Chapter 24

Resonance energy per benzene ring decreases in the order (a) Naphthalene \(>\) Benzene \(>\) Anthracene \(>\) Phenanthrene (b) Benzene \(>\) Naphthalene \(>\) Anthracene \(>\) Phenanthrene (c) Benzene \(>\) Naphthalene \(>\) Phenanthrene \(\rangle\) Anthracene (d) All have equal resonance energy

Which of the following has the most acidic hydrogen: (a) 3 -hexanone (b) 2,4 -hexanedione (c) 2,5 - hexanedione (d) 2,3 - hexanedione

Most stable carbonium ion is (a) \(\mathrm{p}-\mathrm{NO}_{2}-\mathrm{C}_{6} \mathrm{H}_{4}-\mathrm{CH}_{2}^{+}\) (b) \(\mathrm{C}_{6} \mathrm{H}_{3} \mathrm{CH}_{2}^{+}\) (c) \(\mathrm{p}-\mathrm{Cl}-\mathrm{C}_{6} \mathrm{H}_{4}-\mathrm{CH}_{2}^{+}\) (d) \(\mathrm{p}-\mathrm{CH}_{2} \mathrm{O}-\mathrm{C}_{4} \mathrm{H}_{4}-\mathrm{CH}_{2}^{+}\)

Arrange \(\mathrm{CCl}_{3}\left(\mathrm{CH}_{2}\right)_{3} \mathrm{NH}_{2}\) (a), \(\mathrm{CCl}_{3}\left(\mathrm{CH}_{2}\right)_{2} \mathrm{NH}_{2}\) (b) and \(\mathrm{CCl}_{3} \mathrm{CH}_{2} \mathrm{NH}_{2}\) (c)in order of decreasing basic nature. (a) \(\mathrm{C}>\mathrm{B}>\mathrm{A}\) (b) \(C>A>B\) (c) \(\mathrm{A}>\mathrm{C}>\mathrm{B}\) (d) \(\mathrm{B}>\mathrm{A}>\mathrm{C}\)

Which of the following reaction does not involve a carbocation as intermediate? (a) \(\mathrm{C}_{6} \mathrm{H}_{6}+\mathrm{Br}_{2} \quad \mathrm{AlBr}_{3} \quad \mathrm{C}_{6} \mathrm{H}_{5} \mathrm{Br}\) (b) \(\mathrm{CH}_{2}=\mathrm{CH}_{2}^{2} \overline{+\mathrm{Br}_{2} \stackrel{3}{\longrightarrow}}{\longrightarrow} \mathrm{BrCH}_{2}-\mathrm{CH}_{2} \mathrm{Br}\) (c) \(\left(\mathrm{CH}_{3}\right)_{3} \mathrm{COH}+\mathrm{HBr} \mathrm{H}^{+}\left(\mathrm{CH}_{3}\right)_{3} \mathrm{CBr}+\mathrm{H}_{2} \mathrm{O}\) (d) Both (b) and (c)

Consider the following nucleophiles: \(\mathrm{H}_{2} \mathrm{O}, \quad \mathrm{CH}_{3} \mathrm{COO}^{-}, \quad \overline{\mathrm{O} H}, \quad \mathrm{CH}_{3} \mathrm{O}^{-}\) \(\begin{array}{llll}\text { I II II } & \text { II } & \text { III } & \text { IV }\end{array}\) The correct order of decreasing nucleophilicity is, (a) \(\mathrm{I}>\mathrm{II}>\mathrm{III}>\mathrm{IV}\) (b) IV \(>I I I>I I>I\) (c) IV > I > II > III (d) IV > II > III >I

Arrange methyl amine (a), pyridine (b) and guan (c) in decreasing order of basic strength (a) \(\mathrm{C}>\mathrm{A}>\mathrm{B}\) (b) \(\mathrm{A}>\mathrm{B}>\mathrm{C}\) (c) \(\mathrm{B}>\mathrm{A}>\mathrm{C}\) (d) \(\mathrm{B}>\mathrm{C}>\mathrm{A}\)

Arrange in order of decreasing trend towards \(S_{\mathrm{m}}\) reactions: (I) chlorobenzene (II) benzene (III) anilinium chloride (IV) toluene (a) \(\mathrm{IV}>\mathrm{II}>\mathrm{I}>\mathrm{III}\) (b) \(\mathrm{I}>\mathrm{II}>\mathrm{III}>\mathrm{IV}\) (c) \(\mathrm{II}>\mathrm{I}>\mathrm{III}>\mathrm{IV}\) (d) III > I >II > IV

Which one of the following resonating structures of 1-methoxy-1,3-butadiene is least stable? (a) \(\stackrel{\mathrm{C}} \mathrm{C} \mathrm{H}_{2}-\mathrm{CH}=\mathrm{CH}-\mathrm{CH}=\mathrm{O}-\mathrm{CH}_{3}\) (b) \(\mathrm{CH}_{2}=\stackrel{\mathrm{C}}{\mathrm{C}} \mathrm{H}-\mathrm{CH}^{\oplus}-\mathrm{CH}=\mathrm{O}-\mathrm{CH}_{2}^{3}\) (c) \(\stackrel{\mathrm{C}}{\mathrm{C}} \mathrm{H}_{2}-\mathrm{CH}-\mathrm{CH}=\mathrm{CH}-\mathrm{O}-\mathrm{CH}_{3}\) (d) \(\mathrm{CH}_{2}^{2}=\mathrm{CH}-\stackrel{\bullet}{\mathrm{C}} \mathrm{H}-\mathrm{CH}-\mathrm{O}-\mathrm{CH}_{3}^{3}\)

Which of the following statements are correct? 1\. \(\mathrm{SN}^{1}\) mechanism is most commonly given by tertiary alkyl halides. 2\. SN \(^{1}\) mechanism proceeds through the formation of a carbocation. 3\. \(\mathrm{SN}^{2}\) mechanism involves retention of configuration. 4\. \(\mathrm{SN}^{2}\) mechanism proceeds through the formation of a transition state. (a) 1,2 and 4 (b) 1,3 and 4 (c) 2,3 and 4 (d) \(1,2,3\) and 4

Dehydrobromination (-HBr) of the following in increasing order is (1) CCCCBr \((2)\) CCCC(C)Br (3) (a) \(1<2<3\) (b) \(3<2<1\) (c) \(2=3<1\) (d) \(3<1<2\)

Arrange these compounds in order of increasing \(\mathrm{SN}^{2}\) reaction rate (1) CCC(C)Cl (2) CCC(C)Br (3) CC(C)C(C)Cl (4) CC(=O)C(Br)C(C)C (a) \(3<1<2<4\) (b) \(3<2<1<4\) (c) \(4<3<1<2\) (d) \(2>3>1>4\)

Arrange the following compounds in the order of increasing tendency to undergo electrophilic substitution (1) Cyanobenzene (2) Benzene (3) Phenol (4) Toluene (5) Trimethyl phenyl ammonium ion (a) \(5<1<2<4<3\) (b) \(3>2>1>4>5\) (c) \(1>2>5>3>4\) (d) \(5<2<4<1<3\)

Which of the following represent the correct order of nucleophillic addition for (I) HCHO, (II) \(\mathrm{CH}_{3} \mathrm{COCH}_{3}\), (III) \(\mathrm{CH}_{3} \mathrm{CHO}\), (IV) \(\mathrm{CH}_{3} \mathrm{COC}_{2} \mathrm{H}_{5}\) (a) \(\mathrm{I}>\mathrm{II}>\mathrm{III}>\mathrm{IV}\) (b) \(\mathrm{I}>\mathrm{III}>\mathrm{II}>\mathrm{IV}\) (c) IV > II >III >I (d) \(\mathrm{I}>\mathrm{IV}>\mathrm{III}>\mathrm{II}\)

the fo (1) \(\mathrm{CH}_{3}-\stackrel{\Theta}{\mathrm{C}} \mathrm{H}_{2}\) (2) \(\mathrm{CH}_{3}=\stackrel{\Theta}{\mathrm{C}} \mathrm{H}\) (3) \(\mathrm{CH} \equiv \stackrel{\ominus}{\mathrm{C}}\) Correct order of stability of these carbanions in decreasing order is (a) \(1>2>3\) (b) \(2>1>3\) (c) \(3>2>1\) (d) \(3>1>2\)

Consider the following compounds: (1) \(\mathrm{C}_{6} \mathrm{H}_{5}-\mathrm{NH}_{2}\) (2) \(\mathrm{C}_{6} \mathrm{H}_{5}-\mathrm{NH}-\mathrm{C}_{6} \mathrm{H}_{3}\) (3) \(\left(\mathrm{C}_{6} \mathrm{H}_{5}\right)_{3} \mathrm{~N}\) (4) \(\mathrm{CH}_{3}-\mathrm{CH}_{2}-\mathrm{NH}_{2}\) Arrange these compounds in decreasing order of their basicity. (a) \(1>2>3>4\) (b) \(2>3>1>4\) (c) \(3>2>1>4\) (d) \(4>1>2>3\)

C=C1CCCCC1 \(\mathrm{HBr}-\mathrm{X}\) (predominant) Here \(\mathrm{X}\) is (a) (b) CC1CCC(Br)CC1 (c) (d) CC1(Br)CCCCC1

Match the following: List I (Reagents) 1\. (CN) 2\. (ONO) 3\. \(\mathrm{NH}_{3}\) 4\. \(\mathrm{AlCl}\) List II (Nature) (i) Neutral nucleophile (ii) electrophile (iii) Ambident nucleophile (iv) both \(\mathrm{El}\) and \(\mathrm{Nu}\) $$ \begin{aligned} &\text { The correct matching is }\\\ &\begin{array}{|c|c|c|c|c|} \hline & \text { 1 } & \text { 2 } & \text { 3 } & \text { 4 } \\ \hline \text { a } & \text { (i) } & \text { (iii) } & \text { (ii) } & \text { (iv) } \\ \hline \text { b } & \text { (iii) } & \text { (iii) } & \text { (i) } & \text { (ii) } \\ \hline \text { c } & \text { (iv) } & \text { (iii) } & \text { (iii) } & \text { (i) } \\ \hline \text { d } & \text { (ii) } & \text { (iv) } & \text { (i) } & \text { (iii) } \\ \hline \end{array} \end{aligned} $$

When a methyl radical is formed from \(\mathrm{CH}_{3} \mathrm{Cl}\), select the correct statement: (1) bond angle of \(109^{\circ} 28\) ' is retained (2) number of sigma bonds is three (3) carbon undergoes geometric change from tetrahedral to planar (4) hybridization changes \(\mathrm{sp}^{3}\) to \(\mathrm{sp}^{2}\) (a) 2,3 and 4 (b) 1,3 and 4 (c) 2 and 4 (d) 3 and 4

The correct increasing order of the reactivity of halides for \(\mathrm{SN}_{1}\) reaction is (a) \(\mathrm{CH}_{3}-\mathrm{CH}_{2}-\mathrm{X}<\left(\mathrm{CH}_{3}\right)_{2} \mathrm{CH}-\mathrm{X}<\mathrm{CH}_{2}=\mathrm{CH}-\mathrm{CH}_{2}\) \(-\mathrm{X}<\mathrm{Ph} \mathrm{CH}_{2}-\mathrm{X}\) (b) \(\left(\mathrm{CH}_{3}\right)_{2} \mathrm{CH}-\mathrm{X}<\mathrm{CH}_{3}-\mathrm{CH}_{2}-\mathrm{X}<\mathrm{CH}_{2}=\mathrm{CH}-\) \(\mathrm{CH}_{2}-\mathrm{X}<\mathrm{PhCH}_{2}-\mathrm{X}\) (c) \(\mathrm{PhCH}_{2}-\mathrm{X}<\left(\mathrm{CH}_{3}\right)_{2} \mathrm{CH}-\mathrm{X}<\mathrm{CH}_{3}-\mathrm{CH}_{2}-\mathrm{X}<\) \(\mathrm{CH}_{2}=\mathrm{CH}-\mathrm{CH}_{2}-\mathrm{X}\) (d) \(\mathrm{CH}_{2}=\mathrm{CH}-\mathrm{CH}_{2}-\mathrm{X}<\mathrm{PhCH}_{2}-\mathrm{X}<\left(\mathrm{CH}_{3}\right)_{2} \mathrm{CH}\) \(-\mathrm{X}^{2}<\mathrm{CH}-\mathrm{CH}-\mathrm{X}\)

Which of the following statements are correct. (1) \(\overline{\mathrm{N}} \mathrm{H}_{2}\) is better nucleophile than \(\mathrm{NH}_{3}\), but latter \(\left(\mathrm{NH}_{3}\right)\) is better nucleophile than \(\mathrm{NH}_{4}^{+}\) (2) \(\mathrm{C}_{6} \mathrm{H}_{3} \mathrm{O}^{-}\)is better nucleophile than (3) \(\mathrm{OH}\) - is better nucleophile than \(\mathrm{SH}^{-}\)and \(\mathrm{H}_{2} \mathrm{O}\), but \(\mathrm{H}_{2} \mathrm{O}\) is better nucleophile than \(\mathrm{H}_{3} \mathrm{O}^{+}\) (4) \(\mathrm{ClO}^{-}\)is weaker nucleophile than \(\mathrm{ClO}_{4}^{-}\) (a) 1,2 and 3 (b) 1,3 and 4 (c) 2,3 and 4 (d) \(1,2,3\) and 4

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

Consider the following amines: (1) \(\mathrm{C}_{6} \mathrm{H}_{3}-\mathrm{NH}_{2}\) (2) \(0-\mathrm{NO}_{2}-\mathrm{C}_{6} \mathrm{H}_{4}-\mathrm{NH}_{2}\) (3) \(\mathrm{m}-\mathrm{NO}_{2}-\mathrm{C}_{6} \mathrm{H}_{4}-\mathrm{NH}_{2}\) (4) \(\mathrm{p}-\mathrm{NO}_{2}-\mathrm{C}_{6} \mathrm{H}_{4}-\mathrm{NH}_{2}\) Arrange these compounds in decreasing order of basicity. (a) \(1>2>3>4\) (b) \(2>1>3>4\) (c) \(1>3>4>2\) (d) \(1>3>2>4\)

Match the following: List I (Type of reaction) 1\. \(\mathrm{SN}_{1}^{2}\) 2\. \(\mathrm{SN}^{1}\) 3\. \(\mathrm{E}_{2}\) 4\. \(\mathrm{E}_{1 \mathrm{cs}}\) List II (Phenomenon) (i) Walden inversion (ii) Carbanion intermediate (iii) Anti-periplanar configuration (iv) Carbocation intermediate $$ \begin{aligned} &\text { The correct matching is }\\\ &\begin{array}{|c|c|c|c|c|} \hline & \text { 1 } & 2 & 3 & 4 \\ \hline a & \text { (i) } & \text { (iv) } & \text { (iii) } & \text { (ii) } \\\ \hline \text { b } & \text { (i) } & \text { (ii) } & \text { (iii) } & \text { (iv) } \\ \hline \text { c } & \text { (iii) } & \text { (ii) } & \text { (i) } & \text { (iv) } \\ \hline \text { d } & \text { (iv) } & \text { (iii) } & \text { (ii) } & \text { (i) } \\ \hline \end{array} \end{aligned} $$

The correct order of decreasing acidity of the acids given below is 1\. \(\mathrm{Cl}_{3} \mathrm{CCH}=\mathrm{CH}-\mathrm{CH}_{2}-\mathrm{COOH}\) 2\. \(\mathrm{H}_{3} \mathrm{CCH}=\mathrm{CH}-\mathrm{CH}_{2}-\mathrm{COOH}\) 3\. \(\mathrm{Cl}_{3} \mathrm{CCH}=\mathrm{CH}-\mathrm{COOH}\) 4\. \(\mathrm{H}_{3} \mathrm{CCH}_{2} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{COOH}\) (a) \(1>3>2>4\) (b) \(3>1>2>4\) (c) \(3>4>1>2\) (d) \(3>1>4>2\)

Identify the correct statements: (a) \(\mathrm{H}_{2} \mathrm{O}<\mathrm{CH}_{3} \mathrm{COO}^{-}<\mathrm{CH}_{3} \mathrm{O}^{-}\)[basic strength \(]\) (b) \(\mathrm{H}_{2} \mathrm{O}<\mathrm{CH}_{3} \mathrm{COO}^{-}<\mathrm{CH}_{3} \mathrm{O}^{-}\)[nucleophilicity] (c) \(\mathrm{F}^{-}<\mathrm{Cl}^{-}<\mathrm{Br}^{-}<\mathrm{I}^{-} \quad\) [basic strength \(]\) (d) \(\mathrm{F}^{-}<\mathrm{Cl}^{-}<\mathrm{Br}^{-}<\mathrm{I}^{-} \quad\) [nucleophilicity]

The relative order of reactivity of \(\mathrm{F}^{-}, \mathrm{Cl}^{-} \mathrm{Br}\) and \(\mathrm{I}^{-}\)is/ are (a) \(\mathrm{F}^{-}<\mathrm{Cl}^{-}<\mathrm{Br}^{-}<\mathrm{I}^{-}\)in polar solvent (b) \(\mathrm{F}^{-}>\mathrm{Cl}^{-}>\mathrm{Br}>\mathrm{I}^{-}\)in non polar solvent (c) \(\mathrm{F}^{-}<\mathrm{Cl}^{-}<\mathrm{Br}^{-}<\mathrm{I}^{-}\)in non polar solvent (d) \(\mathrm{F}^{-}>\mathrm{Cl}^{-}>\mathrm{Br}^{-}>\mathrm{I}^{-}\)in polar solvent

Which of the following mixture can be separated by steam distillation? (a) Benzoic acid and \(\mathrm{NaCl}\) (b) Acetone and methanol (c) Aniline and chlorobenzene (d) O- Nitrophenol and p-nitrophenol

Which of the following phrases is/are not correctly associated with \(\mathrm{S}_{\mathrm{N}} 1\) reaction? (a) Rate of the reaction is affected by polarity of solvent. (b) The strength of nucleophile is important in determining rate of the reaction. (c) The reaction proceeds with complete inversion of configuration. (d) Neopentyl halide gives no rearranged product by \(\mathrm{S}_{\mathrm{N}} 1\) mechanism.

$$ \begin{aligned} &\text { Match the following }\\\ &\begin{array}{ll} \hline \text { Column-I } & \text { Column-II } \\ \hline \text { (a) } \mathrm{Hg}_{2}^{2+} & \text { (p) Nucleophile } \\ \text { (b) } \mathrm{AlCl}_{3} & \text { (q) Catalyst } \\ \text { (c) } \mathrm{Br} & \text { (r) Lewis acid } \\ \text { (d) } \mathrm{H}^{+} & \text {(s) Soft acid } \\ & \text { (t) Electrophile } \\ \hline \end{array} \end{aligned} $$

Match the following $$ \begin{array}{ll} \hline \text { Column-I } & \text { Column-II } \\ \hline \text { (a) Triphenyl methyl } & \text { (p) Benzyl } \\ \text { carbonium ion is mor } \\ \text { stable than } \\ \text { (b) } 3^{\circ} \text { alkyl carbonium ion is } & \text { (q) Tropylium ion } \\ \text { more stable than } \\ \text { (c) Allyl carbonium ion is } & \text { (r) } \mathrm{CH}^{+}=\mathrm{CH}_{2} \\ \text { less stable than } \\ \text { (d) }{\underline{\phantom{xx}}}^{+} \mathrm{CH}_{3} \text { is less stable than } & \text { (s) } 1^{\circ} \text { alkyl } \\ & \text { (t) } 2^{\circ} \text { alkyl } \end{array} $$

Match the following $$ \begin{array}{ll} \text { Column-I } & \text { Column-II } \\ \hline \begin{array}{ll} \text { (a) } \mathrm{CH}_{3}-\mathrm{CH}_{2}-\mathrm{CH}_{2}^{\oplus} & \text { (p) } \mathrm{sp}^{3} \text { (carbon carry- } \\ \text { ing the charge) } \end{array} \\ \begin{array}{ll} \text { (b) } \mathrm{CH}_{3}-\mathrm{CH}_{2}-\stackrel{\Theta}{\mathrm{C}} \mathrm{H}_{2} & \text { (q) } \mathrm{sp}^{2} \text { (carbon carry- } \\ \text { ing the charge) } \\ \text { (c) } \mathrm{C}_{6} \mathrm{H}_{5}-\mathrm{C} \mathrm{H}_{2} & \text { (r) Nucleophile } \\ \text { (d) } \mathrm{CH}_{3}-\mathrm{C}^{+}=\mathrm{O} & \text { (s) Electrophile } \\ &\text { (t) Planar } \end{array} \\ \end{array} $$

In the molecule \(\mathrm{CH}_{2}=\mathrm{C}=\mathrm{C}=\mathrm{CH}_{2}\), number of carbon atoms in sp hybrid state is

Among the following groups, \(-\mathrm{CH}_{3},-\mathrm{Cl},-\mathrm{OCH}_{3}\), \(-\mathrm{CHO},-\mathrm{CN},-\mathrm{NO}_{2}\) and \(-\mathrm{COOH}\), number of meta directing groups is

In the following benzyl/allyl system \([2002\) or ( \(\mathrm{R}\) is alkyl group) decreasing order of inductive effect is (a) \(\left(\mathrm{CH}_{3}\right)_{3} \mathrm{C}->\left(\mathrm{CH}_{3}\right)_{2} \mathrm{CH}->\mathrm{CH}_{3} \mathrm{CH}_{2}-\) (b) \(\mathrm{CH}_{3} \mathrm{CH}_{2} \rightarrow\left(\mathrm{CH}_{3}\right)_{2} \mathrm{CH}->\left(\mathrm{CH}_{3}\right)_{3} \mathrm{C}-\) (c) \(\left.\mathrm{CH}_{3}\right)_{2} \mathrm{CH}->\mathrm{CH}_{3} \mathrm{CH}_{2}->\left(\mathrm{CH}_{3}\right)_{3} \mathrm{C}-\) (d) \(\left(\mathrm{CH}_{3}\right)_{3} \mathrm{C}->\mathrm{CH}_{3} \mathrm{CH}_{2}->\left(\mathrm{CH}_{3}\right)_{2} \mathrm{CH}-\)

In which of the following compounds, the underlined carbon has \(\mathrm{sp}^{3}\) hybridization? [2002] (a) \(\mathrm{CH}_{3}-\underline{\mathrm{CH}}=\mathrm{CH}_{2}\) (b) \(\mathrm{CH}_{3} \mathrm{CO} \mathrm{NH}_{2}\) (c) \(\mathrm{CH}_{3}-\mathrm{CH}_{2}-\mathrm{OH}\) (d) \(\mathrm{CH}_{3} \mathrm{COOH}\)

The reaction \(\left(\mathrm{CH}_{3}\right)_{3} \mathrm{C}-\mathrm{Br} \stackrel{\mathbf{H}_{2} \mathrm{O}}{\longrightarrow}\left(\mathrm{CH}_{3}\right)_{3} \mathrm{C}-\mathrm{OH}\) is (a) addition reaction (b) substitution reaction (c) free radical reaction (d) elimination reaction

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 \([2003\) (a) \(\mathrm{CH}_{3} \mathrm{NH}_{2}<\mathrm{NH}_{3}<\left(\mathrm{CH}_{3}\right)_{2} \mathrm{NH}\) (b) \(\left(\mathrm{CH}_{3}\right)_{2} \mathrm{NH}<\mathrm{NH}_{3}<\mathrm{CH}_{3} \mathrm{NH}_{2}\) (c) \(\mathrm{NH}_{3}<\mathrm{CH}_{3} \mathrm{NH}_{2}<\left(\mathrm{CH}_{3}\right)_{2} \mathrm{NH}\) (d) \(\mathrm{CH}_{3} \mathrm{NH}_{2}<\left(\mathrm{CH}_{3}\right)_{2} \mathrm{NH}<\mathrm{NH}_{3}\)

During dehydration of alcohols to alkenes by heating with concentration \(\mathrm{H}_{2} \mathrm{SO}_{4}\) the initiation step is [2003] (a) protonation of alcohol molecule (b) formation of carbocation (c) elimination of water (d) formation of an ester

Consider the acidity of the carboxylic acids: \([2\) (i) \(\mathrm{PhCOOH}\) (ii) \(\mathrm{o}-\mathrm{NO}_{2} \mathrm{C}_{6} \mathrm{H}_{4} \mathrm{COOH}\) (iii) \(\mathrm{p}-\mathrm{NO}_{2} \mathrm{C}_{6} \mathrm{H}_{4} \mathrm{COOH}\) (iv) \(\mathrm{m}-\mathrm{NO}_{2} \mathrm{C}_{6} \mathrm{H}_{4} \mathrm{COOH}\) Which of the following order is correct? (a) \(\mathrm{i}>\mathrm{ii}>\mathrm{iii}>\mathrm{iv}\) (b) \(\mathrm{ii}>\mathrm{iv}>\mathrm{iii}>\mathrm{i}\) (c) \(\mathrm{ii}>\mathrm{iv}>\mathrm{i}>\mathrm{iii}\) (d) \(\mathrm{ii}>\mathrm{iii}>\mathrm{iv}>\mathrm{i}\)

Due to the presence of an unpaired electron, free radicals are (a) chemically reactive (b) chemically inactive (c) anions (d) cations

Amongst the following the most basic compound is \([2005]\) (a) benzylamine (b) aniline (c) acetanilide (d) \(\mathrm{p}\)-nitroaniline

2 -methylbutane on reacting with bromine in the presence of sunlight gives mainly \([2005]\) (a) 1-bromo-2-methylbutane (b) 2 -bromo-2-methylbutane (c) 2 -bromo-3-methylbutane (d) 1-bromo-3-methylbutane

Tertiary alkyl halides are practically inert to substitution by SN \(^{2}\) mechanism because of (a) insolubility (b) instability (c) inductive effect (d) steric hindrance

Among the following acids which has the lowest pKa value? (a) \(\mathrm{CH}_{3} \mathrm{COOH}\) (b) \(\mathrm{HCOOH}\) (c) \(\left(\mathrm{CH}_{3}\right)_{2} \mathrm{CH}-\mathrm{COOH}\) (d) \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{COH}\)

Elimination of bromine from 2-bromobutane results in the formation of (a) equimolar mixture of 1 and 2 -butene (b) predominantly 2-butene (c) predominantly 1-butene (d) predominantly 2-butyne

The increasing order of the rate of HCN addition to compounds \(\mathrm{A}-\mathrm{D}\) is (a) \(\mathrm{HCHO}\) (b) \(\mathrm{CH}_{3} \mathrm{COCH}_{3}\) (c) \(\mathrm{Ph} \mathrm{COCH}_{3}\) (d) \(\mathrm{PhCOPh}\) (a) \(a

\(\mathrm{CH}_{3} \mathrm{Br}+\mathrm{Nu}^{-} \longrightarrow \mathrm{CH}_{3}-\mathrm{Nu}+\mathrm{Br} \quad\) [2006] The decreasing order of the rate of the above reaction with nucleophiles \(\left(\mathrm{Nu}^{-}\right) \mathrm{a}\) to \(\mathrm{d}\) is \(\left[\mathrm{Nu}^{-}=\begin{array}{lll}\text { (a) } \mathrm{PhO} & \text { (b) } \mathrm{AcO}^{-} \text {(c) } \mathrm{HO}^{-} & \left.\text {(d) } \mathrm{CH}_{3} \mathrm{O}^{-}\right]\end{array}\right.\) (a) \(\mathrm{d}>\mathrm{c}>\mathrm{a}>\mathrm{b}\) (b) \(\mathrm{d}>\mathrm{c}>\mathrm{b}>\mathrm{a}\) (c) \(a>b>c>d\) (d) \(\mathrm{b}>\mathrm{d}>\mathrm{c}>\mathrm{a}\)

Reaction of trans-2-phenyl-1-bromocyclopentane on reaction with alcoholic KOH produces (a) 4-phenylcyclopentene (b) 2-phenylcyclopentene (c) 1-phenylcyclopentene (d) 3-phenylcyclopentene

The increasing order of stability of the following free radicals is (a) \(\left(\mathrm{CH}_{3}\right)_{2} \dot{\mathrm{C}} \mathrm{H}<\left(\mathrm{CH}_{3}\right)_{3} \dot{\mathrm{C}}<\left(\mathrm{C}_{6} \mathrm{H}_{3}\right)_{2} \dot{\mathrm{C}} \mathrm{H}<\left(\mathrm{C}_{6} \mathrm{H}_{5}\right)_{3} \dot{\mathrm{C}}\) (b) \(\left(\mathrm{C}_{6} \mathrm{H}_{3}\right)_{3} \dot{\mathrm{C}}<\left(\mathrm{C}_{6} \mathrm{H}_{3}\right)_{2} \dot{\mathrm{C}} \mathrm{H}<\left(\mathrm{CH}_{3}\right)_{3} \dot{\mathrm{C}}<\left(\mathrm{CH}_{3}\right)_{2} \dot{\mathrm{C}} \mathrm{H}\) (c) \(\left(\mathrm{C}_{6} \mathrm{H}_{5}\right)_{2} \dot{\mathrm{C}} \mathrm{H}<\left(\mathrm{C}_{6} \mathrm{H}_{3}\right)_{3} \dot{\mathrm{C}}<\left(\mathrm{CH}_{3}\right)_{3} \dot{\mathrm{C}}<\left(\mathrm{CH}_{3}\right)_{2} \dot{\mathrm{C}} \mathrm{H}\) (d) \(\left(\mathrm{CH}_{3}\right)_{2} \dot{\mathrm{C}} \mathrm{H}<\left(\mathrm{CH}_{3}\right)_{3} \dot{\mathrm{C}}<\left(\mathrm{C}_{6} \mathrm{H}_{5}\right)_{3} \dot{\mathrm{C}}<\left(\mathrm{C}_{6} \mathrm{H}_{5}\right)_{2} \dot{\mathrm{C}} \mathrm{H}\)