Class 12Chemistry | Alcohol, Phenol and Ether | MCQs

Class 12Chemistry | Alcohol, Phenol and Ether | MCQs

Question 1:
Williamson’s synthesis of preparing dimethyl ether is an:
(a) SN1reaction
(b) Elimination reaction
(c) SN2reaction
(d) Nucleophilic addition reaction

Answer: (c) SN2 reaction

Alkoxide ion reacts with primary alkyl halide in a single step to form ether.

Question 2:
During dehydration of alcohols to alkenes by heating with concentrated H 2SO4,
theinitiation step is:
(a) protonation of alcohol molecule
(b) formation of carbocation
(c) elimination of water
(d) formation of an ester

Answer: (a) protonation of alcohol molecule

Dehydration of alcohol to alkene in presence of concentrated H 2SO4 involves

the –OH group in the alcohol that donates two electrons to H+ from the acid
Class 12Chemistry | Alcohol, Phenol and Ether | MCQs

reagent, forming an alkyloxonium ion. The deprotonated acid (the nucleophile)

then attacks the hydrogen adjacent to the carbocation and form a double
bond.
Thus, the initiation step is protonation of alcohol.

Question 3:
Which of the following reactions is used to prepare salicylaldehyde?
(a) Kolbe’s reaction
(b) Etard reaction
(c) Reimer- Tiemann reaction
(d) Stephen’s reduction.

Answer: (c) Reimer- Tiemann reaction

Kolbe’s reaction is used to prepare salicylic acid, Etardreaction for
benzaldehyde, Reimer- Tiemann reaction for salicylaldehyde and
Stephen’sreduction for aldehyde.

Question 4:
The boiling points of alcohols are higher than those of hydrocarbons of
comparablemasses due to:
(a) Hydrogen bonding
(b) Ion – dipole interaction
(c) Dipole- dipole interaction
(d) Van der Waal’s forces.

Answer: (a) Hydrogen bonding

Alcohols form intermolecular hydrogen bonds.
Class 12Chemistry | Alcohol, Phenol and Ether | MCQs

Question 5:
Major product obtained on reaction of 3-Phenyl propene with HBr in presence
of organicperoxide
(a) 3- Phenyl 1- bromopropane
(b) 1 –Phenyl -3- bromopropane
(c) 1-Phenyl -2-bromopropane
(d) 3-Phenyl -2- bromopropane

Answer: (b) 1 –Phenyl -3- bromopropane

(C6H5) CH2CH=CH2 + HBr (organic peroxide)  (C6H5)CH2CH2CH2Br anti-
Markovnikovaddition)

Question 6:
Lower molecular mass alcohols are:
(a) miscible in limited amount of water
(b) miscible in excess of water
(c) miscible in water in all proportions
(d) immiscible in water

Answer: (c) miscible in water in all proportions

Lower molecular mass alcohols are able to formhydrogen bonds with water.

Question 7:
Phenol does not undergo nucleophilic substitution reaction easily due to:
(a) acidic nature of phenol
(b) partial double bond character of C-OH bond
(c) partial double bond character of C-C bond
Class 12Chemistry | Alcohol, Phenol and Ether | MCQs

(d) instability of phenoxide ion

Answer: (b) partial double bond character of C-OH bond

The C—O bond in phenols has some double-bond character due to resonance
and hence cannot be easily cleaved by the nucleophile. In contrast, the C—O
bond in alcohol is a pure single bond and hence can be easily cleaved by
nucleophile.

Question 8:
What would be the reactant and reagent used to obtain 2,4-dimethyl pentan-
3-ol?
(a) Propanal and propyl magnesium bromide
(b) 3-methylbutanal and 2-methyl magnesium
(c) 2-dimethylpropanone and methyl magnesium iodide
(d) 2- methylpropanal and isopropyl magnesium iodide

Answer: (d) 2- methylpropanal and isopropyl magnesium iodide

Class 12Chemistry | Alcohol, Phenol and Ether | MCQs

Question 9:
Identify the secondary alcohols from the following set:

(a) (i) and (iv)

(b) (i) and (iii)
(c) (i) and (ii)
(d) (i), (iii) and (iv)

Answer: (a) (i) and (iv)

(i) CH3CH2CH(OH)CH3 (secondary) (ii) (C2H5)3COH (tertiary)

Question 10:
o-hydroxy benzyl alcohol when reacted with PCl3 gives the product a s(IUPAC
name)
(a) o- hydroxy benzyl chloride
(b) 2- chloromethylphenol
(c) o-chloromethyl chlorobenzene
(d) 4-hydroxymethylphenol
Class 12Chemistry | Alcohol, Phenol and Ether | MCQs

Answer: (b) 2- chloromethylphenol

Question 11:
Which are not cleaved by HIO4?
I: glycerol II: glycol
III: 1, 3−propennediol IV: methoxy−2−propanol
(a) I, II, III, IV
(b) I, II
(c) II, III
(d) III, IV

Answer: (d) III, IV

HIO4 will not oxidise, diol from 1, 3 atom & not used for cleavage of ether.
Class 12Chemistry | Alcohol, Phenol and Ether | MCQs

Question 12:
For the following reaction, select the statement that best describes the
change.
RCH2OH+PCC[C5H5NH+ClCrO3-] 
(a) The alcohol is oxidized to an acid, and the Cr(VI) is reduced
(b) The alcohol is oxidized to an aldehyde, and the Cr(VI) is reduced
(c) The alcohol is reduced to an aldehyde, and the Cr(III) is oxidized
(d) The alcohol is oxidized to a ketone, and the Cr(VI) is reduced

Answer: (b) The alcohol is oxidized to an aldehyde, and the Cr (VI) is reduced
Cr6+ Cr3+ (PCC oxidises 10 alcohols to aldehyde).

Question 13:
The common reagent used for dehydration of alcohol is _____.

Answer: Conc. H2SO4 and Al2O3.

Class 12Chemistry | Alcohol, Phenol and Ether | MCQs

The common reagent used for dehydration of alcohol is Conc. H2SO4 and Al2O3
Dehydration of alcohols can be done by:
a) Using aluminium oxide as catalyst.
This is a simple way of making gaseous alkenes like ethene. If ethanol vapour is
passed over heated aluminium oxide powder, the ethanol is essentially cracked
to give ethene and water vapour.
b) Using sulphuric acid at a temperature of 170°C.
Concentrated sulphuric acid produces messy results. Not only is it an acid, but
it is also a strong oxidising agent. It oxidises some of the alcohol to carbon
dioxide and at the same time is reduced itself to sulphur dioxide.
Both of these gases have to be removed from the alkene. It also reacts with
alcohol to produce a mass of carbon. There are other side reactions as well.

Question 14:
An organic compound of molecular formula C 4H10O does not react with
sodium. With excess of HI, it gives only one type of alkyl halide. The compound
is:
(a) Ethoxy ethane
(b) 2- Methoxy propane
(c) 1-Methoxy propane
(d) 1-Butanol

Answer: (a) Ethoxy ethane

Since the organic compound does not react with sodium, it cannot be an
alcohol (butanol). Given, the molecular formula is C 4H10O.
With HI, it gives only one type of alkyl iodide. So, it must be a symmetrical
ether.
Class 12Chemistry | Alcohol, Phenol and Ether | MCQs

Here, among all ethers, ethoxy ethane is symmetrical.

The reaction is as follows:
C2H5OC2H5 + HI  C2H5I + C2H5OH
C2H5OH + HI  C2H5I + H2O

Assertion Reason Based Questions

In the following questions from 15 to 18 a statement of assertion followed by

a statement of reason is given. Choose the correct answer out of the
following choices.

(a) Both A and R are true and R is the correct explanation of A

(b) Both A and R are true but R is not the correct explanation of A.
(c) A is true but R is false.
(d) A is false but R is true.

Question 15:
Assertion (A): Phenols do not react with metal carbonates and metal hydrogen
carbonates.
Reason (R): Metal carbonates and metal hydrogen carbonates are basic in
nature.

Answer: (b) Both A and R are true but R is not the correct explanation of A.
Phenols are weaker acids (Ka = 1.3 x 10-10) than carboxylic acids (Ka = 10-5) and
carbonic acids (Ka=10-7). Therefore, phenols do not react with carbonates and
bicarbonates.
Class 12Chemistry | Alcohol, Phenol and Ether | MCQs

Question 16:
Assertion (A): Phenols are more acidic than aliphatic alcohols.
Reason (R): Phenoxides are stabilized by resonance.

Answer: (a) Both A and R are true and R is the correct explanation of A
When a molecule of phenol loses a proton, it forms phenoxide ion which is
stabilized by resonance as the negative charge is delocalized over aromatic
nucleus.No such resonance is present when an alcohol loses a proton to form
alkoxide ion. Hence, phenols are more acidic than alcohols.

Question 17:
Assertion (A): Lucas reagent can be used to distinguish between methanol and
ethanol.
Reason (R): An equimolar mixture of anhydrous ZnCl2 and conc. HCl is called
Lucas reagent.

Answer: (c) A is true but R is false.

Both methanol and ethanol are 1∘ alcohol and hence cannot be distinguished
by Lucasreagent.

Question 18:
Assertion (A): p-Nitrophenol is less acidic than m-nitrophenol.
Reason (R): Phenol is weaker acid than carbonic acid.

Answer: (d) A is false but R is true.

p-Nitrophenol is more acidic than m-nitrophenol due to +I effect and -m
character of NO2 group. At m-position only -I effect is considered.
Class 12Chemistry | Alcohol, Phenol and Ether | MCQs

Question 19:
Which of the following compound can react with hydroxylamine?

Answer:

Phenols show keto-enol tautomerism and the stability of the keto form
depends upon the number of keto group (more the number of keto groups ,
Class 12Chemistry | Alcohol, Phenol and Ether | MCQs

higher will be stability of the keto tautomer).Thus trihydric phenols should

exist in keto form in considerable amount but only when the two keto groups
are not on adjacent carbon atoms which decreases - stability due to positive
charge on adjacent carbon atoms .

Question 20:
In Williamson's synthesis, ethoxyethane is prepared by:
(a) passing ethanol over heated alumina
(b) heating ethanol with dry Ag2O
(c) heating sodium ethoxide with ethyl bromide
(d) treating ethyl alcohol with excess of H2SO4 at 430-440K

Answer: (c) heating sodium ethoxide with ethyl bromide

Williamson's synthesis is an organic reaction forming an ether from
organohalide and alkoxide.
CH3-CH2-ONa + Br-CH2CH3 CH3CH2-O-CH2CH3
Class 12Chemistry | Alcohol, Phenol and Ether | MCQs

Question 21:
Identify (Z) in the following reaction series:
PBr3 Alc. KOH H2SO4, room temp
Ethanol→ (X) → (Y)  (Z)
H2O, heat
(a) H2C=CH2
(b) CH3CH2OH
(c) CH3CH2OSO3H
(d) C2H5OC2H5

Answer: (b) CH3CH2OH

Question 22:
When phenyl magnesium bromide reacts with tertiary butanol, which of the
following is formed?
(a) benzene
(b) phenol
(c) t-butyl benzene
(d) t-butyl phenyl ether
Class 12Chemistry | Alcohol, Phenol and Ether | MCQs

Answer: (a) benzene

Phenyl magnesium bromide reacts with t-butanol benzene is obtained.
Grignard reagent reacts with compounds containing active hydrogen to form
hydrocarbons corresponding to alkyl(or aryl) part of the reagent.

Question 23:
Anisole is the product obtained from phenol by the reaction known as:
(a) Coupling
(b) Etherification
(c) Oxidation
(d) Esterification

Answer: (b) Etherification

Phenol reacts with alkyl halides in alkali solution to form phenyl ethers
(Williamson's synthesis). The phenoxide ion is a nucleophile and will replace
halogen of alkyl halide.
Class 12Chemistry | Alcohol, Phenol and Ether | MCQs

Case-Study Based Questions

Question 24:
In alcohols, the oxygen of the –OH group is attached to carbon by a sigma (s )
bondformed by the overlap of a sp3hybridised orbital of carbon with a
sp3hybridised orbitalof oxygen. Figure given below depicts structural aspects
of methanol, phenol andmethoxymethane.

1. The bond angle C-O-H in alcohols is slightly less than the tetrahedral angle
(109°28‘). It is due to –
Class 12Chemistry | Alcohol, Phenol and Ether | MCQs

(a) The attraction between C-O and O-H bond pairs.

(b) The repulsion between the unshared electron pairs of oxygen.
(c) The repulsion between neighbouring C-H bonds.
(d) The high electronegativity of oxygen.

2. In phenols, the –OH group is attached to ____ hybridised carbon of an

aromaticring.
(a) sp3
(b) sp
(c) dsp2
(d) sp2

3. The C – O bond length in phenol is slightly less than that in methanol. This is
due to –
(a) Partial double bond character on account of the conjugation of unshared
electron pair of oxygen with the aromatic ring.
(b) Presence of heavier group – phenol.
(c) Positioning of lone pair over oxygen in 3 – D space.
(d) sp3hybridised state of carbon to which oxygen is attached.

4. The bond angle in ethers is slightly greater than the tetrahedral angle due to
(a) Presence of four electron pair around the oxygen.
(b) The repulsive interaction between the two bulky (–R) groups.
(c) Absence of O – H bond.
(d) The attractive interaction between the two bulky (–R) groups.

5. In methoxymethane, the oxygen atom is ____ hybridised.

Class 12Chemistry | Alcohol, Phenol and Ether | MCQs

(a) sp3
(b) sp
(c) dsp2
(d) sp

Answer:
1. (b) The repulsion between the unshared electron pairs of oxygen.
The bond angle in C−O....−H in alcohols is slightly less than tetrahedral is
slightly less than tetrahedral angle (109∘28'). It is due to the repulsion between
the unshared electron pairs of oxygen. In alcohols, two lone pair of electrons
are present. Therefore, three is comparatively more repulsion and less and
angle.
The C−O−C bond angle in their slightly greater than the tetrahedral angle due
to the repulsive interaction between the two bulky (-R) groups.

2. (d) sp2
In phenol carbon atom attached to -OH group is bonded with 3 σ bond and 1 π
bond. Hence, the hybridisation will be sp2.

3. (a) Partial double bond character on account of the conjugation of

unsharedelectron pair of oxygen with the aromatic ring.
Class 12Chemistry | Alcohol, Phenol and Ether | MCQs

(i) In phenol, conjugation of unshared electron pair over oxygen with aromatic
ring results in partial double bond character in carbonoxygen bond.
(ii) In phenol, oxygen is attached to a sp2 hybridised carbon atom while in
methanol, it is attached to a sp3hybridized carbon atom. The bond formed
between oxygen and sp2 hybridised carbon is more stable than that formed
between oxygen and sp3 hybridised carbon.
Therefore, phenolic C — O bond (136 pm ) is slightly less than methanolic C —
O ( 142 pm ) bond .

4. (b) The repulsive interaction between the two bulky (–R) groups.
In the ether, the bond angle is greater than the tetrahedral angle due to
repulsion of bulky alkyl groups in ethers bond angles is slightly greater than
tetrahedral bond angle.

5. (a) sp3
Ether is a compound having alkyl groups which is connected with an oxygen
atom. Each carbon and one oxygen is sp3 hybridized. Dimethyl ether has a bent
Class 12Chemistry | Alcohol, Phenol and Ether | MCQs

structure. It is also known as methoxy methane since two methyl groups are
attached.

Question 25:
By a proper choice of reagents, both symmetrical and unsymmetrical ethers
can beprepared by Williamson synthesis which involves the reaction between
an alkyl halideand an alkoxide ion. The reverse process involves the cleavage of
ethers to giveback the original alkyl halide and the alcohol can be carried out
by heating the etherwith HI at 373 K.

1. The mechanism of Williamson synthesis involves –

(a) Nucleophilic substitution bimolecular
(b) Nucleophilic substitution unimolecular
(c) Electrophilic substitution bimolecular
(d) Electrophilic substitution bimolecular

2. Benzyl ethyl ether reacts with HI to form –

(a) p-iodotoluene and ethyl alcohol.
(b) Benzyl alcohol and ethyl iodide.
(c) Benzyl iodide and ethyl alcohol.
(d) Iodobenzene and ethyl alcohol.

3. Allyl phenyl ether can be prepared by heating –

(a) C6H5Br + CH2=CH-CH2ONa
(b) CH2=CHCH2Br + C6H5ONa
(c) C6H5CH=CHBr + CH3ONa
(d) CH2=CHBr + C6H5CH2ONa
Class 12Chemistry | Alcohol, Phenol and Ether | MCQs

4. Which of the following ethers are not cleaved by HI?

(a) Dicyclohexyl ether
(b) Ethyl phenyl ether
(c) Di – tert – butyl ether
(d) Diphenyl ether

Answer:
1. (a) Nucleophilic substitution bimolecular
When sodium or potassium alkoxide is heated with an alkyl halide to give
ether, this reaction is known as Williamson's synthesis.
RONa+R'X→R−O−R+NaX
This is an example of nucleophilic substitution and follow S N2 mechanism.

2. (c) Benzyl iodide and ethyl alcohol.

3. (b) C6H5OCH2CH=CH2is allyl phenyl ether

Allyl phenyl ether can be prepared by heating
CH2=CH-CH2-Br + C6H5ONa CH2=CH-CH2-O-C6H5 + NaBr
Class 12Chemistry | Alcohol, Phenol and Ether | MCQs

4. (d) Diphenyl ether

In diphenyl ether, oxygen atom is bonded to phenyl ring and both bonds
are strong. They cannot be cleaved by HI.

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