Chapter 29

Nitrobenzene can be prepared from benzene by using a mixture of concentrated \(\mathrm{HNO}_{3}\) and concentrated \(\mathrm{H}_{2} \mathrm{SO}_{4} .\) In the nitrating mixture, nitric acid acts as a (a) base (b) acid (c) reducing agent (d) catalyst

Amongst the following, the most basic compound is (a) benzylamine (b) aniline (c) acetanilide (d) p-nitroaniline

Which of the following compounds is most basic here (a) diphenyl ammonia (b) dimethyl amine (c) guanidine (d) tri methyl amine

The compound that is most reactive towards electrophilic nitration is (a) benzene (b) nitrobenzene (c) benzoic acid (d) toluene

The melting point is highest for (a) primary amines (b) secondary amines (c) tertiary amines (d) quaternary amines

Carbylamine test is performed in alcoholic KOH by heating a mixture of (a) trihalogenated methane and a primary amine (b) an alkyl halide and a primary amine (c) an alkyl cyanide and a primary amine (d) chloroform and silver powder

Acetamide is treated separately with the following reagents. Which one of these would give methylamine? (a) sodalime (b) \(\mathrm{PCl}_{5}\) (c) \(\mathrm{NaOH}+\mathrm{Br}_{2}\) (d) hot conc. \(\mathrm{H}_{2} \mathrm{SO}_{4}\)

Which of the following reacts with \(\mathrm{NaNO}_{2}+\mathrm{HCl}\) at \(273-278 \mathrm{~K}\) to give alcohol/phenol? (a) \(\mathrm{CH}_{3} \mathrm{NH}_{2}\) (b) \(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{NH}_{2}\) (c) \(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{CH}_{2} \mathrm{NHCH}_{3}\) (d) \(\left(\mathrm{CH}_{3}\right)_{2} \mathrm{NH}\)

Hinsberg reagent is (a) \(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{NO}\) (b) \(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{~N}_{2} \mathrm{Cl}\) (c) \(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{SO}_{2} \mathrm{Cl}\) (d) \(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{SO}_{3} \mathrm{H}\)

The compound which one reaction with aqueous nitrous acid at low temperature produces an oily nitrosamine is (a) methylamine (b) ethylamine (c) triethylamine (d) diethylamine

Which is formed when \(\left(\mathrm{CH}_{3}\right)_{4} \mathrm{NOH}\) is heated? (a) \(\mathrm{C}_{2} \mathrm{H}_{5} \mathrm{NH}_{2}\) (b) \(\left(\mathrm{CH}_{2}\right)_{3} \mathrm{~N}\) (c) \(\mathrm{CH}_{3} \mathrm{NH}_{2}\) (d) \(\left(\mathrm{CH}_{3}\right)_{3} \mathrm{~N}\)

Which of the following is most basic in nature? (a) benzylamine (b) acetamide (c) aniline (d) none of these

An organic compound 'A' having molecular formula \(\mathrm{C}_{2} \mathrm{H}_{3} \mathrm{~N}\), on reduction gave another compound 'B'. Upon treatment with nitrous acid, 'B' gave ethyl alcohol. On warming with chloroform and alcoholic \(\mathrm{KOH}\), it formed an effensive smelling compound ' \(\mathrm{C}\) '. The compound ' \(\mathrm{C}^{\prime}\) is (a) \(\mathrm{CH}_{3} \mathrm{C} \equiv \mathrm{N}\) (b) \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{OH}\) (c) \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{NH}_{2}\) (d) \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{~N} \equiv \mathrm{C}\)

Aniline reacts with which of the following to form a Schiff's base (a) benzaldehyde (b) acetone (c) acetic acid (d) both (a) and (b)

Which of the following gives primary amine on reduction? (a) \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{NO}_{2}\) (b) \(\mathrm{CH}_{3} \mathrm{CH}_{2}-\mathrm{O}-\mathrm{N}=\mathrm{O}\) (c) \(\mathrm{C}_{6} \mathrm{H}_{3} \mathrm{~N}=\mathrm{NC}_{6} \mathrm{H}_{5}\) (d) \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{NC}\).

Reaction of aniline with benzaldehyde is a \ldots...... reaction? (a) addition (b) condensation (c) polymerization (d) substitution

The indicator that is obtained by coupling the diazonium salt of sulphanilic acid with \(\mathrm{N}, \mathrm{N}\)-dimethylaniline is (a) methyl orange (b) phenolphthalene (c) indigo (d) phenanthroline

Nitrobenzene on electrolytic reduction in strongly acidic medium gives (a) aniline (b) m-nitroaniline (c) nitrosobenzene (d) p-aminophenol

The reagent that reacts with nitromethane to fo methylhydroxylamine is (a) \(\mathrm{Zn} / \mathrm{NaOH}\) (b) \(\mathrm{Sn} / \mathrm{HCl}\) (c) \(\mathrm{Zn} / \mathrm{NH}_{4} \mathrm{Cl}\) (d) \(\mathrm{Zn} / \mathrm{HCl}\)

Which amine of the following will not give carbylamine reaction? (a) ethylamine (b) dimethylamine (c) methylamine (d) phenylamine

Which is most basic? (a) \(\mathrm{CH}_{3} \mathrm{NH}_{2}\) (b) \(\left(\mathrm{CH}_{3}\right)_{2} \mathrm{NH}\) (c) \(\mathrm{C}_{2} \mathrm{H}_{5} \mathrm{NH}_{2}\) (d) \(\left(\mathrm{C}_{6} \mathrm{H}_{5}\right)_{2} \mathrm{NH}\)

Which of the following reagent can be used to convert benzenediazonium chloride into benzene? (a) \(\mathrm{H}_{3} \mathrm{PO}_{2}\) (b) \(\mathrm{LiAlH}_{4}\) (c) \(\mathrm{Br}_{2}-\mathrm{H}_{2} \mathrm{O}\) (d) \(\mathrm{CH}_{3} \mathrm{OH}\)

Which of the following reactions does not yield an amine? (a) \(\mathrm{R}-\mathrm{X}+\mathrm{NH}_{3} \longrightarrow\) (b) \(\mathrm{R}-\mathrm{CH}=\mathrm{NOH}+[\mathrm{H}] \stackrel{\mathrm{Na}, \mathrm{C}_{2} \mathrm{H}_{3} \mathrm{OH}}{\longrightarrow}\) (c) \(\mathrm{R}-\mathrm{CN}+\mathrm{H}_{2} \mathrm{O} \stackrel{\mathrm{H}^{+}}{\longrightarrow}\) (d) \(\mathrm{R}-\mathrm{CONH}_{2}+4[\mathrm{H}] \stackrel{\mathrm{LiAlH}_{4}}{\longrightarrow}\)

Which of the following reacts with Hinsberg reagent (Benzene sulphonyl chloride) to form a product, soluble in \(\mathrm{KOH}\) ? (a) primary amine (b) secondary amine (c) tertiary amine (d) quaternary amine

Aniline on reaction with acetyl chloride gives (a) phenol (b) acetamide (c) acetanilide (d) benzene

Mark the correct statement: (a) methylamine is slightly acidic (b) methylamine is less basic than ammonia (c) methylamine is a stronger base than ammonia (d) methylamine forms salts with alkalies

Towards electrophilic substitution, the most reactive will be (a) nitrobenzene (b) aniline (c) aniline hydrochloric (d) \(\mathrm{n}\)-acetylaniline

Nitrobenzene gives n-phenylhydroxyl-amine by (a) \(\mathrm{H}_{2} / \mathrm{Pd}-\mathrm{C}\) (b) \(\mathrm{Sn} / \mathrm{HCl}\) (c) \(\mathrm{Zn} / \mathrm{NH}_{4} \mathrm{Cl}\) (d) \(\mathrm{Zn} / \mathrm{NaOH}\)

Which of the following compounds on treatment with \(\mathrm{NaNO}_{2} / \mathrm{HCl}\) and then coupled with phenol, produces p-hydroxyazobenzene? (a) phenol (b) aniline

Among the following, the dissociation constant is highest for (a) \(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{OH}\) (b) \(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{CH}_{2} \mathrm{OH}\) (c) \(\mathrm{CH}_{3} \mathrm{C} \equiv \mathrm{CH}\) (d) \(\mathrm{CH}_{3} \mathrm{NH}_{3}{\underline{\phantom{xx}}}^{+} \mathrm{Cl}^{-}\)

When a mixture of secondary amines is heated with diethyl oxalate, it forms (a) solid oxamic ester (b) liquid oxamic ester (c) form of oxamic ester (d) gaseous oxamic ester

Which of the following is formed when ethyl carbonate reacts with ammonia? (a) urea (b) urea oxalate (c) ethyl cyanate (d) ethyl nitrate

Among the following which one does not act as an intermediate in Hoffmann rearrangement? (a) RNCO (b) \(\mathrm{RCO} \mathrm{O}\) (c) \(" \mathrm{R} \mathrm{CONHBr}\) (d) \(\mathrm{RNC}\)

Pyridine is less basic than triethylamine because (a) pyridine has aromatic character (b) nitrogen in pyridine is sp \(^{2}\) hybridized (c) pyridine is a cyclic system (d) in pyridine, lone pair of nitrogen is delocalized

KCN react readily to form a cyanide with (a) chlorobenzene (b) ethyl alcohol (c) ethyl bromide (d) bromobenzene

When acetamide is treated with \(\mathrm{Br}_{2}\) and caustic soda, then we get (a) bromoacetic acid (b) acetic acid (c) methylamine (d) ethane

Which of the following behaves both as a nucleophile and as an electrophile? (a) \(\mathrm{CH}_{3}-\mathrm{C} \equiv \mathrm{N}\) (b) \(\mathrm{CH}_{3} \mathrm{OH}\) (c) \(\mathrm{CH}_{2}=\mathrm{CH}-\mathrm{CH}_{3}\) (d) \(\mathrm{CH}_{3} \mathrm{NH}_{2}\)

Which of the following compounds cannot by identified by carbylamine test? (a) \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{NH}_{2}\) (b) \(\mathrm{CH}_{3}-\mathrm{CH}_{2}-\mathrm{CH}_{2}-\mathrm{NH}_{2}\) (c) \(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{NH}_{2}\) (d) \(\mathrm{C}_{2} \mathrm{H}_{5}-\mathrm{NH}-\mathrm{C}_{2} \mathrm{H}_{5}\)

\(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{NH}_{2} \stackrel{\left(\mathrm{CH}_{3} \mathrm{CO}\right)_{2} \mathrm{O}}{\longrightarrow} \mathrm{X} \stackrel{\mathrm{Br} / \mathrm{CCl}_{4}}{\longrightarrow}\) \(\mathrm{Y} \frac{\mathrm{HOH}}{\mathrm{H}^{*}}{\longrightarrow} \mathrm{Z}\) (a) bromoacetophenone (b) o-bromoacetophenone (c) p-bromoaniline (d) o-bromoacetanilide

Arrange the following in increasing basicity order: I. \(\mathrm{Cl}_{2} \mathrm{CHCH}_{2} \mathrm{NH}_{2}\) II. \(\mathrm{Cl}_{3} \mathrm{CH}_{2} \mathrm{NH}_{2}\) III. NC1CCCCC1 IV. \(\mathrm{CF}_{3} \mathrm{CH}_{2} \mathrm{NH}_{2}\) (a) \(\mathrm{I}<\mathrm{III}<\mathrm{II}<\mathrm{IV}\) (b) \(\mathrm{II}<\mathbb{I V}<\mathrm{III}<\mathrm{I}\) (c) \(\mathrm{IV}<\mathrm{II}<\mathrm{I}<\mathrm{III}\) (d) \(\mathrm{I}<\mathrm{II}<\mathrm{IV}<\mathrm{III}\)

Which compound will liberate \(\mathrm{CO}_{2}\) from \(\mathrm{NaHCO}_{3}\) solution? (a) \(\mathrm{CH}_{3} \mathrm{NH}_{2}\) (b) \(\mathrm{CH}_{3} \mathrm{CONH}_{2}\) (c) \(\mathrm{CH}_{3} \mathrm{~N}^{+} \mathrm{H}_{3} \mathrm{Cl}^{-}\) (d) \(\left(\mathrm{CH}_{3}\right)_{4} \mathrm{~N}^{+} \mathrm{OH}^{-}\)

A compound 'A' when treated with \(\mathrm{HNO}_{3}\) (in the presence of \(\mathrm{H}_{2} \mathrm{SO}_{4}\) ) gives compound 'B', which is then reduced with \(\mathrm{Sn}\) and \(\mathrm{HCl}\) to aniline? The compound 'A' is (a) acetamide (b) ethane (c) benzene (d) toluene

Consider the following reaction: \(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{NO}_{2} \stackrel{\mathrm{Sn} / \mathrm{HCl}}{\longrightarrow} \mathrm{X} \stackrel{\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{COCl}}{\longrightarrow} \mathrm{Y}+\mathrm{HCl}\) The product \(\mathrm{Y}\) is (a) azobenzene (b) acetanilide (c) benzanilide (d) hydrazobenzene

What is the end product \(\mathrm{C}\) in this series? \(\mathrm{CH}_{3} \mathrm{CN} \stackrel{\mathrm{Na} / \mathrm{C}_{2} \mathrm{H}_{5} \mathrm{OH}}{\longrightarrow}\) \(\mathrm{A} \stackrel{\mathrm{HNO}_{2}}{\longrightarrow} \mathrm{B}\) \({ }^{\mathrm{Cu} / 573 \mathrm{~K}}{\longrightarrow} \mathrm{C}\) (a) \(\mathrm{CH}_{3} \mathrm{COOH}\) (b) \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{NHOH}\) (c) \(\mathrm{CH}_{3} \mathrm{CONH}_{2}\) (d) \(\mathrm{CH}_{3} \mathrm{CHO}\)

Primary nitro compounds react with nitrous acid ts form nitrolic acids which dissolve in \(\mathrm{NaOH}\) giving (a) red solution (b) blue solution (c) vellow solution (d) colourless solution

Which of the following chemicals are used to manufacture methyl isocyanate that caused the Bhopal gas tragedy? (1) methylamine (2) phosgene (3) phosphine (4) dimethylamine (a) 1 and 3 (b) 3 and 4 (c) 1 and 2 (d) 2 and 4

Benzenediazonium chloride on reaction with phenol in weakly basic medium gives (a) diphenyl ether (b) p-hydroxyazobenzene (c) chlorobenzene (d) benzene

Peroxide effect can be checked by the addition of sufficient amount of (a) monophenyl amine (b) diphenyl amine (c) triphenyl amine (d) pentaphenyl amine

Ethyl chloride on heating with \(\mathrm{AgCN}\) forms a compounds \(\mathrm{X}\). The functional isomer of \(\mathrm{X}\) will be (a) \(\mathrm{C}_{2} \mathrm{H}_{5} \mathrm{NH}_{2}\) (b) \(\mathrm{C}_{2} \mathrm{H}_{5} \mathrm{NC}\) (c) \(\mathrm{C}_{2} \mathrm{H}_{5} \mathrm{CN}\) (d) none of these

Identify the correct statement among the following. (a) \(\mathrm{n}, \mathrm{n}\)-dimethylaniline reacts with nitrous acid to give p-nitroso-N,N-dimethyl aniline (b) bromination of p-toluidine produces 3,5 -dibromo, 4-methylaniline (c) aliphatic amines are less basic than ammonia (d) aliphatic primary amines combine with nitrous acid under ice-cold conditions to form stable diazonium salts