This chapter is crucial for CBSE and competitive exams because it links structure with key reactions: preparation and reactions of alcohols and ethers, phenols’ acidity and electrophilic substitution, and stereochemical outcomes in conversions (often tested as assertion/reason and MCQs). Understanding hydrogen bonding, inductive/resonance effects, and SN1/SN2/E2 preferences makes these questions quick and high-scoring.
20
Minutes
15
Questions
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Marking
Q1. Which of the following compounds has the highest boiling point?
(dimethyl ether)
(methylamine)
(ethanol)
(acetaldehyde)
Q2. Which ether among the following is cleaved most readily by under mild conditions (i.e., requires the gentlest conditions for C–O bond cleavage)?
(methyl tert‑butyl ether)
(diethyl ether)
(anisole)
(dimethyl ether)
Q3. Arrange the following phenols in order of increasing acidity (least acidic → most acidic): phenol, ‑nitrophenol, ‑nitrophenol, ‑nitrophenol.
phenol < ‑nitrophenol < ‑nitrophenol < ‑nitrophenol
phenol < ‑nitrophenol < ‑nitrophenol < ‑nitrophenol
‑nitrophenol < phenol < ‑nitrophenol < ‑nitrophenol
phenol < ‑nitrophenol < ‑nitrophenol < ‑nitrophenol
Q4. In an attempted Williamson ether synthesis, which of the following alkyl halide + alkoxide combinations will predominantly give an alkene (E2 elimination) rather than the desired ether (because SN2 is disfavoured)?
Q5. Which reagent is most suitable to remove the methyl group from anisole () and convert it to phenol under mild conditions without nitration or oxidative cleavage of the aromatic ring?
hot concentrated (reflux)
catalytic hydrogenation ()
(boron tribromide)
(oxidative conditions)
Q6. Among the following compounds, which has the lowest boiling point?
Phenol ()
-Nitrophenol (-)
-Nitrophenol (-)
-Nitrophenol (-)
Q7. Arrange the following compounds in order of increasing acidity (least → most acidic):
(i) -Nitrophenol (-), (ii) -Nitrophenol (-), (iii) -Nitrophenol (-), (iv) 2,4-dinitrophenol (-).
(ii) (i) (iii) (iv)
(i) (ii) (iii) (iv)
(i) (iii) (ii) (iv)
(iv) (iii) (ii) (i)
Q8. Which of the following alcohols will react fastest with to give the corresponding alkyl bromide under typical conditions?
1-Butanol ()
2-Butanol ()
tert-Butanol ()
Benzyl alcohol ()
Q9. Assertion (A): -Nitrophenol is a stronger acid than -nitrophenol in aqueous solution.
Reason (R): In -nitrophenol an intramolecular hydrogen bond forms between the OH and NO group, which reduces the extent of ionization of the hydroxyl proton compared to the para isomer.
Both A and R are true, and R correctly explains A.
Both A and R are true, but R does not correctly explain A.
A is true, R is false.
A is false, R is true.
Q10. Which reagent will convert -2-butanol to -2-bromobutane with inversion of configuration as the major stereochemical outcome while minimizing elimination and rearrangement?
Conc. , heat
, hv
(pyridine), then , heat
Q11. Among the following compounds, which has the highest boiling point? (Consider hydrogen bonding and molecular branching.)
(2‑butanol)
(1‑butanol)
(tert‑butanol)
(butanal)
Q12. Which of the following correctly describes the relative acidity and reactivity in Williamson ether synthesis with for ‑nitrophenol and ‑nitrophenol?
‑Nitrophenol is more acidic than ‑nitrophenol, and its phenoxide reacts faster in Williamson synthesis with .
‑Nitrophenol is more acidic than ‑nitrophenol, and its phenoxide reacts faster in Williamson synthesis.
‑Nitrophenol is more acidic, but ‑nitrophenoxide reacts faster in Williamson synthesis with .
‑Nitrophenol is more acidic than ‑nitrophenol, but the phenoxide from ‑nitrophenol is more nucleophilic and reacts faster in Williamson synthesis with .
Q13. On treatment with excess , methyl tert‑butyl ether () undergoes cleavage. The major alkyl halide formed is:
(tert‑butyl bromide)
(methyl bromide)
A 1:1 mixture of and
No reaction under these conditions
Q14. Consider the statements:
S: ‑Nitrophenol is more acidic than ‑nitrophenol in aqueous solution.
R: Intramolecular hydrogen bonding in ‑nitrophenol stabilizes its conjugate base (‑nitrophenoxide), thereby making it less acidic.
Which of the following is correct?
Both S and R are true and R is the correct explanation of S.
Both S and R are true but R is not the correct explanation of S.
S is true but R is false.
S is false and R is true.
Q15. p‑Cresol (‑methylphenol) is subjected to two different bromination conditions: (i) ‑bromosuccinimide (NBS) with light (), and (ii) with . The major organic products X and Y from (i) and (ii) respectively are:
X = ‑hydroxybenzyl bromide (), Y = 2‑bromo‑4‑methylphenol
X = 2‑bromo‑4‑methylphenol, Y = ‑hydroxybenzyl bromide
X = ‑bromophenol (ring‑brominated at para), Y = benzyl bromide
Both (i) and (ii) give a significant mixture of ring‑brominated and benzylic‑brominated products