Chem 7 Organic Chem Principles

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Physical World, Units and Measurements P-1

Organic Chemistry - Some Basic


Principles & Techniques

Numerical

Q.1. The total number of chiral compound/s from the following is


______________.

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Answer Key & Explanation

1. Ans. Correct answer is 2


Explanation
MCQ (Single Correct Answer)

Q.1. Decreasing order of reactivity towards electrophilic


substitution for the following compounds is :

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Q.2. Given below are two statements :

Statement I : Tropolone is an aromatic compound and


has 8π electrons.
Statement II : π electrons of >C=O group in tropolone is involved
in aromaticity.

In the light of the above statements, choose the correct answer


from the options given below:

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Q.3. Given below are two statements, one is labelled as Assertion


A and the other is labelled as Reason R.

Assertion A : Order of acidic nature of the following compounds is


A > B > C.
Reason R : Fluoro is a stronger electron withdrawing group than
Chloro group.

In the light of the above statements, choose the correct answer


from the options given below:

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Q.4. Among the following compounds, the one which shows


highest dipole moment is
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Q.5. Given below are two statements, one is labelled as Assertion


A and the other is labelled as Reason R.

Assertion A : A solution of the product obtained by heating a mole


of glycine with a mole of chlorine in presence of red phosphorous
generates chiral carbon atom.

Reason R : A molecule with 2 chiral carbons is always optically


active.
In the light of the above statements, choose the correct answer
from the options given below:

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Q.6. The decreasing order of hydride affinity for following


carbocations is:
Choose the correct answer from the options given below:

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Q.7. The correct order for acidity of the following hydroxyl


compound is :

A. CH3OH

B.
Choose the correct answer from the options given below:

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Q.8. The pair from the following pairs having both compounds
with net non-zero dipole moment is
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Q.9. The correct IUPAC nomenclature for the following compound


is:
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Q.10. The descending order of acidity for the following carboxylic


acid is-

A. CH3COOH

B. F3C−COOH

C. ClCH2−COOH

D. FCH2−COOH

E. BrCH2−COOH

Choose the correct answer from the options given below:


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Q.11. The strongest acid from the following is


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Q.12. Resonance in carbonate ion is

Which of the following is true?

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Q.13. The most stable carbocation for the following is:

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Q.14. The correct order of pKa values for the following compounds
is:
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Q.15. The increasing order of pKa for the following phenols is

(A) 2, 4 - Dinitrophenol

(B) 4 - Nitrophenol

(C) 2, 4, 5 - Trimethylphenol

(D) Phenol

(E) 3-Chlorophenol

Choose the correct answer from the option given below :


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Q.16. Match List I with List II

List I List II
Isomeric pairs Type of isomers

A. Propanamine and N- I. Metamers


Methylethanamine

B. Hexan-2-one and Hexan-3-one II. Positional


isomers

C. Ethanamide and III. Functional


Hydroxyethanimine isomers

D. o-nitrophenol and p-nitrophenol IV. Tautomers

Choose the correct answer from the options given below :


Q.17. Which of the following conformations will be the most
stable?
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Q.18. The correct order in aqueous medium of basic strength in


case of methyl substituted amines is :

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Q.19. Given below are two statements, one is labelled as Assertion


A and the other is labelled as Reason R

Assertion A : Benzene is more stable than hypothetical


cyclohexatriene

Reason R : The delocalised π electron cloud is attracted more


strongly by nuclei of carbon atoms.
In the light of the above statements, choose the correct answer
from the options given below:

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Q.20. Which will undergo deprotonation most readily in the basic


medium?
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Q.21. Increasing order of stability of the resonance structures is :

Choose the correct answer from the options given below :

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Answer key & Explanation

1. Ans. (D)
Explanation
Higher the electron density on Benzene Ring, Higher its Reactivity
towards electrophilic substitution Reaction

2. Ans. (C)
Explanation
Tropolone is an aromatic compound, and it contains a seven-
membered ring with six carbon atoms and one oxygen atom. The
oxygen atom is doubly bonded to one of the carbon atoms,
forming a carbonyl group (C=O). The remaining carbon atoms
form a conjugated ring system. The oxygen atom's lone pair of
electrons also participates in the conjugation, making the
molecule aromatic.

Let's analyze the given statements:

Statement I: Tropolone is an aromatic compound and has 8 π


electrons. This statement is true. Tropolone is aromatic and has 6
π electrons from the carbon atoms in the ring and 2 π electrons
from the oxygen atom's lone pair, resulting in a total of 8 π
electrons.
Statement II: π electrons of >C=O group in tropolone are involved
in aromaticity. This statement is false. In tropolone, the oxygen
atom's lone pair participates in the conjugation and contributes to
the aromaticity, not the π electrons of the C=O bond.

Based on the analysis, the correct answer is:

Statement I is true, but Statement II is false.


3. Ans. (A)
Explanation

Among A and B; since inductive effect is distance dependent,


Extent of −I effect is higher in A followed by B even though F is
stronger electron withdrawing group than Cl. Thus, A is more
acidic than B.
4. Ans. (D)
Explanation
Among the given compounds, the following compound has the
highest dipole moment because both the +ve and -ve ends
acquire aromaticity.
5. Ans. (C)
Explanation

As for Reason R, it is false. A molecule with 2 chiral carbons is not


necessarily optically active. It may be if the molecule is not
superimposable on its mirror image (i.e., it's chiral). But if the
molecule is superimposable on its mirror image (i.e., it's achiral),
then it will not be optically active. This can occur if the molecule
has a plane of symmetry, in which case it is a meso compound.
6. Ans. (B)
Explanation
Least stable carbocation will have highest hydride affinity.

Stability of carbocation:

7. Ans. (A)
Explanation
8. Ans. (B)
Explanation
The correct option from the pairs having both compounds with a
net non-zero dipole moment is:

Option A: cis-butene, trans-butenecis-butene, trans-butene cis-


butene has a net dipole moment because the two alkyl groups are
on the same side of the molecule, causing an imbalance in the
distribution of electrons. However, trans-butene is symmetric, so
the dipole moments of the two alkyl groups cancel each other out,
giving it a net dipole moment of zero. Therefore, this pair does not
have both compounds with a net non-zero dipole moment.

Option
B: CHClCHClCH2Cl2,CHCl3 Both CHClCH2Cl2 (dichloromethane)
and CHClCHCl3 (chloroform) have a net non-zero dipole moment
due to the difference in electronegativity between the hydrogen
and chlorine atoms. Hence, this pair has both compounds with a
net non-zero dipole moment.

Option C: Benzene, AnisidineBenzene, Anisidine Benzene has a


symmetrical structure, leading to a net zero dipole moment.
Anisidine, however, does have a net dipole moment due to the
asymmetry in its structure. Therefore, this pair does not have
both compounds with a net non-zero dipole moment.

Option D: 1,4-Dichlorobenzene, 1,3-Dichlorobenzene1,4-


Dichlorobenzene, 1,3-Dichlorobenzene 1,4-Dichlorobenzene1,4-
Dichlorobenzene has a symmetrical structure, leading to a net
zero dipole moment. However, 1,3-Dichlorobenzene1,3-
Dichlorobenzene has a non-zero dipole moment due to the
asymmetry in its structure. Therefore, this pair does not have
both compounds with a net non-zero dipole moment.

9. Ans. (D)
Explanation
IUPAC name of the following compound is

2-Methyl-5-oxohexanoic acid
10. Ans. (C)
Explanation
The acidity of carboxylic acids is influenced by the electron-
withdrawing ability of the groups attached to the carboxylic acid.
The stronger the electron-withdrawing ability of the group, the
more it stabilizes the carboxylate anion (formed after losing the
acidic proton), and hence the stronger the acid.

Let's look at the groups attached to the carboxylic acid in each


option:

A. CH3−: Methyl group. It's electron-donating due to the


hyperconjugation effect.

B. F3C−: Trifluoromethyl group. Strong electron-withdrawing


group due to the electronegativity of fluorine atoms and inductive
effect.
C. ClCH2−: Chloromethyl group. It has some electron-withdrawing
ability due to the electronegativity of the chlorine atom, but it's
less than that of fluorine.

D. FCH2−: Fluoromethyl group. It has electron-withdrawing


ability due to the electronegativity of the fluorine atom, but less
than that of the trifluoromethyl group.

E. BrCH2−: Bromomethyl group. It has some electron-


withdrawing ability due to the electronegativity of the bromine
atom, but it's less than that of chlorine and fluorine.

So the order of acidity will be: B > D > C > E > A

11. Ans. (B)


12. Ans. (D)
Explanation
Resonating structure are hypothetical and resonance hybrid is
real structure which is weighted average of all the resonating
structures.
13. Ans. (C)
Explanation

The +M effect of NH2 is stabilizing the carbocation.


14. Ans. (C)
Explanation
Higher the value of Ka or lower the value pKa, stronger will be the
acid.

Presence of electron donating groups destabilises the phonoxide


ion, thus, reduces acidic nature of phenol. Presence of electron
withdrawing group stabilises the phenoxide ion thus increase the
acidic strength of phenol.

Thus, order of acidic strength is:

- Order of pKa will be = b > d > a > c


Acid Strength : -

Acids : Acids are those molecules which donates H+ ion in


aqueous solution (water) and increases concentration of H + ion
in water.

Dissociation constant of this reaction is K a. It is called ionisation


constant.

→ So we can say if a acid form more H+ ion after adding it in H2O


then that acid is called strong acid. If acid produce less H + ion in
H2O then that acid is weak acid.

15. Ans. (D)


Explanation
Order of acidity for following phenol is A > B > E > D > C.

- M and – I increases acidity.

+ M and + I decreases acidity.

∴ Their pKa value is A < B < E < D < C.


16. Ans. (A)
Explanation
A. Propanamine N–Methylethanamine

B. Hexan–2–one Hexan–3–one

C. Ethanamide Hydroxyethanimine

D. o–Nitrophenol p–nitrophenol
17. Ans. (A)
Explanation

18. Ans. (C)


Explanation
In aqueous medium basic strength is dependent on electron
density on nitrogen as well as solvation of cation formed after
accepting H+. After considering all these factors overall basic
strength order is

19. Ans. (B)


Explanation
Benzene is more stable than hypothetical cyclohexatriene due to
the delocalization of electrons in the π electron cloud of the
aromatic ring. This delocalization of electrons leads to a more
stable electronic configuration in benzene, as the electrons are
shared more evenly between all six carbon atoms in the ring. This
is in agreement with Assertion A.

Reason R is also correct, as the delocalized π electron cloud in the


aromatic ring is attracted more strongly by the nuclei of the
carbon atoms. This is due to the fact that the π electrons in the
ring are more spread out and are not localized to a single atom,
which makes them more attracted to the positively charged nuclei
of the carbon atoms. This explanation supports Assertion A.

20. Ans. (A)


Explanation
Most easily deprotonation

21. Ans. (C)


Explanation
2022
Numerical

Q.1. Optical activity of an enantiomeric mixture is +12.6∘ and the specific


rotation of (+) isomer is +30∘. The optical purity is __________%.
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Q.2. Total number of isomers (including stereoisomers) obtained on


monochlorination of methylcyclohexane is ___________.
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Q.3. The total number of monobromo derivatives formed by he alkanes


with molecular formula C5H12 is (excluding stereo isomers) __________.
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Q.4. The number of sp3 hybridised carbons in an acyclic neutral compound


with molecular formula C4H5N is ___________.
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Q.5. Observe structures of the following compounds

The total number of structures/compounds which possess asymmetric


carbon atoms is ______________.
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Q.6. Total number of possible stereoisomers of dimethyl cyclopentane is


____________.
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Q.7. Number of electrophilic centres in the given compound is
_______________.

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Answer Key & Explanation

1. Ans. Correct answer is 42


Explanation

2. Ans. Correct answer is 12


Explanation
Compounds formed on mono-chlorination of methylcyclohexane are :

Total mono-chlorinated products formed = 12

3. Ans. Correct answer is 8


Explanation
Total mono bromo derivatives = 8

4. Ans. Correct answer is 1


Explanation

3 double bond equivalent are present in compound

Only 1 sp3 hybridised carbon is there

(Keeping compound as acyclic)

5. Ans. Correct answer is 3


Explanation

The number of compounds containing asymmetric carbons is three.

6. Ans. Correct answer is 6


Explanation
Dimethyl cyclopentane
will show stereo isomerism, Its stereo isomers are

will show stereo isomerism, Its stereo isomers are


7 Ans. Correct answer is 3
Explanation
Given compounds :

Number of electrophilic centres = 3


MCQ (Single Correct Answer)

Q.1. Given below are two statements.

Statement I : The compound is optically active.

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.

In the light of the above statement, choose the most appropriate answer
from the options given below.

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Q.2. Which among the following is the strongest Bronsted base?


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Q.3. Match List - I with List - II.

Choose the correct answer from the options given below :


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Q.4. Among the following marked proton of which compound shows


lowest pKa value?
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Q.5. Given below are two statements: one is labelled as 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.

Reason R: Planarity is one of the requirements of aromatic systems.

In the light of the above statements, choose the most appropriate answer
from the options given below.
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Q.6. The correct decreasing order of priority of functional groups in


naming an organic Question: compound as per IUPAC system of
nomenclature is

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Q.7. Which of the following compounds is not aromatic?


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Q.8. Arrange the following in decreasing acidic strength.


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Q.9. Which of the following carbocations is most stable?

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Q.10. The correct IUPAC name of the following compound is :

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Q.11. Which of the following structure are aromatic in nature?


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Q.12. Which of the following is most stable?


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Q.13. The correct order of nucleophilicity is

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Q.14. In the following structures, which on is having staggered


conformation with maximum dihedral angle?
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Q.15. The IUPAC name of ethylidene chloride is :

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Q.16. Arrange the following carbocations in decreasing order of stability.


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Q.17. Which of the following is an example of conjugated diketone


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Answer Key & Explanation

1. Ans. (C)
Explanation

Compound (A) in Statement-I and compound in Statement-II is not the


mirror image of (I).

2. Ans. (D)
Explanation

3. Ans. (C)

Explanation
4. Ans. (C)
Explanation
The conjugate base of compound (C) is stabilized by extended conjugation.
Hence the indicated proton of compound C is most acidic i.e. will have
lowest pKa.

5. Ans. (D)
Explanation
[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


aromatic system.

6. Ans. (B)
Explanation
The order of decreasing priority for the functional group is

Hence correct order is

7. Ans. (C)
Explanation
[10] Annulene, although follow (4n + 2)π electron rule, but it is non-aromatic
due to its non planar nature. It is nonplanar due to repulsion of C – H bonds
present inside the ring.

8. Ans. (A)
Explanation
9. Ans. (D)
Explanation

is most stable carbocation

10. Ans. (C)


Explanation

11. Ans. (B)


Explanation

12. Ans. (A)


Explanation

1,3-cyclohexadiene is most stable because it is a neutral molecule. All


others are intermediates and hence less stable.

13. Ans. (D)


Explanation

Conjugate base of acid is always a stronger nucleophile.

14. Ans. (C)


Explanation
It is the staggered conformation with maximum dihedral angle.

15. Ans. (D)


Explanation
Ethylidene chloride is CH3– CHCl2, its IUPAC name is 1,1-Dichloromethane.

16. Ans. (A)


Explanation
The given carbocations are

Carbocation (A) is stabilised by hyperconjugation due to 4α hydrogen


atoms. Carbocation (C) is also stabilised by hyperconjugation due to 4 a
hydrogen atoms but destabilised by −1 effect of O-atom. Carbocation (B) is
most stable as it is stabilised by resonance.

∴ Correct decreasing order of stability is B > A > C

17. Ans. (C)


Explanation
In the rest of the diketones given in the question, the two (C = O) groups are
not in conjugation with each other.
2021
Numerical
Q.1 The dihedral angle in staggered form of Newman projection of 1, 1, 1-Trichloro
ethane is ___________ degree. (Round off to the nearest integer)
27th July Evening Shift 2021

Q.2 The number of sigma bonds in

is _______________.
25th July Morning Shift 2021

Q.3 The number of acyclic structural isomers (including geometrical isomers) for
pentene are ___________.
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Numerical Answer Key

1. Ans. (60)
2. Ans. (10)
3. Ans. (6)

Numerical Explanation

Ans 1. 1, 1, 1-Trichloro ethane [CCl3-CH3]

Ans 2.

Numbers of σ bonds = 10

Ans 3.
MCQ (Single Correct Answer)

Q.1 Arrange the following conformational isomers of n-butane in order of their


increasing potential energy:

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Q.2 Choose the correct name for compound given below :


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Q.3 The compound/s which will show significant intermolecular H-bonding is/are :

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Q.4 The number of stereoisomers possible for 1, 2-dimethyl cyclopropane is :

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Q.5 Which one of the following compounds is not aromatic?


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Q.6 Given below are two statements :
Statement I : Hyperconjugation is a permanent effect.
Statement II : Hyperconjugation in ethyl cation

involves the overlapping of Csp2−H1s bond with empty 2p orbital of other carbon.
Choose the correct option :

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Q.7

The correct order of stability of given carbocation is :


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Q.8 Which among the following is the strongest acid ?

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Q.9 The correct decreasing order of densities of the following compounds is :

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Q.10 Which one among the following resonating structures is not correct?

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Q.11 Which of the following molecules does not show stereo isomerism?

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Q.12 Which of the following compounds does not exhibit resonance?

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Q.13

The correct order of their reactivity towards hydrolysis at room temperature is :

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Q.14 Which one of the following pairs of isomers is an example of metamerism?

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Q.15

Among the given species the Resonance stabilised carbocations are :

20th July Morning Shift 2021

Q.16 Given below are two statements :


Statement I : C2H5OH and AgCN both can generate nucleophile.
Statement II : KCN and AgCN both will generate nitrile nucleophile with all reaction
conditions.
Choose the most appropriate option :

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Q.17 In the following molecule,

Hybridisation of Carbon a, b, and c respectively are :


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Q.18 Compound with molecular formula C3H6O can show :

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Q.19 Which of the following is an aromatic compound?

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Q.20 Which of the following is least basic?

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Q.21 Match List - I with List - II :

List - I List - II
Test/Reagents/Observation(s) Species detected
(a) Lassaigne's Test (i) Carbon
(b) Cu(II) oxide (ii) Sulphur
(c) Silver nitrate (iii) N, S, P, and halogen
(d) The sodium fusion extract (iv) Halogen Specifically
gives black precipitate with
acetic acid and lead acetate

The correct match is :

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Q.22 Among the following, the aromatic compounds are :

Choose the correct answer from the following options :

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Q.23 In

molecule, the hybridization of carbon 1, 2, 3 and 4 respectively, are :

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Q.24 Which of the following is 'a' FALSE statement ?

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Q.25 The correct order of acid character of the following compounds is :

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Q.26 Which one of the following compounds is non-aromatic?

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Q.27 The correct order of the following compounds showing increasing tendency
towards nucleophilic substitution reaction is :

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MCQ Answer Key

1. Ans. (C) 10. Ans. (A) 19. Ans. (A)


2. Ans. (D) 11. Ans. (C) 20. Ans. (A)
3. Ans. (A) 12. Ans. (D) 21. Ans. (C)
4. Ans. (D) 13. Ans. (A) 22. Ans. (B)
5. Ans. (C) 14. Ans. (D) 23. Ans. (A)
6. Ans. (C) 15. Ans. (C) 24. Ans. (A)
7. Ans. (A) 16. Ans. (D) 25. Ans. (C)
8. Ans. (D) 17. Ans. (A) 26. Ans. (D)
9. Ans. (A) 18. Ans. (D) 27. Ans. (D)
MCQ Explanation

Ans 1. More stable less potential energy.


Stability order : I > III > IV > II
So
Potential energy : II > IV > III > I

Ans 2.

First prioritise the groups according to CIP rule


It is (2E)-2-Bromo-hex-2-en-4-yne

Ans 3. (a) Shows intra molecular H-bonding


(b) Shows significant intermolecular H-bonding
(c) It do not show intermolecular H-bonding due to steric hindrance.

Ans 4.
Ans 5.

Ans 6. Statement I : It is correct statement

Ans 7.

Ans 8.

Strongest acid because its conjugate base is aromatic


Ans 9. The density order

Ans 10.

It is unstable Resonating Structure (due to similar charge on adjacent atom).

Ans 11.
Ans 12. CH3−CH2−CH = CH−CH2−NH2
No conjugation thus resonance is not possible.

Ans 13.

Ans 14.

Ans 15.

Ans 16. Both C2H5OH and AgCN can generate nucleophile.


KCN generates nitriles on substitution reactions with haloalkanes where AgCN
generates isonitriles on substitution reactions with haloalkanes. Because KCN is
ionic and has ‘C’ nucleophilic centre whereas AgCN is covalent and has ‘N’
nucleophilic centre.

Ans 17.

Ans 18. C3H6O (degree of unsaturation = 1)

Functional group isomerism.

Ans 19. A compound which has (4n + 2)π electrons completely delocalised over the
cyclic ring is aromatic.

Here 6 π electrons are present which follow the rule.

Ans 20. Basic strength ∝ availability of lone pair.

••
In this case lone pair of is highly participating in resonance.
𝑁
Ans 21. (i) Lassaigne test is used to detect N, S, P, X element
(ii) Carbon and hydrogen are detected by heating the compound with copper (ii)
oxide.
(iii) Halides are detected by silver nitrate
(iv) Sodium fusion extract gives black ppt. with acetic acid and lead acetate to
confirm the presence of sulphur.

Ans 22.

Ans 23.
Ans 24. Carius method is used in the estimation of halogen and sulphur in organic
compounds.

Ans 25. Acidic strength

Since carboxylic acids are more acidic than phenols.


–I and – R effect increase the acidic strength where as +I and +R effect decrease the
acidic strength of carboxylic acids.

Ans 27.
MCQ (More than One Correct Answer)

Q.1 Which one of the following compounds is aromatic in nature?

MCQ Answer Key

1. Ans. A and D
MCQ Explanation
Ans 1. (a) (Acenaphthene)

→ 10 πe− in cyclic conjugation


⇒ Aromatic

(b)

→ 4 πe− in ring conjugation ⇒ Anti Aromatic


(c)

⇒ 4 πe− in ring conjugation ⇒ Antiaromatic


(d)

6πe− in ring conjugation ⇒ Aromatic

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