Chapter 27

Which of the following has lowest solubility in water? (a) \(\left(\mathrm{CH}_{3}\right)_{2} \mathrm{CHOH}\) (b) \(\left(\mathrm{CH}_{3}\right)_{3} \mathrm{COH}\) (c) \(\mathrm{C}_{2} \mathrm{H}_{5} \mathrm{OH}\) (d) \(\mathrm{MeOH}\)

Which of the following has the maximum extent of hydrogen bonding? (a) ethyl amine (b) ammonia (c) ethyl alcohol (d) diethy 1 ether

Which of the following is the most soluble in water? (a) isobutyl alcohol (b) \(\mathrm{n}\)-butyl alcohol (c) sec-hutvl alcohol (d) tert-hutvl alcoholl

An ethyl, alcohol exhibits an acidic character on reaction with (a) hydrogen chloride (b) acetic acid (c) sodium metal (d) acidic \(\mathrm{K}_{2} \mathrm{Cr}_{2} \mathrm{O}_{7}\)

An ether which is liquid at room temperature is (a) \(\mathrm{CH}_{3} \mathrm{OCH}_{3}\) (b) \(\mathrm{C}_{2} \mathrm{H}_{5} \mathrm{OC}_{2} \mathrm{H}_{5}\) (c) \(\mathrm{C}_{2} \mathrm{H}_{5} \mathrm{OCH}_{3}\) (d) none

The most appropriate reagent to convert \(\mathrm{RCOOEt} \longrightarrow \mathrm{RCH}_{2} \mathrm{OH}\) is (a) \(\mathrm{Li} / \mathrm{NH}_{3}\) (liq) (b) \(\mathrm{NaBH}_{4}\) (c) \(\mathrm{LiAlH}_{4}\) (d) \(\mathrm{H}_{2} / \mathrm{Pd}-\mathrm{C}\)

Phenol is less acidic than (a) o-nitrophenol (b) p-methylphenol (c) methanol (d) ethanol

Phenol is less acidic than (a) o-nitrophenol (b) p-methylphenol (c) methanol (d) ethanol

Which of the following does not give iodoform test? (a) \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{OH}\) (b) \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{OH}\) (c) \(\left(\mathrm{CH}_{3}\right)_{2} \mathrm{CHOH}\) (d) \(\mathrm{CH}_{3} \mathrm{COCH}_{3}\)

Diethyl ether is heated with one mole of HI, the products formed are (a) ethyl alcohol and ethyl iodide (b) ethyl iodide only (c) ethyl alcohol only (d) ethyl iodide and ethane

Chemical name of salol is (a) phenyl salicylate (b) methyl salicylate (c) sodium salicylate (d) acetylsalicyclic acid

The only alcohol that can be prepared by the indirect hydration of an alkene is (a) ethyl alcohol (b) propyl alcohol (c) isobutyl alcohol (d) methyl alcohol

Diethyl ether is prepared by passing vapours of ethyl alcohol over a heated catalyst under high temperature and pressure. The catalyst is (a) \(\mathrm{CuO}\) (b) \(\mathrm{Al}_{2} \mathrm{O}_{3}\) (c) \(\mathrm{SiO}_{2}\) (d) \(\mathrm{Ag}_{2} \mathrm{O}\)

Alcohol manufactured from water gas is (a) ethanol (b) butanol (c) isobutanol (d) methanol

Which one of the following compounds will be most readily attacked by an electrophile? (a) phenol (b) toluene (c) benzene (d) chlorobenzene

Carbolic acid is (a) phenyl benzoate (b) salol (c) phenol (d) phenyl acetate

Which compound is known as oil of winter green? (a) phenyl acetate (b) methyl salicylate (c) phenyl salicylate (d) phenyl benzoate

Aspirin is an acetylation product of (a) o-hydroxybenzoic acid (b) p-dihydroxybenzene (c) o-dihydroxybenzene (d) m-hydroxybenzoic acid

Which of the following compounds is resistant to nucleophilic attack by hydroxyl ions? (a) acetonitrile (b) diethyl ether (c) acetamide (d) methyl acetate

Epichlorohydrin is (a) 3-chloropropane (b) 3-chloropropan-1-ol (c) 3 -chloro-1, 2 -epoxypropane (d) none of these

The compound which reacts fastest with Lucas reagent at room temperature is (a) butan - 1-ol (b) butan-2-ol (c) 2 -methylpropan-2-ol (d) 2-methylpropan-1-ol

Glycerol on heating with oxalic acid at \(110^{\circ} \mathrm{C}\) gives (a) ethanol (b) formic acid (c) ethanal (d) ether

Osmium tetroxide is a reagent used for (a) hydroxylation of carbonyl compounds (b) hydroxylation of olefins to form trans-diols (c) hydroxylation of olefins to give cis-diols (d) hydroxylation of acetylenes

In the Libermann's nitroso reaction, sequential changes in the colour of phenol occurs as (a) brown or red \(\longrightarrow\) green \(\longrightarrow\) deep blue (b) red \(\longrightarrow\) deep blue \(\longrightarrow\) green (c) red \(\longrightarrow\) green \(\rightarrow\) white (d) white \(\longrightarrow\) red \(\longrightarrow\) green

Which of the following reactions does not hold true when carried out in the presence of heated copper at \(300^{\circ} \mathrm{C} ?\) (a) phenol \(\longrightarrow\) benzyl alcohol (b) primary alcohol \(\longrightarrow\) aldehyde (c) secondary alcohol \(\longrightarrow\) ketone (d) tertiary alcohol \(\Rightarrow\) olefin

The reaction of Grignard reagent with formaldehyde followed by acidification gives (a) an aldehyde (b) a ketone (c) a carboxylic acid (d) a primary alcohol

When the vapours of ethyl alcohol are passed over red hot copper \(\left(300^{\circ} \mathrm{C}\right)\), the product formed is (a) acetaldehyde (b) acetic acid (c) ethylene (d) none of these

Phenol is heated with phthallic anhydride in presence of conc entrated \(\mathrm{H}_{2} \mathrm{SO}_{4}\). The product gives a pink colour on reacting with an alkali. The product is (a) salicylic acid (b) fluorescein (c) fluorescein (d) phenolphthalein

Which of the following is most acidic? (a) o-cresol (b) phenol (c) p-nitrophenol (d) anisole

The ether that undergoes electrophilic substitution reaction is (a) \(\mathrm{CH}_{3} \mathrm{OCH}_{3}\) (b) \(\mathrm{CH}_{3} \mathrm{OC}_{2} \mathrm{H}_{5}\) (c) \(\mathrm{C}_{2} \mathrm{H}_{5} \mathrm{OC}_{2} \mathrm{H}_{5}\) (d) \(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{OCH}_{3}\)

Organic acid without a carboxylic acid group is (a) picric acid (b) oxalic acid (c) ascorbic acid (d) vinegar

When an ether is exposed to air for sometime, an explosive substance is produced which is (a) TNT (b) super oxide (c) oxide (d) peroxide

HCHO reacts with \(\mathrm{CH}_{3} \mathrm{MgI}\) to give (a) \(\mathrm{CH}_{3} \mathrm{CH}_{2}-\mathrm{OH}\) (b) \(\mathrm{CH}_{3} \mathrm{OH}\) (c) \(\mathrm{CH}_{3} \mathrm{CH}_{2}-\mathrm{I}\) (d) \(\mathrm{CH}_{3} \mathrm{I}\)

Which one of the following sets of reactants is used in Reimer-Tiemann reaction? (a) \(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{OH}+\mathrm{CO}_{2}+\mathrm{KOH}\) (b) \(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{NH}_{2}+\mathrm{CH}_{3} \mathrm{Cl}+\mathrm{KOH}\) (c) \(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{NH}_{2}^{2}+\mathrm{CHCl}_{3}+\mathrm{KOH}\) (d) \(\mathrm{C}_{6} \mathrm{H}_{4} \mathrm{OH}+\mathrm{CHCl}_{3}+\mathrm{KOH}\)

In Williamson synthesis, ethoxyethane is prepared by (a) heating sodium ethoxide with ethyl bromide (b) passing ethanol over heated alumina (c) heating ethanol with dry \(\mathrm{Ag}_{2} \mathrm{O}\) (d) treating ethyl alcohol with excess of at \(430-440 \mathrm{~K}\)

Which of the following reactions will not result in the formation of anisole? (a) sodium phenoxide is treated with methyl iodide (b) phenol and dimethyl sulphate in presence of a base (c) reaction of methylmagnesium iodide with phenol (d) reaction of diazomethane with phenol

Which of the following reactants will react with phenol to give salicylaldehyde after hydrolysis? (a) methyl chloride (b) trichloromethane (c) dichloromethane (d) none of these

Which of the following is a Riemer-Tiemann reaction? (a) \(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{OH}+\mathrm{CCl}_{4} \stackrel{\mathrm{NaOH}}{\longrightarrow}\) salicylic acid (b) \(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{OH}+\mathrm{Zn} \longrightarrow \mathrm{C}_{6} \mathrm{H}_{6}\) (c) \(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{OH}+\mathrm{NaOH} \longrightarrow \mathrm{C}_{6} \mathrm{H}_{5} \mathrm{ONa}\) (d) none of them

Which of the following will not be soluble in sodium bicarbonate? (a) benzenesulphonic acid (b) benzoic acid (c) \(2,4,6\)-trinitrophenol (d) 0 -nitrophenol

Which of the following reactions does not yield an alkyl halide? (a) diethyl ether \(+\mathrm{RCOCl}\) (b) diethyl ether \(+\mathrm{PCl}_{5}\) (c) diethyl ether + HI (d) diethyl ether \(+\mathrm{Cl}_{2}\)

Phenol can be distinguished from ethyl alcohol by all of the following reagents except (a) \(\mathrm{Na}\) (b) \(\mathrm{FeCl}_{3}\) (c) \(\mathrm{Br}_{2} / \mathrm{H}_{2} \mathrm{O}\) (d) \(\mathrm{NaOH}\)

When benzenediazonium chloride is treated with water, the compound formed is (a) \(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{COOH}\) (b) \(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{OH}\) (c) \(\mathrm{C}_{6} \mathrm{H}_{6}\) (d) \(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{NH}_{2}\)

On reacting with oxalic acid at \(503 \mathrm{~K}\), glycerol gives (a) formic acid (b) glyceraldehyde (c) allyl alcohol (d) none of these

Ether is obtained by the reaction of ethyl alcohol and \(\mathrm{H}_{2} \mathrm{SO}_{4}\) at (a) \(474 \mathrm{~K}\) (b) \(383 \mathrm{~K}\) (c) \(413 \mathrm{~K}\) (d) \(273 \mathrm{~K}\)

When phenol is treated with an excess of bromine water, it gives (a) \(2,4,6\)-tribromophenol (b) 2,4 -dibromophenol (c) 0 -and p-bromophenols (d) m-bromophenol

An aromatic ether which is not cleaved by HI even at \(525 \mathrm{~K}\) is (a) \(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{OC}_{6} \mathrm{H}_{5}\) (b) \(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{OC}_{3} \mathrm{H}_{7}\) (c) \(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{OCH}_{3}\) (d) tetrahydrofuran

The alcohol which does not give a stable compound on dehydration is (a) methyl alcohol (b) ethyl alcohol (c) \(\mathrm{n}\)-butyl alcohol (d) n-propyl alcohol

Tert-butyl methyl ether on heating with \(1 \mathrm{M} \mathrm{HI}\) gives (a) \(\mathrm{CH}_{3} \mathrm{I}+\left(\mathrm{CH}_{3}\right)_{3} \mathrm{COH}\) (b) \(\mathrm{CH}_{3} \mathrm{OH}+\left(\mathrm{CH}_{3}\right)_{3} \mathrm{Cl}\) (c) \(\mathrm{CH}_{3} \mathrm{I}+\left(\mathrm{CH}_{3}\right)_{3} \mathrm{Cl}\) (d) none of these

Tert-butyl methyl ether on heating with \(1 \mathrm{M} \mathrm{HI}\) gives (a) \(\mathrm{CH}_{3} \mathrm{I}+\left(\mathrm{CH}_{3}\right)_{3} \mathrm{COH}\) (b) \(\mathrm{CH}_{3} \mathrm{OH}+\left(\mathrm{CH}_{3}\right)_{3} \mathrm{Cl}\) (c) \(\mathrm{CH}_{3} \mathrm{I}+\left(\mathrm{CH}_{3}\right)_{3} \mathrm{Cl}\) (d) none of these

Ethylene reacts with \(1 \%\) cold alkaline \(\mathrm{KMnO}_{4}\) to form (a) ethylene glycol (b) oxalic acid (c) HCHO (d) ethyl alcohol