Chapter 24

Out of these acids, the strongest acid is (a) o-nitrobenzoic acid (b) \(\mathrm{p}-\) nitrobenzoic acid (c) \(\mathrm{m}\) - nitrobenzoic acid (d) benzoic acid

Which one of the following is a sec-allylic carbocation? (a) \(\mathrm{CH}_{2}-\mathrm{CH}=\mathrm{CH}_{2}\) (b) \(\mathrm{CH}_{3}-\mathrm{CH}=\mathrm{CH}-\mathrm{CH}_{2}\) (c) \(\mathrm{C}_{6} \mathrm{H}_{5}-\mathrm{CH}=\mathrm{CH}\) (d) \(\mathrm{CH}_{3}-\mathrm{CH}-\mathrm{CH}=\mathrm{CH}_{2}\)

Which of the following hydrolyzes fastest? (a) \(\mathrm{CH}_{3} \mathrm{Cl}\) (b) \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{Cl}\) (c) \(\mathrm{CH}_{3} \mathrm{OCH}_{2} \mathrm{Cl}\) (d) \(\left(\mathrm{CH}_{3}\right)_{2} \mathrm{CHCl}\)

When pent-2-ene is treated with HI in presence of a peroxy acids the major product obtained is (a) 2-lodo-pentane (b) 3-lodo-pentane (c) both of these (d) none of these

Which is correct about SN reaction? (a) Here reaction intermediate is carbocation (b) It is favoured by polar solvents (c) It is favoured by stability of carbocation (d) all of these

Among the given compounds, the most susceptible to nucleophilic attack at the carbonyl group is (a) \(\mathrm{MeCOCl}\) (b) \(\mathrm{MeCHO}\) (c) \(\mathrm{MeCOOMe}\) (d) \(\mathrm{Me} \mathrm{CO}-\mathrm{O}-\mathrm{CO} \mathrm{Me}\)

The most stable free radical among the following is (1) \(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{CH}_{2}\) (2) \(\mathrm{CH}_{3}-\mathrm{CH}-\mathrm{CH}_{3}\) (3) \(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{CHCH}_{3}\) (4) \(\mathrm{CH}_{3} \mathrm{CH}_{2}\) (a) \(3>1>4>2\) (b) \(1>3>2>4\) (c) \(3>1>2>4\) (d) \(3>2>1>4\)

Arrange the following groups in order of decreasing inductive effects: \(\mathrm{NO}_{2}, \mathrm{C}\left(\mathrm{CH}_{3}\right)_{3}, \mathrm{CH}_{3}, \mathrm{OCH}_{3}, \mathrm{Br}\) (a) \(\mathrm{NO}_{2}>\mathrm{Br}>\mathrm{OCH}_{3}>\mathrm{C}\left(\mathrm{CH}_{3}\right)_{3}>\mathrm{CH}_{3}\) (b) \(\mathrm{NO}_{2}>\mathrm{Br}>\mathrm{OCH}_{3}>\mathrm{CH}_{3}>\mathrm{C}\left(\mathrm{CH}_{3}\right)_{3}\) (c) \(\mathrm{NO}_{2}>\mathrm{OCH}_{3}>\mathrm{Br}>\mathrm{C}\left(\mathrm{CH}_{3}\right)_{3}>\mathrm{CH}_{3}\) (d) \(\mathrm{NO}_{2}>\mathrm{OCH}_{3}>\mathrm{C}\left(\mathrm{CH}_{3}\right)_{3}>\mathrm{Br}>\mathrm{CH}_{3}\)

\(+\mathrm{R}\) power for the following groups decreases in the \(\begin{aligned}&\text { order } \\\&\text { (1) }-\mathrm{NH}_{2} & \text { (2) }-\mathrm{O}\end{aligned}\) (3) \(-\mathrm{OH}\) (4) \(-\mathrm{NHCOCH}_{3}\) (a) \(2>1>3>4\) (b) \(2>3>1>4\) (c) \(1>2>3>4\) (d) \(3>2>1>4\)

In which case, the intermediate involved is incorrect? (a) Pinacol - pinacolone rearrangement - carbocation (b) Hofmann's bromamide reaction \(-\) Nitrene (c) Aldol condensation - carbocation (d) Anti Markonikoff's addition of HBr to propene Free radical.

Arrange the following free radicals in order of stability: (1) Benzyl (2) Allyl (3) Methyl (4) Vinyl (a) \(4>3>2>1\) (b) \(1>2>3>4\) (c) \(1>3>4>2\) (d) \(4>3>1>2\)

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

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) \(C>B>A\) (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) \(\mathrm{C}_{6} \mathrm{H}_{6}+\mathrm{Br}_{2} \mathrm{AlBr}_{3}, \mathrm{C}_{6} \mathrm{H}_{5} \mathrm{Br}\) (b) \(\mathrm{CH}_{2}=\mathrm{CH}_{2}+\mathrm{Br}_{2} \longrightarrow \mathrm{BrCH}_{2}-\mathrm{CH}_{2} \mathrm{Br}\) (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)

In the following compounds C1CCNCC1 C1COCCN1 c1cc[nH]c1 c1cc[nH]c1 (1) (2) (3) (4) The order of basicity is (a) \(4>1>3>2\) (b) \(3>1>4>2\) (c) \(2>1>3>4\) (d) \(1>3>2>4\)

Which of the following will most readily be dehydrated in acidic condition? (a) (b) CCCC(C)O (c) CCC(O)C(C)O (d) CC(=O)C(C)CC(C)O

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

Arrange methyl amine (a), pyridine (b) and guanidine (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) \(\mathrm{B}>\mathrm{C}>\mathrm{A}\)

In which of the following compounds resonance does not lead to stability of the compound? (a) C1CC1 (b) [C+]1C=C1 (c) c1ccccc1 (d) \(\mathrm{CH}=\mathrm{CH}-\mathrm{CH}=\mathrm{CH}_{2}\)

Arrange in order of decreasing trend towards \(\mathrm{S}_{\mathrm{E}}\) 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) \(\mathrm{III}>\mathrm{I}>\mathrm{II}>\mathrm{IV}\)

Which one of the following resonating structures of 1-methoxy-1,3-butadiene is least stable? (a) \(\stackrel{8}{\mathrm{CH}}_{2}-\mathrm{CH}=\mathrm{CH}-\mathrm{CH}=\mathrm{O}-\mathrm{CH}_{3}\) (b) \(\mathrm{CH}_{2}=\mathrm{CH}-\mathrm{CH}^{\circ}-\mathrm{CH}=\mathrm{O}-\mathrm{CH}_{2}^{3}\) (c) \(\mathrm{CH}_{2}-\mathrm{CH}-\mathrm{CH}=\mathrm{CH}-\mathrm{O}-\mathrm{CH}_{3}\) (d) \(\mathrm{CH}_{2}=\mathrm{CH}-\overrightarrow{\mathrm{C}} \mathrm{H}-\mathrm{CH}-\mathrm{O}-\mathrm{CH}_{3}\)

3 phenylpropene on reaction with HBr gives (as a major product) (a) \(\mathrm{C}_{6} \mathrm{H}_{3} \mathrm{CH}_{2} \mathrm{CH}(\mathrm{Br}) \mathrm{CH}_{3}\) (b) \(\mathrm{C}_{6} \mathrm{H}_{3} \mathrm{CH}(\mathrm{Br}) \mathrm{CH}_{2} \mathrm{CH}_{3}\) (c) \(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{Br}\) (d) \(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{CH}(\mathrm{Br}) \mathrm{CH}=\mathrm{CH}_{2}\)

Which of the following statements are correct? 1\. SN mechanism is most commonly given by tertiary alkyl halides. 2\. \(\mathrm{SN}^{1}\) mechanism proceeds through the formation of a carbocation. 3\. 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

Which of the following is correctly matched? (a) \(\mathrm{CH}_{3}-\mathrm{CH}_{2}-\mathrm{CH}_{2}-\mathrm{N}\left(\mathrm{CH}_{2}\right)_{3}^{\circ} \mathrm{OH} . \mathrm{E}_{2}\) reaction (b) CC(C)(C)Br E_reaction (c) \(\mathrm{CH}_{3}-\mathrm{CH}_{2}-\mathrm{CH}_{2} \mathrm{OH}, \mathrm{E}_{1}\) reaction (d) CC(C)(C)O \(\mathrm{E}_{1}\) cb reaction

Which is dehydrated to a maximum extent using conc. \(\mathrm{H}_{2} \mathrm{SO}_{4}\) ? (a) O=C1CCCCC1O (b) O=C1CCC(O)CC1 (c) O=C1CCCC(O)C1 (d) CC1C(=O)CCCC1O

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

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) \(\mid>\mathrm{II}>\mathrm{III}>\mathrm{IV}\) (b) \(\mathrm{I}>\mathrm{III}>\mathrm{II}>\mathrm{IV}\) (c) \(\mathrm{IV}>\mathrm{II}>\mathrm{III}>\mathrm{I}\) (d) \(\mathrm{I}>\mathrm{IV}>\mathrm{III}>\mathrm{II}\)

Consider the following carbanions: (1) \(\mathrm{CH}_{3}-\stackrel{\Theta}{\mathrm{C}} \mathrm{H}_{2}\) (2) \(\mathrm{CH}_{3}=\mathrm{C} \mathrm{H}\) (3) \(\mathrm{CH} \equiv \stackrel{\theta}{\mathrm{C}}\) 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) \(\mathrm{C}_{6} \mathrm{H}_{5}-\mathrm{NH}-\mathrm{C}_{6} \mathrm{H}_{5}\) (3) \(\left(\mathrm{C}_{6} \mathrm{H}_{5}\right)_{3} \mathrm{~N}\) (4) \(\mathrm{CH}_{1}-\mathrm{CH}_{2}-\mathrm{NH}_{2}\) 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) \(4>1>2>3\)

Which hydrogen atom can be abstracted easily from given the compound? CC=CC(C)C (a) \(\alpha\) (b) \(\beta\) (c) \(\gamma\) (d) can't be said

\(\left(\mathrm{H}_{3} \mathrm{C}\right)_{2} \mathrm{C}=\mathrm{CHCH}_{3}+\mathrm{NOBr} \longrightarrow \mathrm{A}\) The structure of the product (a)is given as (a) \(\left(\mathrm{CH}_{3}\right)_{2} \mathrm{C}(\mathrm{Br})-\mathrm{CH}(\mathrm{NO}) \mathrm{CH}_{3}\) (b) \(\left(\mathrm{CH}_{3}\right)_{2} \mathrm{C}(\mathrm{NO})-\mathrm{CH}(\mathrm{Br}) \mathrm{CH}_{3}\) (c) \(\left(\mathrm{CH}_{3}\right)_{2} \mathrm{CH}-\mathrm{C}(\mathrm{NO})(\mathrm{Br}) \mathrm{CH}_{3}\) (d)

When a methyl radical is formed from \(\mathrm{CH}_{3} \mathrm{Cl}\), select the correct statement: (1) bond angle of \(109^{\circ} 28^{\prime}\) is retained (2) number of sigma bonds is three (3) carbon undergoes geometric change from tetrahedral to planar (4) hybridization changes sp' to sp² (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) \(\mathrm{CH}_{3}-\mathrm{CH}_{2}-\mathrm{X}<\left(\mathrm{CH}_{2}\right)_{2} \mathrm{CH}-\mathrm{X}<\mathrm{CH}_{2}=\mathrm{CH}-\mathrm{CH}_{2}\) \(-\mathrm{X}<\mathrm{PhCH}_{2}-\mathrm{X}\) (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) \(\mathrm{CH}_{2}=\mathrm{CH}-\mathrm{CH}_{2}-\mathrm{X}<\mathrm{PhCH}_{2}-\mathrm{X}<\left(\mathrm{CH}_{3}\right)_{2} \mathrm{CH}\) \(-\mathrm{X}<\mathrm{CH}_{3}-\mathrm{CH}_{2}-\mathrm{X}\)

The stability of the following carbocations decreases in the order. (1) [C]1CCCCC1 (2) [C+]1CC1 (3) [C+]1C=CC=C1 (4) [C+]1C=CC=CC=C1 (a) \(3>2>4>1\) (b) \(4>2>3>1\) (c) \(4>3>2>1\) (d) \(4>2>1>3\)

Which of the following statements are correct. (1) \(\overline{\mathrm{NH}}_{2}\) is better nucleophile than \(\mathrm{NH}_{3}\) but latter \(\left(\mathrm{NH}_{3}\right)\) is better nucleophile than \(\mathrm{NH}_{4}{\underline{\phantom{xx}}}^{+}\) (2) \(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{O}^{-}\)is better nucleophile than CC(=O)O (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

The correct order of basicity of the following compound is (1) CC(N)N (2) \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{NH}_{2}\) (3) \(\left(\mathrm{CH}_{3}\right)_{2} \mathrm{NH}\) (4) CC(N)=O (5) \(\mathrm{CH}_{3} \mathrm{CN}\) (a) \(2>1>3>4>5\) (b) \(1>3>2>4>5\) (c) \(3>1>2>5>4\) (d) \(1>3>2>5>4\).

Consider the following carbocations and arranged them in the increasing order of their stability: (1) (2) \(\mathrm{CH}_{3}-\mathrm{CH}-\mathrm{CH}_{3}\) (3) \(\mathrm{C}_{6} \mathrm{H}_{5}-\mathrm{CH}_{2}\) (4) \(\mathrm{C}_{6} \mathrm{H}_{5}-\mathrm{CH}-\mathrm{C}_{6} \mathrm{H}_{5}\) (5) \(\mathrm{CH}_{3}-\mathrm{CO}-\mathrm{C}^{+} \mathrm{H}_{2}\) (a) \(5<2<3<4<1\) (b) \(5<3<2<4<1\) (c) \(5<1<2<4<3\) (d) \(3<2<4<1<5\)

Identify the correct order of reactivity in electrophilic substitution reactions of the following compounds: c1ccccc1 Cc1ccccc1 Clc1ccccc1 O=[N+]([O-])c1ccccc1 (1) (II) (III) (IV) (a) \(\mid>\mathrm{II}>\mathrm{III}>\mathrm{IV}\) (b) IV \(>\mathrm{III}>\mathrm{II}>\mathrm{I}\) (c) \(\mathrm{II}>\mathrm{I}>\mathrm{III}>\mathrm{IV}\) (d) \(\mathrm{II}>\mathrm{III}>\mathrm{I}>\mathrm{IV}\)

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

The reaction, [R]c1ccc(C(Br)Nc2ccccc2)cc1 is influenced by the hyperconjugative effect of group R. Now if R sequentially is I. \(\mathrm{CH}_{3}\) II. \(\mathrm{C}_{2} \mathrm{H}_{5}\) III. \(\left(\mathrm{CH}_{3}\right)_{2} \mathrm{CH}\) IV. \(\left(\mathrm{CH}_{3}\right)_{3} \mathrm{C}\) The increasing order of speed of the above reaction shall be in the sequence (a) I, IV, II, III (b) I, II, III, IV (c) I, III, II, IV (d) IV, I, II, III

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) \(1>3>2>4\)

Which will undergo Friedal-Craft alkylation reaction? (1) Cc1ccc([N+](=O)[O-])cc1 (2) CCc1ccccc1 (3) O=C(O)c1ccccc1 (4) Oc1ccccc1 (a) 1 and 3 (b) 2 and 4 (c) 1 and 2 (d) 1,2 and 4

Match the following. \(\begin{array}{ll}\text { List I } & \text { List II }\end{array}\) 1\. Carbocation (i) delocalization of \(\pi \mathrm{e}\) 2\. Resonance (ii) coplanar 3\. \(\mathrm{NO}_{2}\) (iii) pyramidal 4\. Carbanion (iv) \(-\mathrm{I},-\mathrm{R}\) group The correct matching is: 1 3 4 (a) (ii) (iii) (iv) (i) (b) (ii) (i) (iv) (iii) (c) (i) (iv) (ii) (iii) (d) (ii) (i) (iii) (iv)

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) \(3>4 \geq 1>2\) (d) \(3>1>4>2\)

Which of the following are more stable than \(\mathrm{CH}_{3}-\mathrm{CH}_{2}\) here? (a) \(\mathrm{CH}_{3}-{\mathrm{C}} \mathrm{H}-\mathrm{CH}_{3}\) (b) \(\mathrm{Ph}-\stackrel{\vartheta}{\mathrm{C}} \mathrm{H}\) (c) \(\mathrm{HC}=\hat{\mathrm{C}}\) (d) \(\mathrm{CH}_{2} \mathrm{Cl}\)

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]

Which of the following order/statement (s) is/are correct? (a) In \(\mathrm{S}_{\mathrm{N}} 1\) reactions, \(\mathrm{AgNO}_{3}\) increases the rates of solvolysis (b) Soft bases have enhanced nucleophilicities towards \(\mathrm{S}_{\mathrm{N}} 2\) reactions. (c) \(\mathrm{PhSO}_{3}^{-}>\mathrm{Cl}_{3} \mathrm{CCOO}^{-}>\mathrm{CH}_{3} \mathrm{COO}^{-}>\mathrm{PhO}^{-}\)(leav- ing group ability) (d) HCOOH may lead a tertiary halide towards \(\mathrm{S}_{\mathrm{N}} 2\).

Arrange the following compounds in order of increasing dipole moment. \(\mathrm{Cl}\) Clc1cccc(Cl)c1Cl Clc1ccc(Cl)cc1 Clc1ccc(Cl)c(Cl)c1 (I) (II) (III) ClC=C=C=CCl Clc1cc(Cl)cc(Cl)c1 (IV) (V) (a) \(\mathrm{II}=\mathrm{IV}<\mathrm{V}<\mathrm{I}<\mathrm{III}\) (b) \(\mathrm{IV}<\mathrm{III}<\mathrm{I}\) (c) \(\mathrm{II}<\mathrm{IV}<\mathrm{III}<\mathrm{I}<\mathrm{V}\) (d) \(\mathrm{V}=\mathrm{II}=\mathrm{IV}\)

Which of the following compound(s) has/have delocalized \(\pi\) - electrons? (a) \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{NHCH}=\mathrm{CH}-\mathrm{CH}_{3}\) (b) \(\mathrm{CH}_{3}-\mathrm{C}\left(\mathrm{CH}_{3}\right)-\mathrm{CH}_{2}-\mathrm{CH}=\mathrm{CH}_{2}\) (c) \(\mathrm{CH}_{3} \mathrm{CH}=\mathrm{CH}-\mathrm{CH}_{2}-\mathrm{OCH}_{3}\) (d) C1=CCC=C1

The relative order of reactivity of \(\mathrm{F}^{-}, \mathrm{Cl}^{\prime}, \mathrm{Br}\) and \(\mathrm{I}^{-}\)is/ are (a) \(\mathrm{F}^{-}<\mathrm{Ct}<\mathrm{Br}<\mathrm{I}^{-}\)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