When benzene sulphonic acid and $p - $nitrophenol are treated with ${\rm{NaHC}}{{\rm{O}}_3}$, the gases released respectively are:

${\rm{N}}{{\rm{O}}_2},{\rm{\;C}}{{\rm{O}}_2}$

${\rm{S}}{{\rm{O}}_2},{\rm{\;N}}{{\rm{O}}_2}$

${\rm{S}}{{\rm{O}}_2},{\rm{\;NO}}$

${\rm{S}}{{\rm{O}}_2},{\rm{\;C}}{{\rm{O}}_2}$

An organic compound $A$ containing C, H and O has a pleasant odour with boiling point of 78$^ \circ C$. On boiling $A$ with concentrated ${\rm{\;}}{{\rm{H}}_2}{\rm{S}}{{\rm{O}}_4}$, a colourless gas is produced which decolourises bromine water and alkaline ${\rm{KMn}}{{\rm{O}}_4}$. The organic liquid $A$ is

${{\rm{C}}_2}{{\rm{H}}_5}{\rm{OH}}$

${{\rm{C}}_2}{{\rm{H}}_5}{\rm{Cl}}$

${{\rm{C}}_2}{{\rm{H}}_5}{\rm{COOC}}{{\rm{H}}_3}$

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NEET • CHEMISTRY • ALCOHOLS & PHENOLS & ETHERS

Alcohols & phenols & ethers practice · Hard

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1 Hard

1 of 50

Application +4 | -1

The product 'B' in the following reaction is

{\text{C}}{{\text{H}}_3}{\text{C}}{{\text{H}}_2}{\text{OH}}\xrightarrow{{{\text{PCC}}}}{\text{A}}\xrightarrow[{\left( {{\text{ii}}} \right){\text{ }}{{\text{H}}_2}{\text{O/}}{{\text{H}}^ + }}]{{\left( {\text{i}} \right){\text{ HCN}}}}{\text{B}}

View answer and explanation

Correct option: D

Both (2) and (3)

Option D (Both (2) and (3)) is correct because the reaction sequence involves oxidation of ethanol to ethanal, followed by reaction with HCN to form a cyanohydrin, which upon hydrolysis yields

\alpha

-Hydroxy propionic acid, also known as Lactic acid.

2 Hard

2 of 50

Analyzing +4 | -1

Assertion:- Isopropyl benzene reacts with

\mathrm{O}_2

and acid gives phenol.

Reason:- Initially isopropyl benzene converts into 2-phenyl propan-2-ol.

View answer and explanation

Correct option: D

If both Assertion & reason are False

Option D is correct because isopropyl benzene reacts with oxygen in the presence of a catalyst to give phenol and acetone. The initial product is cumene hydroperoxide, not 2-phenylpropan-2-ol.

3 Hard

3 of 50

Understanding +4 | -1

When an ether is treated with

{\mathrm{P}_2}{\mathrm{S}_5}

we get:

View answer and explanation

Correct option: C

Thio-ether

Option C (Thio-ether) is correct because

{\mathrm{P}_2}{\mathrm{S}_5}

replaces oxygen with sulfur in ethers, forming thioethers.

4 Hard

4 of 50

Analyzing +4 | -1

Find out product

(X)

Ph - CH = C{H_2}\xrightarrow[{\begin{array}{cccccccccccccccccccc} {\left(2 \right)\,HBr} \\ {\left(3 \right)\,Mg,{\text{ dry ether}}} \\ {\left(4 \right)\,HCHO} \end{array}}]{{\left(1 \right){B_2}{H_6}/{\text{THF/}}{H_2}{O_2}/O{H^ - }}}X\left( {{\text{major}}} \right)

View answer and explanation

Correct option: D

{Ph}-{CH}_2-{CH}_2-{CH}_2-{OH}

Option D (

{Ph}-{CH}_2-{CH}_2-{CH}_2-{OH}

) is correct because the hydroboration-oxidation of styrene gives 2-phenylethanol, which then reacts with HBr to give 1-bromo-2-phenylethane. This reacts with Mg to form a Grignard reagent, which then reacts with formaldehyde to give 3-phenylpropan-1-ol.

5 Hard

5 of 50

Application +4 | -1

When benzene sulphonic acid and

p -

nitrophenol are treated with

\mathrm{NaHC}{\mathrm{O}_3}

, the gases released respectively are:

View answer and explanation

Correct option: D

\mathrm{N}{\mathrm{O}_2},\mathrm{\;C}{\mathrm{O}_2}

The correct answer is D (

\mathrm{N}{\mathrm{O}_2},\mathrm{\;C}{\mathrm{O}_2}

) because benzene sulfonic acid is a strong acid that doesn't react with NaHCO3 to release CO2, while p-nitrophenol is acidic enough to react with NaHCO3 to release CO2.

6 Hard

6 of 50

Application +4 | -1

Among the following, the number of compounds which will not give positive iodoform reaction is

(i) 1- Phenylbutane-2-one

(ii) 2-Methylbutan-2-ol

(iii) 3-Methylbutan-2-ol

(iv) 1-Phenylethanol

(v) 3,3-Dimethylbutan-2-one

(vi) 1-Phenylpropan-2-ol

View answer and explanation

Correct option: A

The correct answer is 2. Compounds that do NOT give a positive iodoform test are those lacking a methyl ketone or a secondary alcohol that can be oxidized to a methyl ketone.

7 Hard

7 of 50

Understanding +4 | -1

Diethyl ether and n-propyl methyl ether are

View answer and explanation

Correct option: A

Metamers

Option A (Metamers) is correct because diethyl ether (

\mathrm{C}{\mathrm{H}_3}\mathrm{C}{\mathrm{H}_2}\mathrm{O}{\mathrm{C}{\mathrm{H}_2}\mathrm{C}{\mathrm{H}_3}}

) and n-propyl methyl ether (

\mathrm{C}{\mathrm{H}_3}\mathrm{O}{\mathrm{C}{\mathrm{H}_2}\mathrm{C}{\mathrm{H}_2}\mathrm{C}{\mathrm{H}_3}}

) have the same molecular formula but different alkyl groups attached to the oxygen atom.

8 Hard

8 of 50

Understanding +4 | -1

Diethyl ether is decomposed on heating with:

View answer and explanation

Correct option: D

\mathrm{HI}

Option D (HI) is correct because HI cleaves ethers to form alkyl halides and alcohols.

9 Hard

9 of 50

Analyzing +4 | -1

Assertion:- Dehydration of alcohols always take place in basic medium.

Reason:-

\mathrm{OH}

- is a good leaving group

View answer and explanation

Correct option: D

If both Assertion & reason are False

Option D is correct because dehydration of alcohols typically occurs in acidic medium, and OH- is a poor leaving group.

10 Hard

10 of 50

Understanding +4 | -1

Name the reagent used to convert bromoethane to ethoxy ethane

View answer and explanation

Correct option: A

Sodium ethoxide

Option A (Sodium ethoxide) is correct because sodium ethoxide reacts with bromoethane via Williamson ether synthesis to form ethoxyethane.

11 Hard

11 of 50

Application +4 | -1

To prepare 3-ethylpentane-3-ol, the reactants needed are:

View answer and explanation

Correct option: C

\mathrm{CH}_3 \mathrm{CH}_2 \mathrm{MgBr}+\mathrm{CH}_3 \mathrm{CH}_2 \mathrm{COCH}_2 \mathrm{CH}_3

Option C is correct because the reaction of ethyl magnesium bromide with 3-pentanone will produce 3-ethylpentan-3-ol after hydrolysis.

12 Hard

12 of 50

Analyzing +4 | -1

Assertion: ter-butyl methyl ether is not prepared by the reaction of ter-butyl bromide with sodium methoxide.

Reason: Sodium methoxide is a strong nucleophile.

View answer and explanation

Correct option: B

If both Assertion and Reason are correct, but Reason is not the correct explanation of Assertion.

Option B is correct because both the assertion and reason are correct, but the reason (sodium methoxide being a strong nucleophile) doesn't fully explain why tert-butyl methyl ether isn't formed. The primary reason is steric hindrance around the tert-butyl group, which favors elimination over substitution.

13 Hard

13 of 50

Understanding +4 | -1

Best method to convert alcohol into alkyl chloride is

View answer and explanation

Correct option: A

R - OH + SOC{l_2} \to R - Cl + S{O_2} + HCl

Option A (

R - OH + SOC{l_2} \to R - Cl + S{O_2} + HCl

) is correct because the reaction with thionyl chloride (

SOC{l_2}

) proceeds with retention of configuration and produces gaseous byproducts (

S{O_2}

and

HCl

) that easily escape, leading to a cleaner product.

14 Hard

14 of 50

Application +4 | -1

4.12 \mathrm{~mg}

\mathrm{ROH}

is added to Grignard reagent

\left(\mathrm{CH}_3 \mathrm{Mgl}\right)

. If

1.56 \mathrm{~ml}

of a gas is produced at STP, the molar mass of alcohol will be nearly

View answer and explanation

Correct option: B

59 \mathrm{~g} \mathrm{~mol}^{-1}

Option C (

{B}_6 {H}_6

and alk.

{H}_2 {O}_2

) is correct because this represents hydroboration-oxidation, which converts alkenes to alcohols with anti-Markovnikov addition, resulting in 1-propanol from propene.

15 Hard

15 of 50

Understanding +4 | -1

The simplest alkanol exhibiting optical activity is

View answer and explanation

Correct option: C

S-butyl alcohol

Option C (S-butyl alcohol) is correct because it is the smallest alcohol with a chiral carbon atom, meaning it has four different groups attached to one carbon.

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16 Hard

16 of 50

Application +4 | -1

Which of the ester shown, after reduction with

\mathrm{LiAlH}_4

and aqueous work up, will yield two molecules of only a single alcohol?

View answer and explanation

Correct option: C

\mathrm{C}_6 \mathrm{H}_5-\mathrm{CO}_2-\mathrm{CH}_2 \mathrm{C}_6 \mathrm{H}_5

Option C (

\mathrm{C}_6 \mathrm{H}_5-\mathrm{CO}_2-\mathrm{CH}_2 \mathrm{C}_6 \mathrm{H}_5

) is correct because the ester is derived from benzoic acid and benzyl alcohol, both of which will be reduced to benzyl alcohol upon treatment with

\mathrm{LiAlH}_4

followed by aqueous workup.

17 Hard

17 of 50

Remembering +4 | -1

Glycerol catches fire on mixing with:

View answer and explanation

Correct option: A

\mathrm{KMn}{\mathrm{O}_4}

Option A (

\mathrm{KMn}{\mathrm{O}_4}

) is correct because glycerol reacts vigorously with potassium permanganate, leading to a fire.

18 Hard

18 of 50

Analyzing +4 | -1

\mathrm{C}_4 \mathrm{H}_{10} \mathrm{O}(\mathrm{X}) \xrightarrow{\mathrm{KMnO}_4 / \mathrm{H}^{+}} \mathrm{C}_4 \mathrm{H}_8 \mathrm{O}_2.

'X' can be

A) n-butyl alcohol

B)

2^\circ

butyl alcohol

C) Isobutyl alcohol

D)

3^\circ

butyl alcohol

View answer and explanation

Correct option: C

A and C only

Option C is correct because primary and secondary alcohols can be oxidized to carboxylic acids, while tertiary alcohols are resistant to oxidation under these conditions.

19 Hard

19 of 50

Analyzing +4 | -1

Assertion: Addition of water to but-1-ene in acidic medium yields butan-1-ol.

Reason: Addition the formation of primary carbocation.

View answer and explanation

Correct option: D

If both Assertion and Reason are false

Option D (If both Assertion and Reason are false) is correct because the addition of water to but-1-ene in acidic medium yields butan-2-ol, and the reaction proceeds via the formation of a secondary carbocation.

20 Hard

20 of 50

Analyzing +4 | -1

An organic compound

A

containing C, H and O has a pleasant odour with boiling point of 78

^ \circ C

. On boiling

A

with concentrated

\mathrm{\;}{\mathrm{H}_2}\mathrm{S}{\mathrm{O}_4}

, a colourless gas is produced which decolourises bromine water and alkaline

\mathrm{KMn}{\mathrm{O}_4}

. The organic liquid

A

View answer and explanation

Correct option: C

{\mathrm{C}_2}{\mathrm{H}_5}\mathrm{OH}

Option C is correct because ethanol has a boiling point of 78°C, a pleasant odor, and produces ethene upon reaction with concentrated sulfuric acid, which decolorizes bromine water and alkaline KMnO4.

21 Hard

21 of 50

Analyzing +4 | -1

Decreasing order of reactivity in Williamson's ether synthesis of the following.

I.

{Me}_3 {CCH}_2 {Br}

II.

{CH}_3 {CH}_2 {CH}_2 {Br}

III.

{CH}_2={CHCH}_2 {Cl}

IV.

{CH}_3 {CH}_2 {CH}_2 {CH}_2 {Cl}

View answer and explanation

Correct option: D

>

III

>

>

Option B (III

>

>

>

I) is correct because the reactivity in Williamson's ether synthesis depends on the substrate's ability to undergo SN2 reaction. Allylic halides (III) are most reactive, followed by primary alkyl halides (II and IV), and then sterically hindered halides (I).

22 Hard

22 of 50

Application +4 | -1

Propene,

{CH}_3 {CH}={CH}_2

can be converted into 1-propanol by oxidation. Indicate which set of reagents amongst the following is ideal to effect the above conversion ?

View answer and explanation

Correct option: C

{B}_6 {H}_6

and alk.

{H}_2 {O}_2

Option C (

\mathrm{CH}_3 \mathrm{CH}_2 \mathrm{MgBr}+\mathrm{CH}_3 \mathrm{CH}_2 \mathrm{COCH}_2 \mathrm{CH}_3

) is correct because the Grignard reagent adds to the ketone to form a tertiary alcohol after hydrolysis.

23 Hard

23 of 50

Analyzing +4 | -1

Assertion: Tertiary alcohols gets converted into an alkene instead of a carbonyl Compounds in the presence of heated metallic copper.

Reason: Tertiary alcohols prefer to undergo dehydrogenation instead of dehydration in the presence of heated copper.

View answer and explanation

Correct option: C

Assertion is correct, but reason is wrong statement.

Option C is correct because tertiary alcohols undergo dehydration to form alkenes in the presence of heated copper, not dehydrogenation to form carbonyl compounds.

24 Hard

24 of 50

Remembering +4 | -1

Nobel’s oil is:

View answer and explanation

Correct option: C

Explosive

Option C (Explosive) is correct because Nobel's oil is another name for nitroglycerin, which is a powerful explosive.

25 Hard

25 of 50

Application +4 | -1

Identify the major product that is obtained on treatment of

\mathrm{CH}_3 \mathrm{CH}_2 \mathrm{CH}(\mathrm{F}) \mathrm{CH}_3

with

\mathrm{CH}_3 \mathrm{O}^{-} / \mathrm{CH}_3 \mathrm{OH}

View answer and explanation

Correct option: B

\mathrm{CH}_3 \mathrm{CH}=\mathrm{CHCH}_3

Option B (

\mathrm{CH}_3 \mathrm{CH}=\mathrm{CHCH}_3

) is correct because the major product of the reaction is the more stable alkene, which is the more substituted alkene (Zaitsev's rule).

26 Hard

26 of 50

Remembering +4 | -1

Scientific aspect of fermentation was first studied by:

View answer and explanation

Correct option: C

Buchner

Option C (Buchner) is correct because Eduard Buchner demonstrated that fermentation could occur in the absence of living cells, marking a significant scientific advancement.

27 Hard

27 of 50

Analyzing +4 | -1

Consider the following compounds.

(A) Phenol

(B) Propyne

(C) Benzene sulphonic acid

(D) Benzoic acid

(E) Cyclopentadiene

(F) Ethane

(G) Picric acid

(H) 4-Nitro Cyclohexanol

If

(\mathrm{X})

is the total number of compounds which evolve

\mathrm{H}_2

gas with

\mathrm{Na}

metal and

(\mathrm{Y})

is the total number of compounds which evolve

\mathrm{CO}_2

gas with

\mathrm{NaHCO}_3

. Then find the value of

(\mathrm{X}-\mathrm{Y})

View answer and explanation

Correct option: A

The correct answer is A (4) because Phenol, Propyne, Benzoic acid, and Cyclopentadiene evolve H2 gas with Na metal, while only Benzoic acid reacts with NaHCO3 to evolve CO2 gas. Therefore, X = 4 and Y = 1, so X - Y = 4.

28 Hard

28 of 50

Understanding +4 | -1

Which one of the following does not undergo iodoform reaction

View answer and explanation

Correct option: C

Diethyl ketone

Option C (Diethyl ketone) is correct because it does not contain a

CH_3CO-

group or a

CH_3CH(OH)-

group which are necessary for the iodoform reaction.

29 Hard

29 of 50

Application +4 | -1

{CH}_3-{CH}_2-{CH}={CH}_2 \stackrel{x}{\longrightarrow} {CH}_3 {CH}_2-{CH}_2-{CH}_2 {OH}

What is the suitable reagent

x?

View answer and explanation

Correct option: B

{B}_2 {H}_6\left|{THF}, {H}_2{O}_2\right| {OH}^{-}

Option B (

{B}_2 {H}_6\left|{THF}, {H}_2{O}_2\right| {OH}^{-}

) is correct because it represents hydroboration-oxidation, which converts an alkene to an alcohol with anti-Markovnikov regioselectivity.

30 Hard

30 of 50

Application +4 | -1

An ether contains

60 \%

carbon and

13.3 \%

hydrogen. Formula of the ether is

View answer and explanation

Correct option: B

{C_3}{H_8}O

Option B (

{C_3}{H_8}O

) is correct because the empirical formula derived from the percentage composition matches the molecular formula of an ether with three carbons.

Revision notes and key takeaways

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Key Takeaways

✓ This set contains 50 single-correct-answer MCQs on ALCOHOLS & PHENOLS & ETHERS.
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