264 ogether witk Chemistry-12

SOLVED QUESTION BANK

Objective/Very Short Answer Type Questions [I Mark]
1. Which ofthe following intermediates is fornmed in the reaction shown below: |CBSE 2021|
CH,- CH, - OH + HI’ CH, - CH, -1+H,0
() CH,CH,ÔH, (6) CH,-CH
(c) Both CH,CH,ÖH, and CH,- CH; (4) CH,CH,-0-CH,-CH,
Ans. (c)
2. The reaction:
OH
OH
CHO
1. CHCI, + NaOH,
2. H,0*

is an example of |CBSE 2021)

(a) Reimer-Tiemann reaction (b) Kolbe's reaction
(c) Williamson's synthesis (b) Wurtz reaction
Ans. (a)
3. Phenol is more acidic than ethanol because |CBSE 2021]
(a) Ethoxide ion is more stabie than Phenoxide ion.
(6) Phenoxide ion is more stable than Ethoxide ion.
(c) Phenol undergoes electrophilic substitution reaction.
(d) Phenol undergoes protonation easily.
Ans. (b)
4. The structure(s) of the major product(s) expected from the mononitration of 3-methylphenol willbe |CBSE 20211
OH OH

0,N
and

CH, CH,
NO,
OH OH
NO,
(b) and

CH, CH,

OH
NO, OH
0,N. NO,

(c) and
CH, CH,
OH OH
NO,
(d) and
0,N CH, CH,
Ans. (a)
 Alcohols, Phenols and Ehers 265
5. Complete the following analogy:
o-nitrophenol : A :: 0-eresol : B |CBSE 2021|
(a) A : more acidic than phenol B: less acidic than phenol
(b) A: less acidic than phenol B: more acidic than phenol
(c) A :more acidic than phenol B: more acidic than phenol
(d) A: less acidic than phenol B: less acidic than phenol
Ans. (a)

6. The heating of phenylmethyl ether with HIproduces

(a) lodobenzene (b) Phenol
(c) Benzene (d) Ethyl chloride
OCH, OH

Ans. (b) Phenol. + HI +CH,I

7. Which of the following gives positive iodoform test?
(a) CH,CH,CH,OH (6) CH,ÇH CH,0H
CH,
(c) PhCHOHCH, (d) CH,CH,CH(OH) CH,CH,
I,/NaOH LNaOH
Ans. (c) PhCHOHCH, C,H,CCH, ’ CHI,(S) + C,H,C ONa
Conc. H,SO, is
8. C,H;CH, CH(OH) CH(CH),
(a) CHs CH(CH), (6) H,C,CH,CH,
C-CH,
H
CH,
(c) HC6 (4) CH;CH, CH,
H CH(CH,), H CH,
H*
Ans. () CH,CH, ÇH-CH--CH, ’C,H,CH, CH-CH CH, C,H-CH H ÇH-CH,
OH CH, OH, CH, H CH,
CH, H
-H+
CH CH-CH, CH CH,
CH, H CH CH,
trans- CH,
9. The electrophile involved in Riemer-Tiemann reaction of phenol with CHCI, in presence of NaOH is
(c) HO () CHCI,
(a) :CCI, (6) CI,
OH
Ans. (a) CHCI, CCI,’:CCI, +Cl
266 ogtkcr anek Chemistry--12

10. Arrange the foilowing in decreasing order of acidic

character:
OH OH OH OH

CI CH, NO, OCH,

III IV
(d) III>I>I|> .V
(a) 1V >II|>|>II (b) II> IV > I> III (c) I>II> II| >IV

Ans. (d) - Since, NO, and Cl are electron withdrawing but NO, > C. least acidic.
clectron releasing due to +R effect than -CH, group, therefore, IV is
-OCH, more
11. Identify 'C' in the following:
Anhy. AlCA dil. H,SO,, Phenol+C
+CH,-CH-CH, HCI 130°C 100°C

C
(a) Water (b) Ethanol

(c) Propanone (d) Cumene hydroperoxide

CH,
CH, ÇH CH, CH,-C 0-0 H OH

Ans. (c)
130°C dil. H,SO, +CH,--CH,
100°C 'C'
'A' B Propanone
OH

12.
C,H,COC
base
Nitration, «y: (Major product)

-cooO-, (b) HO -NO,

(c) 0,N (d) -CO0 -NO,

OH OcOc,H, OCOCH,
Conc. HNO,
Ans. (a) c,H,COCI,
base Conc. H,SO,
NO, (Major Product)
13. Find the product of the given reaction:
CH,
H
CH, ’ ?
A
OH

CH, CH, CH,

(a) (b) (c) (d)
CH,
CH, CH, CH, CH,
 Alcohols, Phenols and Ethers 267
CH, CH,
Ans. ()
CH, CH, CH,
OH
A
CH, a,hin
alkyl
CH,
OH,
I, NBS/hy CH, CH,
14.
2. H,OK,Co X is

OH
(a
(c)
CH,0H
(d)

Br OH
NBS/hv Br
Ans. (b) H,0/K,CO,

NBS (N-Bromo succinamide) carries out free radical allylic

substitution reaction.
15. Monochlorination of toluene in sunlight followed by hydrolysis with ag.
NaOH yields. |KVS]
[NCERT Exemplar Problem]
(a) o-Cresol (b) m-Cresol (c) 2, 4-Dihydroxytoluene (d) Benzyl alcohol
CH, CH,CI CH,OH
Ans. (d) KOH(aq)
16. How many alcohols with molecular formula C,H,O are chiral in nature?
|NCERT Exemplar Problem]
(a) 1 (6) 2
(c) 3 (d) 4
Ans. (a) CH, ÇH-CH,-CH, has chiral centre (one).
OH
17. What is the correct order of reactivity of alcohols in the following reaction? |NCERT Exemplar Problem]
R-OH + HCI R-CI + H,0
(a) 1° > 20 > 30 (b) 1° < 2° > 30

(c) 3° > 20 > 1° (d) 3º > 1° > 20

Ans. (c) 3° > 2° > 1° is order of stability of carbocation .:. Reactivity follows the same order.
18. CH,CH,OH can be converted into CH,CHO by INCERT Exemplar Problem]
(a) catalytic hydrogenation (b) treatment with LiAlH,
(c) treatment with pyridinium chlorochromate (PCC) (d) treatment with KMnO,
PCC
Ans. (c) CH,CH,OH ’ CH,CHO
19. IUPACname of the compound CH,-ÇH-0CH, is INCERT Exemplar Problem)
H,
(a) 1-methoxy-1-methylethane (0) 2-methoxy-2-methylethane
(c) 2-methoxyprop ane (d) isopropylmethyl ether
Ans. (c) 2-methoxypropane
268 o9ether wck Chemistry--12

20. Which of the following species

can act as the strongest base? NCERT Exemplar Problem)
(b) OR
(a) °OH

(c) 0C,H,
NO,
Ans. () :: ROH is weakest acid, .. RO is strongest conjugatebase.
21. Identify the product 'C of the following sequence of reactions:
Br
HBr
Mg
dry ether
’ A CH,CHO,B ’'C'

C'is
Br CH,
Br
(b)
(a)
OH
OH

CH CH, CH-CH,
(c)
OH

BI
Dry
MgBr CH,CHO CH,
Ans. (b) + Mg Ether

H C-CH, CH,
Ring H

CH,expansion
CH, B
Br
CH,
22. The number of cyclic isomers of C,H,0H are
(a) 4 (b) 5 (c) 3 (d) 6

OH CH,OH CH OH
Ans. (b) 5,
Cyclobutanol Cyclopropyl 1-Methyl cyclo H ÒH CH,
methanol propanol Trans-2-methyl
Cis-2-methyl
cyclo propano cyclo propanol

Note: In the following questions two or more options may be correct. (Q.23 to 0.25)
23. Which of the following are used to convert RCHO into RCH,OH? [NCERT Exemplar Problem)
(a) H,/Pd (b) LiAIH,
(c) NaBH, (d) Reaction with RMgX folowed by hydrolysis
Ans. (a), (b), (c) will convert RCHO into RCH,0H.
 24. Which of the Alcohols, Phenols and Ethers 269
following renctions will yield plhenol?
CI INCERT Exemplar Probleml
fusion with NaOH at 300 atm (iv) || (d) o-Cresol
(a)
(i) H,0'
OH
NH, OCH,
() NaNO,/HCI
(6)
(i) H,0 (Warning) () || (e) Quinonc

(C
() Oleum OCH,CH,
(i) NaOH, (Heating) Resorcinol
(ii) H* (vi)
C
(g) Anisole
Ans. () (d) (ii) (c) (iii) ) (iv) (a) or quinol
() (g) (ví) (b)
(i) NaOH(aq.), 298K/latm
(a) 27. Match the starting materials
(ü) HCI given in Column I
with the products formed by these
(Column II) in
Ans. (a), (6), (c) will give phenol. (d) will not give phenol the reaction with HI. .NCERT
Exemplar Problem)
because high temperature is needed. ColumnI Column II
25. Which of the following reagents can be used to OH
oxidise primary alcohois to aldehydes?
() CH,-0-CH, (a)
|NCERT Exemplar Problem) +CH,I
(a) Cro, in anhydrous medium.
(b) KMn0, in acidic medium. CH; CH,
(i) CH O CH, (b) CH, 1+CH,0H
(c) Pyridinium chlorochromate.
CH,
(d) Heat in the presence of Cu at 573K. CH,
Ans. (a), (c), (d) can be used. KMn0, converts primary CH,
alcohol to carboxylic acids. (i) H,C o CH,
26. Match the structures of the compounds given in (c) + CH,OH
CH,
ColumnIwith the name of the conpounds given
in Column II. [NCERT Exemplar Problem]
OCH, (d) CHOH + CH,I
Column I Column I (iv) (e)
CH
CH OHCH,I
CH, OH CH,
(a) Hydroquinone CHy
CH-I +CH,OH
CH,
OH
OH

(i) (b) Phenetole (g) CH, OH+CH,I

OH Ans. () (d) (i) (e) (üi) (6) (iv) (a)CH,

In cleavage of ethers, higher alcohol and lower alkyl
(ii) (c) Catechol halide is formed except in tert. butyl methyl ether,
in which (CH,), C* is more stable so (CH),C-I and
OH CH,0H is formed. Anisole with HIgives phenol and
CH,I because phenoxide ion is stabilised by resonance.
270 7ogether wtt0 Chemistry--12
Note: In the following questions a statement of assertion 33. Diethyl ether
followed by a statement of reason is given. Choose molecule.

the correct answer out of the following choices. Ans, True

(Q.28 to Q.30) 34. Ethers have lc
(a) Assertion and reason both are correct statements
and reason is correct explanation for assertion. Ans. True. It is due t
(b) Assertion and reason both are correct in ethers but it
statements but reason is not correct explanation 35. Dettol contai
for assertion.
(c) Assertion is correct statement but reason is Ans. True, phenols
wrong statement. 36. Write the IUI
(d) Assertion is wrong statement but reason is
correct statement. HO
28. Assertion: Ortho-nitrophenol is more acidic than
phenol.
Ans. 3-methyl but
Reason: Nitro group is electron donating group
37. Write the IU
and therefore stabilizes ortho-nitrophenoxide ion.
[CBSE 2021(C))
Ans. (c) Assertion is correct statement but reason is wrong HO
statement.

29. Assertion: Bond angle in ethers is siightly less than

Ans. 2-methyl prc
the tetrahedral angle.
38. Write the IL
Reason: There is a repulsion between the two bulky
(-R)groups. |NCERT Exemplar Problem}

Assertion: The C-0-C bond angle in ethers is Ans. Hex-4-en-3

slightly less than tetrahedral angle. 39. Write IUPA
between
Reason: Due to the repulsive interaction CH,
|CBSE 2020)
the two alkyl groups in ethers.
reason is correct
CH,
Ans. (d) Assertion is Wrong statement but
statement. H,
be
30. Assertion: Ortho and para-nitrophenols can
Ans. 2, 2-Dimeth
separated by steam distillation. 40. Write the
Reason: Ortho isomer associates through CH,CH
intermolecular hydrogen bonding while Para
isomer associates through intramolecular hydrogen
|CBSE 2020|
Ans. 1-Phenylpr
bonding. 41. Write IUE
Ans. (c) Assertion is correct statement but reason is wrong
CH, CH
statement.
31. Phenol reacts with Br, in CS, to give
Ans. Butan-2-o
major product.
42. Write IU
Ans. p-bromophenol
melting point than CH,-C
32. o-nitrophenol has
p-nitrophenol. CH
Ans. 2-methyl
Ans, lower
280 getker wek® Chemistry-12
(v) Why is C-OH bond length in
Case-Based/Passage-Based Integrated Questions than C-OH bond length in phenol? CH,OH longer
84. Read the given passage and answer the questions (CBSE 20201
that follow: Ans. It is due to resonance in phenol, there
is double
Alcohols andphenols are most importantcompounds bond character in C0 bond, therefore shore
used in our daily life. Alcohols are prepared by than single bond in methanol,
hydration of alkenes, fermentation of glucose, OH
reduction of aldehydes, ketones, carboxylic acids
and esters. PCC
Alcohols are soluble inwater. Boiling points increase () Identify the product:
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,SO, Ans.

also follow carbocation mechanism but gives diethyl Cyclohex-2-en-1-one

ether. Alcohols undergo nucleophilic substitution
reactions, esterification with carboxylic acids and
derivatives like amides, acid halides, acid anhydride. (v) Why is R H bond angle in alcohol less
than tetrahedral bond angles? [CBSE 2020]
Phenolis prepared from cumene, diazonium salts,
anisole, chlorobenzene. Phenol is used to prepare Ans. It is due to repulsive interaction between two lone
salicylaldehyde, salicylic acid, aspirin, methyl
pair of electrons in alcohol,
salicylate, p-benzoquinone. Phenol undergoes R H
electrophilic substitution reaction at o &p-position.
Ethers are functional isomers of alcohoBs, have 85. Read the given passage and answer the questions
that follow:
low boiling points. Ethers are used as solvents.
Unsymmnetrical ethers are prepared by Williamson Alcohols play very important role in our daily
synthesis. Ethers react with HI and undergo S,,1 life. Ordinary spirit used as an antiseptic coutains
or S,2 mechanism depending upon stability of methanol. Ethanol is present in cough syrups, tonics,
carbocation formned. Aromatic ethers like anisole wine, beer and whisky, Sugar, starch, cellulose are
undergoes electrophilic substitution at o&p-position. carbohydrates which also contain large number
() Out of tert, butyl alcohol and n-butanol, which -OH groups. Phenol is also an antiseptic in low
will undergo dehydration faster and why? concentration (0.2%) where as 2% solution of
Ans. Tertiary butyl alcohol willundergo dehydration phenol is used as disinfectant. The fragrance of rose
faster because 3° carbocation is more stable. is due tocitronellol (unsaturated alcoho). Phenol
(i) Convert phenol to p-benzoquinone. is used for preparation of many useful compounds
OH like aspirin, methyl salicylate (Todex) and phenyl
Conc. salicylate (salol) used as intestinal antiseptic.
Na,Cr,0,/H,so,
Ans. In these questions, a statement of assertion followed
[O]heat
by a statement of reason is given. Ch00se the correct
Phenol answer out of the following choices.
p-benzoquinone (a) Assertion and reason both are correct statements
(ii) Complete thechemical reaction: and reason iscorrect explanation for assertion.
(b) Assertion and reason both are correct
() CH,MgBr statements but reason is not correct explanation
(i) H,0* for assertion.
(c) Assertion is correct statemnent but reason is
OH CH,
Wrong statement.
() CH,MgBr
Ans. (d) Assertion is wrong statement but reason 1s
(i) H,0*
correct statement.
 Alcohols, Phenols and Ethers 281
) Assertion: Cumene hydroperoxide on hydrolysis
gives phenol and cetone. Ans. (b) Assertion and reason both are correct
Reason: Phenol becomes pink on long statements but reason is not correct explanation
due to oxidation. standing for assertion.
Ans. (b) Assertion and reason (iv) Assertion: Phenol gives violet colour with
both are neutral FeCl,, benzyl alcohol does not.
statements but reason is not correct correct
explanation Reason: Ethanol gives yellow ppt with I, and
for assertion.
NaOH, phenol does not.
(iD Assertion: Phenol reacts with CO,, NaOH at Ans. (b) Assertion and reason both are
3-7 atm. on heating and correct
acidification gives statements but reason is not correct explanation
salicylic acid. for assertion.
Reason: is (v)
Riemer-Tiemann reaction.
Ans. (c) Assertion is correct statement but reason is
Assertion: The bond angle in alcohol and phenol
is more than
tetrahedral angle.
wrong statement. It is Kolbe's reaction. Reason: In phenols, oxygen is attached to sp
(ii) Assertion: Phenol gives picric acid on reaction hybridised carbon.
with conc. HNO, and conc. H,SO,. Ans. (d) Assertion is wrong statement but
reason is
Reason: Picric acid reacts with NaHCO, to Correct statement.
give CO,.
S6. Observe the following table showing boiling points of
alcohol, molar mass. Study the table and answer the
ouestions based on table and related studied concept.
Alcohol
Boiling Point Molar Mass
1. CH,OH 64°C 32 g molH
2. C,H,OH 78°C 46 g moH
3. C,H,0H (2-propylalcohol) 97°C 60 g mol
4. Isopropyl alcohol 82.5°C 60 g mol-!
5. n-butanol 118°C 74 g molH
6. Isobutyl alcohol 108°C 74 g mo}
7. Butan-2-ol 100°C 74 g mo!
8. Tert. butyl alcohol 83°C 74 g molH
() Which of the following has highest boiling (iv) Which of the following is most soluble in water?
point? (a) Ethanol
(a) n-Butane (b) 1-Chloro butane
(b) 1-Propanol
(c) Butan-1-ol (d) Ethoxy ethane (c) 1-Butanol
Ans. (c) It is due to H-bonding.
(d) 2-Pentanol
(i) Which of the folowing has lowest boiling point? Ans. (a) Solubility decreases with increase in alkyl
(a) 1-butanol (b) iso butyl alcohol chain.
(c) 2-butanol (d) 2-methyl-2-propanol (v) Which of the following is most acidic?
Ans. (d) It is due to branching. (a) CH,0H
(iüi) Which of the following has highest boiling (b) C,H,0H
point? (c) Tert. butyl alcohol
(a) CH,0H (b) C,H,OH (d) Isopropyl alcohol
(c) CH,CH,CH,0H Ans. (a) because CH,0 is most stable.
(4) CH,CH,CH,CH,OH
Ans. (d) It is due to longer chain.