Chapter 24

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 \(\mathrm{F}^{-}, \mathrm{Cl}^{-}, \mathrm{Br}\) 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.

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

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

Match the following Column-I (a) C=CC(C)I (b) C=CC(C)(c1cccc([N+](=O)[O-])c1)C(C)C (c) CC(C)C (Singlet) (d) CC(=O)C(F)C(C)=O Column-II (p) resonance (q) \(+\mathrm{I}\) effect (r) \(-\) I effect (s) hyper conjugation (t) intermediate is sp \(^{2}\) hybridized

Cc1ccc(O)c(C(=O)O)c1 is __ . # The number of acidic hydrogen which reacts with RMgBr in the molecule C#Cc1ccc(O)c(C(=O)O)c1 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__ .

The ration of bond orders in \(\mathrm{CO}_{3}^{2-}\) ion and \(\mathrm{SO}_{3}^{2-}\) ion is ___ .

Given below are the four compound which are stabilized either by inductive, mesomeric or hyperconjugation effects.. (a) CC(=O)C1=C(C)CCCC1 (b) BrC1=CCCCC1 (c) CC1=CCCCC1C (d) CC=CCl

In the following benzyl/allyl system or [R]C=C [R]c1ccccc1 ( \(\mathrm{R}\) 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) \(\mathrm{CH}_{3} \mathrm{CH}_{2}->\left(\mathrm{CH}_{3}\right)_{2} \mathrm{CH}->\left(\mathrm{CH}_{3}\right)_{3} \mathrm{C}-\) (c) \(\left.\mathrm{CH}_{3}\right)_{2} \mathrm{CH}->\mathrm{CH}_{3} \mathrm{CH}_{2} \rightarrow\left(\mathrm{CH}_{3}\right)_{3} \mathrm{C}-\) (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? (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 \(\left(\mathrm{CH}_{3}\right)_{3} \mathrm{C}-\mathrm{Br} \stackrel{\mathrm{H}_{2} \mathrm{O}}{\longrightarrow}\left(\mathrm{CH}_{3}\right)_{3} \mathrm{C}-\mathrm{OH}\) 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 (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 (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: (i) \(\mathrm{PhCOOH}\) (ii) \(0-\mathrm{NO}_{2} \mathrm{C}_{6} \mathrm{H}_{4} \mathrm{COOH}\) (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) \(i>\mathrm{ii}>\mathrm{iii}>\mathrm{iv}\) (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 (a) benzylamine (b) aniline (c) acetanilide (d) p-nitroaniline

2 -methylbutane on reacting with bromine in the presence of sunlight gives mainly (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 \(\mathrm{SN}^{2}\) 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) \(\mathrm{PhCOCH}_{3}\) (d) \(\mathrm{PhCOPh}\) (a) \(\mathrm{a}<\mathrm{b}<\mathrm{c}<\mathrm{d}\) (b) \(\mathrm{d}<\mathrm{b}<\mathrm{c}<\mathrm{a}\) (c) \(\mathrm{d}<\mathrm{c}<\mathrm{b}<\mathrm{a}\) (d) \(\mathrm{c}<\mathrm{d}<\mathrm{b}<\mathrm{a}\)

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

The correct order of increasing acid strength of the compound: (1) \(\mathrm{CH}_{3} \mathrm{CO}_{2} \mathrm{H}\) (2) \(\mathrm{MeOCH}_{2} \mathrm{CO}_{2} \mathrm{H}\) (3) \(\mathrm{CF}_{3} \mathrm{CO}_{2} \mathrm{H}\) (4) \((\mathrm{Me})_{2}-\overline{\mathrm{CO}_{2}} \mathrm{H}\) (a) \(2<4<1<3\) (b) \(4<1<3<2\) (c) \(4<1<2<3\) (d) \(1<4<3<2\)

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) \(\left(\mathrm{CH}_{3}\right)_{2} \dot{\mathrm{C}} \mathrm{H}<\left(\mathrm{CH}_{3}\right)_{3} \dot{\mathrm{C}}<\left(\mathrm{C}_{6} \mathrm{H}_{5}\right)_{2} \dot{\mathrm{C}} \mathrm{H}<\left(\mathrm{C}_{6} \mathrm{H}_{3}\right)_{3} \dot{\mathrm{C}}\) (b) \(\left(\mathrm{C}_{6} \mathrm{H}_{3}\right)_{3} \dot{\mathrm{C}}<\left(\mathrm{C}_{6} \mathrm{H}_{5}\right)_{2} \dot{\mathrm{C}} \mathrm{H}<\left(\mathrm{CH}_{3}\right)_{3} \dot{\mathrm{C}}<\left(\mathrm{CH}_{3}\right)_{2} \dot{\mathrm{C}} \mathrm{H}\) (c) \(\left(\mathrm{C}_{6} \mathrm{H}_{5}\right)_{2} \dot{\mathrm{C}} \mathrm{H}<\left(\mathrm{C}_{6} \mathrm{H}_{5}\right)_{3} \dot{\mathrm{C}}<\left(\mathrm{CH}_{3}\right)_{3} \dot{\mathrm{C}}<\left(\mathrm{CH}_{3}\right)_{2} \dot{\mathrm{C}} \mathrm{H}\) (d) \(\left(\mathrm{CH}_{3}\right)_{2} \dot{\mathrm{C}} \mathrm{H}<\left(\mathrm{CH}_{3}\right)_{3} \dot{\mathrm{C}}<\left(\mathrm{C}_{6} \mathrm{H}_{5}\right)_{3} \dot{\mathrm{C}}<\left(\mathrm{C}_{6} \mathrm{H}_{3}\right)_{2} \dot{\mathrm{C}} \mathrm{H}\)

Which of the following is the correct order of decreasing \(\mathrm{SN}^{2}\) reactivity? (a) \(\mathrm{RCH}_{2} \mathrm{X}>\mathrm{R}_{2} \mathrm{CHX}>\mathrm{R}_{3} \mathrm{CX}\) (b) \(\mathrm{R}_{3} \mathrm{CX}>\mathrm{R}_{2} \mathrm{CHX}>\mathrm{RCH}_{2} \mathrm{X}\) (c) \(\mathrm{R}_{2} \mathrm{CHX}>\mathrm{R}_{3} \mathrm{CX}>\mathrm{RCH}_{2} \mathrm{X}\) (d) \(\mathrm{RCH}_{2} \mathrm{X}>\mathrm{R}_{3} \mathrm{CX}>\mathrm{R}_{2} \mathrm{CHX}\)

The correct order of increasing basicity of the given conjugate bases \(\left(\mathrm{R}=\mathrm{CH}_{3}\right)\) is (a) \(\mathrm{RCO} \overline{\mathrm{O}}<\mathrm{HC} \equiv \overline{\mathrm{C}}<\overline{\mathrm{R}}<\overline{\mathrm{N}} \mathrm{H}_{2}\) (b) \(\overline{\mathrm{R}}<\mathrm{HC} \equiv \overline{\mathrm{C}}<\mathrm{RCO} \overline{\mathrm{O}}<\overline{\mathrm{N}} \mathrm{H}_{2}\) (c) \(\mathrm{RCO} \overline{\mathrm{O}}<\overline{\mathrm{N}} \mathrm{H}_{2}<\mathrm{HC} \equiv \overline{\mathrm{C}}<\overline{\mathrm{R}}\) (d) \(\mathrm{RCO} \overline{\mathrm{O}}<\mathrm{HC} \equiv \overline{\mathrm{C}}<\overline{\mathrm{N}} \mathrm{H}_{2}<\overline{\mathrm{R}}\)

The order of stability of the following carbocations: (I) \(\mathrm{CH}_{2}=\mathrm{CH}-\stackrel{\oplus}{\mathrm{C}} \mathrm{H}_{2}\) \(\mathbf{[ 2 0 1 3}]\) (II) \(\mathrm{CH}_{3}-\mathrm{CH}_{2}-\stackrel{\oplus}{\mathrm{C}} \mathrm{H}_{2}\) (III) is: [C+]c1ccccc1 (a) \(\mathrm{I}>\mathrm{II}>\mathrm{III}\) (b) \(\mathrm{III}>\mathrm{I}>\mathrm{II}\) (c) \(\mathrm{III}>\mathrm{II}>\mathrm{I}\) (d) \(\mathrm{II}>\mathrm{III}>\mathrm{I}\)

Considering the basic strength of amines in aqueous solution, which one has the smallest \(\mathrm{pK}_{\mathrm{b}}\) value? (a) \(\left(\mathrm{CH}_{3}\right)_{3} \mathrm{~N}\) (b) \(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{NH}_{2}\) (c) \(\left(\mathrm{CH}_{3}\right)_{2} \mathrm{NH}\) (d) \(\mathrm{CH}_{3} \mathrm{NH}_{2}\)

The reaction of Propene with \(\mathrm{HOCl}\left(\mathrm{Cl}_{2}+\mathrm{H}_{2} \mathrm{O}\right)\) proceeds through the intermediate (a) \(\mathrm{CH}_{3}-\mathrm{CH}(\mathrm{OH})-\mathrm{CH}_{2}^{+}\) (b) \(\mathrm{CH}_{3}-\mathrm{CH}-\mathrm{CH}_{2} \mathrm{Cl}\) (c) \(\mathrm{CH}_{3}-\mathrm{CHCl}-\mathrm{CH}_{2}\) (d) \(\mathrm{CH}_{3}-\mathrm{CH}-\mathrm{CH}_{2} \mathrm{OH}\)