Chapter 18
Sankalp Bharat
Alcohols, Phenols & Ethers
1. Consider the following reaction C. Zn dust, ∆ 3. Salicyl
aldehyde
D. Na2Cr2O7, H2SO4 4. Salicylic acid
Choose the correct answer from the options
Identify products A and B: (2023) given below: (2022)
(a) A-4, B-2, C-1, D-3
(b) A-3, B-4, C-1, D-2
(a) (c) A-2, B-1, C-4, D-3
(d) A-4, B-3, C-2, D-1
4. Which one of the following reaction sequence
(b)
is incorrect method to prepare phenol?
(2022)
(c)
(a)
(b) Aniline, NaNO2 + HCl, H2O, heating
(d)
(c) Cumene, O2, H3O+
2. Which amongst the following will be most
readily dehydrate under acidic conditions?
(2023)
(d)
5. Given below are two statements:
(a) Statement I: The acidic strength of
monosubstituted nitrophenol is higher than
phenol because of electron withdrawing
nitro group.
Statement II: o-nitrophenol, m-nitrophenol
(b) and p-nitrophenol will have same acidic
strength as they have one nitro group
attached to the phenolic ring.
In the light of the above statements, choose
(c) the most appropriate answer from the option
given below: (2022)
(a) Both Statement I and Statement II are
(d) correct.
(b) Both Statement I and Statement II are
3. Match the reagents (List I) with the product
incorrect.
(List II) obtained from phenol.
(c) Statement I is correct but Statement II
List I List II
is incorrect.
A. (i) NaOH (ii) CO2 1. Benzoquinone (d) Statement I is incorrect but Statement II
( iii) H+ is correct.
B. (i) Aqueous 2. Benzene 6. Given below are two statements:
NaOH + CHCl3 Statement I: In Lucas test, primary,
(ii) H+ secondary and tertiary alcohols are
distinguished on the basis of their reactivity
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with conc. HCl + ZnCl2, known as Lucas
Reagent.
Statement II: Primary alcohols are most
reactive and immediately produce turbidity
at room temperature on reaction with Lucas
(d)
Reagent.
In the light of the above statements, choose 9. Reaction between acetone and methyl
the most appropriate answer from the option magnesium chloride followed by hydrolysis
given below: (2022) will give: (2020)
(a) Both Statement I and Statement II are (a) Sec. butyl alcohol
correct. (b) Tert. Butyl alcohol
(b) Both Statement I and Statement II are (c) Isobutyl alcohol
incorrect. (d) Isopropyl alcohol
(c) Statement I is correct but Statement II 10. Anisole on cleavage with HI gives: (2020)
is incorrect.
(d) Statement I is incorrect but Statement II
is correct.
7. What is the IUPAC name of the organic
compound formed in the following chemical
reaction? (2021) (a)
(a) Pentan-2-ol
(b) Pentan-3-ol
(c) 2-methyl butan-2-ol (b)
(d) 2-methyl propan-2-ol
8. The product formed in the following
chemical reaction is: (2021)
(c)
(d)
11. Which of the following substituted phenols
(a) is the strongest acid?
(2020 Covid Re-NEET)
(b)
(a)
(c)
(b)
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(c) (a)
(d) (b)
12.
What is Z? (2020 Covid Re-NEET)
(c)
(a)
(b)
(c)
(d) (d)
13. The compound that is most difficult to 15. Identify the major products P, Q and R in
protonate is: (2019) the following sequence of reactions: (2018)
(a)
(b)
(c)
(d) (a)
14. The structure of intermediate A in the
following reaction, is (2019)
(b)
(c)
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(d)
16. The compound A on treatment with Na gives
B, and with PCl5 gives C. B and C react
(d)
together to give diethyl ether. A, B and C are
in the order: (2018) 20. The oxidation of phenol with chromic acid
(a) C2H5OH, C2H6, C2H5Cl gives (2017-Gujarat)
(b) C2H5OH, C2H5Cl, C2H5ONa (a) An aldehyde
(c) C2H5OH, C2H5Ona, C2H5Cl (b) A simple diketone
(d) C2H5Cl, C2H6, C2H5OH (c) A conjugated diketone
(d) Ortho benzoquinone
17. In the reaction, the electrophile involved is:
(2018) 21. Identify A and predict the type of reaction:
(2017-Delhi)
⊕
(a) Dichloromethyl cation (C HCl2 )
⊕
(b) Formyl cation (C HO) (a)
(c) Dichlorocarbene (:CCl2)
⊕
(d) Dichloromethyl anion (C HCl2)
18. The heating of phenyl-methyl ethers with HI
produces. (2017-Delhi) (b)
(a) Benzene
(b) Ethyl chlorides
(c) Iodobenzene
(d) Phenol (c)
19. Which one is the most acidic compound?
(2017-Delhi)
(d)
22. The reaction:
(a) can be classified as? (2016-I)
(a) Williamson alcohol synthesis reaction
(b) Williamson ether synthesis reaction
(c) Alcohol formation reaction
(d) Dehydration reaction
23. Reaction of phenol with chloroform in
(b) presence of dilute sodium hydroxide finally
introduces which one of the following
functional group? (2015 Re)
(a) –CHO
(c) (b) –CH2Cl
(c) –COOH
(d) –CHCl2
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24. The reaction
(c)
(d)
27. Which of the following will not be soluble in
sodium hydrogen carbonate? (2014)
(a) Benzoic acid
(b) o-Nitrophenol
(c) Benzenesulphonic acid
is called: (2015) (d) 2,4,6-trinitrophenol
(a) Williamson continuous esterification 28. Among the following ethers, which one will
process produce methyl alcohol on treatment with
(b) Etard reaction hot concentrated HI? (2013)
(c) Gatterman – Koch reaction (a)
(d) Williamson synthesis
25. Among the following sets of reactants which
one produces anisole? (2014) (b)
(a) C6H5OH; NaOH; CH3I
(b) C6H5OH; neutral FeCl3
(c) C6H5 – CH3; CH3COCl; AlCl3
(d) CH3CHO; RMgX (c)
26. Identify Z in the sequence of reactions:
(2014) (d)
(a)
(b)
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Answer Key
S1. Ans. (b) S15. Ans. (c)
S2. Ans. (a) S16. Ans. (c)
S3. Ans. (d) S17. Ans. (c)
S4. Ans. (d) S18. Ans. (d)
S5. Ans. (c) S19. Ans. (a)
S6. Ans. (c) S20. Ans. (c)
S7. Ans. (c) S21. Ans. (b)
S8. Ans. (c) S22. Ans. (b)
S9. Ans. (b) S23. Ans. (a)
S10. Ans. (d) S24. Ans. (d)
S11. Ans. (d) S25. Ans. (a)
S12. Ans. (d) S26. Ans. (d)
S13. Ans. (d) S27. Ans. (c)
S14. Ans. (b) S28. Ans. (b)
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Solutions
S1. Ans. (b)
S2. Ans. (a)
Due to presence of conjugation in
product.
S3. Ans. (d) At STP condition substitution at sp2
carbon atom is not feasible.
S5. Ans. (c)
• Nitro group has electron withdrawing
tendency. It can withdraw electrons
both by −I effect and −R effect. Thus
the acidic strength of monosubstituted
nitrophenol is higher than phenol.
• Nitro group present at o- and p-
positions will have strong −R effect
while nitro group present at m-
position will influence only −I effect
hence acidity or o/p isomer will be
more meta isomer.
S6. Ans. (c)
Primary, secondary and tertiary alcohols
can be differentiated by their reaction
with (HCl + anhy ZnCl2) Lucas reagent.
ZnCl2 +HCl
• 3° alcohol → Immediate
turbidity at room temperature.
ZnCl2 +HCl
• 2° alcohol → Turbidity after 5
S4. Ans. (d) minutes at room temperature.
ZnCl2 +HCl
• 1° alcohol → Do not gives
turbidity at room temperature.
S7. Ans.(c)
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Anisole on cleavage with HI gives phenol
and methyliodide
S11. Ans.(d)
Acidic strength of phenol is enhanced by
the presence of electron- withdrawing
groups which stabilized the phenoxide
ion.
While presence of electron- donating
group like CH3,C2H5 destabilizes the
S8. Ans.(c) phenoxide ion, thus decreasing the
acidic strength.
Due to the presence of strong electron-
withdrawing group–NO2(–I, –R), p-nitro
phenol is the strongest acid.
S12. Ans.(d)
The given reaction is hydroboration–
oxidation reaction. It is a two-step
hydration reaction that converts an
alkene into an alcohol.
NaBH4 reduces aldehyde/ketone but
does not reduce ester.
S9. Ans.(b)
Butan-1-ol
S10. Ans.(d) Thus, Z is CH3CH2CH2CH2OH
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S13. Ans.(d)
Due to involvement of lone pair of
electrons present on O-atom is in
resonance in phenol. So, it will have
positive charge (partial), hence incoming
proton will not be able to attack easily.
S14. Ans.(b)
S17. Ans.(c)
It is Reimer-Tiemann reaction the
electrophile formed is : CCl2
(Dichlorocarbene) according to the
following reaction
S18. Ans.(d)
S15. Ans.(c)
In phenyl methyl ether C-O bond is sp2
hybridised. In sp and sp2 hybridisation
(Clarge – O – Csmall) cleavage takes place
but in sp3 hybridisation (Clarge – O –
Csmall) cleavage takes place.
S19. Ans.(a)
Now,
Is a most acidic compound. –NO2 is an
electron withdrawing group. In this
compound, NO2 is attached to the ortho
and para position which increases the
acidic strength of phenol.
S20. Ans.(c)
Phenol + chromic acid = A conjugate
diketone
S16. Ans.(c)
(conjugate diketone)
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S21. Ans.(b)
S22. Ans.(b)
S26. Ans.(d)
In anti Markonikov reaction (presence of
peroxide linkage):
CH3CH2CH=CH2+HBr/H2O2 → CH3CH2–
Williamson ether synthesis CH2Br
S23. Ans.(a) For ether formation:
C2H5ONa → CH3CH2–CH2–CH2–O–C2H5 +
NaBr
Williamson synthesis
The above reaction is Riemer – Tiemann S27. Ans.(b)
reaction which introduces a –CHO Sodium hydrogen carbonate (NaHCO3)
(aldehyde) group to phenol. being an alkali solution will dissolve an
S24. Ans.(d) acid not a base so o-nitrophenol being a
very weak acid than NaHCO3 will not get
The above reaction is called Williamson dissolve.
synthesis of ether.
S28. Ans.(c)
As 3° carbocation formed is stabilized
because of 9 hyperconjugated H’s and 3
S25. Ans.(a) inductive effect inducing –CH3.
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