H3C CH3
H3C CH3 has no H atom ; hence ketoenol tautomerism

is not possible.
13.
Sawhorse Newman Optical
representation representation activity
CH3 OH H H OH OH
OH H OH H
H Optically
(a) H
HO CH3 active
CH3 CH3 H3CCH3

OH H OH Me H H
Me Me H OH
H Optically
(b) H OH inactive
Me
Me OH MeOH

H H OH Me H OH
Me Me OH OH
OH Optically
(c) H OH active
Me
Me H MeH
 CHO H OH HO H H
OH H OH
HO H Optically
(d) H OH active
CH2OH
CH2OH CHO HOH2C
CHO
Me H Br HH Br
H Br H Br Br Optically
(e) H Br inactive
Me
Me Me MeMe

COOH H OH HH OH
H OH H OH OH
Optically
(f) H OH inactive
COOH
COOH COOH HOOCCOOH
N N O
14. (a) OH
H
O O O
CH3
(b) Ph PhC C=CH2
O

(c)
OH O
O O

(d) HO N=O O NOH

O O OH OH
(e)

O OH

(f)

O OH
H
(g) N N

OH
(h) CH3NO2 CH2=N
O
OH
(i) H3C NO2 CH2 N
O

(j) CN C NH
 O OH
CH3
(k) Ph N PhC=NCH3
H
 COOH COOH CH3 CH3 CH3 H
15. (a) H Me Me H (b)
and
H O H H CH3
Et Et O

Me Me Me Me
(c)
H H H H

Me Me
Et Et
(d) C=C=C C=C=C
Me Me
Et Et

Ph COOH H COOH

(e) Ph H H H Ph Ph H H

H COOH H COOH

I I

(f)

Br Br