Chapter 27

Identify the product ' \(\mathrm{P}\) ' in the given reaction \(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{OH}+\mathrm{C}_{2} \mathrm{H}_{5} \mathrm{I} \quad \frac{\mathrm{O}^{-\mathrm{C}}_{2} \mathrm{H}_{5}}{\text { Anhy. }\left(\mathrm{C}_{2} \mathrm{H}_{3} \mathrm{OH}\right)}\) (a) \(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{OC}_{2} \mathrm{H}_{5}\) (b) \(\mathrm{C}_{2} \mathrm{H}_{5} \mathrm{OC}_{2} \mathrm{H}_{5}\) (c) \(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{OC}_{6} \mathrm{H}_{5}\) (d) \(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{I}\).

1-propanol and 2-propanol can be best distinguished by (a) oxidation with \(\mathrm{KMnO}_{4}\) followed by reaction with Fehling solution (b) oxidation with acidic dichromate followed by reaction with Fehling solution (c) oxidation by heating with copper followed by reaction with Fehling solution (d) oxidation with concentrated \(\mathrm{H}_{2} \mathrm{SO}_{4}\) followed by reaction

The ether c1ccc(COc2ccccc2)cc1 when treated with HI produces (1) CCc1ccccc1 (2) OCc1ccccc1 (3) Ic1ccccc1 (4) Oc1ccccc1 (a) 1,3 (b) 1,2 (c) 1,4 (d) all of these

The reaction of the given compound CC=Cc1ccc(O)cc1 with HBr yields (a) (b) CCC(Br)c1ccc(O)cc1 (c) CC(Br)Cc1ccc(Br)cc1 (d) CCCC(Br)c1ccc(Br)cc1

An organic compound \(\mathrm{C}_{3} \mathrm{H}_{6} \mathrm{O}\) does not give a precipitate with 2, 4-dinitrophenylhydrazine and does not react with metallic sodium. It could be (a) \(\mathrm{CH}_{3}-\mathrm{CH}_{2}-\mathrm{CHO}\) (b) \(\mathrm{CH}_{2}=\mathrm{CH}-\mathrm{CH}_{2} \mathrm{OH}\) (c) \(\mathrm{CH}_{3}-\mathrm{CO}-\mathrm{CH}_{3}\) (d) \(\mathrm{CH}_{2}=\mathrm{CH}-\mathrm{O}-\mathrm{CH}_{3}\)

Which of the following reactions will yield propan-2-ol? \(1 \mathrm{CH}_{2}=\mathrm{CH}-\mathrm{CH}_{3}+\mathrm{H}_{2} \mathrm{O} \quad \stackrel{\mathrm{H}^{+}}{\longrightarrow}\) \(2 \mathrm{CH}_{3}-\mathrm{CHO}=\frac{\text { (i) } \mathrm{CH}_{3} \mathrm{MgI}}{\text { (ii) } \mathrm{H}_{2} \mathrm{O}}\) \(\begin{array}{ccc}3 & \mathrm{CH}_{2} \mathrm{O} & \frac{\text { (i) } \mathrm{C}_{2} \mathrm{H}_{5} \mathrm{Mgl}}{\text { (ii) } \mathrm{H}_{2} \mathrm{O}}\end{array}\) \(4 \mathrm{CH}_{2}=\mathrm{CH}-\mathrm{CH}_{3} \stackrel{\text { Neutral } \mathrm{KMnO}_{4}}{\longrightarrow}\) (a) 1 and 2 (b) 2 and 3 (c) 3 and 1 (d) 2 and 4

When phenol is treated with \(\mathrm{CHCl}_{3}\) and \(\mathrm{NaOH}\) followed by acidification, salicylaldehyde is obtained. Which of the following species are involved in the above mentioned reaction as intermediates? 1 . Oc1ccccc1C(Cl)(Cl)Cl 2 Oc1ccccc1C(Cl)Cl 3 . [O-]c1ccccc1C(Cl)Cl 4 . [O-]c1ccccc1C(Cl)Cl (a) 2,4 (b) 2,3 (c) 1,3 (d) 1,4

In the following compounds (I) Oc1ccccc1 (II) Cc1ccc(O)cc1 O=[N+]([O-])c1cccc(O)c1 (IV) O=[N+]([O-])c1ccc(O)cc1 (III) the order of acidity is (a) III \(>\mathrm{IV}>\mathrm{I}>\mathrm{II}\) (b) \(\mathrm{I}>\mathrm{IV}>\mathrm{III}>\mathrm{II}\) (c) \(\mathrm{II}>\mathrm{I}>\mathrm{III}>\mathrm{IV}\) (d) \(\mathrm{IV}>\mathrm{III}>\mathrm{I}>\mathrm{II}\)

Identify the correct order of boiling points of the following compounds: \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{OH}\) (I) \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{CHO}\) (II) \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{COOH}\) (III) (a) \(\mathrm{I}>\tilde{\mathrm{II}}>\overline{\mathrm{III}}\) (b) \(\mathrm{III}>\mathrm{I}>\mathrm{II}\) (c) \(\mathrm{I}>\mathrm{III}>\mathrm{II}\) (d) \(\mathrm{III}>\mathrm{II}>\mathrm{I}\)

What is the major product of the following reaction? C1CCC2OCC2C1 \(\frac{\mathrm{CH}_{3} \mathrm{Mgl}}{\mathrm{Et}_{2} \mathrm{O}} \longrightarrow \stackrel{\mathrm{H}_{3} \mathrm{O}}{\longrightarrow}\) (a) CC1OC2CCCCC12 (b) COC1CCCCC1C (c) CC1CCCCC1CO (d) CCC1CCCCC1O

Match list I (reactants which react with Grignard reagent, \(\mathrm{C}_{2} \mathrm{H}_{5} \mathrm{MgBr}\) ) with list II (products obtained in the reaction) and select the correct answer. List I 1\. ethanol 2\. ethylene chlorohydrin 3\. acetaldehyde 4\. ethylene oxideList II (i) butan-1-ol (ii) butan-2-ol The correct matching is: \(\begin{array}{llll}1 & 2 & 3 & 4\end{array}\) (a) (i) (ii) \((-)\) (i) (b) (i) (ii) (i) ( \(-)\) (c) (-) (i) (ii) (i) (d) (i) (-) (ii) (ii)

Consider the following species: 1\. \(\mathrm{RCHCH}_{3}\) 2\. \(\mathrm{RCH}_{2} \mathrm{CH}_{2}^{+} \quad 3 . \mathrm{RCH}_{2} \mathrm{CH}_{2} \mathrm{OH}_{2}\) In the dehydration of primary alcohols, the correct sequence of formation of the species involved is (a) \(1,2,3\) (b) \(1,3,2\) (c) \(3,2,1\) (d) \(2,1,3\)

Consider the following alcohols 1\. 1-phenyl-1-propanol 2\. 3-phenyl-1-propanol 3\. 1-phenyl-2-propanol The correct sequence of the increasing order of reactivity of these alcohols in their reaction with \(\mathrm{HBr}\) is (a) \(1,3,2\) (b) \(2,3,1\) (c) \(2,1,3\) (d) \(1,2,3\)

An alcohol \(\mathrm{C}_{5} \mathrm{H}_{11} \mathrm{OH}\), on dehydration, gives an alkene, which on oxidation yields a mixture of a ketone and an acid. The alcohol is (a) CCCC(C)O (b) CC(C)C(C)O (c) \(\left(\mathrm{CH}_{3}\right)_{3} \mathrm{CCH}_{2} \mathrm{OH}\) (d) \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}(\mathrm{OH}) \mathrm{CH}_{2} \mathrm{CH}_{3}\)

In the reaction, \(\mathrm{H}_{3} \mathrm{C}-\mathrm{C} \equiv \mathrm{CH} \longrightarrow \mathrm{H}_{3} \mathrm{C}-\mathrm{CH}(\mathrm{OH})-\mathrm{CH}_{3}\), the reagent used would include (a) \(\mathrm{Hg}^{2+} / \mathrm{H}_{2} \mathrm{SO}_{4}\) (b) Na in liquid \(\mathrm{NH}_{3}\), followed by \(\mathrm{CH}_{3} \mathrm{Cl}\) (c) \(1 \mathrm{~mol}\) of \(\mathrm{H}_{2} / \mathrm{Pt}\), followed by \(\mathrm{H}_{2} \mathrm{SO}_{4} / \mathrm{H}_{2} \mathrm{O}\) (d) \(2 \mathrm{~mol}\) of \(\mathrm{H}_{2} / \mathrm{Pt}\), followed by aq. \(\mathrm{NaOH}\)

Compound (X) liberates hydrogen when treated with sodium metal. On oxidation, it gives a compound (Y) with the same number of carbons. Compound (Y) gives orange coloured crystalline 2,4 -dinitrophenyl hydrazone derivative with 2, 4-dinitrophenyl hydrazine hydrochloride. Compound (Y) on treatment with aqueous \(\mathrm{NaOH}\) and iodine gives compound (Z)Compound (Z) on treatment with dilute acid yields benzoic acid. The structure of compound \((\mathrm{X})\) is (a) (b) CC(O)c1ccccc1 C=CC1=CC=CCC1O (c) C=CC1=CC=CC(O)C1 (d) OCCc1ccccc1

Match the following: List I 1\. absolute alcohol 2\. denatured alcohol 3\. \(80 \%\) proof alcoholic liquor 4\. rubbing alcohol List II (i) alcohol made undrinkable by the addition of toxic materials or poisons. (ii) alcoholic liquor containing \(40 \%\) ethanol by volume (iii) anhydrous alcohol (iv) isopropyl alcohol The correct matching is: \(\begin{array}{llll}1 & 2 & 3 & 4\end{array}\) (a) (i) (iii) (ii) (iv) (b) (iii) (i) (ii) (iv) (c) (i) (iii) (iv) (ii) (d) (iii) (i) (ii) (iv)

Under different conditions, nitration of phenol yields 1\. o-nitrophenol 2\. p-nitrophenol 3\. \(2,4,6\)-trinitrophenol The correct sequence of decreasing order of acidic nature of these phenols is (a) \(3,2,1\) (b) \(1,2,3\) (c) \(2,1,3\) (d) \(3,1,2\)

Which of the following reactions will yield 2-propanol? (1) \(\mathrm{CH}_{2}=\mathrm{CH}-\mathrm{CH}_{3}+\mathrm{H}_{2} \mathrm{O} \stackrel{\mathrm{H}^{+}}{\longrightarrow}\) (2) \(\mathrm{CH}_{3} \mathrm{CHO} \stackrel{\text { (i) } \mathrm{CH}_{3} \mathrm{Mgl} \text {, (ii) } \mathrm{H}_{2} \mathrm{O}}{\longrightarrow}\)(3) \(\mathrm{CH}_{2} \mathrm{O} \quad\) (i) \(\mathrm{C}_{2} \mathrm{H}_{5} \mathrm{MgI}\), (ii) \(\mathrm{H}_{2} \mathrm{O}\) (4) \(\mathrm{CH}_{2}=\mathrm{CH}-\mathrm{CH}_{3} \stackrel{\text { Neutral } \mathrm{KMnO}_{4}}{\longrightarrow}\) (a) 1 and 3 (b) 2 and 4 (c) 1 and 2 (d) 3 and 4

When phenol is treated with \(\mathrm{CHCl}_{3}\) and \(\mathrm{NaOH}\) followed by acidification salicylaldehyde is obtained. Which of the following species are involved in the above reaction as intermediates? (a) O=C1C=CC=CC1(Cl)Cl (b) Oc1ccccc1C(Cl)Cl (c) O=C1C=CC=CC1C(Cl)Cl (d) Oc1ccccc1C(Cl)Cl

Identify the correct statements. (a) \(\mathrm{C}_{2} \mathrm{H}_{5}-\mathrm{O}-\mathrm{CH}_{3}\) on cleavage with \(\mathrm{PCl}_{5}\) gives equimolar mixture of ethyl chloride and methyl chloride (b) \(\mathrm{ClCH}_{2} \mathrm{CH}=\mathrm{CH}_{2}\) is more reactive than \(\mathrm{Br} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{CH}_{3}\) to prepare ether using Williamson's synthesis (c) Anisole can be prepared by the reaction of \(\mathrm{CH}_{3}\) ONa on chlorobenzene (d) Sodium metal can be used to dry diethyl ether, benzene and ethyl alcohol.

Which of the following compounds are not stea: volatile? (a) O=[N+]([O-])c1ccccc1O (b) O=[N+]([O-])c1ccc(O)cc1 (c) O=[N+]([O-])c1cc(O)cc([N+](=O)[O-])c1 (d) Cc1cc(C)cc(O)c1

Select wrong statements: (a) Phenols turn blue litmus to red. (b) Reactivity of methanol with sodium metal is more than that of isopropyl alcohol (c) Methanol gives iodoform test. (d) Phenol reacts with \(\mathrm{Na}_{2} \mathrm{CO}_{3}\) and liberates \(\mathrm{CO}_{2}\) gas

Which of the following ethers cannot be synthesized by directly williamson's ether synthesis? (a) c1ccc(COc2ccccc2)cc1 (b) CC=COC=CC (c) \(\left(\mathrm{CH}_{3}\right)_{3} \mathrm{C}-\mathrm{O}-\mathrm{CH}_{3}\)(d) c1ccc(Oc2ccccc2)cc1

Which of the following is/are correct? (a) Phenol gives paraquinol with \(\mathrm{S}_{2} \mathrm{O}_{8}^{-2} / \mathrm{OH}^{-}\)as a major product. (b) Phenol can give electrophilic aromatic substitution reactions in absence of lewis acid. (c) Salicylic acid can give white/yellow solution with \(\mathrm{Br}_{2} / \mathrm{CS}_{2}\) (d) Ipso substitution is possible in phenol derivative if it contains \(-\mathrm{COOH}\) or \(-\mathrm{SO}_{3} \mathrm{H}\) group at ortho or para position with respect to OH group.

2\. \(\mathrm{CH}_{2}=\mathrm{CH}-\mathrm{C}-\mathrm{CH}_{3} \quad \stackrel{\mathrm{LiAlH}_{4}}{\longrightarrow} \mathrm{P}\) \(\mathrm{C}_{6} \mathrm{H}_{5}-\mathrm{CH}=\mathrm{CH}-\mathrm{CHO} \stackrel{\mathrm{LiAlH}_{4}}{\longrightarrow} \mathrm{Q}\)(P) and (Q) are respectively (a) \(\mathrm{CH}_{3}-\mathrm{CH}_{2}-\mathrm{CHOH}-\mathrm{CH}_{3}\) and \(\mathrm{C}_{6} \mathrm{H}_{5}-\mathrm{CH}=\mathrm{CH}-\mathrm{CH}_{2} \mathrm{OH}\) (b) \(\mathrm{CH}_{2}=\mathrm{CH}-\mathrm{CHOH}-\mathrm{CH}_{3}\) and \(\mathrm{C}_{6} \mathrm{H}_{5}-\mathrm{CH}=\mathrm{CH}-\mathrm{CH}_{2} \mathrm{OH}\) (c) \(\mathrm{CH}_{3}-\mathrm{CH}_{2}-\mathrm{CHOH}-\mathrm{CH}_{3}\) and \(\mathrm{C}_{6} \mathrm{H}_{5}-\mathrm{CH}_{2}-\mathrm{CH}_{2}-\mathrm{CH}_{2} \mathrm{OH}\) (d) \(\mathrm{CH}_{2}=\mathrm{CH}-\mathrm{CHOH}-\mathrm{CH}_{3}\) and \(\mathrm{C}_{6} \mathrm{H}_{5}-\mathrm{CH}_{2}-\mathrm{CH}_{2}-\mathrm{CH}_{2} \mathrm{OH}\)

When \(\mathrm{CH}_{3}-\mathrm{CH}=\mathrm{CH}-\mathrm{CHO}\) is reduced with \(\mathrm{NaBH}_{4}\), the product formed is (a) \(\mathrm{CH}_{3}-\mathrm{CH}=\mathrm{CH}-\mathrm{CH}_{2} \mathrm{OH}\) (b) \(\mathrm{CH}_{3}-\mathrm{CH}_{2}-\mathrm{CH}_{2}-\mathrm{CHO}\) (c) \(\mathrm{CH}_{3}-\mathrm{CH}_{2}-\mathrm{CH}_{2}-\mathrm{CH}_{3}\) (d) \(\mathrm{CH}_{3}-\mathrm{CH}_{2}-\mathrm{CH}_{2}-\mathrm{CH}_{2} \mathrm{OH}\)

Match the following \begin{tabular}{ll} Column-I & Column-II \\ \hline (a) \(\mathrm{CH}_{3}-\mathrm{C} \equiv \mathrm{C}-\mathrm{CH}_{2}-\) & \((\mathrm{p})\left(\mathrm{CH}_{2}\right)_{2} \mathrm{C}\) \end{tabular} \(\mathrm{CH}_{3} \frac{\mathrm{Hg}^{2+}, \mathrm{H}_{2} \mathrm{SO}_{4}}{330 \mathrm{~K}}\) (b) \(\left(\mathrm{CH}_{3}\right)_{3} \mathrm{C}-\mathrm{CH}=\) (q) \(\mathrm{CH}_{2} \frac{(1) \mathrm{Hg}(\mathrm{OAc})_{2}}{(2) \mathrm{NaBH}_{4}, \mathrm{OH}}\) (c) \(\left(\mathrm{CH}_{3}\right)_{3} \mathrm{C}-\mathrm{CH}=\) (r) \(\mathrm{CH}_{3} \mathrm{COCH}_{2} \mathrm{CH}_{2} \mathrm{CH}_{3}\) \(\mathrm{CH}_{2} \frac{\mathrm{B}_{2} \mathrm{H}_{6}}{\mathrm{H}_{2} \mathrm{O}_{2}, \mathrm{OH}}\) (d) \(\left(\mathrm{CH}_{3}\right)_{3} \mathrm{C}-\mathrm{CH}=\) (s) \(\mathrm{CH}_{2} \frac{\mathrm{H}_{2} \mathrm{SO}_{4}}{\mathrm{H}_{2} \mathrm{O}} \longrightarrow\) (t) \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{COCH}_{2} \mathrm{CH}_{3}\)

Match the followingColumn-I (a) Neohexyl alcohol (b) Sec -butyl alcohol (c) \(\mathrm{n}\) - hexyl alcohol (d) t- butyl alcohol\begin{tabular}{l} \hline Column-II \\ \hline (p) highest boiling point \\ (q) positive iodoform \\ test \\ (r) highest water \\ solubility \\ (s) susceptible to \\ chromate \(\left(\mathrm{CrO}_{3} / \mathrm{H}^{+}\right)\) \\ oxidation \\ (t) Shows instant reac- \\ tion with \(\mathrm{ZnCl}_{2}+\) \\ conc. HCl \\ \hline \end{tabular}

Match the following Column-I (a) Neohexyl alcohol (b) Sec -butyl alcohol (c) n- hexyl alcohol (d) t- butyl alcohol\begin{aligned} &\text { Column-II } \\ &\hline \text { (p) fastest reaction with } \\ &\text { Luca's reagent } \\ &\text { (q) highest boiling point } \\ &\text { (r) positive iodoform } \\ &\text { test } \\ &\text { (s) highest water } \\ &\text { solubility } \\ &\text { (t) susceptible to } \\ &\text { chromate ( }\left(\mathrm{CrO}_{3} / \mathrm{H}^{+}\right) \\ &\text {oxidation } \\ &\hline \end{aligned}

A compound with molecular formula \(\mathrm{C}_{6} \mathrm{H}_{14} \mathrm{O}_{5}\) is converted by the action of acetyl chloride to a compound with molecular mass 334 . The number of OH groups in the compound is

\(5.2 \mathrm{~g}\) of polyhydric alcohol was treated with an excess of methyl magnesium bromide to produce \(3.36\) litre of \(\mathrm{CH}_{4}\) at STP. Calculate number of OH groups present in polyhydric alcohol (molar mass of alcohol \(=104 \mathrm{~g}\) \(\left.\mathrm{mol}^{-1}\right)\)

Which one of the following is dehydrated maximum by using concentrated \(\mathrm{H}_{2} \mathrm{SO}_{4} ?\) [2002] (a) O=C1CCCC1O (b) O=C1CCC(O)CC1 (c) O=C1CCC(O)CC1 (d) CC1CCCC(O)C1

Picric acid is (a) O=[N+]([O-])c1cc([N+](=O)[O-])c(O)c([N+](=O)[O-])c1 (b) O=C(O)c1cccc([N+](=O)[O-])c1(c) O=C(O)c1cccc(O)c1 (d) Nc1cccc(C(=O)O)c1

An ether is more volatile than an alcohol having the same molecular formula. This is due to (a) dipolar character of ethers (b) alcohols having resonance structures (c) intermolecular hydrogen bonding in ethers (d) inter molecular hydrogen bonding in alcohols

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

Which one of the following undergoes reaction with \(50 \%\) sodium hydroxide solution to give the corresponding alcohol and acid? (a) phenol (b) benzaldehyde (c) butanal (d) benzoic acid

Among the following compounds which one can be dehydrated very easily? (a) \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{OH}\) (b) CCCC(C)O (c) CCC(C)O (d) CCC(C)CCO

The best reagent to convert pent-3-en-2-ol into pent3-en-2-one is (a) acidic permanganate (b) acidic dichromate (c) chromic anhydride in glacial acetic acid (d) pyridinium chlorochromate

Acid catalysed hydration of alkenes, except ethene, leads to the formation of (a) primary alcohol (b) secondary or tertiary alcohol (c) mixture of primary and secondary alcohols (d) mixture of secondary and tertiary alcohols