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JEE • CHEMISTRY • ALCOHOLS & PHENOLS & ETHERS

Alcohols & phenols & ethers practice · Medium

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31 Medium
31 of 96
Understanding +4 | -1
Which one of the following compounds will not react with CH3MgBr\mathrm{C}{\mathrm{H}_3}\mathrm{MgBr}?
View answer and explanation
Correct option: C
Dimethyl ether
Option C (Dimethyl ether) is correct because Grignard reagents react with compounds containing acidic hydrogens or carbonyl groups, which are absent in dimethyl ether.
32 Medium
32 of 96
Understanding +4 | -1
Which of the following statements are correct?

(i) In phenols, the −OH-{OH} group is attached to sp2s p^2 hybridised carbon of an aromatic ring

(ii) The carbon - oxygen bond length (136 pm) in phenol is slightly more than that in methanol

(iii) Partial double bond character is due to the conjugation of unshared electron pair of oxygen with the aromatic ring.

(iv) sp2s p^2 hybridised state of carbon to which oxygen is attached.
View answer and explanation
Correct option: C
(i), (iii) and (iv)
The correct answer is C (VΔPV\Delta P) because the difference between ΔH\Delta H and ΔU\Delta U at constant volume is VΔPV\Delta P.
33 Medium
33 of 96
Remembering +4 | -1
Ether fire can be extinguished by:
View answer and explanation
Correct option: D
All of these
Option D (All of these) is correct because sand, pyrene, and CO2 are all effective fire extinguishers for ether fires.
34 Medium
34 of 96
Understanding +4 | -1
Given below are two statements.

Statement-I: Phenol reacts with bromine in CCl4{CCl}_4 gives a white ppt. of 2,4,6-tribromophenol.

Statement-II : Phenol reacts with dil. HNO3{HNO}_3 at 0−10∘C0-10^{\circ} \mathrm{C} to form o- and p-nitrophenol

Choose the most appropriate answer from given below options:
View answer and explanation
Correct option: D
Statement-I is incorrect and Statement-II is correct
The correct answer is D (Statement-I is incorrect and Statement-II is correct) because phenol reacts with bromine water to give a white precipitate of 2,4,6-tribromophenol, but with bromine in CCl4, it gives a mixture of ortho and para bromophenols. Phenol reacts with dilute HNO3 at 0-10°C to form o- and p-nitrophenol is correct.
35 Medium
35 of 96
Understanding +4 | -1
Assertion: Phenol is a strong acid than ethanol.

Reason: Groups with +M+{M} effect decreases acidity at p-position.
View answer and explanation
Correct option: B
If both Assertion and Reason are correct but Reason is not a correct explanation of the Assertion.
Option B (If both Assertion and Reason are correct but Reason is not a correct explanation of the Assertion) is correct because both statements are true, but the +M effect is not the primary reason for phenol's acidity.
36 Medium
36 of 96
Analyzing +4 | -1
Assertion: Ethanol can be distinguished from methanol using iodoform test.

Reason: Ethanol has a methyl group attached to a carbon containing hydroxyl groups.
View answer and explanation
Correct option: A
Both assertion and reason are correct statements, and reason is the correct explanation of the assertion.
Option A (Both assertion and reason are correct statements, and reason is the correct explanation of the assertion) is correct because ethanol gives a positive iodoform test due to the presence of a methyl group attached to a carbon bearing a hydroxyl group.
37 Medium
37 of 96
Application +4 | -1
Identify (Z)(Z) in the following series,
Ethanol→PBr3(X)→KOHAlc.(Y)→(ii) H2O;  heat(i) H2SO4/Room  temp.(Z){\text{Ethanol}}\xrightarrow{{PB{r_3}}}\left( X \right)\xrightarrow[{KOH}]{{{\text{Alc}}{\text{.}}}}\left( Y \right)\xrightarrow[{(ii)\,{H_2}O;\,\,{\text{heat}}}]{{(i)\,{H_2}S{O_4}/{\text{Room}}\,\,{\text{temp}}{\text{.}}}}\left( Z \right)
View answer and explanation
Correct option: B
CH3−CH2−OHC{H_3} - C{H_2} - OH
The correct answer is B (CH3−CH2−OHC{H_3} - C{H_2} - OH) because the series of reactions converts ethanol to ethene and then back to ethanol.
38 Medium
38 of 96
Understanding +4 | -1
When ethyl alcohol (C2H5OH)\left({C}_2 {H}_5 {OH}\right) reacts with thionyl chloride, in the presence of pyridine, the gas obtained is
View answer and explanation
Correct option: C
HCl,SO2{HCl}, {SO}_2
Option C (HCl,SO2{HCl}, {SO}_2) is correct because the reaction of ethyl alcohol with thionyl chloride in the presence of pyridine produces ethyl chloride, sulfur dioxide, and hydrogen chloride.
39 Medium
39 of 96
Understanding +4 | -1
Replacement of Cl\mathrm{Cl} of chlorobenzene to give phenol requires drastic conditions but chlorine of 2, 4-dinitrochlorobenzene is readily replaced because:
View answer and explanation
Correct option: D
NO2\mathrm{N}{\mathrm{O}_2} withdraws electrons at orthoortho and parapara positions
Option D is correct because the nitro groups (-NO2) are electron-withdrawing groups that stabilize the negative charge formed during the nucleophilic aromatic substitution at the ortho and para positions, making the chlorine more easily replaced.
40 Medium
40 of 96
Analyzing +4 | -1
What is Z in the following sequence of reactions? Z→PCl5X→Alc.KOHY→(ii) H2O ;  boil(i)  Conc. H2SO4ZZ\xrightarrow{{PC{l_5}}}X\xrightarrow{{Alc.KOH}}Y\xrightarrow[{(ii)\,{H_2}O\,;\,\,boil}]{{(i)\,\,Conc.\,{H_2}S{O_4}}}Z
View answer and explanation
Correct option: B
CH3CH(OH)CH3C{H_3}CH(OH)C{H_3}
The correct answer is B (CH3CH(OH)CH3C{H_3}CH(OH)C{H_3}) because the sequence of reactions (treatment with PCl5, alcoholic KOH, and then concentrated H2SO4 followed by water and boiling) leads to the regeneration of the original alcohol.
41 Medium
41 of 96
Analyzing +4 | -1
Assertion: Boiling point of ethanol is higher than that of propane.

Reason: Molecular mass of ethanol is higher than propane.
View answer and explanation
Correct option: B
If both Assertion and Reason are true but Reason is not the correct explanation of Assertion
Option B (If both Assertion and Reason are true but Reason is not the correct explanation of Assertion) is correct because while both statements are true, the higher boiling point of ethanol is primarily due to hydrogen bonding, not its molecular mass.
42 Medium
42 of 96
Understanding +4 | -1
Dehydration of alcohols to alkene by heating with conc. H2SO4{H_2}S{O_4} the initiation step is …….. followed with …. Mechanism.
View answer and explanation
Correct option: C
Protonation of alcohol, carbocation
Option C is correct because the dehydration of alcohols in the presence of conc. H2SO4 proceeds via protonation of alcohol followed by carbocation formation.
43 Medium
43 of 96
Understanding +4 | -1
Primary, secondary and tetiary alcohols are distinguished from one another by
View answer and explanation
Correct option: C
Lucas test
Option C (Lucas test) is correct because the Lucas test differentiates between primary, secondary, and tertiary alcohols based on their reaction rates with Lucas reagent.
44 Medium
44 of 96
Understanding +4 | -1
Which of the following reagent is used to distinguish phenol and benzoic acid?
View answer and explanation
Correct option: D
Neutral FeCl3FeCl_3
Option D (Neutral FeCl3FeCl_3) is correct because phenol reacts with neutral FeCl3FeCl_3 to form a violet-colored complex, while benzoic acid forms a buff-colored precipitate.
45 Medium
45 of 96
Analyzing +4 | -1
Which statement is true regarding following reactions trans −2−-2- Butene ⟶HCO3HA\stackrel{\mathrm{HCO}_{3} H}{\longrightarrow} A cis-2-Butene ⟶HCO3HB\stackrel{\mathrm{HCO}_{3} \mathrm{H}}{\longrightarrow} B
View answer and explanation
Correct option: C
compound AA and BB are formed by anti addition and they are meso and racemic mixture respectively
The correct answer is C because performic acid causes anti-hydroxylation, leading to meso product from trans-2-butene and racemic mixture from cis-2-butene.
46 Medium
46 of 96
Remembering +4 | -1
Which of the following is a gas?
View answer and explanation
Correct option: A
Methane thiol
Option A (Methane thiol) is correct because methane thiol (CH3SH\mathrm{C}{\mathrm{H}_3}\mathrm{SH}) is a gas at room temperature, unlike the other options.
47 Medium
47 of 96
Analyzing +4 | -1
A compound XX with molecular formula C3H8O{\mathrm{C}_3}{\mathrm{H}_8}\mathrm{O} can be oxidised to a compound YY with the molecular formula C3H6O2{\mathrm{C}_3}{\mathrm{H}_6}{\mathrm{O}_2}. XX is most likely to be:
View answer and explanation
Correct option: A
Primary alcohol
Option A (Primary alcohol) is correct because primary alcohols can be oxidized to carboxylic acids with the given molecular formula change.
48 Medium
48 of 96
Analyzing +4 | -1
A compound with molecular formula C4H10O3{\mathrm{C}_4}{\mathrm{H}_{10}}{\mathrm{O}_3} is converted by the action of acetyl chloride to a compound with molecular weight 190. The original compound has:
View answer and explanation
Correct option: B
Two OH\mathrm{OH} groups
Option B is correct because the original compound has two OH groups, which react with acetyl chloride to increase the molecular weight by 84 (2 * 42), resulting in a final molecular weight of 190.
49 Medium
49 of 96
Understanding +4 | -1
The compound formed when Ethyl bromide is heated with dry Silver oxide is
View answer and explanation
Correct option: B
diethylether
Option B is correct because when ethyl bromide is heated with dry silver oxide, it undergoes a Williamson ether synthesis to form diethyl ether.
50 Medium
50 of 96
Analyzing +4 | -1
C2H5OH{\mathrm{C}_2}{\mathrm{H}_5}\mathrm{OH} and C2H5OH{\mathrm{C}_2}{\mathrm{H}_5}\mathrm{OH} can be distinguished by
View answer and explanation
Correct option: D
Both (2) and (3 )
Option D (Both (2) and (3)) is correct because phenol reacts with FeCl3FeCl_3 to give a color and ethanol gives iodoform test with I2+NaOHI_2 + NaOH.
51 Medium
51 of 96
Analyzing +4 | -1
Which of the following alcohols is dehydrated most readily with conc. H2SO4?{\mathrm{H}_2}\mathrm{S}{\mathrm{O}_4}?
View answer and explanation
Correct option: C
p−CH3OC6H4CH(OH)CH3p - \mathrm{C}{\mathrm{H}_3}\mathrm{O}{\mathrm{C}_6}{\mathrm{H}_4}\mathrm{CH}\left( {\mathrm{OH}} \right)\mathrm{C}{\mathrm{H}_3}
Option C (p−CH3OC6H4CH(OH)CH3p - CH_3OC_6H_4CH(OH)CH_3) is correct because the electron-donating methoxy group stabilizes the carbocation intermediate formed during dehydration, accelerating the reaction.
52 Medium
52 of 96
Analyzing +4 | -1
Addition of Grignard reagent to acetaldehyde followed by hydrolysis and then acidic dehydration of the resulting product gives
View answer and explanation
Correct option: B
Alkene
Option B (Alkene) is correct because the Grignard addition to acetaldehyde followed by hydrolysis yields a secondary alcohol, which dehydrates to form an alkene.
53 Medium
53 of 96
Understanding +4 | -1
To obtain unsaturated alcohols from unsaturated aldehydes the following reagent is used for reduction:
View answer and explanation
Correct option: D
LiAlH4\mathrm{LiAl}{\mathrm{H}_4}
Option D is correct. LiAlH4 reduces the carbonyl group of an aldehyde to an alcohol without affecting the carbon-carbon double bond.
54 Medium
54 of 96
Analyzing +4 | -1
Arrange the compounds in order of decreasing acidity:

I. Cl−CH2−CH2−SH{Cl}-{CH}_2-{CH}_2-{SH}

II. Cl2CH−CH2−SH{Cl}_2 {CH}-{CH}_2-{SH}

III. Cl−CH2−CH2−OH{Cl}-{CH}_2-{CH}_2-{OH}

IV. CH3−CH2−OH{CH}_3-{CH}_2-{OH}
View answer and explanation
Correct option: D
II >> I >> III >> IV
Option D (II > I > III > IV) is correct because electron-withdrawing chlorine atoms increase acidity, and thiols are more acidic than alcohols.
55 Medium
55 of 96
Analyzing +4 | -1
C4H8O2(Ester A)+CH3MgBr(2 parts)→H3O+C4H10OAlcohol(B)\underset{\text{(Ester A)}}{\mathrm{C}_4 \mathrm{H}_8 \mathrm{O}_2}+\underset{\text{(2 parts)}}{\mathrm{CH}_3 \mathrm{MgBr}} \xrightarrow{\mathrm{H}_3 \mathrm{O}^{+}} \underset{\text{Alcohol(B)}}{\mathrm{C}_4 \mathrm{H}_{10} \mathrm{O}}

Alcohol B\text{B} reacts faster with Lucas reagent. Hence A\text{A} and B\text{B} are
View answer and explanation
Correct option: A
CH3−COO−C2H5,(CH3)3COH\mathrm{CH}_3-\mathrm{COO}-\mathrm{C}_2 \mathrm{H}_5,\left(\mathrm{CH}_3\right)_3 \mathrm{COH}
Option A is correct because the ester CH3−COO−C2H5\mathrm{CH}_3-\mathrm{COO}-\mathrm{C}_2 \mathrm{H}_5 reacts with excess Grignard reagent to form the tertiary alcohol (CH3)3COH(\mathrm{CH}_3)_3 \mathrm{COH}, which reacts fastest with Lucas reagent.
56 Medium
56 of 96
Understanding +4 | -1
Dehydration of 2-butanol yields
View answer and explanation
Correct option: D
Both (1) and (2)
Option D (Both (1) and (2)) is correct because dehydration of 2-butanol yields both 1-butene and 2-butene as products, with 2-butene being the major product due to Zaitsev's rule.
57 Medium
57 of 96
Application +4 | -1
For the preparation ter-butylmethylether by Williamson’s method the correct choice of reagents is:
View answer and explanation
Correct option: D
Ter-butoxide and methylbromide
The correct answer is D (Ter-butoxide and methylbromide) because tertiary halides are not suitable for Williamson's synthesis due to elimination reactions.
58 Medium
58 of 96
Analyzing +4 | -1
Assertion (A): 7.5 g7.5 \mathrm{~g} of ethoxyethane and 9 g9 \mathrm{~g} of butan-1-ol is miscible to almost same extent while pentane is essentially immiscible with water.

Reason (R): Alcohols and ethers can form hydrogen bonds with the water molecule.
View answer and explanation
Correct option: A
Both A\mathrm{A} and R\mathrm{R} are correct; R\mathrm{R} is the correct explanation of A\mathrm{A}.
Option A (Both A and R are true and R is the correct explanation of A) is correct because the back bonding in BF3BF_3 makes it a weaker Lewis acid compared to BCl3BCl_3.
59 Medium
59 of 96
Remembering +4 | -1
Chlorex which is a good solvent for aromatic impurities is:
View answer and explanation
Correct option: B
Dichlorodiethyl ether
Option B (Dichlorodiethyl ether) is correct because Chlorex, a good solvent for aromatic impurities, is dichlorodiethyl ether.
60 Medium
60 of 96
Analyzing +4 | -1
An alcohol on oxidation is found to give CH3COOHC{H_3}COOH and CH3CH2COOHC{H_3}C{H_2}COOH The alcohol is:
View answer and explanation
Correct option: D
CH3CH(OH)CH2CH2CH3C{H_3}CH(OH)C{H_2}C{H_2}C{H_3}
Option D (CH3CH(OH)CH2CH2CH3C{H_3}CH(OH)C{H_2}C{H_2}C{H_3}) is correct because its oxidation leads to the formation of both acetic acid and propanoic acid via bond cleavage.
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