ALCOHOL PHENOL AND ETHER MCQ

Que 1. Arrange the following compounds in increasing order of boiling

point.
Propan-1-ol, butan-1-ol, butan-2-ol, pentan-1-ol:
(a) Propan-1-ol, butan-1-ol, butan-2-ol, pentan-1-ol
(b) Pentan-1-ol, butan-2-ol, butan-1-ol, propan-1-ol
(c) Pentan-1-ol, butan-1-ol, butan-2-ol, propan-1-ol
(d) Propan-1-ol, butan-2-ol, butan-1-ol, pentan-1-ol
Ans 1. (d) Propan-1-ol, butan-2-ol, butan-1-ol, pentan-1-ol

Que 2. Phenol is less acidic than ______________.

(a) Methanol
(b) p-methylphenol
(c) o-nitrophenol
(d) o-methoxyphenol
Ans 2. (c) o-nitrophenol

Que 3. Which of the following is most acidic?

(a) Benzyl alcohol
(b) Ethanol
(c) Phenol
(d) m-Chlorophenol
Ans 3. (d) m-Chlorophenol

Que 4. Which of the following alcohols gives 2-butene on dehydration by

conc. H2SO4?
(a) 2-methyl propene-2-ol
(b) 2-methyl 1 -propanol
(c) Butane-2-ol
(d) Butane 1-ol
Ans 4. (c) Butane-2-ol

Que 5. One mole of ethyl acetate on treatment with an excess of LiAlH 4 in

dry ether and subsequent acidification produces
(a) 1 mole acetic acid + 1 mole ethyl alcohol
(b) 1 mole ethyl alcohol + 1 mole methyl alcohol
(c) 2 moles of ethyl alcohol
(d) 1 mole of 2-butanol
Ans 5. (c) 2 moles of ethyl alcohol
Que 6. Which of the following reagents cannot, be used to oxidize primary
alcohols to aldehydes?
(a) CrO3 in anhydrous medium
(b) KMnO4 in acidic medium
(c) Pyridinium chlorochromate
(d) Heat in the presence of Cu at 573 K
Ans 6. (b) KMnO4 in acidic medium

Que 7. 1-Phenylethanol can be prepared by the reaction of benzaldehyde

with
(a) Methyl bromide
(b) Ethyl iodide and magnesium
(c) Methyl iodide and magnesium
(d) Methyl bromide and aluminium bromide
Ans 7. (c) methyl iodide and magnesium (Grignard reagent’s).

Que 8. Which of the following alcohols will give the most stable carbocation
during dehydration?
(a) 2-methyl-1-propanol
(b) 2-methyl-2-propanol
(c) 1-Butanol
(d) 2-Butanol
Ans 8. (b) 2-methyl-2-propanol

Que 9. A compound X with the molecular formula C2H8O can be oxidised

to another compound Y whose molecular formulae is C3H6O2. The
compound X may be
(a) CH3CH2OCH3
(b) CH3CH2CHO
(c) CH3CH2CH2OH
(d) CH3CHOHCH3
Ans 9. (c) CH3CH2CH2OH

Que 10. Order of esterification of alcohols are

(a) 3° > 1° > 2°
(b) 2°> 3° > 1°
(c) 1 ° > 2° > 3°
(d) None of these
Ans 10. (c) 1 ° > 2° > 3°

Que 11. What happens when tertiary butyl alcohol is passed over heated
copper at 300°C?
(a) Secondary butyl alcohol is formed
(b) 2-methylpropene is formed
(c) 1-butene is formed
(d) Butanol is formed
Ans 11. (b) 2-methylpropene is formed,
Que 13. CH3CH2OH can be converted into CH3CHO by ______________.
(a) treatment with K2Cr2O7
(b) treatment with LiAlH4
(c) treatment with pyridinium chlorochromate
(d) treatment with KMnO4
Ans 13. (c) treatment with pyridinium chlorochromate

Que 14. What would be the reactant and reagent used to obtain 2, 4-
dimethyl pentan-3-ol?
(a) Propanal and propyl magnesium bromide
(b) 3-methylbutanal and 2-methyl magnesium iodide
(c) 2-dimethylpropanone and methyl magnesium iodide
d) 2-methylpropanal and isopropyl magnesium iodide
Ans 14. (d) 2-methylpropanal and isopropyl magnesium iodide

Que 15. The decreasing order of boiling point of the following alcohols is
(a) 3-methylbuan-2-ol > 2-methylbutan-2-ol > pentan-1-ol
(b) Pentan-1-ol > 3-methylbutan-2-ol > 2-methylbutan-2-ol
(c) 2-methylbutan-2-ol > 3-methylbutan-2-ol > pentan-1-ol
(d) 2-methylbutan-2-ol > pental-1-ol > 3-methylbutan-2-ol
Ans 15. (b) Pentan-1-ol > 3-methylbutan-2-ol > 2-methylbutan-2-ol.

Que 16. Propanone on reaction with alkyl magnesium bromide followed by

hydrolysis will produce
(a) Primary alcohol
(b) Secondary alcohol
(c) Tertiary alcohol
(d) Carboxylic acid
Ans 16. (c) Tertiary alcohol

Que 17. Unknown alcohol is treated with “Lucas reagent” to determine

whether the alcohol is primary, secondary, or tertiary. Which alcohol
reacts fastest and by what mechanism?
(a) Tertiary alcohol by SN2
(b) Secondary alcohol by SN1
(c) Tertiary alcohol by SN1
(d) Secondary alcohol by SN2
Ans 17. (c) Tertiary alcohol by SN1

Que 18. The reaction between phenol and chloroform in the presence of
aqueous NaOH is known as
(a) Etard reaction
(b) Kolbe’s reaction
(c) Reimer Tiemann reaction
(d) None of above
Ans 18. (c) Reimer Tiemann reaction

Que 19. Benzyl alcohol is obtained from benzaldehyde

(a) Wurtz reaction
(b) Etard reaction
(c) Williamson’s synthesis
(d) Cannizzaro’s reaction
Ans 19. (d) Cannizzaro’s reaction

Que 20. Phenol reacts with Br2 in CS2 at low temperature to give
(a) o-Bromophenol
(b) o-and p-Bromophenol
(c) p-Bromophenol
(d) 2,4,6-Tribromophenol
Ans 20. (b) o-and p-Bromophenol

Que 21. Phenol on distillation with zinc dust gives

(a) Benzoquinone
(b) Toluene
(c) Benzaldehyde
(d) Benzene
Ans 21. (d) Benzene

Que 22. Ethanol & Phenol can be distinguished by

(a) Dye test
(b) NaHCO3 test
(c) Carbylamine test
(d) Hinsberg’s test
Ans 22. (a) Dye test

Que 23. During esterification water is removed as soon as it is formed:

(a) To shift the equilibrium in forward reaction
(b) To purify the product
(c) To decrease the rate of reaction
(d) None of above
Ans 23. (a) To shift the equilibrium in forward reaction

Que 24. The compound obtained by the reaction of propene with diborane
followed by hydrolysis with alkaline H2O2 is
(a) n-propyl alcohol
(b) ethanol
(c) triethyl bromide
(d) None of above
Ans 24. (a) n-propyl alcohol

Que 25. Which one of the following will not form yellow precipitate on
heating with an alkaline solution of iodine?
(a) CH3OH
(b) CH3CH2OH
(c) CH3CH2CH(OH)CH3
(d) CH3CH(OH)CH3
Ans 25. (a) CH3OH

Que 26. Four compounds A, B, C, and D have similar molecular masses

were tested for their boiling points. It was found that compound C has the
highest boiling point of all four. What is compound C most likely to be?
(a) Alcohol
(b) Haloalkane
(c) Hydrocarbon
(d) Ether
Ans 26. (a) Alcohol

Que 27. What will be the reactant and reaction condition required for the
given reaction? CH3CH2OH +? → C2H5OC2H5
(a) H2SO4, 443K
(b) H2SO4, 413K
(c) HNO3, 413K
(d) HNO3, 443K
Ans 27. (b) H2SO4, 413K

Que 28. Q-37. Williamson synthesis proceed visa which of the following
mechanism?
a) SN1
b) SN2
c) E1
d) E2
Ans 28. b) SN2

Que 29. The enzyme which breaks down ethanol in the body
(a) Alcohol dehydrogenase (ADH),
(b) Invertase
(c) Trypsin
(d) None of above
Ans 29. (a) Alcohol dehydrogenase (ADH),

Que 30. Cumene hydroperoxide on hydrolysis with dilute H2SO4 gives

(a) Only phenol
(b) Alcohol and phenol
(c) Alcohol and acetone
(d) Phenol and acetone
Ans 30. (d) Phenol and acetone.