Chapter 29

Among the following compounds, which will react with acetone to give a product containing \(>\mathrm{C}=\mathrm{N}-\) ? 1\. \(\mathrm{C}_{6} \mathrm{H}_{3} \mathrm{NH}_{2}\) 2\. \(\left(\mathrm{CH}_{3}\right)_{3} \mathrm{~N}\) 3\. \(\mathrm{C}_{6} \mathrm{H}_{3} \mathrm{NHC}_{6} \mathrm{H}_{5}\) 4\. \(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{NHNH}_{2}\) (a) 3,4 (b) \(1,3,4\) (c) 1,3 (d) 1,4

Identify C in this series. \(\mathrm{CH}_{3} \mathrm{CN} \stackrel{\mathrm{Na} / \mathrm{C}_{2} \mathrm{H}_{3} \mathrm{OH}}{\longrightarrow} \mathrm{A} \stackrel{\mathrm{HNO}_{2}}{\longrightarrow} \mathrm{B} \stackrel{[\mathrm{O}]}{\longrightarrow} \mathrm{C}\) (a) \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{NHOH}\) (b) \(\mathrm{CH}_{3} \mathrm{COOH}\) (c) \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CONH}_{2}\) (d) \(\mathrm{CH}_{3} \mathrm{CHO}\)

Benzamide on reaction with \(\mathrm{POCl}_{3}\) gives (a) aniline (b) chlorobenzene (c) benzyl amine (d) benzonitrile

Reaction of \(\mathrm{RCONH}_{2}\) with a mixture of \(\mathrm{Br}_{2}\) and \(\mathrm{KOH}\) gives \(\mathrm{RNH}_{2}\) as the main product. The intermediate involved in the reaction are 1\. RCONHBr 2\. \(\mathrm{R}-\mathrm{NHBr}\) 3\. \(\mathrm{R}-\mathrm{N}=\mathrm{C}=\mathrm{O}\) 4\. \(\mathrm{RCONBr}_{2}\) (a) \(1,2,3\) (b) \(1,3,4\) (c) 1,3 (d) 1,2

Among the following, the strongest base is (a) \(\mathrm{C}_{6} \mathrm{H}_{3} \mathrm{NH}_{2}\) (b) \(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{CH}_{2}-\mathrm{NH}_{2}\) (c) \(\mathrm{p}-\mathrm{NO}_{2}-\mathrm{C}_{6} \mathrm{H}_{4} \mathrm{NH}_{2}\) (d) \(\mathrm{m}-\mathrm{NO}_{2}-\mathrm{C}_{6} \mathrm{H}_{4} \mathrm{NH}_{2}\)

Compound \(\mathrm{A}\) on reduction gives \(\mathrm{B}\), which on further reaction with \(\mathrm{CHCl}_{3}\) and alcoholic KOH gives compounds \(\mathrm{C}\), which on further hydrolysis gives aniline. The compound \(\mathrm{A}\) is (a) nitrosobenzene (b) methylamine (c) nitromethane (d) nitrobenzene

\(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{Cl} \stackrel{\mathrm{NaCN}}{\longrightarrow} \mathrm{X} \stackrel{\mathrm{Ni} / \mathrm{H}_{2}}{\longrightarrow} \mathrm{Y}\) acetic anhydride \({\longrightarrow} \mathrm{Z}\) \(\mathrm{Z}\) in the above reaction sequence is (a) \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{CONHCONH}_{3}\) (b) \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{NH}_{2}\) (c) \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{CONHCH}_{3}\) (d) \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{NHCOCH}_{3}\)

\(\mathrm{R}-\mathrm{Cl}+\mathrm{AgCN} \longrightarrow \mathrm{A} \stackrel{\text { reductions }}{\longrightarrow} \mathrm{B}\) \(A\) and \(B\) respectively are (a) \(\mathrm{RCN}, \mathrm{RCH}_{2} \mathrm{NH}_{2}\) (b) \(\mathrm{RNC}, \mathrm{RNHCH}_{3}\) (c) \(\mathrm{RCN}, \mathrm{RNHCH}_{3}\) (d) \(\mathrm{RNC}, \mathrm{RCH}_{2} \mathrm{NH}_{2}\)

In a set of reactions propionic acid yielded a compound D. \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{COOH} \stackrel{\mathrm{SOCl}_{2}}{\longrightarrow} \mathrm{B} \stackrel{\mathrm{NH}_{3}}{\longrightarrow} \mathrm{C} \stackrel{\mathrm{KOH}}{\mathrm{Br}_{\mathrm{z}}} \mathrm{D}\) The structure of D would be (a) \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{NHCH}_{3}\) (b) \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{NH}_{2}\) (c) \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{NH}_{2}\) (d) \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CONH}_{2}\)

Identify \(\mathrm{X}\) and \(\mathrm{Y}\) in the following sequence. \(\mathrm{C}_{2} \mathrm{H}_{3} \mathrm{Br} \stackrel{\mathrm{X}}{\longrightarrow}\) product \(\stackrel{\mathrm{Y}}{\longrightarrow} \mathrm{C}_{3} \mathrm{H}_{7} \mathrm{NH}_{2}\) (a) \(\mathrm{X}=\mathrm{KCN}, \mathrm{Y}=\mathrm{LiAlH}_{4}\) (b) \(\mathrm{X}=\mathrm{KCN}, \mathrm{Y}=\mathrm{H}_{3} \mathrm{O}^{+}\) (c) \(\mathrm{X}=\mathrm{CH}_{3} \mathrm{Cl}, \mathrm{Y}=\mathrm{AlCl}_{3} / \mathrm{HCl}\) (d) \(\mathrm{X}=\mathrm{CH}_{3} \mathrm{NH}_{2}, \mathrm{Y}=\mathrm{HNO}_{2}\)

Which of the following is more basic than aniline? (a) p-nitroaniline (b) benzylamine (c) diphenylamine (d) triphenylamine

Which of the following statements relating to aniline is not true? (a) aniline on Schotten-Baumann reaction gives benzanilide (b) aniline cannot be prepared by the reduction of benzonitrile with \(\mathrm{LiAlH}_{4}\) (c) on heating with concentrated \(\mathrm{H}_{2} \mathrm{SO}_{4}\) at \(180^{\circ} \mathrm{C}\), aniline gives sulphanilic acid (d) aniline liberates nitrogen on treatment with ice cold nitrous acid

Aniline is less basic than (a) 4-nitroaniline (b) 4-aminobenzaldehyde (c) anilinium hydrochloride (d) dimethyl amine

para chloroaniline and anilinium hydrochloride can be distinguished by 1\. Sandmeyer reaction 2\. \(\mathrm{AgNO}_{3}\) 3\. Carbylamine reaction 4\. \(\mathrm{NaHCO}_{3}\) (a) \(1,3,4\) (b) \(1,2,4\) (c) \(1,2,3,4\) (d) \(2,3,4\)

Nitrosoamines \(\left(\mathrm{R}_{2} \mathrm{~N}-\mathrm{N}=\mathrm{O}\right)\) are insoluble in water. On heating them with conc. \(\mathrm{H}_{2} \mathrm{SO}_{4}\). They give secondary amines. The reaction is called (a) Fries reaction (b) Etard reaction (c) Lieberman nitroso reaction (d) Perkin reaction

Arrange the following: \(\mathrm{I} \mathrm{CH}_{3} \mathrm{NH}_{2}\) \(\mathrm{II}\left(\mathrm{CH}_{3}\right)_{2} \mathrm{NH}\) \(\mathrm{III} \mathrm{C}_{6} \mathrm{H}_{5} \mathrm{NH}_{2}\) and IV \(\left(\mathrm{CH}_{3}\right)_{3} \mathrm{~N}\) in increasing order of basicity in aqueous medium. (a) \(\mathrm{II}<\mathrm{I}<\mathrm{IV}<\mathrm{III}\) (b) II \(<\mathrm{III}<\mathrm{I}<\mathrm{IV}\) (c) \(\mathrm{I}<\mathrm{II}<\mathrm{III}<\mathrm{IV}\) (d) \(\mathrm{III}<\mathrm{IV}<\mathrm{I}<\mathrm{II}\)

Electrolytic reduction of nitrobenzene in strongly acidic medium gives (a) azoxybenzene (b) aniline (c) p-aminophenol (d) phenylhydroxyl amine

The correct sequence of reagents used for conversion of aniline into benzylamine is (a) \(\mathrm{NaNO}_{2} / \mathrm{HCl}, \mathrm{CuCN}, \mathrm{Sn} / \mathrm{HCl}\) (b) \(\mathrm{NaNO}_{2} / \mathrm{HCl}, \mathrm{CuCN}, \mathrm{H}_{3} \mathrm{O}^{+}\) (c) \(\mathrm{NaNO}_{2} / \mathrm{HCl}, \mathrm{Cu}^{+} / \mathrm{H}_{3} \mathrm{PO}_{2}, \mathrm{CH}_{3} \mathrm{NH}_{2}\) (d) None

Among the following, the strongest base is (a) \(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{NH}_{2}\) (b) \(\mathrm{p}-\mathrm{NO}_{2}-\mathrm{C}_{6} \mathrm{H}_{4} \mathrm{NH}_{2}\) (c) \(\mathrm{m}-\mathrm{NO}_{2}-\mathrm{C}_{6} \mathrm{H}_{4} \mathrm{NH}_{2}\) (d) \(\mathrm{C}_{6} \mathrm{H}_{3} \mathrm{CH}_{2} \mathrm{NH}_{2}\)

Among the following statements on the nitration of aromatic compounds, the false one is (a) the rate of nitration of benzene is almost the same as the hexadeuterobenzene (b) the rate of nitration of toluene is greater than that of benzene (c) nitration is an electrophilic substitution reaction (d) the rate of nitration of benzene is greater than that of hexadeuterobenzene

When nitrobenzene is treated with \(\mathrm{Br}_{2}\) in presence of \(\mathrm{FeBr}_{3}\), the major product formed is m-bromonitrobenzene. The statements which are related to obtain the \(\mathrm{m}\)-isomer are 1\. The electron density on meta carbon is more than at ortho and para positions 2\. the intermediate carbonium ion formed after initial attack of \(\mathrm{Br}^{+}\)at the meta positions is least destabilized 3\. loss of aromaticity when \(\mathrm{Br}^{+}\)attacks at the ortho and para positions and not at m-position 4\. easier loss of \(\mathrm{H}+\) to regain aromaticity from the meta position than from ortho and para positions (a) 1,2 (b) 1,3 (c) \(1,3,4\) (d) 1,4

Which of the following reactions result in the formation of amines? (a) (b) \(\mathrm{C}_{6} \mathrm{H}_{3}-\mathrm{NC} \stackrel{\mathrm{H}^{*} \mid \mathrm{H}_{2} \mathrm{O}}{\longrightarrow}\) (c) \(\mathrm{CH}_{3}-\mathrm{CH}_{2}-\mathrm{N}=\mathrm{C}=\mathrm{O} \stackrel{\text { aq. } \mathrm{KOH}}{\longrightarrow}\) (d) \(\mathrm{CH}_{3}-\mathrm{COOH}+\mathrm{HN}_{3} \stackrel{\text { conc. } \mathrm{H}_{2} \mathrm{SO}_{4}}{\longrightarrow}\)

\(\mathrm{p}-\) Nitroaniline is obtained by (a) 1,4 dinitrobenzene \(\stackrel{\mathrm{NH}_{4} \mathrm{HS}}{\longrightarrow}\) (b) Benzene sulphonic acid \(\stackrel{\mathrm{HNO}_{3} / \mathrm{H}_{2} \mathrm{SO}_{4}}{\longrightarrow}\) (c) Aniline \(\frac{1 . \text { Acetylation } 2 . \mathrm{HNO}_{3} / \mathrm{H}_{2} \mathrm{SO}_{4}}{\text { 3. aq. } \mathrm{NaOH}, \Delta}\) (d) Aniline \(\frac{1 . \mathrm{HNO}_{3} / \mathrm{H}_{2} \mathrm{SO}_{4}}{2 . \mathrm{aq} \cdot \mathrm{NaOH}}\)

An insecticide SEVIN is made by the reaction of 1 - naphthol with methyl isocyanate. A union carbide plant in Bhopal, India, were using this process to make SEVIN for use as an agricultural insecticide. On December 3,1984 , either by accident or by sabotage, a value was opened that admitted water to a large tank of methyl isocyanate. The pressure and temperature within the tank rose very high and the pressure relief value opened to prevent the tank from bursting. A large quantity of methyl isocyanate rushed through the pressure relief valves and the vapours flowed with the breeze into populated areas, killing about 2500 people and injuring many more. The pressure rise in the container (tank) was due to liberation of (a) \(\mathrm{CH}_{4}\) (b) \(\mathrm{NH}_{3}\) (c) \(\mathrm{CO}\) (d) \(\mathrm{CO}_{2}\)

An insecticide SEVIN is made by the reaction of 1 - naphthol with methyl isocyanate. A union carbide plant in Bhopal, India, were using this process to make SEVIN for use as an agricultural insecticide. On December 3,1984 , either by accident or by sabotage, a value was opened that admitted water to a large tank of methyl isocyanate. The pressure and temperature within the tank rose very high and the pressure relief value opened to prevent the tank from bursting. A large quantity of methyl isocyanate rushed through the pressure relief valves and the vapours flowed with the breeze into populated areas, killing about 2500 people and injuring many more. The temperature rise in the tank was attributed to (a) Dissolution of \(\mathrm{CH}_{3}-\mathrm{N}=\mathrm{C}=\mathrm{O}\) in water (b) Dissolution of \(\mathrm{CH}_{3} \mathrm{NH}_{2}\) in water. (c) Dissolution of \(\mathrm{NH}_{3}\) in water. (d) Dissolution of \(\mathrm{CO}_{2}\) in water.

Benzene diazonium chloride is obtained by the diazotization of aniline It gives two types of reactions in which nitrogen atoms are replaced and reactions in which nitrogen atoms are retained. For the above reaction, the reactivity of the diazonium ion will be maximum when \(\mathrm{G}\) is (a) \(-\mathrm{HSO}_{3}\) (b) \(-\mathrm{Cl}\) (c) \(-\mathrm{OCH}_{3}\) (d) \(-\mathrm{CH}_{3}\)

$$ \begin{aligned} &\text { 6. Match the following }\\\ &\begin{array}{ll} \hline \text { Column-I (Substrate) } & \text { Column-II (Reagent) } \\ \hline \text { (a) } \mathrm{R}-\mathrm{CH}_{2}-\mathrm{NH}_{2} & \text { (p) } \mathrm{KMn} \mathrm{O}_{4}, \mathrm{H}^{+} \\ \text {(b) } \mathrm{R}_{2} \mathrm{CH}-\mathrm{NH}_{2} & \text { (q) } \mathrm{H}_{2} \mathrm{SO}_{5} \\ \text { (c) } \mathrm{R}_{2} \mathrm{NH} & \text { (r) } \mathrm{O}_{3} \\ \text { (d) } \mathrm{R}_{3} \mathrm{~N} & \text { (s) } \mathrm{H}_{2} \mathrm{O}_{2} \\ & \text { (t) } \mathrm{HNO}_{2} \\ \hline \end{array} \end{aligned} $$

Piperidine is subjected to exhaustive methylation and the quaternary iodide is heated with moist \(\mathrm{Ag}_{2} \mathrm{O}\) and the number of double bonds present in the product formed is/are

Of the following the number of compounds which answer Fehling's test is Glucose, \(\alpha\)-hydroxyl ketone, glyoxal, p-chlorobenzaldehyde, glyoxalic acid, succinaldehyde.

The number of \(\mathrm{N}-\mathrm{CH}_{2}-\mathrm{N}\) bonds in urotropine is

The \(\mathrm{pK}_{a}\) of the carboxyl group in valine, \(\left(\mathrm{CH}_{3}\right)_{2} \mathrm{CH}\) \(\mathrm{CH} \mathrm{NH}_{2} \mathrm{COOH}\) is \(2.31\) and \(\mathrm{pK}_{\mathrm{a}}\) for the amino group of the acid is \(9.69 .\) The isoelectric point of the valine is

The total number of isomers which are primary amines with a molecular formula \(\mathrm{C}_{4} \mathrm{H}_{7} \mathrm{~N}\), having no \(\mathrm{C} \equiv \mathrm{C}\) bond is

How many of the following amines can be used for the symmetrical cleavage of diborane? \(\mathrm{CH}_{3} \mathrm{NH}_{2},\left(\mathrm{CH}_{3}\right)_{2} \mathrm{NH},\left(\mathrm{C}_{2} \mathrm{H}_{3}\right)_{3} \mathrm{~N},\left(\mathrm{CH}_{3}\right)_{3} \mathrm{~N},\left(\mathrm{C}_{2} \mathrm{H}_{3}\right)_{2} \mathrm{NH}\), \(\mathrm{C}_{2} \mathrm{H}_{5} \mathrm{NH}_{2}, \mathrm{C}_{5} \mathrm{H}_{5} \mathrm{~N}\), (i \(\left.-\mathrm{Pr}\right)_{3} \mathrm{~N}\), quinuclidine

On heating benzyl amine with chloroform and ethanolic KOH, the product obtained is (a) benzyl alcohol (b) benzaldehyde (c) benzonitrile (d) benzyl isocyanide

A substance forms zwitter ion. It can have functional groups \([2002]\) (a) \(-\mathrm{NH}_{2},-\mathrm{COOH}\) (b) \(-\mathrm{NH}_{2},-\mathrm{SO}_{3} \mathrm{H}\) (c) both (d) none of these

In an organic compound of molar mass is \(108 \mathrm{~g} \mathrm{~mol}^{-1}\). \(\mathrm{C}, \mathrm{H}\) and \(\mathrm{N}\) atoms are present in \(9: 1: 35\) by weight in it. Molecular formula can be (a) \(\mathrm{C}_{6} \mathrm{H}_{8} \mathrm{~N}_{2}\) (b) \(\mathrm{C}_{7} \mathrm{H}_{10} \mathrm{~N}\) (c) \(\mathrm{C}_{5} \mathrm{H}_{6} \mathrm{~N}_{3}\) (d) \(\mathrm{C}_{4} \mathrm{H}_{18} \mathrm{~N}_{3}\)

When a primary amine reacts with chloroform in ethanolic KOH, the product formed is (a) an aldehyde (b) an alcohol (c) a cyanide (d) an isocyanide

Ethyl isocyanide on hydrolysis in acidic medium generates [2003] (a) ethylamine salt and methanoic acid (b) propanoic acid and ammonium salt (c) ethanoic acid and ammonium salt (d) methylamine salt and ethanoic acid

The correct order of increasing basic nature for the bases \(\mathrm{NH}_{3}, \mathrm{CH}_{3} \mathrm{NH}_{2}\), and \(\left(\mathrm{CH}_{3}\right)_{2} \mathrm{NH}\) is \([\mathbf{2 0 0 3}]\) (a) \(\mathrm{NH}_{3}<\mathrm{CH}_{3} \mathrm{NH}_{2}<\left(\mathrm{CH}_{3}\right)_{2} \mathrm{NH}\) (b) \(\left(\mathrm{CH}_{3}\right)_{2} \mathrm{NH}<\mathrm{NH}_{3}<\mathrm{CH}_{3} \mathrm{NH}_{2}\) (c) \(\mathrm{CH}_{3} \mathrm{NH}_{2}<\left(\mathrm{CH}_{3}\right)_{2} \mathrm{NH}<\mathrm{NH}_{3}\) (d) \(\mathrm{CH}_{3} \mathrm{NH}_{2}<\mathrm{NH}_{3}<\left(\mathrm{CH}_{3}\right)_{2} \mathrm{NH}\)

Amongst the following, the most basic compound is [2004] (a) benzylamine (b) aniline (c) acetanilide (d) p-nitroaniline

Which one of the following methods is neither meant for the synthesis nor for separation of amines? [2005] (a) Hinsberg method (b) Hoffmann method (c) Wurtz reaction (d) Curtius reaction

An organic compound having molecular mass 60 is found to contain \(\mathrm{C}=20 \%, \mathrm{H}=6.67 \%\) and \(\mathrm{N}=\) \(46.67 \%\) while rest is oxygen. On heating, it gives \(\mathrm{NH}_{3}\) along with a solid residue. The solid residue gives violet colour with alkaline copper sulphate solution. The compound is (a) \(\mathrm{CH}_{3} \mathrm{NCO}\) (b) \(\mathrm{CH}_{3} \mathrm{CONH}_{2}\) (c) \(\left(\mathrm{NH}_{2}\right)_{2} \mathrm{CO}\) (d) \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CONH}_{2}\)

Which of the following is the strongest base in Aqueous solution? (a) Trimethylamine (b) Aniline (c) Dimethylamine (d) Methyl amine

Toluene is nitrated and resulting product is reduced with \(\mathrm{Sn} / \mathrm{HCl}\). The product is now diazotised and then heated with cuprous bromide. The reaction mixture so formed contains. \(\quad\) [2008] (a) mixture of o, p bromo benzene (b) mixture of o, p bromo aniline (c) mixture of o, m bromo toluene (d) mixture of o, p bromo toluene

A compound with molecular mass 180 its acrylated with \(\mathrm{CH}_{3} \mathrm{COCl}\) to get a compound with molecular mass 390 . The number of amino groups present per molecular of the former compound is (a) 4 (b) 6 (c) 2 (d) 5