Chapter 27

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) \(\mathrm{CH}_{3} \mathrm{CCl}_{2}-\mathrm{O}-\mathrm{CHClCH}_{3}\)

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

Benzylamine reacts with nitrous acid to form (a) benzene (b) benzyl alcohol (c) phenol (d) azobenzene

When ethylene glycol is heated with acidified potassium permanganate, the main organic compound obtained is (a) acetaldehyde (b) glyoxal (c) formic acid (d) oxalic acid

n-propyl alcohol and isopropyl alcohol can be chemically distinguished by (a) reduction (b) \(\mathrm{PCl}_{3}\) (c) ozonolysis (d) oxidation with potassium dichromate

The molecule which the highest boiling point is (a) \(\mathrm{CH}_{3}-\mathrm{CHCl}-\mathrm{CH}_{3}\) (b) \(\mathrm{CH}_{3}-\mathrm{CHOH}-\mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{OH}\) (c) \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{Cl}\) (d) \(\mathrm{CH}_{3}-\mathrm{CHOH}-\mathrm{CH}_{3}\)

The major product formed during hydroborationoxidation of 1 -methylcyclopentene is (a) CC1CCCC1O (b) CC1(C=O)CCCC1 (c) CC1(C)CCCC1O (d) CC1CCCC1O

\(\mathrm{H}\) Which of the following reacts fastest with conc. HCl \(\left(\varphi\right.\) is \(\left.\mathrm{C}_{6}-\mathrm{H}_{5}\right) ?\) (a) \(\varphi-\mathrm{CH}_{2}-\mathrm{CH}_{2}-\mathrm{OH}\) (b) \(\varphi-\mathrm{CHOH}-\mathrm{CH}_{3}\) (c) \(\mathrm{CH}_{3}-\mathrm{OH}\) (d) \(\mathrm{CH}_{2}=\mathrm{CH}-\mathrm{CH}_{2} \mathrm{OH}\)

The final product \(\mathrm{B}\) in the following reaction is \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}=\mathrm{CH}_{2} \underset{\left(\mathrm{C}_{6} \mathrm{H}_{3} \mathrm{CO}_{2}\right)_{2}}{\stackrel{\mathrm{NBS}, \mathrm{hv}}{\mathrm{CH}_{2} \mathrm{OH}}} \mathrm{A} \frac{\mathrm{CH}_{3} \mathrm{SNa}}{\longrightarrow} \mathrm{B}\) (a) methyl 1-methylallylsulphide (b) allyl methyl sulphide (c) n-butyl methyl sulphide (d) diallyl sulphide

The correct order of boiling points for primary \(\left(1^{\circ}\right)\), secondary ( \(2^{\circ}\) ) and tertiary ( \(\left.3^{\circ}\right)\) alcohols is (a) \(1^{\circ}>2^{\circ}>3^{\circ}\) (b) \(3^{\circ}>2^{\circ}>1^{\circ}\) (c) \(2^{\circ}>1^{\circ}>3^{\circ}\) (d) \(2^{\circ}>3^{\circ}>1^{\circ}\)

The correct order of increasing boiling points is (a) isobutane \(<\mathrm{n}\)-butane \(<\mathrm{n}\)-butyl chloride \(<\mathrm{n}\)-butanol (b) isobutane \(<\mathrm{n}\)-butyl chloride \(<\mathrm{n}\)-butane \(<\mathrm{n}\)-butanol (c) \(\mathrm{n}\)-butane \(<\mathrm{n}\)-butanol \(<\mathrm{n}\)-butyl chloride \(<\) isobutane (d) \(\mathrm{n}\)-butane \(<\) isobutane \(<\mathrm{n}\)-butyl chloride \(<\mathrm{n}\)-butanol

In the following sequence of reactions, \(\mathrm{CH}_{3}-\mathrm{CH}\left(\mathrm{NH}_{2}\right)-\mathrm{CH}_{3} \stackrel{\mathrm{HNO}_{2}}{\longrightarrow} \mathrm{A}\) \(\stackrel{\text { oxidation }}{\longrightarrow} \mathrm{B} \frac{\text { (i) } \mathrm{CH}_{3} \mathrm{Mgl}}{\text { (ii) } \mathrm{H}^{-} / \mathrm{H}_{2} \mathrm{O}} \mathrm{C}\) the compound \(\mathrm{C}\) formed will be (a) butanol-1 (b) 2-methylpropanol-1 (c) 2 -methylpropanol-2 (d) butanol-2

Which is dehydrated with the greatest ease using concentrated \(\mathrm{H}_{2} \mathrm{SO}_{4} ?\) (a) CC1(O)CCCC(=O)C1 (b) O=C1CCC(O)CC1 (c) O=C1CCCCC1O (d) CC1C(=O)CCCC1O

Which of the following compounds will have the highest value of dipole moment? (a) O=[N+]([O-])c1cccc(O)c1 (b) O=[N+]([O-])c1ccc(O)cc1 (c) O=[N+]([O-])c1ccccc1O (d) O=[N+]([O-])c1ccccc1

An unknown compound dissolves in sulphuric acid, but does not decolourize bromine water and does not react with sodium. Which of the following classes of molecules behave in this manner? (a) phenol (b) alkene (c) alcohol (d) ether

The three products obtained in the reaction between glycerol and excess hydroiodic acid would include in that order (a) allyl iodide, propene and isopropyl iodide (b) allyl iodide, isopropyl iodide and propene (c) isopropyl iodide, allyl iodide and propene (d) propene, allyl iodide and isopropyl iodide

Which one of the following compounds will give a yellow precipitate on warming with a solution of iodine and aqueous alkali? (a) \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{OCH}_{2} \mathrm{CH}_{3}\) (b) \(\left(\mathrm{CH}_{3}\right)_{3} \mathrm{COH}\) (c) CCC(C)O (d) \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{OH}\)

The alcohol, \(\mathrm{C}_{4} \mathrm{H}_{9} \mathrm{OH}\), when shaken with a mixture of anhydrous \(\mathrm{ZnCl}_{2}\) and concentrated HCl gave an immediate oil layer product. The alcohol is (a) \(\left(\mathrm{CH}_{3}\right)_{2} \mathrm{CHCH}_{2}-\mathrm{OH}\) (b) \(\left(\mathrm{CH}_{3}\right)_{3} \mathrm{C}-\mathrm{OH}\) (c) \(\mathrm{H}_{3} \mathrm{C}-\mathrm{CH}(\mathrm{OH}) \mathrm{CH}_{2} \mathrm{CH}_{3}\) (d) \(\mathrm{H}_{3} \mathrm{C}-\left(\mathrm{CH}_{2}\right)_{3}-\mathrm{OH}\)

Periodic acid oxidizes (a) 1,4 -diols (b) 1,3 -diols (c) 1,2 -diols (d) \(\beta\)-ketoaldehyde

When one of the following compounds will react with Grignard reagent to yield a primary alcohol containing two more carbons? (a) \(\mathrm{CH}_{3} \mathrm{CHO}\) (b) C1COC1 (c) HCHO (d) \(\mathrm{CH}_{3} \mathrm{COCH}_{3}\)

Alkene \(\mathrm{R}-\mathrm{CH}=\mathrm{CH}_{2}\) reacts with \(\mathrm{B}_{2} \mathrm{H}_{6}\) in the presence of \(\mathrm{H}_{2} \mathrm{O}_{2}\) to give (a) (b) [R]C(C)=O [R]OC(C)(O)O (c) \(\mathrm{R}-\mathrm{CH}_{2}-\mathrm{CHO}\) (d) \(\mathrm{R}-\mathrm{CH}_{2}-\mathrm{CH}_{2}-\mathrm{OH}\)

For phenol, p-methylphenol, m-nitrophenol and p-nitrophenol the order of increasing acidic strength is (a) Phenol, \(\quad\) p-methylphenol, \(\mathrm{p}\)-nitrophenol, m-nitrophenol (b) p-methylphenol, phenol, m-nitrophenol, p-nitrophenol (c) p-methylphenol, m-nitrophenol, phenol, p-nitrophenol (d) m-nitrophenol, p-nitrophenol, phenol, p-Methylphenol

An organic compound ' \(X\) ' on treatment with acidified \(\mathrm{K}_{2} \mathrm{Cr}_{2} \mathrm{O}_{7}\) gives a compound ' \(\mathrm{Y}\) ' which reacts with \(\mathrm{I}_{2}\) and sodium carbonate to form triiodomethane. The compound ' \(\mathrm{X}^{\prime}\) is (a) \(\mathrm{CH}_{3} \mathrm{CHOHCH}_{3}\) (b) \(\mathrm{CH}_{3} \mathrm{CHO}\) (c) \(\mathrm{CH}_{3} \mathrm{COCH}_{3}\) (d) \(\mathrm{CH}_{3} \mathrm{OH}\)

The compound obtained by the reaction of ethene with diborane, followed by hydrolysis with alkaline hydrogen peroxide is (a) ethanal (b) ethanol (c) triethyl boride (d) propanol

Heating methyl phenyl ether with HI gives (a) methanol + iodobenzene (b) methyl alcohol + benzyl alcohol (c) methyl iodide \(+\) phenol (d) methyl iodide + iodobenzene

Higher homologues of ethers can be prepared by (a) diazomethane (b) Grignard reagent (c) alkyl halides (d) none of these

\(\mathrm{CH}_{2}=\mathrm{CH}_{2} \frac{\mathrm{X}}{\mathrm{Ag}} \rightarrow \mathrm{X} \frac{\text { steam }}{473 \mathrm{~K}}-\mathrm{Y}\) The compound \(Y\) is (a) ethylene glycol (b) epoxyethane (c) ethanal (d) ethanol

To prepare 3 -ethylpentan-3-ol, the reagents needed are (a) \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{MgBr}+\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{COCH}_{2} \mathrm{CH}_{3}\) (b) \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{MgBr}+\mathrm{CH}_{3} \mathrm{COCH}_{2} \mathrm{CH}_{3}\) (c) \(\mathrm{CH}_{3} \mathrm{MgBr}+\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{COCH}_{2} \mathrm{CH}_{3}\) (d) \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{MgBr}+\mathrm{CH}_{3}^{2} \mathrm{COCH}_{2} \mathrm{CH}_{3}\)

1-phenylethanol can be prepared by the reaction of benzaldehyde with (a) methyl iodide and magnesium (b) methyl bromide and aluminium bromide (c) ethyl iodide and magnesium (d) methyl bromide

Conversion of cyclohexene to cyclohexanol can be conveniently achieved by (a) hyboration-hydrolysis (b) hydroboration-oxidation (c) \(\mathrm{NaOH}-\mathrm{H}_{2} \mathrm{O}\) (d) \(\mathrm{Br}_{2}-\mathrm{H}_{2} \mathrm{O}\)

An organic compound (A) reacts with sodium metal and forms (B). On heating with concentrated \(\mathrm{H}_{2} \mathrm{SO}_{4}\), (A) gives diethyl ether. (A) and (B) are respectively (a) \(\mathrm{C}_{2} \mathrm{H}_{5} \mathrm{OH}\) and \(\mathrm{C}_{2} \mathrm{H}_{5} \mathrm{ONa}\) (b) \(\mathrm{C}_{3} \mathrm{H}_{7} \mathrm{OH}\) and \(\mathrm{CH}_{3} \mathrm{ONa}\) (c) \(\mathrm{CH}_{3} \mathrm{OH}\) and \(\mathrm{CH}_{3} \mathrm{ONa}\) (d) \(\mathrm{C}_{4} \mathrm{H}_{9} \mathrm{OH}\) and \(\mathrm{C}_{4} \mathrm{H}_{9} \mathrm{ONa}\)

Which of the following facts explains as to why p-nitrophenol is more acidic than phenol? 1\. \(-\) I effect of nitro group 2\. Greater resonance effect of p-nitrophenoxy group 3\. Steric effect of bulky nitro group Select the correct answer using the codes given below: (a) 2 and 3 (b) 1 and 3 (c) 1 and 2 (d) 2 alone

Ethanol and dimethyl ether form a pair of functional isomers. The boiling point of ethanol is higher than that of dimethyl ether due to the presence of (a) H-bonding in dimethyl ether (b) H-bonding in ethanol (c) \(\mathrm{CH}_{3}\) group in ethanol (d) \(\mathrm{CH}_{3}\) group in dimethyl ether

What amount of bromine will be required to convert \(2 \mathrm{~g}\) of phenol into \(2,4,6\)-tribromophenol? (a) \(6.0\) (b) \(8.0\) (c) \(10.22\) (d) \(20.44\)

The reaction of elemental sulphur with Grignard reagent followed by acidification leads to the formation of (a) sulphoxide (b) mercaptan (c) sulphonic acid (d) thioester

Which of the following is the most suitable method for removing the traces of water from ethanol? (a) Heating with sodium metal (b) Hassing dry HCl gas through it (c) Distilling it (d) Reacting with \(\mathrm{Mg}\)

Product \(\mathrm{C}\) in the following reaction, will be \(\mathrm{C}_{2} \mathrm{H}_{5} \mathrm{Br} \stackrel{\mathrm{aq} \cdot \mathrm{NaOH}}{\longrightarrow} \mathrm{A} \stackrel{\mathrm{Na}}{\longrightarrow} \mathrm{B} \stackrel{\mathrm{CH}_{3} \mathrm{I}}{\longrightarrow} \mathrm{C}\) (a) ethane (b) ethyl methyl ether (c) ethyl iodide (d) propane

Isopropyl alcohol is obtained by reacting which of the following alkenes with concentrated \(\mathrm{H}_{2} \mathrm{SO}_{4}\) followed by boiling with water? (a) 2 -methylpropene (b) ethylene (c) isoprene (d) propylene

The reaction of \(\mathrm{CH}_{3} \mathrm{MgBr}\) with acetone and hydrolysis of the resulting product gives (a) \(\left(\mathrm{CH}_{3}\right)_{3} \mathrm{COH}\) (b) \(\left(\mathrm{CH}_{3}\right)_{2} \mathrm{CHOH}\) (c) \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{OH}\) (d) \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{OH}\)

Which of the following compounds on reaction with \(\mathrm{CH}_{3} \mathrm{MgBr}\) will give a tertiary alcohol? (a) CC1COC1C (b) \(\mathrm{C}_{2} \mathrm{H}_{5} \mathrm{CO}_{2} \mathrm{CH}_{3}\) (c) \(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{CHO}\) (d) \(\mathrm{C}_{2} \mathrm{H}_{5} \mathrm{COOH}\)

Oxymercuration-demercuration reaction of 1 -methylcyclohexene gives (a) trans-2-methyl cyclohexanol (b) cis-2-methylcyclohexanol (c) 1 -methylcyclohexanol (d) mixture of cis-and trans-2-methylcyclohexanol

In the reaction sequence, \(\mathrm{Z}\) will be Glycerol \(\stackrel{\mathrm{KHSO}_{4} / \Delta}{\longrightarrow} \mathrm{X} \stackrel{\mathrm{Zn}-\mathrm{Hg} / \mathrm{conc} \mathrm{HCl} / \Delta}{\longrightarrow}\) \(\mathrm{Y} \stackrel{\mathrm{NBS} / \mathrm{CCl}_{4}}{\longrightarrow} \mathrm{Z}\) (a) 1,2 -dibromopropane (b) 1-bromopropane (c) 2-bromopropane (d) 3-bromopropene

2-phenylethanol may be prepared by the reaction of phenylmagnesium bromide with (a) \(\mathrm{HCHO}\) (b) \(\mathrm{CH}_{3} \mathrm{COCH}_{3}\) (c) C1CO1 (d) \(\mathrm{CH}_{3} \mathrm{CHO}\)

The reagent used for the preparation of higher ethers from halogenated ethers is (a) sodium alkoxide (b) Grignard reagent (c) concutrated \(\mathrm{H}_{2} \mathrm{SO}_{4}\) (d) dry silver oxide

A compound is soluble in concentrated \(\mathrm{H}_{2} \mathrm{SO}_{4}\). It does not decolourize bromine in carbon tetrachloride but is oxidized by chromic anhydride in aqueous sulphuric acid within two seconds, turning the orange solution to blue, then green and finally opaque. The original compound is (a) an alkane (b) an ether (c) a tertiary alcohol (d) a primarv alcohol