MCQs on Alcohols, Phenols and Ethers for NEET and JEE

Alcohol is a compound containing one or more hydroxyl groups (-OH) directly attached to an aliphatic carbon atom. The simplest alcohol is me...

Alcohol is a compound containing one or more hydroxyl groups (-OH) directly attached to an aliphatic carbon atom. The simplest alcohol is methyl alcohol. Alcohols and phenols both contain a hydroxyl group (-OH). A hydroxyl group is also present in carboxylic acids, but it is bonded to a carbonyl carbon atom. Alcohols and phenols can be viewed as organic relatives of water in which one hydrogen atom is replaced by an alkyl group or an aryl group. Alcohols contain a hydroxyl group bonded to an sp3 hybridised carbon atom. Phenols have a hydroxyl group bonded to an sp2 hybridised carbon atom of an aromatic ring.

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NEET 2017:











NEET 2017:










The reaction

can be classified as [NEET 2016]

 (A) Dehydration reaction

 (B) Williamson alcohol synthesis reaction

 (C) Williamson ether synthesis reaction

 (D) Alcohol formation reaction

Reaction of phenol with chloroform in the presence of dilute sodium hydroxide finally introduces, which one of the following functional group? NEET 2015

(a) -CH2CI (b) -COOH 
(c) -CHCl2 (d) -CHO 
Concept Questions :-Phenols: Preparation, Properties, Acidic Nature of Phenol

NEET 2015:

The reaction

is called [AIPMT 2015]

 (A) Williamson synthesis

 (B) Williamson continuous etherification process

 (C) Etard reaction

 (D) Gatterman - Koch reaction

NEET 2013:

Which of the following will not be soluble in sodium hydrogen carbonate? [AIPMT 2014]

 (A) 2,4,6-trinitrophenol

 (B) Benzoic acid

 (C) o-Nitrophenol

 (D) Benzenesulphonic acid

Among the following sets of reactants which one produces anisole? [AIPMT 2014]

 (A) CH3CHO; RMgX

 (B) C6H5OH; NaOH; CH3I

 (C) C6H5OH; neutral FeCl3

 (D) C6H5 – CH3; CH3COCl; AlCl3

NEET 2009:

NEET 2008: 

NEET 2007: 

NEET 2006: 

NEET 2006: 

Which one of the following can be oxidised to the corresponding carbonyl compound: [CBSE AIPMT 2004]

 (A) o-Nitrophenol

 (B) Phenol

 (C) 2-methyl-2-hydroxy propane

 (D) 2-hydroxy propane

Which of the following will not form a yellow precipitate on heating with an alkaline solution of iodine: [CBSE AIPMT 2004]

 (A) CH3CH2CH(OH)CH3

 (B) CH3OH

 (C) CH3CH2OH

 (D) CH3CH(OH)CH3

Ethanol is converted into ethoxy ethane, [KARNATAKA CET 2016]

 (A) by heating excess of ethanol with conc. H2SO4 at 140°C

 (B) by heating Ethanol with excess of conc. H2SO4 at 443 K

 (C) by treating with conc. H2SO4 at room temperature

 (D) by treating with conc. H2SO4 at 273 K

Isopropyl methyl ether when treated with cold hydrogen iodide gives [MHT CET 2016]

 (A) isopropyl iodide and methyl iodide

 (B) isopropyl alcohol and methyl iodide

 (C) isopropyl alcohol and methyl alcohol

 (D) isopropyl iodide and methyl alcohol

The reaction which involves dichlorocarbene as an electrophile is [KARNATAKA CET 2016]

 (A) Reimer – Tiemann reaction

 (B) Kolbe’s reaction

 (C) Friedel – Craft’s acylation

 (D) Fittig’s reaction

Which among the following phenolic compounds is most acidic in nature? [MHT CET 2016]

 (A) p-aminophenol

 (B) phenol

 (C) m-nitrophenol

 (D) p-nitrophenol

Reaction of which among the following ethers with HI in cold leads to formation of methyl alcohol ? [MH-CET 2015]

 (A) ethyl methyl ether

 (B) methyl propyl ether

 (C) isopropyl methyl ether

 (D) tert-butyl methyl ether

During dehydration of alcohols to alkenes by heating with conc. H2SO4 the initiation step is [AIEEE 2003]

 (A) formation of carbocation

 (B) elimination of water

 (C) formation of an ester

 (D) protonation of alcohol molecule

Name the catalyst used in commercial method of preparation of phenol. [MHT CET 2016]

 (A) Silica

 (B) Calcium phosphate

 (C) Anhydrous aluminium chloride

 (D) Cobalt naphthenate

Arrange the following compounds in the increasing order of their acidic strength: [KARNATAKA CET 2015]

i. m-nitrophenol

ii. m-cresol

iii. phenol

iv. m-chlorophenol

 (A) iii < ii < i < iv

 (B) ii < iv < iii < i

 (C) ii < iii < iv < i

 (D) ii < iii < i < iv

Select the ether among following that yields methanol as one of the products on reaction with cold hydroiodic acid [MH-CET 2014]

 (A) 1-Methoxybutane

 (B) 1-Methoxy-2-methylpropane

 (C) 2-Methoxy-2-methylpropane

 (D) Methoxybenzene

Iodoform can be prepared from all except: [AIEEE 2012]

 (A) Ethyl methyl ketone

 (B) Isopropyl alcohol

 (C) 3-Methyl-2-butanone

 (D) Isobutyl alcohol

Which of the following compounds has highest boiling point? [MH-CET 2015]

 (A) Propan-1-ol

 (B) n-Butane

 (C) Chloroethane

 (D) Propanal

The most suitable reagent for the conversion of

R – CH2 – OH → R – CHO is: [JEE MAIN 2014]

 (A) K2Cr2O7

 (B) CrO3

 (C) PCC (Pyridinium Chlorochromate)

 (D) KMnO4

A liquid was mixed with ethanol and a drop of concentrated H2SO4 was added. A compound with a fruity smell was formed. The liquid was [AIEEE 2009]

 (A) HCHO

 (B) CH3COCH3

 (C) CH3COOH

 (D) CH3OH

Dehydration of alcohol is an example of .. [ AFMC 2000] 

a) Redox reaction

b) Elimination

c) Substitution reaction

d) Addition reaction

Phenol is more readily soluble in [ AFMC 2001

a) NaOH solution 

b) dil. HCI

c) both NaOH and HCI

d) NaHCO3

Excess of ethanol and con. H2SO4 on heating up to 140°C produces [ AFMC 2002] 

a) diethyl ether 

b) diethyl sulphate 

c) ethyl hydrogen sulphate 

d) ethylene

Which of the following has the maximum viscosity .. [ AFMC 2003] 

a) Glycol b) Ethanol c) Water d) Acetone 

The only alcohol that can be prepared by the indirect hydration of alkene is .. [ AFMC 2005] 

a) ethyl alcohol

b) propyl alcohol

c) isobutyl alcohol

d) methyl alcohol

Q3) Which of the following represents Lucas reagent? [ AFMC2006]

a) H2SO4 + HCI

b) Mn02 + H2S4

c) ZnCl2 + conc. HCI

d) ZnCl2 +Conc. H2S04

AFMC 2007: 

Which of the following is added to chloroform to slow down its aerial oxidation in presence of light?  [ AFMC 2008] 

a) Carbonyl chloride
b) Ethyl alcohol 
c) Sodium hydroxide 
d) Nitric acid 

The catalyst used in the preparation of an alkyl chloride by the action of dry HCI on the alcohol is [AFMC 2008] 

a) anhydrous AlC13 
b) FeCl3 
c) anhydrous ZnCl2 
d) Cu 

Chlorobenzene can be prepared by reacting aniline with [ IIT 1984] 

a) hydrochloric acid
b) cuprous chloride
c) chlorine in presence of anhydrous aluminum chloride
d) nitrous acid followed by heating cuprous chloride

The reaction of toluene with chlorine in presence of ferric chloride gives predominantly ..[ IIT 1986]

a) benzoyl chloride 
b) m-chlorotoluene 
c) benzyl chloride 
d) o- and p- chlorotolunene 

[ IIT 1986]: 

Which of the following is most acidic?

 (A) m-Chlorophenol

 (B) Benzyl alcohol

 (C) Phenol

 (D) Cyclohexanol

Acid catalysed hydration of alkenes except ethene leads to the formation of

A)mixture of secondary and tertiary alcohols

B)mixture of primary and secondary alcohols

C)secondary or tertiary alcohol

D)primary alcohol

Among the alkenes which one produces tertiary butyl alcohol on acid hydration

A   (CH3)2C = CH2

B   CH3 – CH = CH – CH3

C   CH3 – CH2 – CH = CH2

D   CH3 – CH = CH2

Among the following, which is least acidic?

A)     phenol

B)     o-cresol

C)     p-nitrophenol

D)     p-chlorophenol

An ether is more volatile than an alcohol having the same molecular formula. This is due to

A)dipolar character of ethers

B)alcohols having resonance structures

C)inter-molecular hydrogen bonding in ethers

D)inter-molecular hydrogen bonding in alcohols

An organic compound A containing C, H and O has a pleasant odour with boiling point of 78°C. On boiling A with concentrated H2SO4, a colourless gas is produced gas is produced which decolourises bromine water and alkaline KMnO4. The organic liquid A is

A)C2H5COOCH3

B)C2H5OH

C)C2H5Cl

D)C2H6

An organic compound A(C4H9Cl) on reaction with Na/diethyl ether gives a hydrocarbon which on monochlorination gives only one chloro derivative then, A is:

A)iso-butyl chloride

B)secondary butyl chloride

C)t-butyl chloride

D)n-butyl chloride

An oxygen containing organic compound upon oxidation forms a carboxylic acid as the only organic product with its molecular mass higher by 14 units. The organic compound is ______.

A)a ketone

B)an aldehyde

C)a primary alcohol

D)a secondary alcohol

Anisole can be prepared by the action of methyl iodide on sodium phenate. The reaction is called

A)Fittig’s reaction

B)Williamson’s reaction

C)Wurtz’s reaction

D)Etard’s reaction

Catalytic dehydrogenation of a primary alcohol gives a

A)ketone

B)aldehyde

C)secondary alcohol

D)ester

Chloro ethane reacts with X to form diethyl ether. What is X

A)NaOH

B)H2SO4

C)C2H5ONa

D)Na2S2O3

Consider the following reaction
C2H5OH + H2SO4  → Product
Among the following, which one cannot be formed as a product under any conditions?

A.Ethylene

B.Ethyl-hydrogen sulphate

C.Diethyl ether

D.Acetylene

Denatured alcohol is

A.Rectified spirit + methanol + naphtha

B.Undistilled ethanol

C.Rectified spirit

D.Ethanol + methanol

Ethyl chloride is converted into diethyl ether by

A.Perkin's reaction

B.Grignard reagent

C.Wurtz reaction

D.Williamson's synthesis

Formation of diethyl ether from ethanol is based on a

A.dehydration reaction

B.dehydrogenation reaction

C.hydrogenation reaction

D.heterolytic fission reaction

From amongst the following alcohols the one that would react fastest with conc. HCl and anhydrous ZnCl2, is

A.2-Methylpropan-2-ol

B.2-Butanol

C.1-Butanol

D.2-Methylpropanol

In preparation of alkene from alcohol using Al2O3 which is effective factor:

A.Porosity of Al2O3

B.Temperature

C.Concentration

D.Surface area of Al2O3

In Williamson's synthesis

A.an alcohol is heated with conc. H2SO4 at 140°C

B.an alkyl halide is treated with sodium

C.an alkyl halide is treated with sodium alkoxide

D.None of the above

Methanol cannot be dried with anhydrous CaCl2 because

A.CaCl2 dissolves in it

B.it is not good dehydrating agent

C.it forms a solid CaCl2 × 4CH3OH

D.it reacts with CH3OH

Methyl phenyl ether can be obtained by reacting

A.phenolate ions and methyl iodide

B.methoxide ions and bromobenzene

C.methanol and phenol

D.bromobenzene and methyl bromide


Question and Answer on "MCQ on Alcohols, Phenols and Ethers"

1. Benzenediazonium chloride on reaction with phenol in weakly basic medium gives

  1. diphenyl ether
  2. p-hydroxyazobenzene
  3. chlorobenzene
  4. Benzene

Answer: (2)

2. Phenol reacts with bromine in CS2 at low temperature to give

  1. m-bromophenol
  2. o-and p-bromophenol
  3. p-bromophenol
  4. 2,4,6-tribromophenol

Answer: (2)

3. When phenol is treated with excess bromine water it gives

  1. m-bromophenol
  2. o- and p-bromophenol
  3. 2,4-dibromophenol
  4. 2,4,6-tribromophenol

Answer: (4)

4. Phenol on reduction with H2 in the presence of Ni catalyst gives

  1. benzene
  2. toluene
  3. cyclohexane
  4. Cyclohexanol

Answer: (4)

5. Dehydration of alcohol is an example of

  1. addition reaction
  2. elimination reaction
  3. substitution reaction
  4. redox reaction

Answer: (b)

6. The compound obtained by the reaction of ethene with diborane followed by hydrolysis with alkaline H2O2 is

  1. ethanol
  2. propanol
  3. ethanol
  4. triethyl bromide

Answer: (1)

7. Which of the following is formed when phenol is exposed to air?

  1. o-Benzoquinone
  2. p-Benzoquinone
  3. Phenoquinone
  4. o-and p-Benzoquinone

Answer: (4)

8. Which of the following is formed when glycerol is heated with oxalic acid at 503K?

  1. Glyceric acid
  2. Acrolein
  3. Allyl alcohol
  4. Methanoic acid

Answer: (c)

9. The alcohol which does not react with Lucas reagent is

  1. isobutyl alcohol
  2. n-butanol
  3. tert-butyl alcohol
  4. sec-butyl alcohol

Answer: (2)

10. Phenol is less acidic than

  1. acetic acid
  2. p-methoxyphenol
  3. p-nitrophenol
  4. Ethanol

Answer: (1,3)

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Advanced Chemistry: MCQs on Alcohols, Phenols and Ethers for NEET and JEE
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