SOME BASIC PRINCIPLES OF ORGANIC CHEMISTRY

SOME BASIC PRINCIPLES OF ORGANIC CHEMISTRY

1. Arrange the following carbocations in decreasing order (d) 1,1-Dichloroethane
of stability.
•
4.  C7 H 5O2 2 
hv
  X   2 C6 H 5  2CO2
Consider the above reaction and identify the
intermediate ‘X’
(a)

(a) B > A > C (b) A > B > C

(c) C > B > A (d) C > A > B
(b)
2. In the following structures, which one is having
staggered conformation with maximum dihedral angle?
(a) (c)

(d)

(b)
5. Which will have the highest enol content?
(a)

(c)

(b)

(c)
(d)

(d)

3. The IUPAC name of ethylidene chloride is:

(a) 1-Chloroethene
(b) 1-Chloroethyne
(c) 1,2-Dichloroethane
SOME BASIC PRINCIPLES OF ORGANIC CHEMISTRY

6. Which of the following is most stable? (a) 4-methyl-2-nitro-5-oxohept-3-enal

(a) (b) 4-methyl-5-oxo-2-nitrohept-3-enal
(c) 4-methyl-6-nitro-3-oxohept-4-enal
(d) 6-formyl-4-methyl-2-nitrohex-3-enal

11. Which of the following carbocations is most stable?

(b) (a)

(b)
(c)

(c)
(d)

(d)

7. Which one of the following techniques is not used to

spot components of a mixture separated on a thin layer 12. Arrange the following in decreasing acidic strength.
chromatographic plate?
(a) I2 (Solid) (b) U.V. Light
(c) Visualisation agent as a component of mobile phase
(d) Spraying of an appropriate reagent

8. Which of the following structures are aromatic in

nature?
(a) A > B > C > D (b) B > A > C > D
(c) D > C > A > B (d) D > C > B > A

13. Which of the following compounds is not aromatic?

(a)

(a) A, B, C and D (b) Only A and B

(c) Only A and C (d) Only B, C and D

9. The formula of the purple colour formed in (b)

Laissaigne’s test for sulphur using sodium
nitroprusside is
(a) NaFe[Fe(CN)6] (b) Na[Cr(NH3)2(NCS)4]
(c) Na2[Fe(CN)5(NO)] (d) Na4[Fe(CN)5(NOS)]
(c)
10. The correct IUPAC name of the following compound is

(d)
 SOME BASIC PRINCIPLES OF ORGANIC CHEMISTRY

14. The correct stability order of the following diazonium 17. Given below are two statements. One is labelled as
salt is Assertion A and the other is labelled as Reason R.
Assertion A: [6] Annulene. [8] Annulene and cis –[10]
Annulene, are respectively aromatic, not-aromatic and
aromatic.

[6] Annulene

[8] Annulene

Cis-[10] Annulene
(a) (A) > (B) > (C) > (D)
Reason R: Planarity is one of the requirements of
(b) (A) > (C) > (D) > (B)
aromatic systems.
(c) (C) > (A) > (D) > (B)
In the light of the above statements, choose the most
(d) (C) > (D) > (B) > (A)
appropriate answer from the options given below.
(a) Both A and R are correct and R is the correct
15. The correct decreasing order of priority of functional
explanation of A.
groups in naming an organic compound as per IUPAC
(b) Both A and R are correct but R is NOT the correct
system of nomenclature is :
explanation of A.
(a) –COOH > –CONH2 > –COCl > –CHO
(c) A is correct but R is not correct.
(b) –SO3H > –COCl > –CONH2 > –CN
(d) A is not correct but R is correct.
(c)
18. In Carius method of estimation of halogen, 0.45 g of an
(d) –COOH > –COOR > –CONH2 > –COCl organic compound gave 0.36 g of AgBr. Find out the
percentage of bromine in the compound.
(Molar masses: AgBr = 188 g mol-1, Br = 80 g mol–1)
16. Which of the following is not an example of benzenoid
(a) 34.04% (b) 40.04%
compound ?
(a) (c) 36.03% (d) 38.04%

19. Match List-I with List-II

List-I List-II
(Mixture) (Purification Process)
(b) (A) Chloroform & Aniline (I) Steam distillation
(B) Benzoic acid &
(II) Sublimation
Napthalene
(C) Water & Aniline (III) Distillation
(c) (D) Napthalene & Sodium
(IV) Crystallisation
chloride

(a) (A)-(IV), (B)-(III), (C)-(I), (D)-(II)

(d) (b) (A)-(III), (B)-(I), (C)-(IV), (D)-(II)
(c) (A)-(III), (B)-(IV), (C)-(II), (D)-(I)
SOME BASIC PRINCIPLES OF ORGANIC CHEMISTRY

(d) (A)-(III), (B)-(IV), (C)-(I), (D)-(II)

20. Which among the following is the strongest Bronsted

base ?
(a) (d)

(b) 22. Given below are two statements.

(c) Statement I: The compound is

optically active.

(d) Statement II: is mirror image

of above compound A.
In the light of the above statement, choose the most
appropriate answer from the options given below.
(a) Both Statement I and Statement II are correct
(b) Both Statement I and Statement II are incorrect.
(c) Statement I is correct but Statement II is incorrect.
21. Correct structure of  -methylcyclohexane
(d) Statement I is incorrect but Statement II is correct.
carbaldehyde is :
(a) 23. Number of electrophillic centres in the given
compound is_____.

(b)

24. Total number of possible stereoisomers of dimethyl

(c) cyclopentane is _____.

25. Observe structures of the following compounds

 SOME BASIC PRINCIPLES OF ORGANIC CHEMISTRY

The total number of structures/compounds which

posses asymmetric carbon atoms is ____.

26. The number of chiral alcohol(s) with molecular

formula C4H10O is_____.

27. The number of sp3 hybridised carbons in an acyclic

neutral compound with molecular formula C4H5N
is :

28. Optical activity of an enantiomeric mixture is

+12.6° and the specific rotation of (+) isomer is
+30°. The optical purity is____%

29. The number of stereoisomers formed in a reaction

of (±) Ph(C=O) C(OH)(CN)Ph with HCN is_____.
SOME BASIC PRINCIPLES OF ORGANIC CHEMISTRY

Answer Key
1. (a) 2. (c) 3. (d) 4. (d) 5. (c) 6. (a) 7. (c) 8. (b) 9. (d) 10. (c)
11. (d) 12. (a) 13. (c) 14. (b) 15. (b) 16. (b) 17. (d) 18. (a) 19. (d) 20. (d)
21. (a) 22. (c) 23. 3 24. 6 25. 3 26. 1 27. 1 28. 42 29. 3

Solutions
1. Among the given carbocations, B is most stable as Lone pair of oxygen will be involved in resonance due to which B
carbocation gets stabilised. Then, Carbocation A will show +I effect and has 4 alpha hydrogens which stabilises
carbocation A .But Carbocation C shows -I effect due to which it is least stable. So, the correct order is B > A > C

2. In anti conformation the dihedral angle is 180o (maximum)

3.

1,1-Dichloreoethane

4.

5. Enol form of (c) is most stable due to formation of aromatic benzene-1,3,5-triol.

So, option (c) has maximum enol content.

6.
 SOME BASIC PRINCIPLES OF ORGANIC CHEMISTRY

Aromatic molecule is the most stable

Hence (a) is correct.

7. The function of the mobile phase is to carry the components present on a thin layer chromatographic plate.

are aromatic as they are cyclic, planar and have (4n  2) e

8. and

9. Na2S + Na2[Fe(CN)5NO] → Na4[Fe(CN)5NOS]

Sodium sulphide reacts with sodium nitroprusside to form a violet colour compound, which confirms the presence of
sulphur.

10.

4-methyl-6-nitro-3-oxohept-4-enal

11. More is the delocalization of charge, more will be the stability of carbonation. Hence, (d) is correct.

12.

-I effect of -NO2 group is stronger than -OCH3 group.

So, the order is A > B > C > D
SOME BASIC PRINCIPLES OF ORGANIC CHEMISTRY

13.
is a non-planar compound, hence it is not aromatic.
All other molecules follow Huckel rule, hence they are aromatic.

14. Diazonium salt containing aryl group directly linked to electron donating group is most stable due to resonance. The +M
effect stabilizes the intermediate whereas the electron withdrawing group on benzene destabilizes the intermediate at para
position.

Order will be (A) > (C) > (D) > (B)

15. The order of decreasing priority for functional group is

Hence correct order is

–SO3H > –COCl > –CONH2 > –CN

16. Option (b) is not a benzenoid compound, and it exists in tub shape (non-aromatic molecule).

17. [6] Annulene is aromatic because it is planar. [8] Annulene and [10] Annulene are both not aromatic because they are not
planar. So, Assertion (A) is not correct. Reason (R) is correct because planarity is one of the requirements of an aromatic
system.

18. 188 g of AgBr = 80 g of Br

80
0.36 g of AgBr   0.36
188
% of Br in given organic compound
80  0.36
  100  34.04%
188  0.45

19.
List-I (Mixture) List-II (Purification Process)
 SOME BASIC PRINCIPLES OF ORGANIC CHEMISTRY

(A) Chloroform & Aniline (III) Distillation

(B) Benzoic acid & Napthalene (IV) Crystallisation
(C) Water & Aniline (I) Steam distillation
(D) Napthalene & Sodium chloride (II) Sublimation

20.

is the strongest base among the given compounds due to maximum +I effect over ‘N’ atom.

21.

22.

Therefore, statement I is true, but statement II is false.

23.

This compound has 3 electrophilic centers.

SOME BASIC PRINCIPLES OF ORGANIC CHEMISTRY

24.

This will not show stereoisomer

This will show stereoisomers

Total stereoisomers possible = 6

25.
 SOME BASIC PRINCIPLES OF ORGANIC CHEMISTRY

All these compound possess asymmetric carbon atoms.

26. Possible structure of alcohols with molecular formula C4H10O are

Only 1 isomer is chiral in nature.

2C  2  N  H  X
27. Degree of unsaturation 
2


 2  4  2 1 5  0  8  3  5  3
2 2

Answer is 1

Totalrotation
28. Optical purity   100
Specificrotation
12.6
  100  42%
30

29.