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) diethyl ether

Which of the following is the most soluble in water? (a) isobutyl alcohol (b) n-butyl alcohol (c) sec-butyl alcohol (d) tert-butyl alcohol

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

The compound which gives the most stable carbonium ion on dehydration is (a) \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{OH}\) (b) \(\left(\mathrm{CH}_{3}\right)_{3} \mathrm{COH}\) (c) \(\left(\mathrm{CH}_{3}\right)_{2} \mathrm{CHCH}_{2} \mathrm{OH}\) (d) \(\mathrm{CH}_{3} \mathrm{CHOHCH}_{2} \mathrm{CH}_{3}\)

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

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) \(\mathrm{Ag}_{2} \mathrm{O}\)

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

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 \(\longrightarrow\) 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) \(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{NH}_{2}+\mathrm{CHCl}_{3}+\mathrm{KOH}\) (d) \(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{OH}^{2}+\mathrm{CHCl}_{3}+\mathrm{KOH}\)

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 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 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 \(+\mathrm{Cl}_{2}\)

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) \(273 \mathrm{~K}\)

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) \(273 \mathrm{~K}\)

The reaction of an aromatic aryl chloride and phenol in the presence of the base \(\mathrm{NaOH}\) or pyridine, is called (a) Kolbe's reaction (b) Perkin reaction (c) Sandmeyer's reaction (d) Schotten-Baumann reaction

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 \(1 \mathrm{M}\) 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

Ethyl chloride is converted into diethyl ether in (a) Wurtz reaction (b) Grignard reaction (c) Perkin reaction (d) Williamson synthesis

The reaction of \(\mathrm{CO}_{2}\) with sodium phenoxide at \(400 \mathrm{~K}\) results in the formation of (a) salicyaldehdye (b) sodium benzoate (c) benzoic acid (d) sodium salicylate

The distillation of phenol with zinc dust gives (a) \(\mathrm{C}_{6} \mathrm{H}_{5}-\mathrm{C}_{6} \mathrm{H}_{5}\) (b) \(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{OC}_{6} \mathrm{H}_{5}\) (c) \(\mathrm{C}_{6} \mathrm{H}_{6}\) (d) \(\mathrm{C}_{6} \mathrm{H}_{12}\)

When diethyl ether is treated with an excess of \(\mathrm{Cl}_{2}\) in the presence of sunlight, the product formed is (a) \(\mathrm{CH}_{3} \mathrm{CHCl}-\mathrm{O}-\mathrm{CH}_{2} \mathrm{CH}_{3}\) (b) \(\mathrm{CH}_{3} \mathrm{CHCl}-\mathrm{O}-\mathrm{CHClCH}_{3}\) (c) \(\mathrm{CCl}_{3} \mathrm{CCl}_{2}-\mathrm{O}-\mathrm{CCl}_{2} \mathrm{CCl}_{3}\) (d) \(\mathrm{CH}_{7} \mathrm{CCl}_{2}-\mathrm{O}-\mathrm{CHClCH}_{3}\)

The ionization constant of phenol is higher than that of ethanol because (a) phenoxide ion is a stronger base than ethoxide ion (b) phenoxide ion is stabilized through delocalization electron (c) phenoxide ion is less stable than ethoxide ion (d) phenoxide ion is bulkier than ethoxide ion

Absolute alcohol (100\% alcohol) is prepared by 6 distilling rectified spirit over (a) \(\mathrm{Mg}\left(\mathrm{OC}_{2} \mathrm{H}_{5}\right)_{2}\) (b) \(\mathrm{CaCl}_{2}\) (c) \(\mathrm{Na}\) (d) \(\mathrm{Mg}\)

Three moles of ethanol react with one mole of phosphorus tribromide to form 3 moles of bromoethane and one mole of \(\mathrm{X}\). Which of the following is \(X ?\) (a) \(\mathrm{H}_{3} \mathrm{PO}_{3}\) (b) \(\mathrm{H}_{3} \mathrm{PO}_{2}\) (c) \(\mathrm{H}_{3} \mathrm{PO}_{4}\) (d) \(\mathrm{HPO}_{3}\)