CUET UG Chemistry Booster Test - 3 Chemical Reactions and Uses
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QUESTION 1 OF 20
QUESTION 2 OF 20
QUESTION 3 OF 20
The reaction of an alkoxide ion with water suggests that:
QUESTION 4 OF 20
Match List-I (Substituent on Phenol) with List-II (Effect on Acidic Strength)
| List I | List II |
|---|---|
| 1. Electron withdrawing group at ortho/para | a. Decreases acid strength |
| 2. Electron releasing group (alkyl) | b. Serves as a reference (pKa ≈ 10.0) |
| 3. Nitro group | c. Highly enhances acid strength |
| 4. Unsubstituted phenol | d. Enhances acidic strength |
QUESTION 5 OF 20
Statements concerning the acidity of alcohols and phenols:
1. Phenol is millions of times more acidic than ethanol.
2. In phenoxide ion, the negative charge is delocalized.
3. Alcohols are stronger acids than water.
4. Alkoxides are stronger bases than hydroxide ions.
QUESTION 6 OF 20
Arrange the following in decreasing order of their acid strength based on pKa and substituent effects:
1. 2,4,6-Trinitrophenol
2. Phenol
3. 3-Nitrophenol
4. 4-Methylphenol
QUESTION 7 OF 20
To drive the reversible esterification equilibrium of an alcohol with a carboxylic acid to the right-hand side, what action is necessary?
QUESTION 8 OF 20
Identify the reaction type that produces aspirin from salicylic acid.
QUESTION 9 OF 20
What is the IUPAC name of the product formed when tert-butyl alcohol reacts with HCl in the Lucas test?
QUESTION 10 OF 20
Arrange the ease of cleavage of the C–O bond by hydrogen halides for the following alcohols in decreasing order:
1. 2-Methylpropan-2-ol
2. Propan-2-ol
3. Methanol
4. Propan-1-ol
QUESTION 11 OF 20
Statements about dehydration of alcohols:
1. Tertiary alcohols are the easiest to dehydrate.
2. The ease of dehydration follows: Primary > Secondary > Tertiary.
3. The rate-determining step forms a carbocation.
4. Protic acids like H₂SO₄ or H₃PO₄ are used.
QUESTION 12 OF 20
In the mechanism of dehydration of ethanol, how is the equilibrium driven to the right?
QUESTION 13 OF 20
Arrange the sequence of products formed during the strong oxidation of a primary alcohol:
1. Aldehyde
2. Primary alcohol
3. Carboxylic acid
4. Strong oxidising agent (KMnO₄/K₂Cr₂O₇) completes the oxidation.
QUESTION 14 OF 20
When tertiary alcohols are subjected to strong oxidising agents (KMnO₄) at elevated temperatures, what happens?
QUESTION 15 OF 20
Match List-I (Reaction Condition) with List-II (Product)
| List I | List II |
|---|---|
| 1. Dilute HNO₃ at 298 K | a. Picric acid (poor yield) |
| 2. Concentrated HNO₃ | b. Picric acid (high yield industrially) |
| 3. Concentrated H₂SO₄ followed by concentrated HNO₃ | c. Mixture of o- and p-nitrophenols |
| 4. Bromine water | d. 2,4,6-Tribromophenol |
QUESTION 16 OF 20
The reaction of phenol with bromine in CS₂ at low temperature yields monobromophenols. The temperature at which dilute nitric acid reacts with phenol is:
QUESTION 17 OF 20
Statements regarding Kolbe's reaction:
1. Phenoxide ion is more reactive than phenol towards electrophilic substitution.
2. Carbon dioxide acts as a weak electrophile.
3. Ortho hydroxybenzoic acid is formed as the main product.
4. Chloroform is used as a reagent.
QUESTION 18 OF 20
In the Reimer-Tiemann reaction, what is the intermediate formed before hydrolysis to salicylaldehyde?
QUESTION 19 OF 20
Arrange the following hydrogen halides in decreasing order of their reactivity towards the cleavage of ethers:
1. HF
2. HBr
3. HCl
4. HI
QUESTION 20 OF 20
Identify the reaction type when anisole reacts with an alkyl halide in the presence of anhydrous aluminium chloride.
Test Complete!
Answer Review
1
�� Oxygen possesses lone pairs. �� Alcohols can accept protons. �� Hence, they behave as Brønsted bases.
As stated in the passage, alcohols act as Brønsted bases because the oxygen atom possesses unshared electron pairs that can accept a proton. Thus, alcohols behave as proton acceptors. Therefore, option D is correct.
- �� Option A → Brønsted bases accept protons rather than donate them.
- �� Option B → The polar O–H bond explains acidic behaviour, not basic behaviour.
- �� Option C → C–O bond cleavage is unrelated to Brønsted basicity.
Used
- Contextual/Tonal Matching
Application:
- Identify the statement directly supported by the passage.
Final Logic:
- Lone Pair → Proton Acceptor → Brønsted Base.
Lone Pair = Base
2
�� Protonation converts –OH into a good leaving group. �� Protonated alcohols undergo C–O bond cleavage. �� They behave as electrophiles.
The passage clearly states that alcohols react as electrophiles in their protonated form. Protonation converts the hydroxyl group into water, making it a good leaving group and facilitating nucleophilic attack. Therefore, option B is correct.
- �� Option A → Alkoxide ions are nucleophiles, not electrophiles.
- �� Option C → Phenoxide ions are also nucleophilic.
- �� Option D → Neutral alcohols are much less reactive as electrophiles.
Used
- Contextual/Tonal Matching
Application:
- Identify the electrophilic species mentioned in the passage.
Final Logic:
- Protonated Alcohol = Electrophile.
H⁺ Makes Alcohol Reactive
3 The reaction of an alkoxide ion with water suggests that:
�� Alkoxide ions abstract a proton from water. �� Water donates the proton. �� Therefore, water is the stronger acid.
The reaction RO⁻ + H₂O → ROH + OH⁻ shows that water donates a proton to the alkoxide ion. Since proton transfer occurs from water to the alkoxide ion, water behaves as the stronger acid, while alkoxide is the stronger base. Therefore, option A is correct.
- �� Option B → Alcohols are weaker acids than water.
- �� Option C → Alkoxide ions are stronger bases than hydroxide ions.
- �� Option D → Alkoxide ions are strong proton acceptors.
Used
- Elimination
Application:
- Compare the acid-base strengths using the proton-transfer reaction.
Final Logic:
- Water Donates H⁺ → Stronger Acid.
Water Gives, Alkoxide Takes
4 Match List-I (Substituent on Phenol) with List-II (Effect on Acidic Strength)
| List I | List II |
|---|---|
| 1. Electron withdrawing group at ortho/para | a. Decreases acid strength |
| 2. Electron releasing group (alkyl) | b. Serves as a reference (pKa ≈ 10.0) |
| 3. Nitro group | c. Highly enhances acid strength |
| 4. Unsubstituted phenol | d. Enhances acidic strength |
�� Electron-withdrawing groups increase acidity. �� Alkyl groups decrease acidity. �� Phenol serves as the reference compound.
1 → c : Electron-withdrawing groups at the ortho or para position strongly stabilize the phenoxide ion and highly enhance acidity. 2 → a : Electron-releasing alkyl groups destabilize the phenoxide ion and decrease acidity. 3 → d : The nitro group is an electron-withdrawing group and enhances acidic strength. 4 → b : Unsubstituted phenol has a pKa of about 10.0 and serves as the reference. Therefore, option D is correct.
- �� Option A → Multiple incorrect pairings are present.
- �� Option B → Electron-withdrawing groups are incorrectly matched.
- �� Option C → Nitro and alkyl effects are incorrectly matched.
Used
- Option Grouping
Application:
- Match each substituent with its effect on phenol acidity.
Final Logic:
- EWG ↑ Acidity; EDG ↓ Acidity.
Nitro Up, Alkyl Down
5 Statements concerning the acidity of alcohols and phenols:
1. Phenol is millions of times more acidic than ethanol.
2. In phenoxide ion, the negative charge is delocalized.
3. Alcohols are stronger acids than water.
4. Alkoxides are stronger bases than hydroxide ions.
�� Phenoxide ion is resonance stabilized. �� Alcohols are weaker acids than water. �� Alkoxides are stronger bases than hydroxide ions.
Statement 1 is correct because phenol is much more acidic than ethanol due to resonance stabilization of the phenoxide ion. Statement 2 is correct because the negative charge in the phenoxide ion is delocalized over the aromatic ring. Statement 3 is incorrect because alcohols are weaker acids than water. Statement 4 is correct because alkoxide ions are stronger bases than hydroxide ions owing to the weaker acidity of alcohols. Therefore, option A is correct.
- �� Option B → Includes statement 3, which is incorrect.
- �� Option C → Includes statement 3 and omits statement 1.
- �� Option D → Includes statement 3, which is incorrect.
Used
- Elimination
Application:
- Verify each statement using NCERT concepts on acidity and resonance.
Final Logic:
- Statements 1, 2 and 4 are correct; statement 3 is incorrect.
Phenol Stable, Alkoxide Strong Base
6 Arrange the following in decreasing order of their acid strength based on pKa and substituent effects:
1. 2,4,6-Trinitrophenol
2. Phenol
3. 3-Nitrophenol
4. 4-Methylphenol
�� Nitro groups increase acidity. �� Methyl groups decrease acidity. �� Picric acid is the strongest phenol.
Statement 1 represents 2,4,6-trinitrophenol (picric acid), which is the strongest acid because three nitro groups strongly stabilize the phenoxide ion. Statement 2 represents phenol, which is less acidic than nitrophenols. Statement 3 represents 3-nitrophenol, whose nitro group increases acidity through the −I effect. Statement 4 represents 4-methylphenol, where the methyl group exerts a +I effect, decreasing acidity. Therefore, the decreasing order of acid strength is: 2,4,6-Trinitrophenol > 3-Nitrophenol > Phenol > 4-Methylphenol. Hence, option D is correct.
- �� Option A → Places phenol above 3-nitrophenol.
- �� Option B → Gives the reverse order.
- �� Option C → Places 3-nitrophenol above picric acid.
Used
- Option Grouping
Application:
- Compare the effects of electron-withdrawing and electron-donating substituents.
Final Logic:
- More −NO₂ → Stronger Acid; CH₃ → Weaker Acid.
Three Nitro > One Nitro > Phenol > Methyl Phenol
7 To drive the reversible esterification equilibrium of an alcohol with a carboxylic acid to the right-hand side, what action is necessary?
�� Esterification is reversible. �� Removing water shifts equilibrium forward. �� Ester yield increases.
The esterification of an alcohol with a carboxylic acid is a reversible reaction. According to Le Chatelier's principle, continuous removal of water shifts the equilibrium towards ester formation, thereby increasing the yield. Therefore, option B is correct.
- �� Option A → HCl is not used to shift the equilibrium.
- �� Option C → A base neutralizes the acid catalyst and suppresses esterification.
- �� Option D → Low temperature does not effectively drive the equilibrium towards ester formation.
Used
- Elimination
Application:
- Recall the condition used to favour ester formation.
Final Logic:
- Remove Water → More Ester.
Remove H₂O, Make Ester
8 Identify the reaction type that produces aspirin from salicylic acid.
�� Salicylic acid undergoes acetylation. �� An acetyl group is introduced. �� Aspirin is produced.
Aspirin is prepared by acetylating salicylic acid using an acetylating agent such as acetic anhydride or acetyl chloride. The reaction introduces an acetyl (CH₃CO–) group and is known as acetylation (acylation). Therefore, option A is correct.
- �� Option B → No halogen atom is introduced.
- �� Option C → No alkyl group is introduced.
- �� Option D → Water elimination is not the principal reaction.
Used
- Contextual/Tonal Matching
Application:
- Identify the named reaction used to prepare aspirin.
Final Logic:
- Aspirin = Acetylation.
Aspirin = Acetyl
9 What is the IUPAC name of the product formed when tert-butyl alcohol reacts with HCl in the Lucas test?
�� tert-Butyl alcohol undergoes substitution. �� The –OH group is replaced by chlorine. �� A tertiary alkyl chloride is formed.
tert-Butyl alcohol reacts rapidly with concentrated HCl in the presence of ZnCl₂ (Lucas reagent). The hydroxyl group is replaced by chlorine through an SN1 mechanism, producing 2-chloro-2-methylpropane. Therefore, option A is correct.
- �� Option B → This is the product from butan-1-ol.
- �� Option C → This is obtained from butan-2-ol.
- �� Option D → This is not the product of tert-butyl alcohol.
Used
- Elimination
Application:
- Identify the substitution product of tert-butyl alcohol.
Final Logic:
- tert-Butyl Alcohol → tert-Butyl Chloride.
tert-Butyl → tert-Butyl Chloride
10 Arrange the ease of cleavage of the C–O bond by hydrogen halides for the following alcohols in decreasing order:
1. 2-Methylpropan-2-ol
2. Propan-2-ol
3. Methanol
4. Propan-1-ol
�� Tertiary alcohols react fastest. �� Secondary alcohols react more slowly. �� Primary alcohols react slower than secondary alcohols.
Statement 1 represents 2-methylpropan-2-ol, a tertiary alcohol that undergoes C–O bond cleavage most readily through the SN1 mechanism. Statement 2 represents propan-2-ol, a secondary alcohol with intermediate reactivity. Statement 3 represents methanol, which shows the least tendency for C–O bond cleavage among these alcohols. Statement 4 represents propan-1-ol, a primary alcohol that reacts more slowly. Therefore, the decreasing order of reactivity is: 2-Methylpropan-2-ol > Propan-2-ol > Propan-1-ol > Methanol. Hence, option A is correct.
- �� Option B → Gives the reverse order.
- �� Option C → Places secondary alcohol above tertiary alcohol.
- �� Option D → Places primary alcohol above secondary alcohol.
Used
- Option Grouping
Application:
- Arrange alcohols according to carbocation stability and ease of substitution with hydrogen halides.
Final Logic:
- 3° > 2° > 1° > Methyl Alcohol.
3° Fast → 2° Medium → 1° Slow → CH₃OH Slowest
11 Statements about dehydration of alcohols:
1. Tertiary alcohols are the easiest to dehydrate.
2. The ease of dehydration follows: Primary > Secondary > Tertiary.
3. The rate-determining step forms a carbocation.
4. Protic acids like H₂SO₄ or H₃PO₄ are used.
�� Tertiary alcohols dehydrate most readily. �� Carbocation formation is the slow step. �� Protic acids catalyse dehydration.
Statement 1 is correct because tertiary alcohols form the most stable carbocations and therefore undergo dehydration most easily. Statement 2 is incorrect because the correct order is: Tertiary > Secondary > Primary. Statement 3 is correct because carbocation formation is the rate-determining step in acid-catalysed dehydration. Statement 4 is correct because concentrated H₂SO₄ or H₃PO₄ acts as the acid catalyst. Therefore, option B is correct.
- �� Option A → Includes statement 2, which is incorrect.
- �� Option C → Includes statement 2, which is incorrect.
- �� Option D → Includes statement 2, which is incorrect.
Used
- Elimination
Application:
- Verify each statement using the NCERT dehydration mechanism.
Final Logic:
- Statements 1, 3 and 4 are correct; statement 2 is incorrect.
3° First, Carbocation Next
12 In the mechanism of dehydration of ethanol, how is the equilibrium driven to the right?
�� Dehydration is reversible. �� Ethene escapes from the reaction mixture. �� Equilibrium shifts towards products.
During acid-catalysed dehydration, ethene is continuously removed as it is formed because it is a gas. According to Le Chatelier's principle, removal of the product shifts the equilibrium towards further formation of ethene. Therefore, option B is correct.
- �� Option A → More catalyst increases the rate but does not shift equilibrium.
- �� Option C → Increased pressure opposes gaseous product formation.
- �� Option D → Addition of water shifts equilibrium towards alcohol.
Used
- Elimination
Application:
- Apply Le Chatelier's principle to the reaction.
Final Logic:
- Remove Product → More Product Forms.
Gas Leaves, Reaction Proceeds
13 Arrange the sequence of products formed during the strong oxidation of a primary alcohol:
1. Aldehyde
2. Primary alcohol
3. Carboxylic acid
4. Strong oxidising agent (KMnO₄/K₂Cr₂O₇) completes the oxidation.
�� Primary alcohol first forms an aldehyde. �� Further oxidation gives a carboxylic acid. �� Strong oxidants complete the conversion.
Statement 1 represents the primary alcohol. Statement 2 represents the aldehyde formed during the first stage of oxidation. Statement 3 represents the carboxylic acid obtained after further oxidation. Statement 4 is a correct NCERT fact indicating that strong oxidising agents such as KMnO₄ or K₂Cr₂O₇ complete the oxidation to the acid. Therefore, the sequence is: Primary alcohol → Aldehyde → Carboxylic acid. Hence, option C is correct.
- �� Option A → Begins with the intermediate.
- �� Option B → Reverses the oxidation sequence.
- �� Option D → Places carboxylic acid before aldehyde.
Used
- Option Grouping
Application:
- Arrange compounds according to the oxidation pathway.
Final Logic:
- Alcohol → Aldehyde → Acid.
Alcohol → Aldehyde → Acid
14 When tertiary alcohols are subjected to strong oxidising agents (KMnO₄) at elevated temperatures, what happens?
�� Tertiary alcohols lack α-hydrogen. �� Normal oxidation does not occur. �� Strong oxidation cleaves C–C bonds.
Tertiary alcohols do not undergo ordinary oxidation because they lack a hydrogen atom on the carbon bearing the hydroxyl group. Under vigorous oxidation with strong oxidising agents at high temperatures, cleavage of carbon-carbon bonds occurs, producing smaller carboxylic acids. Therefore, option C is correct.
- �� Option A → Oxidation cannot produce secondary alcohols.
- �� Option B → Ketones are formed from secondary alcohols.
- �� Option D → Under vigorous conditions they undergo C–C bond cleavage.
Used
- Elimination
Application:
- Recall the oxidation behaviour of tertiary alcohols.
Final Logic:
- No α-H → C–C Cleavage.
3° Alcohol = Break Carbon Chain
15 Match List-I (Reaction Condition) with List-II (Product)
| List I | List II |
|---|---|
| 1. Dilute HNO₃ at 298 K | a. Picric acid (poor yield) |
| 2. Concentrated HNO₃ | b. Picric acid (high yield industrially) |
| 3. Concentrated H₂SO₄ followed by concentrated HNO₃ | c. Mixture of o- and p-nitrophenols |
| 4. Bromine water | d. 2,4,6-Tribromophenol |
�� Dilute nitric acid gives mono-nitrophenols. �� Concentrated nitric acid forms picric acid. �� Sulphonation followed by nitration improves picric acid yield.
1 → c : Dilute nitric acid at 298 K produces a mixture of ortho- and para-nitrophenols. 2 → a : Direct nitration with concentrated nitric acid gives picric acid in poor yield because of oxidation side reactions. 3 → b : Sulphonation followed by nitration is the industrial method for obtaining picric acid in high yield. 4 → d : Bromine water reacts with phenol to give 2,4,6-tribromophenol as a white precipitate. Therefore, option A is correct.
- �� Option B → Dilute and concentrated nitration products are interchanged.
- �� Option C → Multiple incorrect pairings are present.
- �� Option D → Concentrated nitric acid and industrial nitration are interchanged.
Used
- Option Grouping
Application:
- Match each reaction condition with its characteristic product.
Final Logic:
- Dilute → Mono Nitro; Conc. → Picric; Sulphonation + Nitration → High Yield; Br₂ Water → Tribromo.
Dilute–Mono, Conc.–Picric, Br₂–Tribromo
16 The reaction of phenol with bromine in CS₂ at low temperature yields monobromophenols. The temperature at which dilute nitric acid reacts with phenol is:
�� Dilute nitric acid reacts at room temperature. �� The reaction produces o- and p-nitrophenols. �� The temperature is 298 K.
According to NCERT, phenol reacts with dilute nitric acid at 298 K to produce a mixture of ortho- and para-nitrophenols. This mild temperature favours mononitration of the activated aromatic ring. Therefore, option A is correct.
- �� Option B → 337 K is not the NCERT condition for nitration of phenol.
- �� Option C → 443 K is associated with dehydration reactions of alcohols.
- �� Option D → 573 K is used in oxidation/dehydrogenation reactions of alcohols.
Used
- Elimination
Application:
- Recall the standard NCERT temperature for nitration of phenol.
Final Logic:
- Dilute HNO₃ + Phenol → 298 K.
Nitration = 298 K
17 Statements regarding Kolbe's reaction:
1. Phenoxide ion is more reactive than phenol towards electrophilic substitution.
2. Carbon dioxide acts as a weak electrophile.
3. Ortho hydroxybenzoic acid is formed as the main product.
4. Chloroform is used as a reagent.
�� Phenoxide ion is highly activated. �� CO₂ behaves as a weak electrophile. �� Salicylic acid is the major product.
Statement 1 is correct because the phenoxide ion has greater electron density than phenol and undergoes electrophilic substitution more readily. Statement 2 is correct because carbon dioxide acts as a weak electrophile in Kolbe's reaction. Statement 3 is correct because the major product obtained after acidification is ortho hydroxybenzoic acid (salicylic acid). Statement 4 is incorrect because chloroform is used in the Reimer–Tiemann reaction, not in Kolbe's reaction. Therefore, option D is correct.
- �� Option A → Includes statement 4, which is incorrect.
- �� Option B → Includes statement 4, which is incorrect.
- �� Option C → Includes statement 4, which is incorrect.
Used
- Elimination
Application:
- Verify each statement using the NCERT description of Kolbe's reaction.
Final Logic:
- Statements 1, 2 and 3 are correct; statement 4 is incorrect.
Kolbe = CO₂, Reimer = CHCl₃
18 In the Reimer-Tiemann reaction, what is the intermediate formed before hydrolysis to salicylaldehyde?
�� Chloroform reacts in alkaline medium. �� A substituted benzal chloride intermediate is formed. �� Hydrolysis gives salicylaldehyde.
In the Reimer–Tiemann reaction, phenol reacts with chloroform and sodium hydroxide to produce a substituted benzal chloride intermediate. Hydrolysis of this intermediate yields salicylaldehyde. Therefore, option B is correct.
- �� Option A → Phenoxide ion is the reactant, not the intermediate before hydrolysis.
- �� Option C → Benzoquinone is not formed in this reaction.
- �� Option D → Ortho-hydroxybenzoic acid is the product of Kolbe's reaction.
Used
- Contextual/Tonal Matching
Application:
- Identify the characteristic intermediate of the Reimer–Tiemann reaction.
Final Logic:
- CHCl₃ → Benzal Chloride → Salicylaldehyde.
Reimer = Benzal Chloride
19 Arrange the following hydrogen halides in decreasing order of their reactivity towards the cleavage of ethers:
1. HF
2. HBr
3. HCl
4. HI
�� HI is the most reactive. �� HBr is less reactive than HI. �� HCl and HF are much less effective.
Statement 1 represents HF, which is the least reactive because of its weak nucleophilicity. Statement 2 represents HBr, which is less reactive than HI but more reactive than HCl. Statement 3 represents HCl, which is comparatively ineffective for ether cleavage. Statement 4 represents HI, which is the most effective hydrogen halide for ether cleavage because iodide is a strong nucleophile and HI is a strong acid. Therefore, the decreasing order is: HI > HBr > HCl > HF. Hence, option A is correct.
- �� Option B → Places HBr above HI.
- �� Option C → Gives the reverse trend.
- �� Option D → Incorrectly places HBr and HCl.
Used
- Option Grouping
Application:
- Arrange hydrogen halides according to their effectiveness in ether cleavage.
Final Logic:
- HI > HBr > HCl > HF.
I > Br > Cl > F
20 Identify the reaction type when anisole reacts with an alkyl halide in the presence of anhydrous aluminium chloride.
�� Anisole activates the benzene ring. �� Alkyl halide provides the electrophile. �� Alkylation occurs on the aromatic ring.
Anisole undergoes electrophilic aromatic substitution with alkyl halides in the presence of anhydrous AlCl₃. This reaction is known as Friedel-Crafts alkylation, in which an alkyl group is introduced mainly at the ortho and para positions. Therefore, option A is correct.
- �� Option B → Reimer–Tiemann reaction introduces a –CHO group using CHCl₃ and NaOH.
- �� Option C → Williamson synthesis prepares ethers using alkoxides and alkyl halides.
- �� Option D → Kolbe's reaction introduces a –COOH group using CO₂.
Used
- Contextual/Tonal Matching
Application:
- Identify the named reaction from the reagents used.
Final Logic:
- Alkyl Halide + AlCl₃ = Friedel-Crafts Alkylation.
Alkyl + AlCl₃ = Friedel Alkylation
