11.Alcohols, Phenols And Ethers

1. Which of the following alcohols is prepared by acid catalysed hydration of alkenes?

(a) Butan \(-1-o \ell\).

(c) ethanol

(d) methanol

2. Which of the following alcohols can be prepared by direct hydration of corresponding alkene in presence of \(50 \%\) sulphuric acid?

(a) Butan \(-1-o \ell\)

(b) Butan \(-2-o \ell\)

(c) 2 -Methylpropan \(-1-o \ell\)

(d) 2-Methylpropan \(-2-o \ell\)

3. Which of the following alcohols cannot be prepared by reduction of carbonyl compounds?

(a) Pentan \(-1-o \ell\)

(b) Pentan \(-2-o \ell\)

(c) 2 - Methylpentan \(-2-\mathrm{o} \ell\)

(d) 3 - Methylpentan - \(2-\mathrm{o}\) l

4. Which of the following conversions explains the acidic nature of alcohols?

(a) Ethanol \(\stackrel{\mathrm{H} \mathrm{Br}\}}{\longrightarrow}\) Bromoethane

(b) Ethanol \(\stackrel{\mathrm{N}_2}{\longrightarrow}\) Sodium ethoxide

(c) Ethanol \(\stackrel{\mathrm{Pa}_3}{\longrightarrow}\) Chloroethane

(d) Ethanol \(\stackrel{\mathrm{SOCl}_2}{\longrightarrow}\) Chloroethane

5. Which of the following compounds gives 3 -ethylpentan-3-0 \(\boldsymbol{\ell}\) by the action of ethyl magnesium iodide followed by acid hydrolysis?

(a) Propanone

(b) Butanone

(c) Pentan - 2 - one

(d) Pentan - 3 - one

6. Which of the following compound is obtained as major product on reaction of ethoxybenzene with nitrating mixture?

(a) 2 -Nitro ethoxybenzene

(b) 3 - Nitro ethoxybenzene

(c) 4 - Nitro ethoxybenzene

(d) Nitrobenzene

7. Benzyl phenyl ether reacts with hydrogen bromide to give

(a) benzyl bromide and phenol

(b) benzyl alcohol and bromobenzene

(c) benzyl bromide and bromobenzene

(d) benzyl alcohol and phenol

8. Ethers are considered as

(a) monoalkyl derivatives of water

(b) alkoxy derivatives of alkanes

(c) alkyl derivatives of fatty acids

(d) condensation products of acid and alcohol

9. Which of the following compounds is not isomeric with ethoxyethane?

(a) 1 - Methoxypropane

(b) 2 - Methoxypropane

(c) 2 - Methylpropan - 2 - ol 

(d) 2 - Methylbutan - \(2-\mathrm{ol}\) 

10. Which one of the following compounds dissolves in hot dilute sulphuric acid but does not reacts with sodium metal?

(a) ethyl bromide

(b) acetic acid

(c) ethyl alcohol

(d) diethyl ether

11. Which of the following alcohol will have the fastest rate of dehydration?

12. The phenol having lowest acidity is

13. Pyrogallol is

(a) 1,2-Dihydroxybenzene

(b) Methoxy benzene

(c) 2-Bromophen ol

(d) 1,2,3-Trihydroxybenzene

14. Which of the following is an excellent antiseptic?

(a) Benzaldehyde

(b) Benzyl alcohol

(c) Phenol

(d) Acetia acid

15. Carbolic acid is

16. Which of the following gives anisole?

(a) Phenyl and methyl chloride

(b) Benzyl alcohol and sodium hydroxide

(c) Aniline with nitrous acid

(d) Sodium phenoxide and methyl chloride

17. In the reaction

the compound \(\mathrm{X}\) is

(a) Ethyl alcohol

(b) Isopropyl alcohol

(c) Tert-butyl alcohol

(d) n-Propyl alcohol

18. Which of the following methods does not give phenol?

19. Which of the following groups increases the acidity of phenol?

(a) \(-\mathrm{CN}\)

(b) \(-X\) (halogen)

(c) \(-\mathrm{NO}_2\)

(d) all

20. The reaction

is an example of

(a) Schotten Baumann reaction

(b) Friedel Craft's reaction

(c) Etard reaction

(d) Perkin reaction

21. Vinyl carbinol is

22. Intramolecular hydrogen bonding is found in

(a) o-bromophenol

(b) o-nitrophenol

(c) m-nitrophenol

(d) p-nitrophenol

23. How many isomeric acyclic alcohols and ethers are possible for \(\mathrm{C}_4 \mathrm{H}_8 \mathrm{O}\) ?

(a) 3

(b) 4

(c) 5

(d) 7

24. Unknown compound \((X)\) on hydration by conc. \(\mathrm{H}_2 \mathrm{SO}_4\) gives \((\mathrm{Y})\). The compound \((\mathrm{Y}\) ) on oxidation gives acetone. The compound \((X)\) is

(a) \(\mathrm{CH}_3 \mathrm{CH}=\mathrm{CH}_2\)

(b) \(\mathrm{CH}_3 \mathrm{CH}_2 \mathrm{OH}\)

(c) \(\mathrm{CH}_3 \mathrm{CHOHCH}_3\)

(d) \(\mathrm{CH}_2=\mathrm{CH}_2\)

25. An example of benzylic alcohol is

26. Which of the following isomers of butanol has a chiral structure?

(a) \((\mathrm{CH} 3)_3 \mathrm{CH}_2 \mathrm{OH}\)

(b) \(\left(\mathrm{CH}_3\right)_2 \mathrm{CHCH}_2 \mathrm{OH}\)

(c) \(\mathrm{CH}_3 \mathrm{CH}(\mathrm{OH}) \mathrm{CH}_2 \mathrm{CH}_5\)

(d) \(\mathrm{CH}_3\left(\mathrm{CH}_2\right)_3 \mathrm{OH}\)

27. A compound \(\mathrm{X}\) with molecular formula \(\mathrm{C}_3 \mathrm{H}_8 \mathrm{O}\) can be oxidised to a compound \(Y\) with the molecular formula \(\mathrm{C}_3 \mathrm{H}_6 \mathrm{O}_2 \times \mathrm{X}\) is most likely to be

(a) Primary alcohol

(b) sec. alcohol

(c) aldehyde

(d) ketone

28. Raney nickel is a/an

(a) alloy of \(\mathrm{Al}\) and \(\mathrm{Ni}\) leached in sodium hydroxide solution

(b) alloy of \(\mathrm{Al}\) and Fe leached in caustic soda solution

(c) alloy of \(\mathrm{Fe}\) and \(\mathrm{Co}\) leached in soda bicarbonate

(d) all of these

29. Phenol is less acidic than

(a) Ethanol

(b) Methanol

(c) o-Nitrophenol

(d) p-Methyl phenol

30. The increasing orded of acidity among phenol: p-methyl, m-nitrophenol and p-nitrophenol is

(a) phenol, p-methyl phenol, p-nitriphenol, m-nitrophenol

(b) p-methyl phenol, phenol, m-nitrophenol, p-nitriphenol

(c) p-nitrophenol, m-nitriphenol, phenol, p-methyl phenol

(d) m-nitrophenol, p-nitriphenol, phenol, p-methyl phenol

31. An alcohol having molecular formula \(\mathrm{C}_6 \mathrm{H}_{11} \mathrm{OH}\) on dehydration gives an alkene, which on oxidation yield a mixture of ketone and acid. The alcohol is

32. The correct IUPAC name of the compound \(\mathrm{CH}_3 \mathrm{CH}\left(\mathrm{C}_2 \mathrm{H}_5\right) \mathrm{CH}_2 \mathrm{CH}_2(\mathrm{OH}) \mathrm{CH}_3\) is

(a) 2-Ethylpentan-4-ol

(b) 2-Hyxroxy-4-methyl pentane

(c) 4-Ethylpentan-2-ol

(d) 4-Methylhexan-2-ol

33. Phenol can be industrially prepared from cumene. It is

(a) Isopropyl benzene

(b) o-Dimethylbenzene

(c) Phenyl acetate

(d) 2-Acetoxylbenzoic acdi

34. Consider the following alkyl halides

1) \(\left(\mathrm{CH}_3\right)_3 \mathrm{CBr}\)

2) \(\mathrm{CH}_3 \mathrm{Br}\)

3) \(\mathrm{C}_2 \mathrm{H}_5 \mathrm{Br}\)

4) \(\mathrm{CH}_3 \mathrm{CHBrCH}_3\)

Arrange these alkyl halides in decreasing order of reactivity in Williamson's reaction.

(a) \(2>3>4>1\)

(b) \(4>3>2>1\)

(c) \(1>4>3>2\)

(d) \(1>2>3>4\)

35. Which one of the following compound is most acidic

36. In the reaction

Which of the following compounds will be formed

37. During dehydration of alcohols to alkenes by heating with conc. \(\mathrm{H}_2 \mathrm{SO}_4\), the initial step is

(a) formation of an ester

(b) protonation of alcohol molecule

(c) formation of carbocation

(d) elimination of water

38. Which of the following alcohols cannot be prepared by the action of a suitable Grignard reagent as an aldehyde or a ketone followed by hydrolysis?

(a) Ethyl alcohol

(b) Isopropyl alcohol

(c) n-Propyl alcohol

(d) Methanol

39. The best reagent to convert pent-2-en-2-ol into pent-3-en-2-one is

(a) acidic permagnate

(b) acidc dichromate

(c) chromic anhydride in glacial acetic acid

(d) pyridinium chloro chromate

40. Arrange the following compounds according to decreasing boiling points

(a) (IV) \(>\) (III) \(>\) (II) \(>\) (I)

(b) (III) \(>\) (IV) \(>\) (II) \(>\) (I)

(c) (I) \(>\) (II) \(>\) (III) \(>\) (IV)

(d) (III) \(>\) (II) \(>\) (I) \(>\) (IV)

41. In the following sequence of reactions

The compound ' \(\mathrm{D}\) ' is

(a) n-butyl alcohol

(b) n-propyl alcohol

(c) propanal

(d) butanal

42. Hydrolysis of 2-bromo-2-methylbutane by \(\mathrm{SN}^1\) mechanism gives mainly

(a) 3-methylbutan-2-ol

(b) 2-methylbutan-2-ol

(c) 2,2-dimethylpropan-2-ol

(d) 2-methylbutan-1-ol

43. In the following reaction, \(C\) is

(a) \(\mathrm{H}_2 \mathrm{C}=\mathrm{CH}\)

(b) \(\mathrm{CH}_3 \mathrm{CH}_2 \mathrm{OH}\)

(c) \(\mathrm{C}_2 \mathrm{H}_3-\mathrm{OC}_2 \mathrm{H}_5\)

(d) \(\mathrm{C}_2 \mathrm{H}_5-\mathrm{OS} \mathrm{O}_3 \mathrm{H}\)

44. The compound which is not isomeric with diethyl ether is

(a) n-Propyl methyl ether

(b) butan-1-ol

(c) 2-Methylpropan-2-ol

(d) Butanone

45. The most suitable reagent for the conversion of primary alcohol into aldehyde with the same number of carbon is

(a) acidic \(\mathrm{K}_2 \mathrm{Cr}_2 \mathrm{O}_7\)

(b) acidified \(\mathrm{KMnO}_4\)

(c) Pyridinium chlorochromate

(d) \(\mathrm{CrO}_3\)

46. A compound ' \(X\) ' undergoes reduction with \(\mathrm{LiAlH}_4\) to yield ' \(Y\) '. when vapours of ' \(Y\) ' are passed over freshly reduced copper at \(300^{\circ} \mathrm{C}\), ' \(X\) ' is formed. What is ' \(Y\) '?

(a) \(\mathrm{CH}_3 \mathrm{COCH}_3\)

(b) \(\mathrm{CH}_3 \mathrm{CHO}\)

(c) \(\mathrm{CH}_3 \mathrm{CH}_2 \mathrm{OH}\)

(d) \(\mathrm{CH}_3 \mathrm{OCH}_3\)

47. n-Propyl alcohol and isopropyl alcohol can be chemically distinguished by which reagent?

(a) \(\mathrm{PCl}_5\)

(b) reduction

(c) oxidation with potassium dichromate

(d) ozonolysis

48. When \(\mathrm{CH}_2=\mathrm{CH}-\mathrm{COOH}\) is reduced with \(\mathrm{LiAlH}_4\), the compound obtained will be

(a) \(\mathrm{CH}_3-\mathrm{CH}_2-\mathrm{COOH}\) (b) \(\mathrm{CH}_2=\mathrm{CH}-\mathrm{CH}_2 \mathrm{OH}\)

(c) \(\mathrm{CH}_3-\mathrm{CH}_2-\mathrm{CH}_2 \mathrm{OH}\) (d) \(\mathrm{CH}_3-\mathrm{CH}_2-\mathrm{CHO}\)

49. Which type of carbocation is formed as an intermediate during the dehydration 4,4-dimethylpentanol?

(a) \(1^0\)

(b) \(2^0\)

(c) \(3^0\)

(d) All the three

50. The relative acidic character of \(\mathrm{CH}_3 \mathrm{CH}_2 \mathrm{OH}\), \(\left(\mathrm{CH}_3\right)_2 \mathrm{CHOH}\) and \(\left(\mathrm{CH}_3\right)_3 \mathrm{COH}\) can be explained on the basis of

(a) resonance

(b) inductive effect

(c) hyperconjugation

(d) hybridisation