CAPS - 3

CHEMISTRY Isomerism
TARGET : JEE Advanced – 2023

SINGLE CHOICE QUESTIONS

1. Which of the following is the diastereoisomers of the compound

(A) (B)

(C) (D)

2. Stereoisomers possible for following compound is

(A) 8 (B) 16 (C) 32 (D) 64

3. How many stereoisomer may have this natural occuring compound.

(A) 8 (B) 16 (C) 64 (D) 128

4. The S-enantiomers of ibuprofein is reversible for its pain relieving properties. Which one of the structure
shown is S-ibuprofein?

(A) (B)

(C) (D)

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5. Give the correct order of initials T or F for following statements. Use T if statement is true
and F if it is false.
I. Me–CH=C=C=CH–Br is optically active.
II. All optically active compound are chiral.
III. All chiral pyramidal molecules are optically inactive.
IV CH3 – CH2 – CH2 – COOH and are positional isomers.

(A) TTTF (B) FTFT (C) FTFF (D) TFTT

6. Which pairs of the salts should have identical solubilities in methanol?

(I) (II)

(III) (IV)

(A) I & IV (B) I & III (C) I & II (D) II & IV

MULTIPLE CHOICE QUESTIONS

7. Which of the following compounds has a stereoisomer that is a meso compound?
(A) 2,4-dibromohexane (B) 2,3-dibromobutane
(C) 2,4-dimethylpentane (D) hexane-2,5-diol
8. True statement(s) about the following compound is/are

(A) It shows geometrical isomerism (B) It shows optical isomerism

(C) It configuration is E (D) It is having two stereocenters

9. Consider the following statements regarding the given projection and select the correct
statement(s)?

(W) (X) (Y) (Z)

(A) W & Y are diastereoisomers (B) Z is the newmann projection of X

(C) W, X, Y and Z are optically active (D) Y & Z are meso.

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INTEGER ANSWER TYPE
10. Indicate the stereo centres in the following molecule and total number of stereomers in
the following molecule.

11. The number of structurally isomeric ketones with molecular formula C 6H12O are :
12. The number of structurally isomeric esters with molecular formula C5H10O2 are.
13. Classify the following compounds as homocyclic, heterocyclic, alicyclic, aliphatic,
aromatic, saturated and unsaturated.

(a) (b) (c) (d)

14. What is the relation between following compounds ?

(a) , (b) , (c) , (d) ,

15. Write all structurally isomeric ethers with molecular formula C5H12O.
16. What is the number of all (structurally isomeric) alkynes with molecular formula C6H10.
17. How many aromatic have benzen ring structural isomers are possible for C7H8O.
18. 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.

Match the column:

19. Match the column :
Column I Column II

(A) Compound show geometrical isomerism (P)

(B) Compound shows optical isomerism (Q)

(C) Compound having plane of symmetry (R)

(D) Compound having centre of symmetry (S)

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SUBJECTIVE ANSWER TYPE

20. How many stereoisomers are possible for following compounds:

(a) (b) CH3–CH=CH–CH=CH–CH=C=CH2

(c) (d) 1,2-dichlorocyclopropane

(e) 1,3- dimethylcyclobutane (f) 2-bromo-3- chlorobutane

(g) 1,3-dimethyl cyclohexane

21. Find relationship between following pairs.

(a)

(b)

(c)

(d)

(e)

(f)

22. Discuss the optical activity of the following two compounds and also label them as polar and non polar.

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23. Identify chiral and achiral compounds from the list given below.

(a) (b)

(c) (d)

(e) (f)

(g) (h)

24. Ectocarpene is a volatile, sperm cell attracting material released by the eggs at the sea wood
Ectocarpus Siliculosus and is shown below:–

All the double bonds are cis & the absolute configuration of the stereocentre is S. Write a stereo
chemically accurate representation of ectocarpene.

25. Consider the following six structures:

(I) (II)

(III) (IV)

(V) (VI)

Establish the stereochemical relationship between: (a) I and II, (b) III and IV, (c) II and III, (d) I and V, (e)
IV and (VI)

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26. Find relationship between following pairs.

(a) &

(b) &

(c) CH2CH2CH2 – CHO &

(d) &

(e) &

(f) &

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 ANSWER KEY CAPS-3

1. (D) 2. (A) 3. (C) 4. (D) 5. (C)

6. (A) 7. (BD) 8. (ABCD) 9. (ABC) 10. 8
11. 6 12. 9
13. (a) Homocyclic, alicyclic, unsaturated (b) Heterocyclic, aromatic, unsaturated
(c) Heterocyclic, alicyclic, saturated (d) Aliphatic, saturated.
14. (a) Chain isomers (b) Position isomers (c) Identical (d) Chain isomers

15. (i) CH3–O–CH2–CH2–CH2–CH3 (ii) (iii)

(iv) (v) CH3–CH2–O–CH2–CH2–CH3 (vi)

16. 7 17. 5 18. 30 19. (A) P, Q, R; (B) P, Q, S; (C) R ; (D) R

20. (a) 8 (b) 4 (c) 3 (d) 3 (e) 2 (f) 4 (g) 3

21. (a) Diastereoisomers (b) Identical (c) Metamer (d) Identical (e) Geometrical isomer (f) Identical
22. Compound I is optically inactive since it contain a plane of symmetry. Compound II is enantiomeric
since it does not contain plane of symmetry, hence chiral. Also compound I is polar while II is non polar
23. (a) chiral, (b) achiral, Plane of symmetry (c) achiral, Plane of symmetry (d) chiral, (e) chiral, (f) achiral,
meso (g) chiral, trans (h) achiral, Plane of symmetry

24.

25. (a) Both I and II are optically, but they are not mirror image of one another, hence, they are distereomers;
(b) Distereomers ; (c) Enantiomers; (d) I and V are enantiomers; (e) IV and VI are distereomers
26. (a) identical (b) diasteroisomers (c) chain isomer
(d) positional isomer (e) Geometrical isomer (f) Enantiomer

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