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

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) \(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{SO}_{3} \mathrm{H}\)

When acetamide is treated with \(\mathrm{NaOBr}\), the product formed is (a) \(\mathrm{CH}_{3} \mathrm{OH}\) (b) \(\mathrm{CH}_{3} \mathrm{NH}_{2}\) (c) \(\mathrm{CH}_{3} \mathrm{CN}\) (d) \(\mathrm{CH}_{3} \mathrm{COBr}\)

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

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 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)

Among the following compound \(\mathrm{C}_{3} \mathrm{H}_{7} \mathrm{NH}_{2}, \mathrm{NH}_{3}\), \(\mathrm{CH}_{3} \mathrm{NH}_{2}, \mathrm{C}_{2} \mathrm{H}_{5} \mathrm{NH}_{2}\) and \(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{NH}_{2}\) the least basic com- pound is (a) \(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{NH}_{2}\) (b) \(\mathrm{C}_{2} \mathrm{H}_{5} \mathrm{NH}_{2}\) (c) \(\mathrm{CH}_{3} \mathrm{NH}_{2}\) (d) \(\mathrm{NH}_{3}\)

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) \(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{~N}=\mathrm{NC}_{6} \mathrm{H}_{5}\) (d) \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{NC}\).

Reaction of aniline with benzaldehyde is a ...... 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

Treatment of ammonia with excess of ethyl iodide will yield (a) diethylamine (b) ethylamine (c) triethylamine (d) tetraethylammonium iodide

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 form 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) \(\mathrm{C}_{2} \mathrm{H}_{3} \mathrm{NH}_{2}\) (d) \(\left(\mathrm{C}_{6} \mathrm{H}_{3}\right)_{2} \mathrm{NH}\)

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) \(\mathrm{R}-\mathrm{X}+\mathrm{NH}_{3} \longrightarrow \longrightarrow\) (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) \(\mathrm{R}-\mathrm{CONH}_{2}+4[\mathrm{H}] \stackrel{\text { LiAlH }_{4}}{\longrightarrow}\)

Which of the following reacts with Hinsberg reagent (Benzene sulphonyl chloride) to form a product, soluble in 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) 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) \(\mathrm{Zn} / \mathrm{NaOH}\)

Among the following, the weakest base is (a) \(\mathrm{CH}_{3} \mathrm{NHCHO}\) (b) \(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{CH}_{2} \mathrm{NH}_{2}\) (c) \(\mathrm{O}_{2} \mathrm{NCH}_{2} \mathrm{NH}_{2}\) (d) \(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{CH}_{2} \mathrm{NHCH}_{3}\)

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 (c) azobenzene (d) nitrobenzene

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) \(\mathrm{RCON}\) (c) \(\mathrm{R} \mathrm{CONHBr}\) (d) 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) \(\mathrm{C}_{2} \mathrm{H}_{5}-\mathrm{NH}-\mathrm{C}_{2} \mathrm{H}_{5}\)

Arrange the following in increasing basicity order: I. \(\mathrm{Cl}_{2} \mathrm{CHCH}_{2} \mathrm{NH}_{2}\) II. \(\mathrm{Cl}_{3} \mathrm{CH}_{2} \mathrm{NH}_{2}\) IV. \(\mathrm{CF}_{3} \mathrm{CH}_{2} \mathrm{NH}_{2}\) (a) \(\mathrm{I}<\mathrm{III}<\mathrm{II}<\mathrm{IV}\) (b) \(\mathrm{II}<\mathrm{IV}<\mathrm{III}<\mathrm{I}\) (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) \(\left(\mathrm{CH}_{3}\right)_{4} \mathrm{~N}^{+} \mathrm{OH}^{-}\)

Which of the following cannot be identified by carbyl amine test? 1\. \(\mathrm{C}_{3} \mathrm{H}_{7} \mathrm{NH}_{2}\) 2\. \(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{NH}_{2}\) 3\. \(\mathrm{C}_{6}{\underline{\phantom{xx}}}^{3} \mathrm{H}_{5}-\mathrm{NH}-\mathrm{C}_{6} \mathrm{H}_{5}\) 4\. \(\left(\mathrm{C}_{3} \mathrm{H}_{7}\right)_{3} \mathrm{~N}\) (a) 2,3 (b) \(1,2,4\) (c) 3,4 (d) \(1,3,4\)

Consider the following reaction: \(\mathrm{C}_{6} \mathrm{H}_{3} \mathrm{NO}_{2} \stackrel{\mathrm{Sn} / \mathrm{HCl}}{\longrightarrow} \mathrm{X} \stackrel{\mathrm{C}_{\mathrm{o}} \mathrm{H}_{3} \mathrm{COCl}}{\longrightarrow} \mathrm{Y}+\mathrm{HCl}\) The product \(\mathrm{Y}\) is (a) azobenzene (b) acetanilide (c) benzanilide (d) hydrazobenzene

What is the end product \(\mathrm{C}\) in this series? \(\mathrm{CH}_{3} \mathrm{CN} \stackrel{\mathrm{Na} / \mathrm{C}_{2} \mathrm{H}_{3} \mathrm{OH}}{\longrightarrow} \mathrm{A} \stackrel{\mathrm{HNO}_{2}}{\longrightarrow} \mathrm{B}\) \(\stackrel{\mathrm{Cu} / 573 \mathrm{~K}}{\longrightarrow} \mathrm{C}\) (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 to form nitrolic acids which dissolve in \(\mathrm{NaOH}\) giving (a) red solution (b) blue solution (c) yellow solution (d) colourless solution

What is the end product in the following sequence of operations? \(\mathrm{C}_{2} \mathrm{H}_{5} \mathrm{NH}_{2} \stackrel{\mathrm{HNO}_{2}}{\longrightarrow} \mathrm{A} \stackrel{\mathrm{PCl}_{3}}{\longrightarrow} \mathrm{B} \stackrel{\mathrm{NH}_{3}}{\longrightarrow} \mathrm{C}\) (a) ethyl cyanide (b) methylamine (c) ethylamine (d) acetamide

The common statement(s) between Curtuis and Hoffmann degradation is/are 1\. Both involve nitrene reaction intermediate 2\. Both involve intramolecular alkyl shift 3\. Curtius reaction gives primary amine while Hoffimann degradation gives secondary amine 4\. Curtius reaction uses \(\mathrm{NaN}_{3}\) while Hofmann degradation uses \(\mathrm{NaOBr}\) (a) \(1,2,3\) (b) \(1,2,4\) (c) \(2,3,4\) (d) \(1,3,4\)

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) \(\mathrm{l}\) and 2 (d) 2 and 4