Chapter 26

Which of the following compound reacts with chlorobenzene to produce DDT? (a) trichloroacetaldehyde (b) m-chloroacetaldehyde (c) acetaldehyde (d) nitrobenzene

Chloroform is slowly oxidized by air in the presence of light and air to form (a) phosgene (b) formyl chloride (c) formaldehyde (d) trichloroethanol

The reaction of the formation of bromobenzyl chloride with \(\mathrm{NaCN}\) in ethanol leads to (a) 4-bromo-2-cyanobenzyl chloride (b) 4 -cyanobenzyl cyanide (c) 4 -cyanobenzyl chloride (d) 4 -bromobenzyl cyanide

The end product [B] in the following sequence of reactions is \(\mathrm{CH}_{3} \mathrm{Cl} \stackrel{\mathrm{KCN}}{\longrightarrow}[\mathrm{A}] \stackrel{\mathrm{H} / \mathrm{H}_{2} \mathrm{O}}{\longrightarrow}[\mathrm{B}]\) (a) \(\mathrm{HCOOH}\) (b) \(\mathrm{CH}_{3} \mathrm{COCH}_{3}\) (c) \(\mathrm{CH}_{3} \mathrm{NH}_{2}\) (d) \(\mathrm{CH}_{3} \mathrm{COOH}\)

\(\mathrm{CH}_{3}-\mathrm{CH}_{2}-\mathrm{CH}_{2}-\mathrm{Cl} \stackrel{\text { alc. } \mathrm{KOH}}{\longrightarrow}(\mathrm{X}) \stackrel{\mathrm{HBr}}{\longrightarrow}(\mathrm{Y}) \stackrel{\mathrm{Na}_{\text {ether }}}{\longrightarrow}(\mathrm{Z})\) In the above sequence of reaction, the product \((Z)\) is (a) propane (b) hexane (c) 2,3 -dimethylbutane (d) allyl bromide

\(\mathrm{R}-\mathrm{OH}+\mathrm{HX} \longrightarrow \mathrm{R}-\mathrm{X}+\mathrm{H}_{2} \mathrm{O}\) In the above reaction, the reactivity of different alcohols is (a) tertiary \(>\) secondary \(>\) primary (b) tertiary \(>\) secondary \(<\) primary (c) tertiary \(<\) secondary \(>\) primary (d) secondary \(<\) primary < tertiary

Under which of the following conditions would toluene \(\mathrm{C}_{6} \mathrm{H}_{5}-\mathrm{CH}_{3}\), be converted into bromomethyl benzene, \(\mathrm{C}_{6} \mathrm{H}_{3}-\mathrm{CH}_{2} \mathrm{Br} ?\) (a) reaction with \(\mathrm{Br}_{2}\) in dark (b) reaction with \(\mathrm{Br}_{2} / \mathrm{FeBr}_{3}\) (c) reaction with \(\mathrm{Br}_{2}^{-}\)in sunlight (d) reaction with \(\mathrm{HBr}\)

The number of isomeric alkyl halides possible for \(\mathrm{C}_{5} \mathrm{H}_{11} \mathrm{Cl}\) is (a) 5 (b) 6 (c) 4 (d) 8

Chlorination of toluene in the presence of light and heat followed by treatment with aqueous \(\mathrm{NaOH}\) gives (a) p-cresol (b) o-cresol (c) benzoic acid (d) 2,4 -dihydroxytoluene

The reaction of benzyl chloride with sodium cyanide followed by reduction with hydrogen in the presence of nickel gives (a) n-isobutylaniline (b) \(\beta\)-phenylethylamine (c) aniline (d) benzylamine

Which of the following is an example of \(\mathrm{S}_{\mathrm{N}^{2}}\) reaction? (a) \(\mathrm{CH}_{3} \mathrm{Br}+\mathrm{OH} \longrightarrow \mathrm{CH}_{3} \mathrm{OH}+\mathrm{Br}\) (b) CC(Br)CC(O)CBr (c) \(\mathrm{CH}_{3}-\mathrm{CH}_{2}-\mathrm{OH} \underset{\text { Heat }}{\mathrm{H}_{2}} \longrightarrow \mathrm{H}_{2} \mathrm{O}+\mathrm{H}_{2} \mathrm{C}=\mathrm{CH}_{2}\) (d)

The pesticide DDT slowly changes to (a) p, p-dichlorodiphenyldichloroethene (b) p, p'-dichlorodiphenyldichloroethane (c) p, p'-dichlorodiphenylethene (d) \(\mathrm{CCl}_{3}-\mathrm{CHO}\) and chlorobenzene

An alkyl chloride produces a single alkene on reaction with sodium ethoxide and ethanol. The alkene further undergoes hydrogenation to yield 2 -methylbutane. Identify the alkyl chloride from amongst the following. (a) \(\mathrm{ClCH}_{2} \mathrm{CH}\left(\mathrm{CH}_{3}\right) \mathrm{CH}_{2} \mathrm{CH}_{3}\) (b) \(\mathrm{ClCH}_{2} \mathrm{C}\left(\mathrm{CH}_{3}\right)_{2} \mathrm{CH}_{3}\) (c) \(\mathrm{ClCH}_{2} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{CH}_{3}\) (d) \(\mathrm{CH}_{3} \mathrm{C}(\mathrm{Cl})\left(\mathrm{CH}_{3}\right) \mathrm{CH}_{2} \mathrm{CH}_{3}\)

A set of compounds in which the reactivity of halogen atom in the ascending order is (a) chloroethane, chlorobenzene, vinyl chloride (b) chlorobenzene, vinyl chloride, chloroethane (c) vinyl chloride, chloroethane, chlorobenzene (d) vinyl chloride, chlorobenzene, chloroethane

In the following groups: 1\. \(-\) OAc 2\. - OMe 3\. \(-\mathrm{OSO}_{2} \mathrm{Me}\) 4\. \(-\mathrm{OSO}_{2} \mathrm{CF}_{3}\) the order of leaving group ability is (a) \(1>2>3>4\) (b) \(4>3>1>2\) (c) \(4>2>1>3\) (d) \(2>3>4>1\)

At higher temperature, iodoform reaction is given by (a) \(\mathrm{CH}_{3} \mathrm{CO}_{2} \mathrm{CH}_{3}\) (b) \(\mathrm{CH}_{3} \mathrm{CO}_{2} \mathrm{C}_{6} \mathrm{H}_{5}\) (c) \(\mathrm{CH}_{3} \mathrm{CO}_{2} \mathrm{C}_{2} \mathrm{H}_{5}\) (d) \(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{CO}_{2} \mathrm{CH}_{3}\)

Allyl chloride on dehydrochlorination gives (a) propylene (b) acetone (c) propadiene (d) allyl alcohol

Identify \(Z\) in the following series: \(\mathrm{CH}_{2}=\mathrm{CH}_{2} \stackrel{\mathrm{HBr}}{\longrightarrow} \mathrm{X} \stackrel{\text { Hydrolysis }}{\rightarrow} \mathrm{Y} \stackrel{\mathrm{I}_{2} \text { Excess }}{\longrightarrow} \mathrm{Z}\) (a) \(\mathrm{CHI}_{3}\) (b) \(\mathrm{CH}_{3} \mathrm{CHO}\) (c) \(\mathrm{C}_{2} \mathrm{H}_{5} \mathrm{I}\) (d) \(\mathrm{C}_{2} \mathrm{H}_{5} \mathrm{OH}\)

During debromination of meso-dibromobutane, the major compound formed is (a) n-butane (b) 1 -butane (c) cis-2-butene (d) trans-2-butene

The products formed when alcoholic silver nitrile reacts with ethyl bromide are 1\. cthyne 2\. ethene 3\. nitroethane 4\. ethyl alcohol 5\. ethyl nitrile (a) 3,5 (b) 3,4 (c) \(2,3,5\) (d) 1,5

1-chlorobutane on reaction with alcoholic potash gives (a) 1 -butene (b) 1 -butanol (c) 2 -butene (d) 2-butanol

n-propyl bromide on treatment with ethanolic potassium hydroxide produces (a) propane (b) propene (c) propyne (d) propanol

Which one of the following compounds undergoes substitution at a slower rate than benzene and yet yields predominantly ortho and para products? (a) phenol (b) chlorobenzene (c) nitrobenzene (d) benzene sulphonic acid

An organic compound \(\mathrm{X}\left(\mathrm{C}_{4} \mathrm{H}_{4} \mathrm{Cl}\right)\) on reaction with \(\mathrm{Na} /\) diethylether gives a hydrocarbon which on monochlorination gives only one chloro derivative then, \(\mathrm{X}\) is (a) t-butyl chloride (b) s-butyl chloride (c) iso-butyl chloride (d) \(\mathrm{n}\)-butyl chloride

Propyl benzene reacts with bromine in presence of light or heat to give (a) CC(Br)Cc1ccccc1 (b) CCC(Br)c1ccccc1 (c) CCCc1ccccc1Br (d) BrCCCc1ccccc1

Identify the final product (C) in the following sequence of reactions. \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{I} \stackrel{\text { Alc. } \mathrm{KOH}, \Delta}{\longrightarrow}(\mathrm{A}) \stackrel{\mathrm{Br}_{2}}{\longrightarrow}(\mathrm{B}) \stackrel{\mathrm{KCN}}{\longrightarrow}(\mathrm{C})\) (a) \(\mathrm{NCCH}_{2} \mathrm{CH}_{2} \mathrm{CN}\) (b) \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{Br}\) (c) \(\mathrm{CH}_{3} \mathrm{CH}_{2}^{2} \mathrm{CN}\) (d) \(\mathrm{BrCH}_{2} \mathrm{CH}_{2} \mathrm{CN}\)

Consider the following sequence of reactions \(\left(\mathrm{CH}_{3}\right)_{2} \mathrm{CHBr} \stackrel{\text { Ethanolic KOH }}{\longrightarrow}(\mathrm{X}) \stackrel{\mathrm{Br}_{2}}{\longrightarrow}(\mathrm{Y})\) \(\frac{\mathrm{NaNH}_{2}}{\mathrm{liq} \cdot \mathrm{NH}_{3}}\) The end product \((Z)\) is (a) propane (b) propyne (c) propene (d) propan-2-al

Which one is the correct statement? (a) 2 -butene is Saytzeff's product (b) 1 -butene is the Hofmann product (c) both (a) and (b) are correct (d) none is correct

Replacement of \(\mathrm{Cl}\) of chlorobenzene to give phenol requires drastic conditions, but chlorine of 2,4 dinitrochlorobenzene is readily replaced because (a) \(-\mathrm{NO}_{2}\) makes the ring electron rich at ortho and para positions (b) \(-\mathrm{NO}_{2}\) withdraws electrons at meta position (c) \(-\mathrm{NO}_{2}\) donates electrons at meta position (d) \(-\mathrm{NO}_{2}\) withdraws electrons at ortho and para positions

The refluxing of the silver salt of the carboxylic acid in \(\mathrm{CCl}_{4}\) to form haloalkane or haloarene is called (a) Friedel-Crafts reaction (b) Wittig reaction (c) Hoffmann's bromamide reaction (d) Hunsdiecker reaction

A compound \(\mathrm{P}\left(\mathrm{C}_{3} \mathrm{H}_{6} \mathrm{Cl}_{2}\right)\) on reaction with an alkali either gives a compound \(\mathrm{Q}\left(\mathrm{C}_{3} \mathrm{H}_{6} \mathrm{O}\right)\) or \(\mathrm{R}\left(\mathrm{C}_{3} \mathrm{H}_{4}\right) .\) On oxidation, \(Q\) gives a compound \(\mathrm{C}_{2} \mathrm{H}_{6} \mathrm{O}_{2} . \mathrm{R}\), on reacting with dilute \(\mathrm{H}_{2} \mathrm{SO}_{4}\) containing \(\mathrm{Hg}^{2+}\) ion, gives a compound \(\mathrm{S}\left(\mathrm{C}_{3} \mathrm{H}_{6} \mathrm{O}\right)\), which reacts with bromine and alkali to give sodium salt of \(\mathrm{C}_{2} \mathrm{H}_{4} \mathrm{O}_{2}\). Then \(\mathrm{P}\) is (a) \(\mathrm{CH}_{2} \mathrm{ClCH}_{2} \mathrm{CH}_{2} \mathrm{Cl}\) (b) \(\mathrm{CH}_{3}^{2} \mathrm{CCl}_{2} \mathrm{CH}_{3}^{2}\) (c) \(\mathrm{CH}_{1} \mathrm{CHClCH}_{2} \mathrm{Cl}\) (d) \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CHCl}_{2}\)

Which of the following product is obtained when o-xylene is treated with \(\mathrm{Br}_{2}\) in the presence of iron?

A compound \(\mathrm{X}\left(\mathrm{C}_{3} \mathrm{H}_{\mathrm{s}} \mathrm{Br}_{2}\right)\) gives an aldehyde \(\mathrm{Y}\) upon hydrolysis. Oxidation of \(\mathrm{Y}\) gives a dibasic acid of which only one mono-nitro derivative can be obtained. Identify X.

Which of the following statements is/are correct? 1\. \(\mathrm{CH}_{3} \mathrm{CHCl}_{2} \mathrm{CH}_{3}\) is a secondary alkyl halide. 2\. Acetylene is formed when \(\mathrm{CH}_{2}=\mathrm{CH}-\mathrm{Cl}\) is heated with water. 3\. Iodoform gives a precipitate with AgNO, solution on heating, whereas chloroform does not. 4\. Freon \(\left(\mathrm{CCl}_{2} \mathrm{~F}_{2}\right)\) is prepared by the action of \(\mathrm{CCl}_{4}\) and \(\mathrm{SbF}_{3}\) in the presence of \(\mathrm{SbCl}_{5}\) as a catalyst. (a) 1,2 and 3 (b) 2,3 and 4 (c) 1,3 and 4 (d) 3 and 4

The decreasing order of reactivity of I. m-nitrobromobenzene II. 2, 4, 6-trinitrobromobenzene III. p-nitrobromobenzene IV. and 2,4 -dinitrobromobenzene towards \(\mathrm{OH}\) ions is (a) \(\mathbb{I}>\mathrm{II}>\mathrm{III}>\mathrm{IV}\) (b) \(\mathrm{II}>\mathrm{IV}>\mathrm{I}>\mathrm{III}\) (c) \(\mathrm{II}>\mathrm{IV} \geq \mathrm{III}>\mathrm{I}\) (d) \(\mathrm{IV}>\mathrm{II} \geq \mathrm{III}>1\)

Match List I (compound) with List II (use) and select the correct answer using the codes given below the lists: List I List II (Compound) (Use) I. acetylsalicylic A. insecticide II. DDT B. drug III. naphthalene C. moth repellent IV. carbon tetrachloride D. fire extinguisher \(\mathrm{E}\). refrigerant (a) \(I-E, I I-A, I I I-C, I V-D\) (b) I-B, II-C, III-D, IV-A (c) \(\mathrm{I}-\mathrm{E}, \mathrm{II}-\mathrm{C}, \mathrm{III}-\mathrm{D}, \mathrm{IV}-\mathrm{A}\) (d) I-B, II-A, III-C, IV-D

Consider the following haloalkanes: 1\. \(\mathrm{CH}_{3} \mathrm{~F}\) 2\. \(\mathrm{CH}_{3} \mathrm{Cl}\) 3\. \(\mathrm{CH}_{3} \mathrm{Br}\) 4\. \(\mathrm{CH}_{3} \mathrm{I}\) The increasing order of reactivity in nucleophilic substitution reaction is (a) \(4<3 \leq 2<1\) (b) \(1<3<2<4\) (c) \(1<2<3<4\) (d) \(1<2<4<3\)

Which of the following will give a positive carbylamine test? 1\. \(\mathrm{H}_{3} \mathrm{C}-\mathrm{NH}_{2}\) 2\. \(\mathrm{H}_{3} \mathrm{C}-\mathrm{NH}-\mathrm{CH}_{3}\) 3\. \(\left(\mathrm{CH}_{3}\right)_{3} \mathrm{~N}\) 4\. \(\mathrm{C}_{6} \mathrm{H}_{5}-\mathrm{NH}_{2}\) Select the correct answer using the codes given below. (a) 1 and 3 (b) 2 and 4 (c) 1 and 4 (d) 3 and 4

Aryl halides are less reactive towards nucleophilic substitution reactions as compared to alkyl halides due to 1\. the formation of less stable carbonium ion 2\. resonance stabilization 3\. longer carbon-halogen bond 4\. the inductive effect 5\. sp \(^{2}\) hybridized carbon attached to halogen (a) \(1,2,3\) (b) \(2,4,5\) (c) 2,5 (d) 4,5

Which of the following order represents the increasing order of reactivity towards \(\mathrm{Br}\) under \(\mathrm{S}_{\mathrm{N}}{\underline{\phantom{xx}}}^{1}\) conditions? 1\. vinyl chloride 2\. methyl chloride 3\. ethyl chloride 4\. allyl chloride (a) \(4<3 \leq 2<1\) (b) \(1<2 \leq 3<4\) (c) \(2<1<3<4\) (d) \(2<1<4<3\)

Which of the following will not form a Grignard reagent on treatment with \(\mathrm{Mg}\) in dry ether? (a) \(\mathrm{BrCH}_{2} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{Br}\) (b) \(\mathrm{Br} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{Br}\) (c) \(\mathrm{BrCH}_{2} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{Br}\) (d) All the three above can form Grignard reagent.

Ethyl bromide can be convert into ethyl alcohol by: (a) Heating with aqueous KOH. (b) Heating with alc \(\mathrm{KOH}\) (c) Heating with dry silver oxide (d) Heating with moist silver oxide.

Identify the reaction in which Hofmann product could be the major product? (a) 2- chlorohexane \(\frac{\mathrm{C}_{2} \mathrm{H}_{5} \mathrm{O}^{-}}{\mathrm{C}_{2} \mathrm{H}_{3} \mathrm{OH}}\) (b) 2 - fluorohexane \(\frac{\mathrm{C}_{2} \mathrm{H}, \mathrm{O}^{-}}{\mathrm{C}_{2} \mathrm{H}_{6} \mathrm{OH}}\) (c) 2-iodohexane \(\frac{\mathrm{C}_{2} \mathrm{H}_{5} \mathrm{O}^{-}}{\mathrm{C}_{2} \mathrm{H}_{3} \mathrm{OH}}\) (d) 2 - bromohexane \(\frac{\mathrm{C}_{2} \mathrm{H}_{3} \mathrm{O}^{-}}{\mathrm{C}_{2} \mathrm{H}_{3} \mathrm{OH}}\)

Consider the following statements for Friedel Craft's reaction. Which of the following statement is incorrect? (a) The entering alkyl group is an activating group; hence polyalkylation is possible. (b) Rearrangement in alkylating group is possible when the Lewis acid used is \(\mathrm{AlCl}_{3}\). (c) Aryl halides are more effect than alkyl halide as halide component. (d) Aromatic compounds containing m-directing group cannot give this reaction

Match the following: List I (Reactants) 1\. \(\mathrm{CH}_{3}\left(\mathrm{CH}_{2}\right), \mathrm{OH} \stackrel{\text { Nalfr. } \mathrm{H}_{1} \mathrm{SO}_{4} \mathrm{~A}}{\longrightarrow}\) 2\. \(\left(\mathrm{CH}_{3}\right)_{3} \mathrm{COH} \frac{\mathrm{Com} \cdot \mathrm{HCl}}{\text { Roan } \mathrm{km}}\) 3\. \(\mathrm{CH}_{3} \mathrm{CH}(\mathrm{OH})\left(\mathrm{CH}_{2}\right)_{2} \mathrm{CH}_{3} \stackrel{\mathrm{Hat}_{2}}{\longrightarrow}\) 4\. \(\mathrm{Me}_{2} \mathrm{CHCH}_{2} \mathrm{OH} \stackrel{\mathrm{soc}_{2}}{\longrightarrow}\) List II (Alkyl halides) A. \(\mathrm{CH}_{3} \mathrm{CHBr}\left(\mathrm{CH}_{2}\right)_{2} \mathrm{CH}_{3}\) B. \(\mathrm{Me}_{2} \mathrm{CHCH}_{2} \mathrm{Cl}\) C. \(\left(\mathrm{CH}_{3}\right)_{3} \mathrm{CCl}\) D. \(\mathrm{CH}_{3}\left(\mathrm{CH}_{2}\right)_{3} \mathrm{Br}\) The correct matching is \(\begin{array}{llll}1 & 2 & 3 & 4 \\ \text { (a) } \mathrm{C} & \mathrm{D} & \mathrm{B} & \mathrm{A}\end{array}\) (b) \(\mathrm{C} \quad \mathrm{D} \quad \mathrm{A} \quad \mathrm{B}\) (c) \(\mathrm{D} \quad \mathrm{C}\) A \(\quad\) B (d) \(\mathrm{D} \quad \mathrm{C}\) B \(A\)

Match the following: List I (Reactants) 1\. \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{Br}+\) alc. \(\mathrm{KOH}\) 2\. \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}(\mathrm{Br}) \mathrm{CH}_{3}+\) alc. \(\mathrm{KOH}\) 3\. \(\left(\mathrm{CH}_{3}\right)_{3} \mathrm{CBr}+\) alc. \(\mathrm{KOH}\) List II (Products) A. cis-but-2-ene B. trans-but-2-ene C. but-1-ene D. 2-methylprop-1-ene The correct matching is \(\begin{array}{lll}1 & 2 & 3\end{array}\) \(\begin{array}{lll}1 & 2 & 3\end{array}\) (a) C B D (b) \(\mathrm{C} \mathrm{A} \mathrm{D}\) (c) \(\mathrm{C} \mathrm{D} \quad \mathrm{A}\) (d) B A C

Match the following \begin{tabular}{ll} \hline Column-I & Column-II \\ \hline (a) \(\mathrm{RI}>\mathrm{RBr}>\mathrm{RCl}\) \(>\) RF & (p) Order of reactivity \\ (b) \(\mathrm{RF}>\mathrm{RCl}>\mathrm{RBr}\) & (q) Decreasing order \\ \(>\mathrm{RI}\) & of B.pt. \\ (c) \(3^{\circ}>2^{\circ}>1^{\circ}\) (hydrocarbon) & (r) Decreasing order of \\\ (d) \(1^{\circ}>2^{\circ}>3^{\circ}\) & density \\ (alkyl halide) & (s) stability order \\ & (t) Order of replacement \\ of \(\mathrm{H}\) atom \end{tabular}

Match the following \begin{tabular}{ll} \hline Column-1 & Column-II \\ \hline (a) Acetylsalicylic acid & (p) Insecticide \\ (b) DDT & (q) Drug \\ (c) Naphthalene & (r) Moth repellent \\ (d) Carbon tetrahcloride & (s) Fire extinguisher \\ & (t) Sublimation \end{tabular}

How many moles of alkyl halides will react with a mole of ethylamine converting it into its ammonium salt?

How many elimination products are possible when 1chloromethyl cyclopentane is treated with alcoholic \(\mathrm{KOH} ?\)