Chapter 24

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) \(\mathrm{O}^{-}\)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.

Hyper conjugation is possible in (a) \(\mathrm{CH}_{3} \mathrm{CH}_{2}^{\ominus}\) (b) Cc1ccccc1 (c) \(\mathrm{CH}_{2}=\mathrm{CH}_{2}\) (d) CCC(C)(C)C

Match the following \begin{tabular}{ll} \hline Column-1 & Column-II \\ \hline (a) \(\mathrm{Hg}_{2}^{2+}\) & (p) Nucleophile \\ (b) \(\mathrm{AlCl}_{3}\) & (q) Catalyst \\ (c) \(\mathrm{Br}\) & (r) Lewis acid \\ (d) \(\mathrm{H}^{+}\) & (s) Soft acid \\ & (t) Electrophile \end{tabular}

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 12002 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) \(\left.\mathrm{CH}_{2}\right)_{2} \mathrm{CH}->\mathrm{CH}_{3} \mathrm{CH}_{2} \rightarrow\left(\mathrm{CH}_{2}\right)_{3} \mathrm{C}-\) (d) \(\left(\mathrm{CH}_{2}\right)_{3} \mathrm{C}->\mathrm{CH}_{3} \mathrm{CH}_{2}->\left(\mathrm{CH}_{3}\right)_{2} \mathrm{CH}-\)

The reaction \(\left(\mathrm{CH}_{3}\right)_{3} \mathrm{C}-\mathrm{Br} \stackrel{\mathrm{H}, \mathrm{O}}{\longrightarrow}\left(\mathrm{CH}_{3}\right)_{3} \mathrm{C}-\mathrm{OH}\) is \([2003 \mid\) (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 12003 (a) \(\mathrm{CH}_{3} \mathrm{NH}_{2}<\mathrm{NH}_{3}<\left(\mathrm{CH}_{3}\right)_{2} \mathrm{NH}\) (b) \(\left(\mathrm{CH}_{3}\right)_{2} \mathrm{NH}<\mathrm{NH}_{1}<\mathrm{CH}_{3} \mathrm{NH}_{2}\) (c) \(\mathrm{NH}_{3}<\mathrm{CH}_{3} \mathrm{NH}_{2}<\left(\mathrm{CH}_{2}\right)_{2} \mathrm{NH}\) (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 \([\mathbf{2 0 0 3} \mid\) (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) \(\mathrm{ii}>\mathrm{iv}>\mathrm{ui}>\mathrm{i}\) (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) p-nitroanil

Tertiary alkyl halides are practically inert to substitution by SN² mechanism because of \(\quad\) [2005] (a) insolubility (b) instability (c) inductive effect (d) steric hindrance

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

\(\mathrm{CH}_{3} \mathrm{Br}+\mathrm{Nu} \longrightarrow \mathrm{CH}_{1}-\mathrm{Nu}+\mathrm{Br} \quad\) [2006] The decreasing order of the rate of the above reaction with nucleophiles \(\left(\mathrm{Nu}^{-}\right)\)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) \(b>d>c>a\)

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) \((\mathrm{Me})_{2}-\mathrm{CO}_{2} \mathrm{H}\) (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-phenyleyclopentene

The increasing order of stability of the following free radicals is \(\quad\) [2006] (a) \(\left(\mathrm{CH}_{3}\right)_{2} \mathrm{CH}<\left(\mathrm{CH}_{3}\right)_{3} \mathrm{C}<\left(\mathrm{C}_{6} \mathrm{H}_{3}\right)_{2} \mathrm{C} \mathrm{H}<\left(\mathrm{C}_{6} \mathrm{H}_{3}\right)_{3} \dot{\mathrm{C}}\) (b) \(\left(\mathrm{C}_{6} \mathrm{H}_{5}\right), \dot{\mathrm{C}}<\left(\mathrm{C}_{5} \mathrm{H}_{5}\right)_{2} \overrightarrow{\mathrm{C}} \mathrm{H}<\left(\mathrm{CH}_{3}\right)_{3} \dot{\mathrm{C}}<\left(\mathrm{CH}_{3}\right)_{2} \mathrm{CH}\) (c) \(\left(\mathrm{C}_{6} \mathrm{H}_{3}\right)_{2} \dot{\mathrm{C}} \mathrm{H}<\left(\mathrm{C}_{6} \mathrm{H}_{3}\right), \overrightarrow{\mathrm{C}}<\left(\mathrm{CH}_{3}\right)_{3} \overrightarrow{\mathrm{C}}<\left(\mathrm{CH}_{3}\right)_{2} \mathrm{CH}\) (d) \(\left(\mathrm{CH}_{3}\right)_{2} \mathrm{CH}<\left(\mathrm{CH}_{3}\right)_{3} \overrightarrow{\mathrm{C}}<\left(\mathrm{C}_{6} \mathrm{H}_{3}\right)_{3} \mathrm{C}<\left(\mathrm{C}_{6} \mathrm{H}_{4}\right)_{2} \mathrm{CH}\)

Which of the following is the correct order of decreasing SN \(^{2}\) reactivity? \(\quad\) [2007] (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 |2010] (a) \(\mathrm{RCO} \overline{\mathrm{O}}<\mathrm{HC} \equiv \overline{\mathrm{C}}<\overline{\mathrm{R}}<\overline{\mathrm{N}} \mathrm{H}_{2}\) (b) \(\overline{\mathrm{R}}<\mathrm{HC}=\overline{\mathrm{C}}<\mathrm{RCO} \overline{\mathrm{O}}<\overline{\mathrm{N}} \mathrm{H}_{2}\) (c) \(\mathrm{RCO} \overline{\mathrm{O}}<\overline{\mathrm{N} H}_{2}<\mathrm{HC} \equiv \overline{\mathrm{C}}<\overline{\mathrm{R}}\) (d) \(\mathrm{RCO} \overline{\mathrm{O}}<\mathrm{HC} \equiv \overline{\mathrm{C}}<\overline{\mathrm{N}} \mathrm{H}_{2}<\overline{\mathrm{R}}\)

The strongest acid amongst the following compounds is: (a) \(\mathrm{HCOOH}\) (b) \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}(\mathrm{Cl}) \mathrm{CO}_{2} \mathrm{H}\) (c) \(\mathrm{ClCH}_{2} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{COOH}\) (d) \(\mathrm{CH}_{3} \mathrm{COOH}\)

Arrange the following compound in order of decreasing acidity: \(|2013|\) Oc1ccc(Cl)cc1 Cc1ccc(O)cc1 O=[N+]([O-])c1ccc(O)cc1 COc1ccc(O)cc1 (I) (II) (III) (IV) (a) \(\mathrm{III}>\mathrm{I}>\mathrm{II}>\mathrm{IV}\) (b) IV \(>\mathrm{III}>\mathrm{I}>\mathrm{II}\) (c) \(\mathrm{II}>\mathrm{IV} \geq \mathrm{I}>\mathrm{III}\) (d) \(\mathrm{I}>\mathrm{II}>\mathrm{III}>\mathrm{IV}\)

A solution of \((-)-1\)-chloro-1-phenylethane in toluene racemizes slowly in the presence of a small amount of \(\mathrm{SbCl}_{5}\) due to formation of: \(|\mathbf{2 0 1 3}|\) (a) carbocation (b) free radical (c) carbanion (d) carbene

Considering the basic strength of amines in aqueous solution, which one has the smallest \(\mathrm{pK}_{b}\) value? [2014] (a) \(\left(\mathrm{CH}_{3}\right)_{3} \mathrm{~N}\) (b) \(\mathrm{C}_{6} \mathrm{H}_{3} \mathrm{NH}_{2}\) (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) \(\mathrm{CH}_{3}-\mathrm{CH}-\mathrm{CH}_{2} \mathrm{OH}\)