12th; Chemistry Practice Sheet Unit 11: Alcohol, Phenol & Ether

PART – A (MCQ based)

1)Ethanol on heating with conc. H2SO4 at 443 K gives-

a- diethyl sulphate b- Ethylene c- Diethyl ether d- Ethyl hydrogen sulphate
2) Which of the following is most acidic?
a- H2O b- CH3OH c- C2H5OH d- CH3 – CH2 – CH2 – OH
3) C6H5Cl ---- NaOH(aq)-------------------623 K; 300 atm -------  A, where A is
a- Phenol b- Sodium phenoxide c- Benzene d- Cyclohexyl chloride
5) The order of acidic strength among i)Phenol ii) p-nitrophenol iii) 2,4 Dinitrophenol following is..
a- (i) = (ii) = (iii) b- (i) < (ii) < (iii) c- (ii) < (iii) = (iv) d- (i) < (iii) < (ii)
6) Phenol can be distinguished from ethyl alcohol by all reagents except-
a-NaOH b-FeCl3 c- Br2/ H2O d- Na
7) Which of the following compounds is least acidic?

a- o-Nitrophenol b- m-Nitrophenol c- p-Nitrophenol d- Phenol

8) The product obtained from the following sequence of reactions is..

HC ≡ CH ----- HgSO4 / H2SO4 ---------
a- Acetaldehyde b- Ethanol c- Glycol d- Acetic Acid
9) Which of the following compounds will be most readily attacked by an electrophile?
a- Chlorobenzene b-Benzene c-Phenol d-Toluene
11) 2- Methoxy – 2- methyl propane on heating with HI would produce-
a- Methyl alcohol and sec-propyl iodide. b- Methyl iodide and tert-butyl alcohol.
c- Methyl iodide and isobutene. d- Methyl alcohol and tert- butyl iodide.
13. Which of the following will give yellow ppt with I 2 /NaOH
a. CH3CH2COCH2CH3 b. CH3COOCOCH3 c. CH3CONH2 d. CH3CH(OH)CH2CH3
14. Aspirin is an acetylation product of:
a. p-dihydroxybezene b. o-hydroxybenzoic acid c. o-dihydroxybenzene d. m-hydroxybenzoic acid
15) Carbolic acid is...
a- Phenol b- Benzene c- Phenyl Acetate d- Salicylic acid
17) The reaction of Lucas reagent is fastest with
a- (CH3)3COH b- (CH3)2CHOH c- CH3(CH2)2OH d- CH3CH2OH
18) Which of the following is most acidic ?
a- Phenol b- Benzyl alcohol c- m- Chlorophenol d- Cyclohexanol
19) The correct order of boiling points for primary (1˚), secondary (2˚) and tertiary alcohol (3˚) is...
a- 1˚ > 2˚ > 3˚ b- 3˚ > 2˚ > 1˚ c- 2˚ > 1˚ > 3˚ d- 2˚ > 3˚ > 1˚
20) Which of the following is the most suitable method for removing the traces of water from ethanol ?
a- Heating with Na metal b- Passing dry HCl gas through it c- Distilling it d- Reacting with Mg
21) The most suitable method of separation of a mixture of ortho and para-nitro-phenols mixed in the ratio of 1:1 is..
a- Steam distillation b- Crystallisation c- Vaporization d- Colour Spectrum
22) IUPAC name of the compound H3CCH(OH)CH2CH(CH3)CH3 is..
a-4-methylpentene – 2- ol b- 2-methylpentanol – 4 c- 4,4- dimethyl- butan – 2- ol d- 4-methyl pentan – 2 – ol
23) The most suitable reagent for the conversion of RCH 2OH RCHO is
a- KMnO4 b- K2Cr2O7 c- CrO3 d- PCC
24) When Phenol is treated with CHCl3and NaOH, the product formed is –
a- Benzoldehyde b- Salicylaldehyde c- Salicylic acid d- Benzoic acid

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 12th; Chemistry Practice Sheet Unit 11: Alcohol, Phenol & Ether

25) When ether is exposed to air for sometimes, and explosive substance produced is-
a- Peroxide b- TNT c- Picric acid d- Superoxide
PART – B (True/False)

1. Ethanol is more acidic than methanol. ( )

2. Phenol is more reactive than benzene towards electrophilic substitution reaction.( )
3. Phenol undergoes Kolbe’s reaction, Ethanol does not.( )
4. Resorcinol have phenolic group.( )
5. The pKa of acetic acid is lower than that of phenol.( )
6. The water solubility of the alcohols follow the order t-butyl alcohol >sec- butyl alcohol>n-butyl alcohol.( )
7. Electron withdrawing group increase the acidity of Phenol.( )
8. Alcohols are difficult to protonate than phenol.( )
9. Both symmetrical and unsymmetrical ethers can be prepared by Williamson’s synthesis. ( )
10. P.C.C is a reducing agent.( )
11. Salicylic acid is also known as carbolic acid.()
12. Addition of alkenes through hydroboration follows anti-markovnikov rule.( )
13. Intramolecular Hydrogen bonding is present in p-nitro phenol.( )
14. Methanol is used as a solvent in paints & varnishes.( )
15. Ethers are the least reactive of the functional groups.( )
16. Isopropyl alcohol and 1-propanol are two names for the same compound.( )
17. Primary and secondary alcohols gives the same type of product when subjected to mild oxidizing agent.( )
18. Cyclic ethers are examples of heterocyclic organic compounds.( )
19. Phenols react with Na2CO3 and liberate CO2.( )
20. Methanol gives Iodoform test.( )
21. Methylated alcohol is unfit for drinking.( )
22. 2-Butanol can exhibit enantiomerism.( )
23. Reactivity of Methanol with sodium is more than that of isopropyl alcohol.( )
24. Straight chain alcohols are less soluble in water than their branched chain isomers.( )

PART – C (FIB)

1. Upon reacting with Grignard’s Reagent; formaldehyde forms _______________ degree alcohol
2. Phenoxide ion is more acidic than ethoxide ion due to ______effect.
3. The preparation of Ethers by Williamson’s synthesis follows___________ mechanism.
4. Alcohols are highly soluble in water due to _______ bonding.
5. The Hydroboration-Oxidation process proceeds through _______________ Rule.
6. When the vapours of a tertiary alcohol are passed over heated copper at 573K_____________ is formed.
7. Picric acid is more acidic than phenol due to _________ effect .
8. In Kolbe’s reaction ;Carbon Dioxide works as a weak _____________ agent.
9. Trinitrophenols are more acidic than phenol as it has lower _________ values .
10. Acidic dehydration of alcohols at lower temperatures form __________ due to SN 2 mechanism.

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 12th; Chemistry Practice Sheet Unit 11: Alcohol, Phenol & Ether

11. In IUPAC nomenclature of Ethers; the larger _________group is chosen as the parent hydrocarbons.
12. In case of reaction with HI, when one of the alkyl groups of the reacting ether is tertiary , then the halide formed
is a ______________ degree halide.
13. Anisole undergoes bromination with bromine in ethanoic acid to form ______________as the major product .
14. During preparation of Phenol from Cumene, __________ is formed as an important by-product.
15. Orthonitrophenol (ONP) is _________ volatile due to presence of weak intramolecular Hydrogen Bonding.
16. The chemical composition of Lucas Reagent is ____________.
17. The chemical test which can be used to distinguish between Methanol and Ethanol is ________ test.
18. Ethers are the least reactive of the functional groups due to ______________ hindrance.
19. The Lewis Acid catalyst used in the Friedel Crafts alkylation of Anisole is ________.
20. On Zinc dust distillation of Phenol __________ is formed.
21. The IUPAC name of the major product formed on acetylation of Salicylic acid is _________.
22. Two common by-products of fermentation of Cane Sugar are Ethanol and____.
23. Controlled oxidation of Alcohols gives rise to/ yields__________.
24. On prolonged exposure of Ethanol to atmosphere, it gives vinegar like smell due to _______ process.
25. A better reagent for oxidation of primary allylic alcohols to aldehydes in good yield is ____________.
PART – D (Case based)

I. Read the given passage and answer the questions that follow:
Alcohols and phenols are most important compounds used in our daily life. Alcohols are prepared by hydration of alkenes,
fermentation of glucose, reduction of aldehydes, ketones, carboxylic acids and esters.
Alcohols are soluble in water. Boiling points increase with increase in molar mass and decrease with branching. Alcohols on
dehydration gives alkene at 443K, follow carbocation mechanism. Excess of alcohol at 413K on dehydration with conc. H 2SO4
also follow carbocation mechanism but gives diethyl ether. Alcohols undergo nucleophilic substitution reactions, esterification
with carboxylic acids and derivatives like amides, acid halides, acid anhydride.
Phenol is prepared from cumene, diazonium salts, anisole, chlorobenzene. Phenol is used to prepare salicylaldehyde, salicylic
acid, aspirin, methyl salicylate, p-benzoquinone. Phenol undergoes electrophilic substitution reaction at o & p-position. Ethers are
functional isomers of alcohols, have low boiling points. Ethers are used as solvents. Unsymmetrical ethers are prepared by
Williamson synthesis. Ethers react with HI and undergo S N1 or SN2 mechanism depending upon stability of carbocation formed.
Aromatic ethers like anisole undergoes electrophilic substitution at o & p-position.

(a) Write IUPAC name of CH3—C—CH2CH3OHCH3?

(b) Out of tert, butyl alcohol and n-butanol, which will undergo dehydration faster and why?
(c) Convert phenol to p-benzoquinone.
(d) Cyclohexanone + CH3MgBr + H30+ -------------
(e) (e) Why is C—OH bond length in CH3OH longer than C—OH bond length in phenol?
(f) Cyclohex 2 ene -1-ol + PCC -----------------
(g) (g) Why is ROH bond angle in alcohol less than tetrahedral bond angles?

II. Read the given passage and answer the questions that follow:
Alcohols play very important role in our daily life. Ordinary sprit used as an antiseptic contains methanol. Ethanol is present
in cough syrups, tonics, wine, beer and whisky, Sugar, starch, cellulose are carbohydrates which also contain large
number —OH groups. Phenol is also an antiseptic in low concentration (0.2%) where as 2% solution of phenol is used
as disinfectant. The fragrance of rose is due to citronellol (unsaturated alcohol). Phenol is used for preparation of
many useful compounds like aspirin, methyl salicylate (Iodex) and phenyl salicylate (salol) used as intestinal
antiseptic.

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 12th; Chemistry Practice Sheet Unit 11: Alcohol, Phenol & Ether

(a) How is phenol prepared from cumene? What is advantage of this method?
(b) How is phenol converted into salicylic acid?
(c) Convert phenol to picric acid.
(d) Distinguish between phenol and benzyl alcohol?
(a) Why does phenol turn pink after long standing?

PART – E (Assertion Reason based)

Note : In the following questions a statement of assertion followed by a

statement of reason is given. Choose the correct answer out of the following
choices.
(i) Assertion and reason both are correct and reason is correct explanation
of assertion.
(ii) Assertion and reason both are wrong statements.
(iii) Assertion is correct but reason is wrong statement.
(iv) Assertion is wrong but reason is correct statement.
(v) Assertion and reason both are correct statements but reason is not correct explanation of assertion.

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

Reason : Addition of water in acidic medium proceeds through the formation of primary carbocation.

2. Assertion : p-nitrophenol is more acidic than phenol.

Reason : Nitro group helps in the stabilisation of the phenoxide ion by dispersal of negative charge due to resonance.

3. Assertion : IUPAC name of the compound is 2-Ethoxy-2-methylethane.

Reason : In IUPAC nomenclature, ether is regarded as hydrocarbon derivative in which a hydrogen atom is replaced by —OR
or —OAr group [where R = alkyl group and Ar = aryl group]

4. Assertion : Bond angle in ethers is slightly less than the tetrahedral angle.
Reason : There is a repulsion between the two bulky (—R) groups.

5. Assertion : Boiling points of alcohols and ethers are high.

Reason : They can form intermolecular hydrogen-bonding.

6. Assertion : Like bromination of benzene, bromination of phenol is also carried out in the presence of Lewis acid.
Reason : Lewis acid polarises the bromine molecule.

7. Assertion : o-Nitrophenol is less soluble in water than the m- and p-isomers.

Reason : m- and p- Nitrophenols exist as associated molecules.

8. Assertion : Ethanol is a weaker acid than phenol.

Reason : Sodium ethoxide may be prepared by the reaction of ethanol with aqueous NaOH.

9. Assertion : Phenol forms 2, 4, 6 – tribromophenol on treatment with Br2 in carbon disulphide at 273K.
Reason : Bromine polarises in carbon disulphide.

10. Assertion : Phenols give o- and p-nitrophenol on nitration with conc. HNO3 and H2SO4 mixture.
Reason : —OH group in phenol is o–, p– directing.

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 12th; Chemistry Practice Sheet Unit 11: Alcohol, Phenol & Ether

PART – F (Subjective based)

1. Write IUPAC structure of following: Ethoxyethane; 3-methoxypropane; 2-ethoxy-1, 1-

dimethylcycloheaxane; Benzene 1,3 di-ol; m-cresol; 4-chloro -2,3-dimethylpentan -1-ol;
Cyclohexylmethanol; Cyclopent -3-en- 1-ol
2. Give equations of following:
a) Oxidation of propan -1-ol with alkaline KMnO4 solution
b) Bromine in CS2 with phenolDilute HNO3 with phenol
c) Treating phenol with CHCl3 in presence of aq. NaOH
d) Write the following reactions in context of Phenols
e) Electrophilic aromatic substitution
f) Kolbe`s reaction
g) Reamer –Tiemann reaction
h) Reaction with Zn dust
i) Oxidation in presence of chromic acid
j) Write reaction of C-O bond cleavage in Ethers with mechanism.
3. Write conversions of the following:
a) Propene to propan-2-ol b) Benzyl chloride to benzyl alcohol c) Ethyl magnesium chloride to propan
-1-ol
4. Show synthesis of:
a) 1-phenylethanol from a suitable alkene b) Pentan-1-ol using a suitable alkyl halide
5. Give reason for the higher B.P. of ethanol in compare to methoxymethane.
6. Write reaction of:
a) Friedal –craft acetylation of anisole b) Nitration of anisole c) Bromination of anisole in ethanoic acid
medium d) Friedal craft alkylation of anisole
7. Write limitations of Williamson`s synthesis in the preparation of certain ethers, give example. Comment on
ortho and para isomers of nitrophenol upon the Volatile nature with structural formula.
8. Write structure of : Picric acid; Salicylic acid; Aspirin
9. Mention the following test of 1°, 2° and 3° alcohol: Lucas test; Victor Meyer`s test; Libermann`s test;
Reaction with Ferric chloride; Iodoform test
10. Why phenol has higher B.P. than toluene?
11. Why phenols have smaller dipole moment than methanol?
12. Write the reaction of preparation of phenol from cumene.
13. Write coupling reaction in terms of phenols.
14. An alkoxide is a stronger base than hydroxide ion. Justify. Phenols are more acidic than alcohol. Justify
15. Compare the acidic strength of aminophenols and methoxyphenols. Alcohols are easily protonated than
phenols. Why?

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