SUBJECT : CHEMISTRY

Topic : Alcohol, Ether, Phenol Test-2 - Phenol and Ether

1. Assertion (A): Phenols are more acidic than 4. Correct sequence of decreasing order of acid
aliphatic alcohols. strength of the given compounds is -
Reason (R): Phenoxides are stabilized by
[Propan-1-ol, 2,4,6-trinitrophenol, 3-nitrophenol,
resonance.
3,5-dinitrophenol, phenol, 4-methylphenol.]
(1) Both Assertion & Reason are correct,
Reason is the correct explanation for (1) 2,4,6-trinitrophenol > 3-nitrophenol > 3,5-
Assertion. dinitrophenol > phenol < 4-methylphenol >
Propan-1-ol.
(2) Both Assertion & Reason are correct,
Reason is not the correct explanation (2) 2,4,6-trinitrophenol > 3,5-dinitrophenol > 3-
of Assertion. nitrophenol > phenol > 4-methylphenol >
Propan-1-ol.
(3) Assertion is correct but Reason is incorrect.
(3) 2,4,6-trinitrophenol > 3-nitrophenol > phenol
(4) Assertion is incorrect but Reason is correct. > 3,5-dinitrophenol > 4-methylphenol >
2. Select the correct option based on statements Propan-1-ol
below: (4) 3-nitrophenol > phenol > 3,5-dinitrophenol
Assertion (A): The solubility of alcohols in > 4-methylphenol > Propan-1-ol > 2,4,6-
water decreases with an increase in the number trinitrophenol
of carbon atoms. 5. The major product (A) obtained in the given
Reason (R): The non-polar alkyl group or the reaction is
hydrophobic portion supports the solubility of
alcohol.
(1) Both (A) and (R) are true and (R) is the
correct explanation of (A).
(2) Both (A) and (R) are true but (R) is not the
correct explanation of (A).
(1)
(3) (A) is true but (R) is false.
(4) Both (A) and (R) are false.
3. What is the compound 'C' in the following
sequence of the reaction.
NaOH CO2 , 410K HCl
P henol −−−−→ A −−−−−−−→ B −−→ C? (2)
4−7 atm

(1) Benzoic acid

(2) Salicylic acid
(3) Benzaldehyde (3) CH2=CH2

(4) Salicylaldehyde (4) CH3 − CH = CH2

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6. Which of the following are used to convert 10. Identify the major products P, Q and R in the
RCHO into RCH2OH ? following sequence of reaction :
(a) H2 / Pd or Pt
(b) LiAlH4
(c) NaBH4
P, Q & R will be respectively :
(d) Reaction with RMgX followed by
hydrolysis.
Choose the correct option. (1)

(1) a, b, c (2) b, c, d
(3) a, c, d (4) a, b, d (2)
7. The product formed when phenol is treated with
bromine water is (3)

(1) (2) (4)

11.

(3) (4)
P & Q are :-

8. Reaction of sodium ethoxide and ethyl

iodide will give:-
(1)
(1) Ether
(2) Ethyl alcohol
(3) Acetaldehyde
(4) Acetic acid (2)
9. The reaction of SOCl2 on alkanols to form alkyl
chlorides gives good yields because :
(1) Alkyl chlorides are immiscible with SOCl2
(3)
(2) The other products of the reaction are
gaseous and escape out
(3) Alcohol and SOCl2 are soluble in water
(4) The reaction does not occurs via (4)
intermediate formation of an alkyl chloro
sulphite
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12. Phenol can be distinguished from ethyl alcohol 16. Which molecule on reaction with Cu/573 K may
by all reagents except not give aldehyde or ketone ?
(1) Na (2) F eCl3

(3) Br2 /H2 O (4) NaOH (1) (2)

13. Select the correct option based on statements

below: (3) (4)
Assertion (A): Ether behave as bases in the
17. An organic compound X on treatment with
presence of mineral acids.
acidified K2Cr2O7 gives a compound Y which
Reason (R): It is due to the presence of lone reacts with I2 and sodium hydroxide to form tri
pairs of electrons on the oxygen atom. iodomethane, the compound X is:
(1) Both (A) and (R) are true and (R) is the (1) CH3OH (2) CH3COCH3
correct explanation of (A). (3) CH3CHO (4) CH3CHOHCH3
(2) Both (A) and (R) are true but (R) is not the 18. Which of the following gives turbidity after 30
correct explanation of (A). min or on heating during Lucas test :-
(3) (A) is true but (R) is false. (1) n-butyl alcohol (2) Sec. butyl alcohol
(4) Both (A) and (R) are false. (3) Tert butyl alcohol (4) Benzyl alcohol
14. 19. What is major product of following reaction?
,
Con.HNO3
−−−−−−−→ Product
then A and B are Con.H2 SO4

(1) (1) (2)

(2) (3) (4)

(3) Both (1) and (2)

20.
(4) P hOH + CH3 CH2 CH2 I ; true statement
15. When acetone reacts with Grignard reagent it
for X is
gives :-
(1) red coloured is appeared in Victor Meyer test.
(1) 1°alcohol (2) responds to iodoform test
(2) 2° – alcohol (3) when heated with Cu gives compound that
responds Baeyer's reagent test
(3) 3° alcohol
(4) gives turbidity only when heating with
(4) Methyl alcohol Lucas reagent
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21. Cu Al O
2 3
26. Which of the following does not reduces the
A←− − −C2H5OH−−−→ B, A and B respectively
o
300 C Δ carboxylic acids into alcohol?
are :-
1. LiAlH /ether 1. B H
(1) Alkene, alkanal (2) Alkyne, alkanal (1) −−−−−−4−+−−−→ (2) −−−2−+→
6

2. H3 O 2.H3 O

(3) Alkanal, Alkene (4) Alkene, alkyne (3) NaBH4 (4) −−−
ROH 2
→−−−−−→
H
+ Catalyst
H
22. Which among the following reaction not possible?
27. Which of the following is not the product of
(1)
dehydration of
(2)
(3) (1) (2)
(4)
23. (3) (4)
P Br3
28. CH3CH2CH2OH−−−→(A)
The electrophile involved in the above reaction is :
Alc.KOH HBr NH3
(1) dichlorocarbene (: CCl2) −−−−−−→ (B) −−−
→ (C) −−
−→ (D), (D) is :
(1) CH3 − CH2 − CH − NH2
(2) trichloromethyl anion
(2)
(3) formyl cation
(3)
(4) dichloromethyl cation

24. Bayer ′ s reagent HIO4

H3C – CH=CH – CH3 −−−−−−−−−→ X −−−→ Y (4)
Y is :-
29. HBr Aq.KOH
(1) (2) H3C – CH=O Consider, CH3 – CH=CH2−−−→(A) −−−−−→(B)
NaOH +I2
−−−−−−→ + (D)
(3) CH3 – COOH (4)
Identify (C) and (D) respectively :-
25. In the given reaction : (1) CHCl3 and
(2) CHI3 +
(3) CH3 – OH + CH3 – CH2 – OH
(A) and (B) respectively by: (4) CHI3 +
(1) CH3CHO and CH3CHO 30. Na CH3 −−Br
CH3 − −OH −−
→ (A) −−−−−−→ (B)
(2) CH3COCH3 and CH3CHO what will be "B" ?
(3) CH3COCH3 and CH3COCH3 (1) CH3 – O – CH3 (2) CH3CH2OCH3
(4) CH3COOH and CH3COCH3 (3) CH3OH (4) CH3ONa

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 CLASSROOM CONTACT PROGRAMME
(Academic Session : 2024 - 2025)

ENTHUSIAST COURSE
PHASE : I(A)
TARGET : PRE-MEDICAL-2025
Test Type :REVISION Test Pattern :NEET (UG)
TEST DATE : 05-10-2024
ANSWER KEY
Q. 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30
A. 1 3 2 2 2 1 4 1 2 4 3 1 1 1 3 1 4 1 3 3 3 4 1 2 2 3 4 2 2 1

HINT – SHEET

1. Ans ( 1 ) 4. Ans ( 2 )
When a molecule of phenol loses a proton, it * Phenol is a stronger acid than alcohol.
forms phenoxide ion which is stabilized by * Methyl ( – CH3) group being electron releasing
resonance as the negative charge is delocalized in nature, decreases the acidic strength of phenol.
over aromatic nucleus. No such resonance is * Nitro ( – NO2) group being electron withdrawing
present when an alcohol loses a proton to form in nature, increases the acidic strength of phenol.
alkoxide ion. 5. Ans ( 2 )
Hence, phenols are more acidic than alcohols. Tertiary halides on treatment with base, such as sodium
2. Ans ( 3 ) methoxide, readily undergo elimination resulting in the
As the molecular weight increases, non-polar formation of alkenes. (Williamson's Synthesis)
part increases and solubility decreases.
So, Assertion is correct. Reason is
incorrect, because hydrogen bonding is not
affected by an increase in the non-polar part. 6. Ans ( 1 )
Aldehydes and ketones are reduced to the
3. Ans ( 2 ) corresponding alcohols by addition of hydrogen in
the presence of catalysts (catalytic hydrogenation).
It is also prepared by treating aldehydes and
ketones with sodium borohydride (NaBH4) or
lithium aluminium hydride (LiAlH4).
H2 +Catalyst
RCHO −−−−−−−−→ RCH2 OH
LiAlH4 or NaBH4
RCHO −−−−−−−−−−−→ RCH2 OH
The reaction of RMgX with any aldehyde other
than methanal gives secondary alcohols not the
primary alcohols.

1803CMD24A00C021 HS-1/2
 Target:PRE-MEDICAL-2025/05-10-2024
7. Ans ( 4 ) 13. Ans ( 1 )
When phenol is treated with bromine water, Due to the presence of lone pair of electrons on
2,4,6-tribromophenol is formed as white oxygen atom, ethers behave as base and form
precipitate. stable oxonium salts with mineral acids.
8. Ans ( 1 )
Allen module.
9. Ans ( 2 )
ROH + SOCl2 → RCl + SO2↑ → + HCl↑ 14. Ans ( 1 )

10. Ans ( 4 )
Mech:

15. Ans ( 3 )

18. Ans ( 1 )

give turbidity after 30 min.

19. Ans ( 3 )

+ conc. HNO3 —→

21. Ans ( 3 )

23. Ans ( 1 )

11. Ans ( 3 )
27. Ans ( 4 )
does not form in dehydration of

12. Ans ( 1 ) 29. Ans ( 2 )

Na reacts both with phenol and ethyl alcohol to
evolve H2 gas and hence can not be used to
distinguish phenol from ethyl alcohol. All the
remaining reagents react only with phenol but
not with ethyl alcohol and can be distinguishing
phenol from ethyl alcohol
HS-2/2 1803CMD24A00C021