CUET UG Chemistry Booster Test - 2 Properties and Reactions of Amines
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QUESTION 1 OF 20
Which of the following specific amines is most likely to exist as a gas with a fishy odour at room temperature?
QUESTION 2 OF 20
As the carbon chain grows, primary amines transition from liquids to higher solids. This physical state change is primarily correlated with:
QUESTION 3 OF 20
Identify the accepted IUPAC name of the simplest aromatic amine, which is colourless but becomes coloured on storage due to oxidation.
QUESTION 4 OF 20
The transformation of colourless aniline into coloured products upon storage in air is chemically classified as:
QUESTION 5 OF 20
Consider the solubility of butan-1-ol and butan-1-amine in water. Which statement correctly explains their relative solubility?
(I) Butan-1-ol is more soluble because oxygen is more electronegative than nitrogen (3.5 vs 3.0), forming stronger hydrogen bonds.
(II) Butan-1-amine is more soluble because it has more hydrogen atoms available for bonding.
QUESTION 6 OF 20
Arrange the following compounds in decreasing order of their solubility in water:
C₆H₅NH₂, (C₂H₅)₂NH, C₂H₅NH₂
QUESTION 7 OF 20
Which of the following amines will lack intermolecular hydrogen bonding completely?
QUESTION 8 OF 20
Why does a secondary amine possess a lower degree of intermolecular association compared to a primary amine?
(I) It has only one hydrogen atom available for hydrogen bond formation.
(II) It completely lacks an unshared pair of electrons.
QUESTION 9 OF 20
Arrange the following compounds of similar molecular masses in decreasing order of their boiling points:
n-C₄H₉OH, n-C₄H₉NH₂, (C₂H₅)₂NH, C₂H₅N(CH₃)₂
QUESTION 10 OF 20
The boiling point of N,N-Dimethylethanamine is 310.5 K, which is significantly lower than that of its isomer n-Butan-1-amine (350.8 K). This is fundamentally because N,N-Dimethylethanamine:
QUESTION 11 OF 20
| List 1 (Basicity Term) | List 2 (Mathematical Expression / Meaning) |
|---|---|
| 1. Base dissociation constant (Kb) | a. [RNH₃⁺][OH⁻] / [RNH₂] |
| 2. pKb | b. –log Kb |
| 3. Stronger base | c. Larger Kb or smaller pKb |
| 4. Weaker base | d. Smaller Kb or larger pKb |
QUESTION 12 OF 20
When an amine salt is treated with an aqueous solution of sodium hydroxide (NaOH), the parent amine is regenerated. This specific transformation represents:
QUESTION 13 OF 20
QUESTION 14 OF 20
QUESTION 15 OF 20
Arrange the following methyl-substituted amines in decreasing order of basic strength in aqueous solution:
(A) (CH₃)₂NH
(B) CH₃NH₂
(C) (CH₃)₃N
(D) NH₃
QUESTION 16 OF 20
Based on the dimensionless pKb values provided in the text (Methanamine = 3.38, N,N-Dimethylmethanamine = 4.22, Benzenamine = 9.38), which of the following represents the weakest base?
QUESTION 17 OF 20
Arrange the following alkyl halides in decreasing order of their reactivity with amines during an alkylation reaction:
QUESTION 18 OF 20
What is the primary disadvantage of preparing primary amines via the ammonolysis of alkyl halides?
(I) It requires an extremely high temperature that destroys the amine.
(II) It yields a mixture of primary, secondary, and tertiary amines, and also a quaternary ammonium salt.
QUESTION 19 OF 20
During the acylation of a primary amine with an acid chloride, a stronger base like pyridine is typically added. What is the chemical purpose of pyridine in this mixture?
QUESTION 20 OF 20
When methanamine reacts with benzoyl chloride, the hydrogen atom of the amine is replaced by a benzoyl group. What is the IUPAC name of the product?
Test Complete!
Answer Review
1 Which of the following specific amines is most likely to exist as a gas with a fishy odour at room temperature?
�� Methanamine is a lower aliphatic amine. �� Lower aliphatic amines are gases. �� They have fishy odour.
- Methanamine is the simplest lower aliphatic amine. Lower aliphatic amines exist as gases at room temperature and possess a fishy odour. Hence, methanamine best matches the given condition.
- �� Option B → Hexane-1,6-diamine is a higher amine, not a gaseous lower amine.
- �� Option C → Benzenamine is aromatic and not the best example of lower aliphatic gaseous amine.
- �� Option D → Propan-1-amine is generally liquid at room temperature.
Used
- Elimination
Application:
- �� Eliminate higher, aromatic, and liquid amines.
Final Logic:
- �� Lower aliphatic amine = gas with fishy odour.
- Methanamine = Fishy Gas
2 As the carbon chain grows, primary amines transition from liquids to higher solids. This physical state change is primarily correlated with:
�� Longer alkyl chains increase molecular mass. �� Intermolecular forces become stronger. �� Higher amines may become solids.
- As the alkyl chain becomes larger, the hydrophobic part and molecular mass increase. This increases intermolecular attractions, causing higher amines to shift from liquid to solid state.
- �� Option A → Amines do not lose their lone pair.
- �� Option C → The main reason is increased molecular size, not loss of H-bonding capacity.
- �� Option D → Chain growth does not convert amines into aromatic compounds.
Used
- Contextual/Tonal Matching
Application:
- �� Connect physical state trend with molecular size.
Final Logic:
- �� Larger alkyl chain increases molecular mass and changes physical state.
- Long Chain = Heavy = Solid
3 Identify the accepted IUPAC name of the simplest aromatic amine, which is colourless but becomes coloured on storage due to oxidation.
�� Simplest aromatic amine is aniline. �� IUPAC name of aniline is benzenamine. �� It becomes coloured due to atmospheric oxidation.
- The simplest aromatic amine is C₆H₅NH₂, commonly called aniline. Its accepted IUPAC name is benzenamine. Arylamines like aniline are colourless but become coloured on storage due to atmospheric oxidation.
- �� Option A → N-Methylethanamine is an aliphatic secondary amine.
- �� Option C → Prop-2-en-1-amine is an unsaturated aliphatic amine.
- �� Option D → N,N-Dimethylmethanamine is a tertiary aliphatic amine.
Used
- Elimination
Application:
- �� Identify the only aromatic amine among the options.
Final Logic:
- �� Aniline = Benzenamine.
- Benzene + NH₂ = Benzenamine
4 The transformation of colourless aniline into coloured products upon storage in air is chemically classified as:
�� Aniline is colourless when pure. �� It becomes coloured on exposure to air. �� This is due to oxidation.
- Aniline and other arylamines become coloured on storage because atmospheric oxygen oxidizes them slowly. The coloured products formed are responsible for the observed colour change.
- �� Option A → No acid-base salt formation is involved.
- �� Option C → Electrophilic substitution is not the storage effect.
- �� Option D → Nucleophilic substitution is unrelated here.
Used
- Contextual/Tonal Matching
Application:
- �� Link colour formation on storage with air oxidation.
Final Logic:
- �� Air exposure causes atmospheric oxidation.
- Aniline + Air = Oxidation Colour
5 Consider the solubility of butan-1-ol and butan-1-amine in water. Which statement correctly explains their relative solubility?
(I) Butan-1-ol is more soluble because oxygen is more electronegative than nitrogen (3.5 vs 3.0), forming stronger hydrogen bonds.
(II) Butan-1-amine is more soluble because it has more hydrogen atoms available for bonding.
�� Alcohols form stronger hydrogen bonds than amines. �� Oxygen is more electronegative than nitrogen. �� Therefore, butan-1-ol is more water soluble.
- Butan-1-ol forms stronger hydrogen bonds with water because oxygen is more electronegative than nitrogen. Amines can also form hydrogen bonds, but they are generally weaker than those formed by alcohols.
- �� Option B → Statement II is incorrect; more hydrogen atoms alone does not make butan-1-amine more soluble.
- �� Option C → Statement II is incorrect.
- �� Option D → Statement I is correct.
Used
- Option Grouping
Application:
- �� Compare hydrogen bond strength of O–H and N–H groups.
Final Logic:
- �� Stronger O–H hydrogen bonding makes alcohol more soluble.
- O bonds stronger than N
6 Arrange the following compounds in decreasing order of their solubility in water:
C₆H₅NH₂, (C₂H₅)₂NH, C₂H₅NH₂
�� Smaller aliphatic amines are more soluble. �� Larger hydrophobic groups reduce solubility. �� Aromatic amines are least soluble here.
- Ethylamine is a lower aliphatic primary amine and forms hydrogen bonds with water effectively. Diethylamine has a larger hydrophobic part, so it is less soluble. Aniline has an aromatic ring, making it least soluble among the given compounds.
- �� Option A → Incorrectly places aniline as most soluble.
- �� Option C → Incorrectly places diethylamine above ethylamine.
- �� Option D → Again wrongly places aniline highest.
Used
- Ordering
Application:
- �� Compare hydrophobic alkyl/aryl size and hydrogen bonding.
Final Logic:
- �� Smaller aliphatic amine > larger aliphatic amine > aromatic amine.
- Small aliphatic dissolves best
7 Which of the following amines will lack intermolecular hydrogen bonding completely?
�� Tertiary amines lack N–H bonds. �� Intermolecular hydrogen bonding requires N–H hydrogen. �� N,N-Diethylbutan-1-amine is tertiary.
- N,N-Diethylbutan-1-amine has three carbon groups attached to nitrogen and no hydrogen directly bonded to nitrogen. Therefore, it cannot form intermolecular hydrogen bonds among its own molecules.
- �� Option A → Propan-1-amine is primary and has N–H bonds.
- �� Option B → N-Methylethanamine is secondary and has one N–H bond.
- �� Option D → Ethanamine is primary and has two N–H bonds.
Used
- Elimination
Application:
- �� Identify the tertiary amine with no N–H bond.
Final Logic:
- �� No N–H bond means no intermolecular hydrogen bonding.
- Tertiary = 0 N–H
8 Why does a secondary amine possess a lower degree of intermolecular association compared to a primary amine?
(I) It has only one hydrogen atom available for hydrogen bond formation.
(II) It completely lacks an unshared pair of electrons.
�� Secondary amines have one N–H hydrogen. �� Primary amines have two N–H hydrogens. �� Amines still possess a lone pair.
- Secondary amines have the formula R₂NH, so only one hydrogen atom is available for hydrogen bond formation. Primary amines have two such hydrogens, so they show stronger intermolecular association. → Statement II is incorrect because secondary amines still contain an unshared pair on nitrogen.
- �� Option B → Statement II is false.
- �� Option C → Statement II is false.
- �� Option D → Statement I is true.
Used
- Option Grouping
Application:
- �� Compare primary and secondary amine structures.
Final Logic:
- �� Secondary amine has fewer N–H hydrogens than primary amine.
- Secondary = 1 H only
9 Arrange the following compounds of similar molecular masses in decreasing order of their boiling points:
n-C₄H₉OH, n-C₄H₉NH₂, (C₂H₅)₂NH, C₂H₅N(CH₃)₂
�� Alcohols form stronger hydrogen bonds than amines. �� Primary amines form stronger H-bonds than secondary amines. �� Tertiary amines lack N–H hydrogen.
- n-C₄H₉OH has the highest boiling point because alcohols form stronger hydrogen bonds due to more electronegative oxygen. → Among amines, boiling point order is: Primary amine > Secondary amine > Tertiary amine Therefore: n-C₄H₉OH > n-C₄H₉NH₂ > (C₂H₅)₂NH > C₂H₅N(CH₃)₂
- �� Option B → Gives nearly reverse order.
- �� Option C → Incorrectly places secondary amine above primary amine.
- �� Option D → Incorrectly places primary amine above alcohol.
Used
- Ordering
Application:
- �� Rank based on hydrogen-bonding strength.
Final Logic:
- �� Alcohol > Primary amine > Secondary amine > Tertiary amine.
- O–H strongest, then 1°, 2°, 3° amines
10 The boiling point of N,N-Dimethylethanamine is 310.5 K, which is significantly lower than that of its isomer n-Butan-1-amine (350.8 K). This is fundamentally because N,N-Dimethylethanamine:
�� N,N-Dimethylethanamine is tertiary. �� Tertiary amines lack N–H bonds. �� Hence intermolecular hydrogen bonding is absent.
- N,N-Dimethylethanamine is a tertiary amine. It has no hydrogen atom attached directly to nitrogen, so it cannot form intermolecular hydrogen bonds with its own molecules. → n-Butan-1-amine is a primary amine and forms intermolecular hydrogen bonds, giving it a higher boiling point.
- �� Option A → Both are isomeric and have similar molecular formula/molar mass.
- �� Option B → Water solubility is not the main boiling point reason.
- �� Option D → Tertiary amine does not have stronger intermolecular attraction than primary amine.
Used
- Elimination
Application:
- �� Compare hydrogen-bonding ability of isomeric amines.
Final Logic:
- �� No N–H bond means lower boiling point.
- 3° Amine = No H-bond Donor
11
| List 1 (Basicity Term) | List 2 (Mathematical Expression / Meaning) |
|---|---|
| 1. Base dissociation constant (Kb) | a. [RNH₃⁺][OH⁻] / [RNH₂] |
| 2. pKb | b. –log Kb |
| 3. Stronger base | c. Larger Kb or smaller pKb |
| 4. Weaker base | d. Smaller Kb or larger pKb |
�� Kb measures basic strength. �� pKb is the negative logarithm of Kb. �� Stronger bases have larger Kb values.
- The base dissociation constant (Kb) is given by: Kb = [RNH₃⁺][OH⁻] / [RNH₂] → pKb is defined as: pKb = –log Kb → A stronger base has a larger Kb and therefore a smaller pKb. → A weaker base has a smaller Kb and a larger pKb. Hence: 1-a, 2-b, 3-c, 4-d
- �� Option B → Interchanges Kb and pKb definitions.
- �� Option C → Incorrectly assigns stronger base relation.
- �� Option D → Gives incorrect expression for Kb.
Used
- Option Grouping
Application:
- �� Match each basicity term with its mathematical definition.
Final Logic:
- �� Larger Kb means stronger basic character.
- High Kb = High Base
12 When an amine salt is treated with an aqueous solution of sodium hydroxide (NaOH), the parent amine is regenerated. This specific transformation represents:
�� Amine salts are acidic in nature. �� NaOH removes the proton. �� Free amine is regenerated.
- Amines react with acids to form ammonium salts. Example: RNH₂ + HCl → RNH₃⁺Cl⁻ → Treatment with NaOH regenerates the amine: RNH₃⁺Cl⁻ + NaOH → RNH₂ + NaCl + H₂O → This is an acid-base neutralization/displacement reaction.
- �� Option A → No addition reaction occurs.
- �� Option C → No alkyl group is introduced.
- �� Option D → Nitrous acid is required for diazotisation.
Used
- Contextual/Tonal Matching
Application:
- �� Identify the role of NaOH in the reaction.
Final Logic:
- �� Base regenerates amine from its salt.
- Salt + Base → Free Amine
13
�� Alkylamines do not undergo resonance with a benzene ring. �� Lone pair remains available. �� Protonation occurs more readily.
- In aniline, the nitrogen lone pair participates in resonance with the benzene ring. → Because of this delocalization, the lone pair becomes less available for protonation. → In alkylamines, such resonance does not occur. Therefore, the lone pair remains localized and can readily accept a proton. Hence alkylamines are stronger bases than aniline.
- �� Option A → This is true for aniline, not alkylamines.
- �� Option B → Alkylamines possess a lone pair.
- �� Option D → Five resonance structures belong to aniline.
Used
- Elimination
Application:
- �� Compare lone-pair availability in aniline and alkylamines.
Final Logic:
- �� Greater lone-pair availability means stronger basicity.
- No Resonance = Stronger Base
14
�� Aniline is resonance stabilized. �� Lone pair is delocalized. �� Protonation becomes less favorable.
- The lone pair on nitrogen in aniline participates in resonance with the benzene ring. → Aniline is stabilized by several resonance structures. → Upon protonation, the anilinium ion loses much of this stabilization and has fewer resonance forms. → Therefore, aniline is less willing to accept a proton and behaves as a weaker base than ammonia.
- �� Option A → Five resonance structures belong to aniline, not anilinium ion.
- �� Option C → Ammonia does not show this resonance.
- �� Option D → Carbocation formation is irrelevant.
Used
- Contextual/Tonal Matching
Application:
- �� Focus on resonance stabilization described in the passage.
Final Logic:
- �� Greater stabilization of aniline reduces proton acceptance.
- More Resonance → Less Basic
15 Arrange the following methyl-substituted amines in decreasing order of basic strength in aqueous solution:
(A) (CH₃)₂NH
(B) CH₃NH₂
(C) (CH₃)₃N
(D) NH₃
�� Aqueous basicity depends on +I effect and solvation. �� Secondary amines are best balanced. �� Tertiary amines suffer steric hindrance.
- In aqueous solution, basicity depends on: +I effect of alkyl groups Solvation of the conjugate acid Steric hindrance → Secondary amines receive sufficient electron donation and are effectively solvated. → Tertiary amines have stronger +I effect but poorer solvation due to steric hindrance. Thus: (CH₃)₂NH > CH₃NH₂ > (CH₃)₃N > NH₃
- �� Option B → Incorrectly places tertiary amine first.
- �� Option C → Places primary amine above secondary amine.
- �� Option D → Gives reverse trend.
Used
- Ordering
Application:
- �� Apply aqueous basicity order from NCERT.
Final Logic:
- �� Solvation makes secondary amines strongest in water.
- 2° > 1° > 3° > NH₃
16 Based on the dimensionless pKb values provided in the text (Methanamine = 3.38, N,N-Dimethylmethanamine = 4.22, Benzenamine = 9.38), which of the following represents the weakest base?
�� Higher pKb means weaker base. �� Benzenamine has the highest pKb value. �� Therefore, it is the weakest base.
- Basic strength is inversely related to pKb value. A smaller pKb indicates a stronger base, while a larger pKb indicates a weaker base. Given values: Methanamine = 3.38 N,N-Dimethylmethanamine = 4.22 Ammonia = 4.75 Benzenamine = 9.38 Since Benzenamine has the highest pKb value, it is the weakest base among the given options.
- �� Option A → Methanamine has a lower pKb, so it is stronger than benzenamine.
- �� Option B → N,N-Dimethylmethanamine has a lower pKb than benzenamine.
- �� Option D → Ammonia is weaker than many aliphatic amines but stronger than benzenamine here.
Used
- Dimensional/Unit Analysis
Application:
- �� Compare the numerical pKb values.
Final Logic:
- �� Highest pKb = weakest base.
- High pKb = Poor base
17 Arrange the following alkyl halides in decreasing order of their reactivity with amines during an alkylation reaction:
�� Reactivity depends on leaving group ability. �� Iodide is the best leaving group. �� Chloride is the least reactive.
- In alkylation of amines, alkyl halides react through nucleophilic substitution. The reactivity depends mainly on the ease of C–X bond cleavage. Leaving group ability: I⁻ > Br⁻ > Cl⁻ Therefore, the decreasing order is: RI > RBr > RCl
- �� Option B → Gives reverse order.
- �� Option C → Places RBr above RI incorrectly.
- �� Option D → Places RCl above RBr incorrectly.
Used
- Ordering
Application:
- �� Arrange alkyl halides based on leaving group ability.
Final Logic:
- �� Better leaving group gives faster reaction.
- I > Br > Cl
18 What is the primary disadvantage of preparing primary amines via the ammonolysis of alkyl halides?
(I) It requires an extremely high temperature that destroys the amine.
(II) It yields a mixture of primary, secondary, and tertiary amines, and also a quaternary ammonium salt.
�� Primary amine formed can react further. �� Further alkylation gives higher amines. �� Final product may include quaternary ammonium salt.
- During ammonolysis, the primary amine formed still has a lone pair on nitrogen and can react further with alkyl halide. This leads to formation of secondary amines, tertiary amines, and quaternary ammonium salts. Hence, the major disadvantage is product mixture formation. Statement I is incorrect because destruction by extremely high temperature is not the main disadvantage.
- �� Option A → Statement I is incorrect.
- �� Option C → Statement I is incorrect.
- �� Option D → Statement II is correct.
Used
- Option Grouping
Application:
- �� Identify the actual limitation of ammonolysis.
Final Logic:
- �� Further alkylation causes mixture formation.
- Ammonolysis = Mixture problem
19 During the acylation of a primary amine with an acid chloride, a stronger base like pyridine is typically added. What is the chemical purpose of pyridine in this mixture?
�� Acylation produces HCl. �� Pyridine removes HCl. �� This drives product formation.
- In acylation of amines with acid chlorides, HCl is produced as a by-product. Pyridine, being a stronger base, removes this HCl and prevents the amine from being converted into its salt. This shifts the equilibrium towards amide formation.
- �� Option A → Pyridine is not used as an oxidizing agent.
- �� Option B → Electrophilic addition is not involved.
- �� Option D → Pyridine does not replace the acyl group.
Used
- Contextual/Tonal Matching
Application:
- �� Identify the role of base in acylation.
Final Logic:
- �� Removing HCl favours amide formation.
- Pyridine pulls HCl
20 When methanamine reacts with benzoyl chloride, the hydrogen atom of the amine is replaced by a benzoyl group. What is the IUPAC name of the product?
�� Methanamine contains a methyl group on nitrogen. �� Benzoyl chloride introduces benzoyl group. �� Product is N-Methylbenzamide.
- Methanamine, CH₃NH₂, reacts with benzoyl chloride, C₆H₅COCl, by acylation. One hydrogen attached to nitrogen is replaced by the benzoyl group. Product: C₆H₅CONHCH₃ This compound is named N-Methylbenzamide because the methyl group is attached to the nitrogen atom of benzamide.
- �� Option B → N-Phenylacetamide has a phenyl group on nitrogen and an acetyl group, not benzoyl.
- �� Option C → Benzenamine is aniline, not the acylation product.
- �� Option D → Benzamide lacks the N-methyl group.
Used
- Substitution
Application:
- �� Add benzoyl group to methanamine and name the N-substituted amide.
Final Logic:
- �� Benzoyl chloride + methanamine = N-Methylbenzamide.
- Methanamine + Benzoyl = N-Methylbenzamide
