1. Question: What is acidity in organic 1.

Question: What is basicity in organic

chemistry? chemistry?
Answer: Acidity refers to the ability of a Answer: Basicity refers to the ability of a
compound to donate a proton (H⁺) when compound to accept a proton (H⁺) when
dissolved in a solvent. dissolved in a solvent.
2. Question: How does the presence of
electronegative atoms influence the acidity of 2. Question: How does the presence of
organic compounds? electron-donating groups affect the basicity of
Answer: Electronegative atoms stabilize the organic compounds?
resulting conjugate base, increasing the acidity Answer: Electron-donating groups increase
of the compound. the basicity of compounds by stabilizing the
resulting conjugate acid.
3. Question: Compare the acidity of alkanes,
alkenes, and alkynes. 3. Question: Compare the basicity of alkanes,
Answer: Alkynes are more acidic than alkenes, alkenes, and alkynes.
which are more acidic than alkanes due to the Answer: Alkynes are more basic than alkenes,
increasing s-character of the hybridized orbital which are more basic than alkanes due to the
in the C-H bond. increasing s-character of the hybridized orbital
in the C-H bond.
4. Question: How does the acidity of carboxylic
acids compare to that of alcohols? 4. Question: How does the basicity of amines
Answer: Carboxylic acids are more acidic than compare to that of alcohols?
alcohols because the carbonyl group stabilizes Answer: Amines are more basic than alcohols
the resulting carboxylate ion. due to the presence of a lone pair of electrons
on nitrogen.
5. Question: What factors influence the acidity
of phenols? 5. Question: What factors influence the basicity
Answer: The acidity of phenols is influenced of aromatic amines?
by substituents on the aromatic ring and Answer: Basicity of aromatic amines is
resonance stabilization of the phenoxide ion. influenced by the electron-donating or
withdrawing nature of substituents on the
6. Question: What role does resonance aromatic ring.
stabilization play in determining acidity?
Answer: Resonance stabilization delocalizes 6. Question: What role does resonance
the negative charge, making the conjugate base stabilization play in determining basicity?
more stable and increasing acidity. Answer: Resonance stabilization delocalizes
the positive charge, making the resulting
7. Question: Compare the acidity of aromatic conjugate acid more stable and increasing
and aliphatic compounds. basicity.
Answer: Aromatic compounds are generally
more acidic due to resonance stabilization of 7. Question: Compare the basicity of aromatic
the resulting conjugate base. and aliphatic compounds.
Answer: Aromatic compounds are generally
8. Question: How do substituents affect the less basic than aliphatic compounds due to
acidity of organic molecules? resonance stabilization of the lone pair on
Answer: Substituents can donate or withdraw nitrogen.
electron density, affecting the stability of the
conjugate base and acidity of the molecule. 8. Question: How do substituents affect the
basicity of organic molecules?
9. Question: Discuss the acidity trends in Answer: Substituents can either donate or
carboxylic acids with increasing alkyl group size. withdraw electron density, affecting the
Answer: As the size of the alkyl group stability of the resulting conjugate acid and the
increases, the acidity of carboxylic acids basicity of the molecule.
decreases due to decreased electron
withdrawal. 9. Question: Discuss the basicity trends in
amines with increasing alkyl group size.
10. Question: What happens to acidity when a Answer: Basicity decreases with increasing
compound undergoes protonation? alkyl group size due to decreased electron
Answer: Acidity decreases because the density on nitrogen.
protonated form is less likely to donate a
proton. 10. Question: What happens to basicity when a
compound accepts a proton?
11. Question: What effect does conjugation Answer: Basicity decreases when a
have on acidity? compound accepts a proton because the
Answer: Conjugation increases the stability of resulting conjugate acid is less likely to accept
the conjugate base, making the compound another proton.
more acidic.
11. Question: What effect does conjugation
12. Question: Compare the acidity of primary, have on basicity?
secondary, and tertiary alcohols. Answer: Conjugation decreases basicity by
Answer: Tertiary alcohols are more acidic stabilizing the lone pair of electrons on
than secondary alcohols, which are more acidic nitrogen.
than primary alcohols due to stability of the
resulting alkoxide ion. 12. Question: Compare the basicity of primary,
secondary, and tertiary amines.
13. Question: How do different functional Answer: Tertiary amines are less basic than
groups affect organic acid acidity? secondary amines, which are less basic than
Answer: Functional groups that stabilize primary amines due to decreased electron
negative charge increase acidity, while those density on nitrogen.
that destabilize decrease acidity.
13. Question: How do different functional
14. Question: How does a compound's groups affect the basicity of organic
structure influence its ability to donate a compounds?
proton? Answer: Functional groups that stabilize the
Answer: Presence of acidic hydrogen or a resulting conjugate acid decrease basicity, while
partial positive charge on carbon increases those that destabilize increase basicity.
ability to donate a proton.
14. Question: How does a compound's
15. Question: Explain the significance of pKa in structure influence its ability to accept a
determining acidity. proton?
Answer: pKa is the negative logarithm of the Answer: Presence of a lone pair of electrons
acid dissociation constant (Ka). Lower pKa on an electronegative atom increases ability to
values indicate stronger acids. accept a proton.

16. Question: What trends are observed in α- 15. Question: Explain the significance of pKa in
hydrogens of carbonyl compounds? determining basicity.
Answer: α-Hydrogens of carbonyl compounds Answer: pKa is the negative logarithm of the
are acidic due to the electron-withdrawing base dissociation constant (Kb). Higher pKa
carbonyl group. values indicate stronger bases.

17. Question: How does the presence of 16. Question: What trends are observed in the
multiple functional groups affect overall basicity of heterocycles?
acidity? Answer: Basicity of heterocycles increases
 Answer: It depends on specific functional with the electron-donating nature of the
groups and their effects; multiple groups can heteroatom and the absence of resonance
either increase or decrease acidity. stabilization.

18. Question: Compare the acidity of terminal 17. Question: How does the presence of
and internal alkynes. multiple functional groups affect overall
Answer: Terminal alkynes are more acidic due basicity?
to presence of a hydrogen atom directly Answer: It depends on specific functional
bonded to a sp-hybridized carbon atom. groups and their effects; multiple groups can
either increase or decrease basicity.
19. Question: What effect does solvent polarity
have on acidity? 18. Question: Compare the basicity of aromatic
Answer: Polar solvents stabilize charged and non-aromatic nitrogen-containing
species, increasing acidity compared to compounds.
nonpolar solvents. Answer: Aromatic nitrogen-containing
compounds are generally less basic than non-
20. Question: Explain acidity strength in terms aromatic nitrogen-containing compounds due
of conjugate base stability. to resonance stabilization.
Answer: More stable conjugate bases result
in stronger acids. 19. Question: What effect does solvent polarity
have on basicity?
21. Question: How does the size of the Answer: Polar solvents stabilize charged
conjugate base influence acidity? species, increasing basicity compared to
Answer: Larger conjugate bases are less nonpolar solvents.
stable and lead to weaker acids.
20. Question: Explain basicity strength in terms
22. Question: Compare the acidity of alcohols of conjugate acid stability.
and thiols. Answer: More stable conjugate acids result in
Answer: Thiols are generally more acidic than stronger bases.
alcohols due to the lower electronegativity of
sulfur compared to oxygen. 21. Question: How does the size of the
conjugate acid influence basicity?
23. Question: What is the effect of inductive Answer: Larger conjugate acids are less stable
effects on acidity? and lead to weaker bases.
Answer: Electronegative atoms can withdraw
electron density through sigma bonds, 22. Question: Compare the basicity of amines
increasing acidity. and phosphines.
Answer: Amines are generally more basic
24. Question: Explain the acidity trend in than phosphines due to the lower
haloalkanes. electronegativity of nitrogen compared to
Answer: Acidity increases with increasing size phosphorus.
and electronegativity of the halogen due to
increased stabilization of the conjugate base. 23. Question: What is the effect of inductive
effects on basicity?
25. Question: How does the presence of Answer: Electron-withdrawing groups
resonance affect acidity in organic molecules? decrease basicity, while electron-donating
Answer: Resonance stabilization increases groups increase basicity.
acidity by spreading charge over multiple
atoms. 24. Question: Explain the basicity trend in
haloalkanes.
26. Question: Compare the acidity of terminal Answer: Basicity decreases with increasing
alkynes with terminal alkenes. size and electronegativity of the halogen due to
Answer: Terminal alkynes are more acidic due decreased stabilization of the resulting
to the presence of a sp-hybridized carbon conjugate acid.
directly bonded to a hydrogen.
25. Question: How does the presence of
27. Question: Discuss the acidity trend in α- resonance affect basicity in organic molecules?
carbon atoms of carbonyl compounds. Answer: Resonance stabilization decreases
Answer: α-Carbon atoms adjacent to carbonyl basicity by delocalizing the lone pair of
groups are acidic due to resonance stabilization electrons.
of the resulting enolate ion.
26. Question: Compare the basicity of terminal
28. Question: How does the acidity of a alkynes with terminal alkenes.
compound change with increasing electron Answer: Terminal alkynes are less basic than
density on the conjugate base? terminal alkenes due to the absence of a lone
Answer: Acidity decreases as electron density pair of electrons on the sp-hybridized carbon.
on the conjugate base increases, leading to
greater stability. 27. Question: Discuss the basicity trend in α-
carbon atoms of carbonyl compounds.
29. Question: Explain the effect of aromaticity Answer: α-Carbon atoms adjacent to carbonyl
on acidity. groups are less basic due to resonance
Answer: Aromatic compounds are more stabilization of the resulting enolate ion.
acidic due to increased stability of the
conjugate base resulting from resonance. 28. Question: How does the basicity of a
compound change with increasing electron
30. Question: How does hybridization of the density on the conjugate acid?
acidic hydrogen atom affect acidity? Answer: Basicity increases as electron density
Answer: Hybridization influences the strength on the conjugate acid increases, leading to
of the C-H bond and the ease of proton greater stability.
removal, affecting acidity.
29. Question: Explain the effect of aromaticity
on basicity.
Answer: Aromatic compounds are less basic
due to decreased availability of the lone pair of
electrons for protonation.

30. Question: How does hybridization of the

nitrogen atom affect basicity?
Answer: Sp³-hybridized nitrogen atoms are
more basic than sp²-hybridized nitrogen atoms
due to increased electron density.
Q1. Arrange the following in order of decreasing acidity:
(a) CH₃CH₂OH, (b) CH₃COOH, (c) CH₃CH₂NH₂.
[6 marks]

Solution:

 CH₃COOH is most acidic (carboxylate anion stabilized by resonance).

 CH₃CH₂OH less acidic (no resonance).

 CH₃CH₂NH₂ weakest (N⁻ conjugate base is very unstable).

Order: CH₃COOH > CH₃CH₂OH > CH₃CH₂NH₂.

Q2. Compare the acidity of CH₃COOH, ClCH₂COOH, and CCl₃COOH. Explain.

[6 marks]

Solution:

 –Cl group withdraws electrons (–I effect), stabilizing conjugate base.

 More Cl → stronger acid.

Order: CCl₃COOH > ClCH₂COOH > CH₃COOH.

Q3. Arrange in decreasing basicity: NH₃, CH₃NH₂, (CH₃)₃N.

[6 marks]

Solution:

 CH₃ groups donate electrons by +I effect, increasing basicity.

 But (CH₃)₃N has steric hindrance, lowering availability of lone pair.

Order: CH₃NH₂ > (CH₃)₃N > NH₃.

Q4. Between ethanol (CH₃CH₂OH) and thiol (CH₃SH), which is more acidic? Explain.
[4 marks]

Solution:

 S–H bond is weaker than O–H, so thiol proton is easier to remove.

 CH₃SH more acidic than CH₃CH₂OH.

Q5. Arrange HC≡CH, CH₂=CH₂, CH₃CH₃ in decreasing acidity.

[6 marks]

Solution:

 Acidity increases with % s-character of C–H bond.

 sp > sp² > sp³.

Order: HC≡CH > CH₂=CH₂ > CH₃CH₃.
Q6. Why is NaNH₂ a stronger base than NaOH?
[4 marks]

Solution:

 N less electronegative than O, so NH₂⁻ holds electrons less tightly and donates them more
easily.

 Hence NaNH₂ > NaOH in basicity.

Q7. Arrange the following in order of increasing acidity: CH₃COOH, HCOOH, (CH₃)₂CHCOOH.
[6 marks]

Solution:

 Formic acid (HCOOH) most acidic, no +I effect.

 Acetic acid weaker (–CH₃ donates electrons).

 Isobutyric acid (CH(CH₃)₂)₂CHCOOH) weakest due to strong +I effect.

Order: HCOOH > CH₃COOH > (CH₃)₂CHCOOH.

Q8. Explain why amides (RCONH₂) are much less basic than amines (RNH₂).
[4 marks]

Solution:

 Lone pair on N in amides is delocalized with C=O group.

 Reduced availability for protonation → less basic.

Q9. Between CH₃⁻ and NH₂⁻, which is stronger base? Explain.

[4 marks]

Solution:

 CH₃⁻ less electronegative than NH₂⁻ → electrons are donated more easily.

 CH₃⁻ stronger base than NH₂⁻.

Q10. Rank the acidity of CH₃CH₂OH, CF₃CH₂OH, and CCl₃CH₂OH.

[6 marks]

Solution:

 Electronegative substituents withdraw electrons (–I effect).

 CF₃ group is stronger –I than CCl₃.

Order: CF₃CH₂OH > CCl₃CH₂OH > CH₃CH₂OH.
🔹 Aromatic Compounds (10 Questions)

Q11. Arrange phenol, o-nitrophenol, and p-nitrophenol in order of increasing acidity.

[6 marks]

Solution:

 –NO₂ withdraws electrons → more acidic.

 o-nitrophenol has intramolecular H-bond, slightly more acidic than p.

Order: phenol < p-nitrophenol < o-nitrophenol.

Q12. Which is more basic: aniline or p-methylaniline? Explain.

[4 marks]

Solution:

 –CH₃ donates electrons (+I), increasing basicity.

 p-methylaniline > aniline.

Q13. Arrange in acidity: benzoic acid, p-nitrobenzoic acid, p-methylbenzoic acid.

[6 marks]

Solution:

 –NO₂ withdraws → increases acidity.

 –CH₃ donates → decreases acidity.

Order: p-nitrobenzoic acid > benzoic acid > p-methylbenzoic acid.

Q14. Compare basicity of aniline and acetanilide.

[4 marks]

Solution:

 In acetanilide, lone pair delocalized into C=O → less basic.

 Aniline more basic.

Q15. Why is phenol more acidic than cyclohexanol?

[4 marks]

Solution:

 Phenoxide ion stabilized by resonance with benzene ring.

 Cyclohexanol lacks resonance.

Q16. Arrange in decreasing basicity: pyridine, pyrrole, piperidine.
[6 marks]

Solution:

 Piperidine (aliphatic) most basic.

 Pyridine: lone pair available, but less basic than aliphatic.

 Pyrrole: lone pair part of aromatic sextet → least basic.

Order: piperidine > pyridine > pyrrole.

Q17. Arrange in increasing acidity: phenol, o-chlorophenol, p-chlorophenol.

[6 marks]

Solution:

 –Cl withdraws electrons (–I), increases acidity.

 Ortho effect (inductive + H-bonding) makes o-chloro strongest.

Order: phenol < p-chlorophenol < o-chlorophenol.

Q18. Which is stronger acid: benzoic acid or salicylic acid? Explain.

[4 marks]

Solution:

 Salicylic acid has intramolecular H-bond stabilizing conjugate base.

 Salicylic acid > benzoic acid.

Q19. Why is aniline less basic than methylamine?

[4 marks]

Solution:

 In aniline, lone pair on N is delocalized into benzene ring.

 Reduced availability for protonation → less basic.

Q20. Arrange in acidity: phenol, 2,4,6-trinitrophenol (picric acid), and cresol (p-CH₃–C₆H₄–OH).
[6 marks]

Solution:

 Multiple –NO₂ groups withdraw strongly → picric acid most acidic.

 Phenol intermediate.

 Cresol weakest due to +I effect of –CH₃.

Order: picric acid > phenol > cresol.
 1. Key chemical principle (pKa, resonance, inductive effect, hybridization, etc.)

2. Comparison/Reasoning (why one is stronger/weaker vs others)

3. Final conclusion (order/ranking/choice)

Q1. Arrange the following in order of decreasing acidity:

(a) CH₃CH₂OH, (b) CH₃COOH, (c) CH₃CH₂NH₂.
[6 marks]

Solution:

1. Acetic acid (CH₃COOH) is most acidic because the conjugate base (CH₃COO⁻) is resonance-
stabilized.

2. Ethanol (CH₃CH₂OH) is less acidic since its conjugate base (CH₃CH₂O⁻) has no resonance
stabilization.

3. Ethylamine (CH₃CH₂NH₂) is the weakest acid; nitrogen is less electronegative than oxygen, so
it holds negative charge poorly.
Order: CH₃COOH > CH₃CH₂OH > CH₃CH₂NH₂.

Q2. Compare the acidity of CH₃COOH, ClCH₂COOH, and CCl₃COOH.

[6 marks]

Solution:

1. Chlorine is strongly electron-withdrawing (–I effect), stabilizing the carboxylate anion.

2. The more chlorine atoms attached, the stronger the acidity.

3. Therefore, trichloroacetic acid (CCl₃COOH) is strongest, followed by chloroacetic acid

(ClCH₂COOH), then acetic acid (CH₃COOH).
Order: CCl₃COOH > ClCH₂COOH > CH₃COOH.

Q3. Arrange in decreasing basicity: NH₃, CH₃NH₂, (CH₃)₃N.

[6 marks]

Solution:

1. Alkyl groups donate electrons by the +I effect, increasing electron density on nitrogen.

2. CH₃NH₂ is more basic than NH₃ due to one +I group; (CH₃)₃N has three +I groups but steric
hindrance lowers availability of the lone pair.

3. Therefore, CH₃NH₂ is strongest base, followed by (CH₃)₃N, then NH₃.

Order: CH₃NH₂ > (CH₃)₃N > NH₃.
Q4. Between ethanol (CH₃CH₂OH) and thiol (CH₃SH), which is more acidic?
[4 marks]

Solution:

1. Bond strength: O–H bond is stronger than S–H, so H⁺ is released more easily from thiols.

2. Electronegativity: Oxygen is more electronegative than sulfur, but sulfur’s larger size
stabilizes the negative charge on S⁻ better.

3. Thus, thiols are more acidic than alcohols.

Answer: CH₃SH is more acidic.

Q5. Arrange HC≡CH, CH₂=CH₂, CH₃CH₃ in decreasing acidity.

[6 marks]

Solution:

1. Hybridization: sp (acetylene) has 50% s-character, sp² (ethylene) has 33%, sp³ (ethane) has
25%.

2. Higher s-character = more electronegative carbon = stronger acidity.

3. Therefore, acetylene is most acidic, followed by ethylene, then ethane.

Order: HC≡CH > CH₂=CH₂ > CH₃CH₃.

Q6. Why is NaNH₂ a stronger base than NaOH?

[4 marks]

Solution:

1. Nitrogen is less electronegative than oxygen, so it holds negative charge less tightly.

2. This makes NH₂⁻ more willing to donate electrons/protons → stronger base.

3. OH⁻ is more stabilized due to oxygen’s high electronegativity, making it weaker.

Answer: NaNH₂ > NaOH in basicity.

Q7. Arrange the following in order of increasing acidity: CH₃COOH, HCOOH, (CH₃)₂CHCOOH.
[6 marks]

Solution:

1. Formic acid (HCOOH) has no +I group, making it strongest.

2. Acetic acid (CH₃COOH) has a +I group (–CH₃), reducing acidity.

3. Isobutyric acid ((CH₃)₂CHCOOH) has stronger +I groups, so weakest.

Order: HCOOH > CH₃COOH > (CH₃)₂CHCOOH.
Q8. Explain why amides (RCONH₂) are much less basic than amines (RNH₂).
[4 marks]

Solution:

1. In amides, nitrogen’s lone pair delocalizes into the carbonyl group (resonance).

2. This reduces the availability of the lone pair for protonation.

3. Amines do not have this delocalization, so they are more basic.

Answer: Amides << amines in basicity.

Q9. Between CH₃⁻ and NH₂⁻, which is stronger base?

[4 marks]

Solution:

1. Basicity depends on electronegativity: carbon is less electronegative than nitrogen.

2. CH₃⁻ holds electrons less tightly, so donates more easily.

3. NH₂⁻ is more stable, so weaker base.

Answer: CH₃⁻ > NH₂⁻.

Q10. Rank the acidity of CH₃CH₂OH, CF₃CH₂OH, and CCl₃CH₂OH.

[6 marks]

Solution:

1. –CF₃ and –CCl₃ groups withdraw electrons strongly (–I effect).

2. The stronger the electron withdrawal, the more stabilized the conjugate base.

3. CF₃ is more electronegative than CCl₃, so CF₃CH₂OH is most acidic.

Order: CF₃CH₂OH > CCl₃CH₂OH > CH₃CH₂OH.

Q11. Arrange in decreasing basicity: CH₃NH₂, CH₃CH₂NH₂, (CH₃)₂NH.

[6 marks]

Solution:

1. Alkyl groups donate electrons (+I effect), increasing basicity.

2. Secondary amine ((CH₃)₂NH) has two +I groups, making it more basic than primary amines.

3. Between CH₃NH₂ and CH₃CH₂NH₂, both are primary, but ethyl donates slightly more than
methyl.
Order: (CH₃)₂NH > CH₃CH₂NH₂ > CH₃NH₂.
Q12. Compare acidity of CH₃CH₂OH and CH₃CH₂NH₂.
[4 marks]

Solution:

1. O–H bond is more polar than N–H, making H⁺ release easier.

2. The conjugate base CH₃CH₂O⁻ is more stabilized than CH₃CH₂NH⁻.

3. Oxygen is more electronegative than nitrogen, favoring acidity.

Answer: Alcohol > Amine in acidity.

Q13. Which is more basic: NH₃ or PH₃?

[4 marks]

Solution:

1. N is more electronegative than P, but its lone pair is in a smaller orbital, easily available for
bonding.

2. In PH₃, lone pair is more diffuse, less available.

3. Hence NH₃ accepts protons more readily.

Answer: NH₃ is more basic than PH₃.

Q14. Arrange in order of acidity: H₂O, H₂S, H₂Se.

[6 marks]

Solution:

1. Down the group, bond strength decreases (O–H > S–H > Se–H).

2. Weaker bonds break more easily, releasing H⁺.

3. Hence acidity increases down the group.

Order: H₂O < H₂S < H₂Se.

Q15. Explain why CH₃CH₂COOH is more acidic than CH₃CH₂OH.

[4 marks]

Solution:

1. Carboxylate ion (RCOO⁻) is resonance-stabilized.

2. Alkoxide ion (RO⁻) has no resonance stabilization.

3. Greater stability of conjugate base → stronger acid.

Answer: Carboxylic acid > Alcohol in acidity.
Q16. Which is more basic: CH₃Li or CH₃MgBr?
[4 marks]

Solution:

1. Basicity depends on ionic character of C–M bond.

2. C–Li bond is more ionic, giving carbon more negative charge.

3. Hence CH₃Li is stronger base than CH₃MgBr.

Answer: CH₃Li > CH₃MgBr.

Q17. Arrange in decreasing acidity: CH₃COOH, CF₃COOH, NO₂CH₂COOH.

[6 marks]

Solution:

1. Both –CF₃ and –NO₂ are strong electron withdrawing groups.

2. –CF₃ has strong –I effect, –NO₂ has both –I and –M effect.

3. Hence: NO₂CH₂COOH > CF₃COOH > CH₃COOH.

Answer: Nitroacetic acid > Trifluoroacetic acid > Acetic acid.

Q18. Compare basicity of CH₃O⁻ and CH₃S⁻.

[4 marks]

Solution:

1. Oxygen is more electronegative than sulfur, holding negative charge more tightly.

2. Sulfur is larger, delocalizing charge better, making CH₃S⁻ less reactive.

3. Thus CH₃O⁻ is stronger base.

Answer: CH₃O⁻ > CH₃S⁻.

Q19. Arrange in order of acidity: HC≡CH, H₂C=CH–CH₃, CH₃CH₃.

[6 marks]

Solution:

1. Acetylene (sp C) is most acidic due to high s-character.

2. Alkene (sp²) is less acidic.

3. Alkane (sp³) is weakest.

Order: HC≡CH > H₂C=CH–CH₃ > CH₃CH₃.

Q20. Explain why carbanions are stronger bases than amide ions.
[4 marks]

Solution:
 1. Carbon is less electronegative than nitrogen, holds negative charge poorly.

2. Thus carbanion is highly reactive, strong base.

3. Amide ion (NH₂⁻) is stabilized by electronegativity of N, less basic.

Answer: Carbanions > Amides in basicity.

Great 👍 Thanks for confirming!

Let’s continue with the Aromatic section.

I’ll now generate the 20 Aromatic Q&As (Q21–Q40), each with at least 3 explanation points. These
will cover acidic and basic properties in benzene derivatives, phenols, anilines, substituted
aromatics, etc.

🔹 Aromatic Q&As (Q21–Q40)

Q21. Arrange in order of acidity: Benzyl alcohol, Phenol, p-Nitrophenol.

[6 marks]

Solution:

1. Phenol is more acidic than benzyl alcohol due to resonance stabilization of phenoxide ion.

2. –NO₂ at para position withdraws electrons, stabilizing phenoxide further.

3. Benzyl alcohol lacks resonance stabilization of conjugate base.

Order: p-Nitrophenol > Phenol > Benzyl alcohol.

Q22. Compare basicity of aniline and cyclohexylamine.

[6 marks]

Solution:

1. In aniline, the lone pair on N delocalizes into the aromatic ring, reducing availability for
protonation.

2. In cyclohexylamine, no resonance → lone pair fully available.

3. Hence cyclohexylamine is more basic.

Answer: Cyclohexylamine > Aniline.

Q23. Explain why phenol is more acidic than cyclohexanol.

[6 marks]

Solution:

1. Phenoxide ion is resonance stabilized over the aromatic ring.

2. Cyclohexoxide ion has no resonance stabilization.

3. Resonance increases conjugate base stability → greater acidity.

Answer: Phenol > Cyclohexanol.
Q24. Arrange in increasing acidity: Phenol, o-Cresol, o-Nitrophenol.
[6 marks]

Solution:

1. –CH₃ group (o-cresol) donates electrons → decreases acidity.

2. Phenol is more acidic than o-cresol.

3. –NO₂ group withdraws strongly → stabilizes conjugate base → highest acidity.

Order: o-Cresol < Phenol < o-Nitrophenol.

Q25. Which is more basic: Aniline or p-Nitroaniline?

[6 marks]

Solution:

1. –NO₂ group withdraws electrons by –M and –I effect.

2. This reduces electron density on N, lowering basicity.

3. Aniline has lone pair more available than p-nitroaniline.

Answer: Aniline > p-Nitroaniline.

Q26. Arrange in order of basicity: Aniline, N-Methylaniline, N,N-Dimethylaniline.

[6 marks]

Solution:

1. In aniline, lone pair partially delocalizes → moderate basicity.

2. N-Methylaniline has +I effect of methyl, increasing basicity slightly.

3. In N,N-dimethylaniline, steric hindrance and resonance reduce basicity.

Order: N-Methylaniline > Aniline > N,N-Dimethylaniline.

Q27. Explain why p-Nitrophenol is more acidic than phenol.

[4 marks]

Solution:

1. –NO₂ group withdraws electrons, stabilizing phenoxide ion.

2. Resonance increases stability of conjugate base.

3. Phenol lacks this extra stabilization.

Answer: p-Nitrophenol > Phenol.
Q28. Arrange in decreasing acidity: Phenol, o-Methoxyphenol, o-Chlorophenol.
[6 marks]

Solution:

1. –OCH₃ group donates by +M, reducing acidity.

2. –Cl group withdraws inductively, stabilizing conjugate base.

3. Phenol lies in between.

Order: o-Chlorophenol > Phenol > o-Methoxyphenol.

Q29. Compare acidity of benzoic acid and p-Methoxybenzoic acid.

[6 marks]

Solution:

1. –OCH₃ group donates by +M effect, destabilizing carboxylate ion.

2. This reduces acidity compared to benzoic acid.

3. Benzoic acid has no such destabilization.

Answer: Benzoic acid > p-Methoxybenzoic acid.

Q30. Which is more basic: Aniline or p-Toluidine (p-Methylaniline)?

[6 marks]

Solution:

1. –CH₃ group donates by +I effect, increasing electron density on N.

2. This increases basicity compared to aniline.

3. Aniline has no extra electron-donating effect.

Answer: p-Toluidine > Aniline.

Q31. Arrange in acidity: Phenol, o-Nitrophenol, p-Nitrophenol.

[6 marks]

Solution:

1. Both o- and p-nitro increase acidity vs phenol.

2. p-Nitrophenol is more stabilized by resonance than o-isomer.

3. Phenol is least acidic.

Order: p-Nitrophenol > o-Nitrophenol > Phenol.
Q32. Why is aniline less basic in water than expected?
[6 marks]

Solution:

1. In water, aniline undergoes resonance, delocalizing lone pair into ring.

2. Protonated anilinium ion is less stabilized.

3. Hence basicity in aqueous solution is reduced.

Answer: Lone pair delocalization reduces aqueous basicity.

Q33. Compare acidity of salicylic acid (o-hydroxybenzoic acid) and benzoic acid.
[6 marks]

Solution:

1. In salicylic acid, –OH at ortho position forms intramolecular H-bond, stabilizing conjugate
base.

2. This increases acidity compared to benzoic acid.

3. Benzoic acid lacks this extra stabilization.

Answer: Salicylic acid > Benzoic acid.

Q34. Arrange in decreasing basicity: Pyridine, Aniline, Piperidine.

[6 marks]

Solution:

1. Piperidine is aliphatic → no delocalization → highest basicity.

2. Pyridine has lone pair outside aromatic ring, moderately basic.

3. Aniline lone pair delocalizes into ring, least basic.

Order: Piperidine > Pyridine > Aniline.

Q35. Compare acidity of phenol and thiophenol.

[6 marks]

Solution:

1. S–H bond is weaker than O–H bond → H⁺ release easier.

2. Sulfur is larger, charge is more delocalized → greater stability.

3. Hence thiophenol is more acidic.

Answer: Thiophenol > Phenol.
Q36. Arrange in acidity: o-Aminobenzoic acid, m-Aminobenzoic acid, p-Aminobenzoic acid.
[6 marks]

Solution:

1. –NH₂ donates electrons by resonance, reducing acidity.

2. Effect strongest at para, weakest at meta.

3. Intramolecular H-bond in ortho slightly increases acidity vs para.

Order: m-Aminobenzoic acid > o-Aminobenzoic acid > p-Aminobenzoic acid.

Q37. Why is p-Nitroaniline less basic than aniline?

[6 marks]

Solution:

1. –NO₂ group strongly withdraws electrons.

2. Lone pair on N is less available for protonation.

3. Resonance delocalization reduces electron density further.

Answer: p-Nitroaniline < Aniline in basicity.

Q38. Arrange in acidity: Phenol, 2,4,6-Trinitrophenol, p-Cresol.

[6 marks]

Solution:

1. Trinitrophenol has multiple –NO₂ groups → very strong acidity.

2. Phenol is moderate.

3. p-Cresol has +I effect → weakest acid.

Order: 2,4,6-Trinitrophenol > Phenol > p-Cresol.

Q39. Compare basicity of aniline and acetanilide.

[6 marks]

Solution:

1. In acetanilide, –NHCOCH₃ group delocalizes lone pair into carbonyl.

2. Lone pair less available for protonation.

3. Aniline has more available lone pair → more basic.

Answer: Aniline > Acetanilide.
Q40. Arrange in basicity: Pyrrole, Pyridine, Imidazole.
[6 marks]

Solution:

1. Pyrrole: lone pair part of aromatic sextet → not available → weakest base.

2. Pyridine: lone pair outside ring → moderately basic.

3. Imidazole: one lone pair delocalized, one available → stronger base than pyridine.
Order: Imidazole > Pyridine > Pyrrole.

Perfect 👍
We already completed Q1–Q40 (20 aliphatic + 20 aromatic).

Now let’s move on to Q41–Q50.

This set will still focus on aromatic systems (acid–base properties in substituted aromatics,
heteroaromatics, etc.), each with ≥3 explanations.

🔹 Aromatic Q&As (Q41–Q50)

Q41. Arrange in acidity: Phenol, p-Chlorophenol, p-Bromophenol.

[6 marks]

Solution:

1. Both –Cl and –Br withdraw electrons by –I effect.

2. –Cl is more electronegative than –Br, stronger –I effect.

3. Hence p-chlorophenol is more acidic than p-bromophenol.

Order: p-Chlorophenol > p-Bromophenol > Phenol.

Q42. Why is picric acid (2,4,6-trinitrophenol) a much stronger acid than phenol?
[6 marks]

Solution:

1. Three –NO₂ groups withdraw strongly via –M and –I effects.

2. Phenoxide ion is highly stabilized by resonance.

3. In phenol, conjugate base is less stabilized.

Answer: Picric acid >> Phenol in acidity.
Q43. Compare basicity of aniline and m-nitroaniline.
[6 marks]

Solution:

1. –NO₂ group withdraws strongly, lowering electron density on N.

2. In meta position, resonance effect is weak but –I effect still operates.

3. Hence m-nitroaniline is less basic than aniline.

Answer: Aniline > m-Nitroaniline.

Q44. Arrange in decreasing basicity: Pyridine, Quinoline, Isoquinoline.

[6 marks]

Solution:

1. Pyridine: lone pair free and available → good base.

2. Quinoline and isoquinoline have extended conjugation → lone pair less localized.

3. Pyridine is more basic, followed by quinoline ≈ isoquinoline.

Order: Pyridine > Quinoline ≈ Isoquinoline.

Q45. Explain why o-nitrophenol is more acidic than m-nitrophenol.

[6 marks]

Solution:

1. –NO₂ group at ortho position withdraws electrons strongly.

2. Intramolecular H-bond stabilizes conjugate base in o-nitrophenol.

3. Meta position lacks resonance stabilization.

Answer: o-Nitrophenol > m-Nitrophenol.

Q46. Which is more basic: p-Anisidine (p-methoxyaniline) or aniline?

[6 marks]

Solution:

1. –OCH₃ donates electrons by +M effect.

2. This increases electron density on N, making lone pair more available.

3. Hence p-anisidine is more basic than aniline.

Answer: p-Anisidine > Aniline.
Q47. Arrange in acidity: o-Nitrobenzoic acid, m-Nitrobenzoic acid, p-Nitrobenzoic acid.
[6 marks]

Solution:

1. –NO₂ group withdraws electrons → increases acidity.

2. Ortho and para positions allow resonance stabilization, meta does not.

3. Intramolecular H-bond further stabilizes ortho.

Order: o-Nitrobenzoic acid > p-Nitrobenzoic acid > m-Nitrobenzoic acid.

Q48. Compare basicity: Imidazole vs Pyridine.

[6 marks]

Solution:

1. Imidazole has two nitrogens, one lone pair delocalized, one available.

2. This makes it more basic than pyridine, where lone pair is only moderately available.

3. Protonated imidazole is stabilized by resonance.

Answer: Imidazole > Pyridine.

Q49. Arrange in acidity: Benzoic acid, o-Hydroxybenzoic acid, p-Hydroxybenzoic acid.

[6 marks]

Solution:

1. –OH group donates by resonance, reducing acidity.

2. At ortho position, intramolecular H-bond stabilizes carboxylate.

3. Para effect is purely resonance, less stabilizing.

Order: o-Hydroxybenzoic acid > Benzoic acid > p-Hydroxybenzoic acid.

Q50. Why is pyrrole almost neutral in water?

[6 marks]

Solution:

1. Lone pair of N in pyrrole participates in aromatic sextet.

2. This makes it unavailable for protonation.

3. Protonation breaks aromaticity, which is highly unfavorable.

Answer: Pyrrole shows very weak basicity (almost neutral).
Perfect — I’ll expand the reasoning for each question into at least three clear explanations so you
can use them for teaching or exam prep.

Q51. Why is picric acid (2,4,6-trinitrophenol) very acidic?

Answer: Strong –NO₂ groups withdraw strongly.

Explanations:

1. The –NO₂ groups have a strong –I (inductive effect), pulling electron density away from the
O–H bond, weakening it and making the proton easier to remove.

2. After deprotonation, the phenoxide ion is stabilized by resonance with all three nitro
groups, which delocalize the negative charge.

3. The combined effect of three nitro groups at 2, 4, and 6 positions maximizes electron
withdrawal, making picric acid one of the strongest phenols.

Q52. Arrange acidity: phenol, p-chlorophenol, o-chlorophenol.

Answer: o-chloro > p-chloro > phenol.

Explanations:

1. –Cl is an electron-withdrawing group (–I effect), which increases acidity by stabilizing the
phenoxide ion.

2. In the ortho position, –Cl has both –I effect and an ortho effect (proximity effect), which
increases acidity more than at para.

3. Steric repulsion at ortho may also weaken the O–H bond, making deprotonation easier
compared to para- and unsubstituted phenol.

Q53. Which is more basic: aniline or acetanilide?

Answer: Aniline.
Explanations:

1. In aniline, the –NH₂ group is free, and its lone pair is available for protonation.

2. In acetanilide, the lone pair is delocalized into the carbonyl group (–CONH–), reducing its
availability for bonding with H⁺.

3. Resonance in acetanilide stabilizes the nitrogen, but lowers basicity compared to free amine
(aniline).

Q54. Which is stronger acid: salicylic acid or benzoic acid?

Answer: Salicylic acid.

Explanations:

1. In salicylic acid, the ortho –OH group forms intramolecular H-bonding with the carboxylate,
stabilizing the conjugate base.
 2. The –OH group has –I and mesomeric effects, which withdraw electrons and enhance
acidity.

3. The stabilization of conjugate base in salicylic acid lowers pKa compared to benzoic acid.

Q55. Why is aniline less basic than methylamine?

Answer: Lone pair delocalized into benzene.

Explanations:

1. In aniline, the lone pair on N participates in resonance with the aromatic ring, reducing its
availability to accept protons.

2. In methylamine, the lone pair is localized and fully available for protonation.

3. The aromatic ring is electron withdrawing by resonance, which further decreases the
basicity of aniline.

Q56. Arrange acidity: phenol, 2,4,6-trinitrophenol, cresol.

Answer: 2,4,6-trinitrophenol > phenol > cresol.

Explanations:

1. Trinitrophenol has three strong –NO₂ groups, which strongly withdraw electrons and
stabilize the conjugate base.

2. Cresol has a +I donating –CH₃ group, which destabilizes the conjugate base and lowers
acidity.

3. Phenol is intermediate because it has no strongly withdrawing or donating substituents.

Q57. Which is more basic: pyridine or pyrrole?

Answer: Pyridine.
Explanations:

1. In pyridine, the lone pair on N is not part of aromatic sextet, so it is free for protonation.

2. In pyrrole, the lone pair participates in aromaticity, so it is unavailable for protonation.

3. Protonation of pyridine keeps aromaticity intact, but protonation of pyrrole destroys

aromaticity, making it less basic.
Q58. Why is benzoic acid acidic while toluene is not?

Answer: Carboxylate stabilized by resonance.

Explanations:

1. Benzoic acid’s –COOH group can delocalize the negative charge over two oxygens, stabilizing
the conjugate base.

2. The benzene ring has a –I effect, slightly withdrawing electrons and increasing acidity.

3. In contrast, toluene has only a –CH₃ substituent, which is electron donating (+I), giving no
stabilization to a possible conjugate base.

Q59. Arrange in basicity: pyridine, aniline, piperidine.

Answer: piperidine > pyridine > aniline.

Explanations:

1. Piperidine is an aliphatic amine, where the lone pair is fully available, making it the most
basic.

2. Pyridine is less basic since lone pair is in sp² orbital (more electronegative, less available).

3. Aniline is least basic since lone pair delocalizes into the benzene ring, reducing availability.

Q60. Which is more acidic: o-nitrophenol or p-nitrophenol?

Answer: o-nitrophenol.
Explanations:

1. At ortho, the –NO₂ group strongly withdraws electrons by –I effect, increasing acidity.

2. Intramolecular H-bonding in o-nitrophenol stabilizes the conjugate base.

3. At para, the effect is weaker since there is no stabilizing H-bond and the nitro group is farther
from OH.

Q61. Why is phenol less acidic than picric acid?

Answer: –NO₂ stabilizes phenoxide strongly.

Explanations:

1. Picric acid has three –NO₂ groups, which withdraw electrons strongly by –I and –M effects,
stabilizing the negative charge on oxygen.

2. In phenol, no such electron-withdrawing substituents exist, so the phenoxide ion is less

stabilized.

3. Resonance with nitro groups spreads charge across the aromatic ring, making picric acid
much more acidic.
Q62. Arrange acidity: benzoic acid, o-hydroxybenzoic acid, p-hydroxybenzoic acid.

Answer: o-hydroxy > p-hydroxy > benzoic.

Explanations:

1. In o-hydroxybenzoic acid (salicylic acid), intramolecular H-bonding stabilizes the conjugate

base, increasing acidity.

2. In p-hydroxybenzoic acid, the –OH group can donate electron density by resonance, slightly
decreasing acidity compared to ortho.

3. Simple benzoic acid has no –OH substituent, so it is least acidic.

Q63. Which is more basic: aniline or N,N-dimethylaniline?

Answer: Aniline.
Explanations:

1. In N,N-dimethylaniline, steric hindrance reduces accessibility of the lone pair for protonation.

2. The lone pair in dimethylaniline is also delocalized into the benzene ring (–M effect),
reducing basicity.

3. In aniline, lone pair is more available, although partially delocalized, so it is more basic.

Q64. Which is stronger acid: cinnamic acid or benzoic acid?

Answer: Cinnamic acid.

Explanations:

1. Cinnamic acid has a conjugated double bond adjacent to –COOH, which helps delocalize the
negative charge after deprotonation.

2. The extended resonance stabilizes the carboxylate anion more than in benzoic acid.

3. The alkene exerts a mild –I effect, slightly increasing acidity compared to benzoic acid.

Q65. Why is phenol acidic while anisole is neutral?

Answer: In anisole, O is bonded via C–O–C, no acidic H.

Explanations:

1. Phenol has an O–H bond, and the proton can be donated to form a stable phenoxide ion.

2. In anisole, oxygen is bonded to two carbons (ether), so no acidic proton is present.

3. The lone pairs on oxygen in anisole are stabilized by resonance with benzene, making it
neutral rather than acidic.
Q66. Arrange in basicity: pyridine, imidazole, pyrrole.

Answer: imidazole > pyridine > pyrrole.

Explanations:

1. Imidazole has two nitrogens: one lone pair participates in aromaticity, but the other is free
and more available than in pyridine.

2. Pyridine’s nitrogen lone pair is free but less basic than imidazole due to electron deficiency of
the ring.

3. Pyrrole’s lone pair is part of aromaticity, so unavailable for protonation → least basic.

Q67. Which is more acidic: benzoic acid or p-fluorobenzoic acid?

Answer: p-fluorobenzoic acid.

Explanations:

1. Fluorine is highly electronegative, exerting a strong –I effect, withdrawing electron density

and stabilizing the carboxylate.

2. At para position, resonance donation is weak, so inductive withdrawal dominates.

3. Thus, p-fluorobenzoic acid has lower pKa than benzoic acid.

Q68. Why is sulfanilic acid amphoteric?

Answer: –NH₂ basic, –SO₃H acidic.

Explanations:

1. The –SO₃H group can donate a proton, showing acidic character.

2. The –NH₂ group can accept a proton, showing basic character.

3. In water, sulfanilic acid can act as a zwitterion, proving both acidic and basic properties.

Q69. Arrange acidity: phenol, 2,4-dinitrophenol, cresol.

Answer: 2,4-dinitrophenol > phenol > cresol.

Explanations:

1. 2,4-dinitrophenol has two strong electron-withdrawing –NO₂ groups, strongly stabilizing the
conjugate base.

2. Phenol has moderate acidity due to resonance stabilization of phenoxide.

3. Cresol has a +I donating –CH₃ group, destabilizing phenoxide, so it is least acidic.

Q70. Which is more basic: pyridine or quinoline?

Answer: Quinoline slightly less.

Explanations:

1. In quinoline, the nitrogen lone pair is delocalized into the fused aromatic ring, reducing
availability.

2. Pyridine’s nitrogen lone pair is more localized, making it slightly more basic.

3. Larger conjugated systems (quinoline) withdraw electrons more, lowering basicity.

Q71. Why is benzoic acid stronger than acetic acid?

Answer: Benzene ring withdraws slightly by –I effect.

Explanations:

1. The aromatic ring is electron withdrawing compared to the methyl group of acetic acid,
stabilizing carboxylate anion.

2. In acetic acid, –CH₃ is electron donating, which destabilizes the conjugate base.

3. Thus, benzoic acid has lower pKa than acetic acid.

Q72. Which is less basic: pyridine or pyrrole?

Answer: Pyrrole.
Explanations:

1. Pyrrole’s nitrogen lone pair is part of the aromatic sextet, so unavailable for protonation.

2. Protonation of pyrrole would break aromaticity, making it very unfavorable.

3. In pyridine, the lone pair is outside the ring’s aromaticity, so it can accept H⁺.

Q73. Arrange acidity: phenol, benzyl alcohol, benzoic acid.

Answer: benzoic acid > phenol > benzyl alcohol.

Explanations:

1. Benzoic acid forms a stabilized carboxylate anion → most acidic.

2. Phenol is weaker since phenoxide is less stabilized than carboxylate.

3. Benzyl alcohol has no resonance stabilization after deprotonation → least acidic.

Q74. Which is more basic: aniline or o-toluidine?

Answer: Aniline.
Explanations:

1. In o-toluidine, the –CH₃ group causes steric hindrance, reducing lone pair availability.

2. Steric crowding also reduces solvation of the conjugate acid.

3. Aniline has no such steric hindrance, so it is more basic.

Q75. Which is stronger acid: phthalic acid or benzoic acid?

Answer: Phthalic acid.

Explanations:

1. Phthalic acid has two –COOH groups, and one can stabilize the other by intramolecular H-
bonding.

2. The electron-withdrawing effect of one –COOH increases the acidity of the other.

3. Benzoic acid has only one –COOH, so weaker acid.

Q76. Arrange acidity: p-nitrophenol, phenol, p-methoxyphenol.

Answer: p-nitrophenol > phenol > p-methoxyphenol.

Explanations:

1. –NO₂ strongly withdraws electrons, stabilizing phenoxide → highest acidity.

2. Phenol has moderate acidity.

3. –OCH₃ is electron donating (+M effect), destabilizing phenoxide → least acidic.

Q77. Which is more basic: pyridine or pyrazine?

Answer: Pyridine.
Explanations:

1. Pyrazine has two nitrogens, which withdraw electron density from each other, reducing
basicity.

2. Pyridine has only one nitrogen, so lone pair is more available.

3. Extra electronegativity in pyrazine ring decreases basicity compared to pyridine.

Q78. Why is aniline less basic in water?

Answer: Protonated form destabilized due to delocalization.

Explanations:

1. The lone pair on aniline is partially delocalized into the ring, reducing basicity.

2. Protonated aniline (–NH₃⁺) loses resonance stabilization, making it less stable in water.

3. Hydration energy is lower for protonated aniline compared to aliphatic amines, reducing
basicity in water.

Q79. Arrange acidity: phenol, 2-nitrophenol, 4-methylphenol.

Answer: 2-nitrophenol > phenol > 4-methylphenol.

Explanations:

1. The ortho –NO₂ group strongly withdraws electrons and stabilizes the conjugate base.

2. Phenol has moderate acidity.

3. 4-methyl is electron donating (+I), destabilizing phenoxide → least acidic.

Q80. Which is more basic: pyridine or piperazine?

Answer: Piperazine.
Explanations:

1. Piperazine is aliphatic, so nitrogen lone pairs are localized and more available for
protonation.

2. Pyridine’s lone pair is in sp² orbital, held more tightly, less basic.

3. Piperazine has two amine groups, which can donate electrons, increasing basicity.

Got it 👍 You want 40 organic chemistry questions with answers (20 aliphatic, 20 aromatic) focusing
on acidity and basicity trends, electron donating/withdrawing groups, and relationships with Ka,
pKa, Kb, pKb.

Here’s a structured set:

Aliphatic Compounds (20 Questions)

Conceptual / Trend Questions

1. Q: Between ethanol (CH₃CH₂OH) and acetic acid (CH₃COOH), which is more acidic?
A: Acetic acid, because the –COOH group has resonance stabilization of its conjugate base.
 2. Q: Which is more basic: NH₃ or CH₃NH₂?
A: CH₃NH₂, because the –CH₃ group donates electrons by +I effect.

3. Q: Which has lower pKa: HF or CH₃CH₂OH?

A: HF (pKa ≈ 3.2 vs ethanol ≈ 16).

4. Q: Why is chloroacetic acid more acidic than acetic acid?

A: –Cl is electron-withdrawing (–I effect), stabilizing the conjugate base.

5. Q: Rank acidity: CH₃COOH, ClCH₂COOH, CCl₃COOH.

A: CCl₃COOH > ClCH₂COOH > CH₃COOH.

6. Q: Which is more basic: CH₃NH₂ or (CH₃)₃N?

A: CH₃NH₂, because steric hindrance reduces basicity in (CH₃)₃N.

7. Q: Between CH₃OH and CH₃SH, which is more acidic?

A: CH₃SH, because S–H bond is weaker than O–H.

8. Q: Arrange acidity: CH₃CH₂OH, CH₃CH₂COOH, CH₃CH₂NH₂.

A: CH₃CH₂COOH > CH₃CH₂OH > CH₃CH₂NH₂.

9. Q: Between CH₃⁻ and NH₂⁻, which is stronger base?

A: CH₃⁻, because it is less electronegative and holds electrons more loosely.

10. Q: Why is acetylene (HC≡CH) more acidic than ethane?

A: sp-hybridized carbon is more electronegative, stabilizing negative charge.

Application / Numerical / Comparative

11. Q: Compare acidity: phenol vs ethanol.

A: Phenol > ethanol, due to resonance stabilization in phenoxide ion.

12. Q: Which is more basic: pyrrolidine or acetamide?

A: Pyrrolidine, because lone pair on N in amide is delocalized with C=O.

13. Q: Why is nitroethane more acidic than ethane?

A: –NO₂ group strongly withdraws electrons, stabilizing anion.

14. Q: Compare acidity: CH₃–CH₂–COOH vs CH₂Cl–CH₂–COOH.

A: CH₂Cl–CH₂–COOH is more acidic (–I effect).

15. Q: Arrange in increasing basicity: CH₃NH₂, NH₃, CF₃NH₂.

A: CF₃NH₂ < NH₃ < CH₃NH₂.

16. Q: Which is more acidic: formic acid or acetic acid?

A: Formic acid, because –H is less electron donating than –CH₃.

17. Q: Between NaNH₂ and NaOH, which is stronger base?

A: NaNH₂, because NH₂⁻ is less electronegative than O⁻.

18. Q: Which is more acidic: HC≡CH or CH₂=CH₂?

A: HC≡CH, due to sp carbon’s higher electronegativity.

19. Q: Why is CH₃CONH₂ less basic than CH₃NH₂?

A: Lone pair on N in amide delocalizes with carbonyl.

20. Q: Which has lower pKb: CH₃NH₂ or (C₂H₅)₂NH?

A: (C₂H₅)₂NH, stronger base due to more +I groups.
Aromatic Compounds (20 Questions)

Conceptual / Trend Questions

1. Q: Which is more acidic: phenol or cresol (p-CH₃–C₆H₄–OH)?

A: Phenol, since –CH₃ donates electrons and reduces acidity.

2. Q: Which is more acidic: phenol or nitrophenol?

A: Nitrophenol, because –NO₂ withdraws electrons.

3. Q: Why is aniline less basic than aliphatic amines?

A: Lone pair on N is delocalized with aromatic ring.

4. Q: Arrange in acidity: phenol, p-nitrophenol, p-methoxyphenol.

A: p-nitrophenol > phenol > p-methoxyphenol.

5. Q: Which is stronger base: aniline or p-methylaniline?

A: p-methylaniline, because –CH₃ donates electrons.

6. Q: Which is stronger acid: benzoic acid or p-methylbenzoic acid?

A: Benzoic acid, because –CH₃ donates electrons.

7. Q: Why is p-nitrobenzoic acid stronger than benzoic acid?

A: –NO₂ withdraws electrons, stabilizing carboxylate anion.

8. Q: Arrange in basicity: aniline, p-nitroaniline, p-methoxyaniline.

A: p-nitroaniline < aniline < p-methoxyaniline.

9. Q: Which is more acidic: benzoic acid or phenol?

A: Benzoic acid (pKa ≈ 4.2 vs phenol ≈ 10).

10. Q: Why is phenol more acidic than cyclohexanol?

A: Phenoxide ion stabilized by resonance.

Application / Numerical / Comparative

11. Q: Which has higher pKa: aniline or NH₃?

A: Aniline, because resonance lowers basicity.

12. Q: Arrange in acidity: benzoic acid, o-nitrobenzoic acid, p-nitrobenzoic acid.

A: o-nitrobenzoic acid > p-nitrobenzoic acid > benzoic acid.

13. Q: Which is more basic: pyridine or pyrrole?

A: Pyridine, because lone pair is not delocalized in aromatic sextet.

14. Q: Why is picric acid (2,4,6-trinitrophenol) very acidic?

A: Multiple –NO₂ groups strongly withdraw electrons, stabilizing phenoxide ion.

15. Q: Compare acidity: salicylic acid vs benzoic acid.

A: Salicylic acid is stronger (intramolecular H-bond stabilizes anion).

16. Q: Which is more basic: pyridine or piperidine?

A: Piperidine (aliphatic), because lone pair not delocalized.

17. Q: Arrange acidity: phenol, o-chlorophenol, p-chlorophenol.

A: o-chlorophenol > p-chlorophenol > phenol.
18. Q: Which is more basic: aniline or acetanilide?
A: Aniline, because in acetanilide lone pair delocalizes into C=O.

19. Q: Why is sulfanilic acid amphoteric?

A: Contains both –NH₂ (basic) and –SO₃H (acidic).

20. Q: Arrange in basicity: pyridine, aniline, piperidine.

A: aniline < pyridine < piperidine.