Chapter 27

Benzylamine reacts with nitrous acid to form (a) benzene (b) benzyl alcohol (c) phenol (d) azobenzene

When ethylene glycol is heated with acidified potassium permanganate, the main organic compound obtained is (a) acetaldehyde (b) glyoxal (c) formic acid (d) oxalic acid

n-propyl alcohol and isopropyl alcohol can be chemically distinguished by (a) reduction (b) \(\mathrm{PCl}_{5}\) (c) ozonolysis (d) oxidation with potassium dichromate

The molecule which the highest boiling point is (a) \(\mathrm{CH}_{3}-\mathrm{CHCl}-\mathrm{CH}_{3}\) (b) \(\mathrm{CH}_{3}-\mathrm{CHOH}-\mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{OH}\) (c) \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{Cl}\) (d) \(\mathrm{CH}_{3}-\mathrm{CHOH}-\mathrm{CH}_{3}\)

The major product formed during hydroborationoxidation of 1 -methylcyclopentene is

Which of the following reacts fastest with conc. HCl \(\left(\varphi\right.\) is \(\left.C_{6}-H_{3}\right) ?\) (a) \(\varphi-\mathrm{CH}_{2}-\mathrm{CH}_{2}-\mathrm{OH}\) (b) \(\varphi-\mathrm{CHOH}-\mathrm{CH}_{3}\) (c) \(\mathrm{CH}_{3}-\mathrm{OH}\) (d) \(\mathrm{CH}_{2}=\mathrm{CH}-\mathrm{CH}_{2} \mathrm{OH}\)

\(\mathrm{A} \frac{\mathrm{K}_{2} \mathrm{Cr}_{2} \mathrm{O}_{7}}{\mathrm{H}_{2} \mathrm{SO}_{4}}-\mathrm{B} \underset{\text { vigrous oxidation }}{[\mathrm{O}]} \mathrm{CH}_{3} \mathrm{COOH}\) Here, B is propanone so A will be (a) Ethyl alcohol (b) Isopropyl alcohol (c) n-propyl alcohol (d) tertiary butyl alcohol

The correct order of boiling points for primary \(\left(1^{\circ}\right)\), secondary \(\left(2^{\circ}\right)\) and tertiary \(\left(3^{\circ}\right)\) alcohols is (a) \(1^{\circ}>2^{\circ}>3^{\circ}\) (b) \(3^{\circ}>2^{\circ}>1^{\circ}\) (c) \(2^{\circ}>1^{\circ}>3^{\circ}\) (d) \(2^{\circ}>3^{\circ}>1^{\circ}\)

In the following sequence of reactions, \(\mathrm{CH}_{3}-\mathrm{CH}\left(\mathrm{NH}_{2}\right)-\mathrm{CH}_{3} \stackrel{\mathrm{HNO}_{2}}{\longrightarrow} \mathrm{A}\) oxidation \(\underset{\text { (ii) } \mathrm{H}^{\prime} / \mathrm{H}_{2} \mathrm{O}}{\longrightarrow} \mathrm{B} \frac{\text { (i) } \mathrm{CH}_{3} \mathrm{Mgl}}{\mathrm{C}}\) the compound \(\mathrm{C}\) formed will be (a) butanol-1 (b) 2 -methylpropanol-1 (c) 2 -methylpropanol-2 (d) butanol-2

Which one of the following is more reactive than the rest towards a mixture of anhydrous. \(\mathrm{ZnCl}_{2}\) and concentrated \(\mathrm{HCl}\) ? (a) 2 -methylpropan-2-ol (b) methanol (c) butan-2-ol (d) butan-1-ol

An unknown compound dissolves in sulphuric acid, but does not decolourize bromine water and does not react with sodium. Which of the following classes of molecules behave in this manner? (a) phenol (b) alkene (c) alcohol (d) ether

The three products obtained in the reaction between glycerol and excess hydroiodic acid would include in that order (a) allyl iodide, propene and isopropyl iodide (b) allyl iodide, isopropyl iodide and propene (c) isopropyl iodide, allyl iodide and propene (d) propene, allyl iodide and isopropyl iodide

Higher homologues of ethers can be prepared by (a) diazomethane (b) Grignard reagent (c) alkyl halides (d) none of these

The alcohol, \(\mathrm{C}_{4} \mathrm{H}_{9} \mathrm{OH}\), when shaken with a mixture of anhydrous \(\mathrm{ZnCl}_{2}\) and concentrated HCl gave an immediate oil layer product. The alcohol is (a) \(\left(\mathrm{CH}_{3}\right)_{2} \mathrm{CHCH}_{2}-\mathrm{OH}\) (b) \(\left(\mathrm{CH}_{3}\right)_{3} \mathrm{C}-\mathrm{OH}\) (c) \(\mathrm{H}_{3} \mathrm{C}-\mathrm{CH}(\mathrm{OH}) \mathrm{CH}_{2} \mathrm{CH}_{3}\) (d) \(\mathrm{H}_{3} \mathrm{C}-\left(\mathrm{CH}_{2}\right)_{3}-\mathrm{OH}\)

Periodic acid oxidizes (a) 1,4 -diols (b) 1, 3-diols (c) 1,2 -diols (d) \(\beta\)-ketoaldehyde

Alkene \(\mathrm{R}-\mathrm{CH}=\mathrm{CH}_{2}\) reacts with \(\mathrm{B}_{2} \mathrm{H}_{6}\) in the presence of \(\mathrm{H}_{2} \mathrm{O}_{2}\) to give (a) [R]C(C)=O (b) [R]OC(C)O (c) \(\mathrm{R}-\mathrm{CH}_{2}-\mathrm{CHO}\) (d) \(\mathrm{R}-\mathrm{CH}_{2}-\mathrm{CH}_{2}-\mathrm{OH}\)

An organic compound ' \(X\) ' on treatment with acidified \(\mathrm{K}_{2} \mathrm{Cr}_{2} \mathrm{O}_{7}\) gives a compound ' \(\mathrm{Y}^{\prime}\) which reacts with \(\mathrm{I}_{2}\) and sodium carbonate to form triodomethane. The compound ' \(\mathrm{X}^{\prime}\) is (a) \(\mathrm{CH}_{3} \mathrm{CHOHCH}_{3}\) (b) \(\mathrm{CH}_{3} \mathrm{CHO}\) (c) \(\mathrm{CH}_{3} \mathrm{COCH}_{3}\) (d) \(\mathrm{CH}_{3} \mathrm{OH}\)

The compound obtained by the reaction of ethene with diborane, followed by hydrolysis with alkaline hydrogen peroxide is (a) ethanal (b) ethanol (c) triethyl boride (d) propanol

Heating methyl phenyl ether with HI gives (a) methanol + iodobenzene (b) methyl alcohol + benzyl alcohol (c) methyl iodide \(+\) phenol (d) methyl iodide + iodobenzene

\(\mathrm{CH}_{2}=\mathrm{CH}_{2} \frac{\mathrm{X}}{\mathrm{Ag}} \rightarrow \mathrm{X} \frac{\text { steam }}{473 \mathrm{~K}}-\mathrm{Y}\) The compound \(\mathrm{Y}\) is (a) ethylene glycol (b) epoxyethane (c) ethanal (d) ethanol

To prepare 3 -ethylpentan-3-ol, the reagents needed are (a) \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{MgBr}+\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{COCH}_{2} \mathrm{CH}_{3}\) (b) \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{MgBr}+\mathrm{CH}_{3} \mathrm{COCH}_{2} \mathrm{CH}_{3}\) (c) \(\mathrm{CH}_{3} \mathrm{MgBr}+\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{COCH}_{2} \mathrm{CH}_{3}\) (d) \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{MgBr}+\mathrm{CH}_{3} \mathrm{COCH}_{2} \mathrm{CH}_{3}\)

1-phenylethanol can be prepared by the reaction of benzaldehyde with (a) methyl iodide and magnesium (b) methyl bromide and aluminium bromide (c) ethyl iodide and magnesium (d) methyl bromide

Conversion of cyclohexene to cyclohexanol can be conveniently achieved by (a) hyboration-hydrolysis (b) hydroboration-oxidation (c) \(\mathrm{NaOH}-\mathrm{H}_{2} \mathrm{O}\) (d) \(\mathrm{Br}_{2}-\mathrm{H}_{2} \mathrm{O}\)

An organic compound (A) reacts with sodium metal and forms (B). On heating with concentrated \(\mathrm{H}_{2} \mathrm{SO}_{4}\), (A) gives diethyl ether. (A) and (B) are respectively (a) \(\mathrm{C}_{2} \mathrm{H}_{5} \mathrm{OH}\) and \(\mathrm{C}_{2} \mathrm{H}_{5} \mathrm{ONa}\) (b) \(\mathrm{C}_{3} \mathrm{H}_{7} \mathrm{OH}\) and \(\mathrm{CH}_{3} \mathrm{ONa}\) (c) \(\mathrm{CH}_{3} \mathrm{OH}\) and \(\mathrm{CH}_{3} \mathrm{ONa}\) (d) \(\mathrm{C}_{4} \mathrm{H}_{9} \mathrm{OH}\) and \(\mathrm{C}_{4} \mathrm{H}_{9} \mathrm{ONa}\)

Which of the following facts explains as to why p-nitrophenol is more acidic than phenol? 1\. \(-\) I effect of nitro group 2\. Greater resonance effect of p-nitrophenoxy group 3\. Steric effect of bulky nitro group Select the correct answer using the codes given below: (a) 2 and 3 (b) 1 and 3 (c) 1 and 2 (d) 2 alone

Ethanol and dimethyl ether form a pair of functional isomers. The boiling point of ethanol is higher than that of dimethyl ether due to the presence of (a) H-bonding in dimethyl ether (b) H-bonding in ethanol (c) \(\mathrm{CH}_{3}\) group in ethanol (d) \(\mathrm{CH}_{3}\) group in dimethyl ether

The reaction of elemental sulphur with Grignard reagent followed by acidification leads to the formation of (a) sulphoxide (b) mercaptan (c) sulphonic acid (d) thioester

Which of the following is the most suitable method for removing the traces of water from ethanol? (a) Heating with sodium metal (b) Hassing dry HCl gas through it (c) Distilling it (d) Reacting with \(\mathrm{Mg}\)

Product C in the following reaction, will be \(\mathrm{C}_{2} \mathrm{H}_{5} \mathrm{Br} \stackrel{\mathrm{aq} \cdot \mathrm{NaOH}}{\longrightarrow} \mathrm{A} \stackrel{\mathrm{Na}}{\longrightarrow \mathrm{B}} \stackrel{\mathrm{CH}_{3} \mathrm{I}}{\longrightarrow} \mathrm{C}\) (a) ethane (b) ethyl methyl ether (c) ethyl iodide (d) propane

Isopropyl alcohol is obtained by reacting which of the following alkenes with concentrated \(\mathrm{H}_{2} \mathrm{SO}_{4}\) followed by boiling with water? (a) 2 -methylpropene (b) ethylene (c) isoprene (d) propylene

The reaction of \(\mathrm{CH}_{3} \mathrm{MgBr}\) with acetone and hydrolysis of the resulting product gives (a) \(\left(\mathrm{CH}_{3}\right)_{3} \mathrm{COH}\) (b) \(\left(\mathrm{CH}_{3}\right)_{2} \mathrm{CHOH}\) (c) \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{OH}\) (d) \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{OH}\)

Which of the following compounds on reaction with \(\mathrm{CH}_{3} \mathrm{MgBr}\) will give a tertiary alcohol? CC(C)(C)C 11 (a) (b) \(\mathrm{C}_{2} \mathrm{H}_{5} \mathrm{CO}_{2} \mathrm{CH}_{3}\) (c) \(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{CHO}\) (d) \(\mathrm{C}_{2} \mathrm{H}_{5} \mathrm{COOH}\)

Oxymercuration-demercuration reaction of 1 -methylcyclohexene gives (a) trans-2-methyl cyclohexanol (b) cis-2-methylcyclohexanol (c) 1 -methylcyclohexanol (d) mixture of cis-and trans-2-methylcyclohexanol

In the reaction sequence, \(\mathrm{Z}\) will be Glycerol \(\stackrel{\mathrm{KHSO}_{4} / \Delta}{\longrightarrow} \mathrm{X} \stackrel{\mathrm{Zn}-\mathrm{Hg} / \mathrm{conc} \mathrm{HCl} / \Delta}{\longrightarrow}\) \(\mathrm{Y} \stackrel{\mathrm{NBS} / \mathrm{CCl}_{4}}{\longrightarrow} \mathrm{Z}\) (a) 1, 2-dibromopropane (b) 1-bromopropane (c) 2-bromopropane (d) 3-bromopropene

2 -phenylethanol may be prepared by the reaction of phenylmagnesium bromide with (a) HCHO (b) \(\mathrm{CH}_{3} \mathrm{COCH}_{3}\) (c) C1CO1 (d) \(\mathrm{CH}_{3} \mathrm{CHO}\)

The reagent used for the preparation of higher ethers from halogenated ethers is (a) sodium alkoxide (b) Grignard reagent (c) concutrated \(\mathrm{H}_{2} \mathrm{SO}_{4}\) (d) dry silver oxide

A compound is soluble in concentrated \(\mathrm{H}_{2} \mathrm{SO}_{4}\). It does not decolourize bromine in carbon tetrachloride but is oxidized by chromic anhydride in aqueous sulphuric acid within two seconds, turning the orange solution to blue, then green and finally opaque. The original compound is (a) an alkane (b) an ether (c) a tertiary alcohol (d) a primary alcohol

Vinyl carbinol is (a) \(\mathrm{HO}-\mathrm{CH}_{2}-\mathrm{CH}=\mathrm{CH}_{2}\) (b) \(\mathrm{CH}_{3}-\mathrm{C}\left(\mathrm{CH}_{2} \mathrm{OH}\right)=\mathrm{CH}_{2}\) (c) \(\mathrm{CH}_{3}-\mathrm{CH}=\mathrm{CH}-\mathrm{OH}\) (d) \(\mathrm{CH}_{3} \mathrm{C}(\mathrm{OH})=\mathrm{CH}_{2}\)

Schotten-Baumann reaction is (a) sodium phenate \(+\) methyl iodide \(\quad{ }_{-\mathrm{HCl}}\) phenyl benzoate (b) benzenediazonium chloride \(+\) phenol \(\longrightarrow\) p-Hydroxyazobenzene (c) phenol + benzoyl chloride \(\stackrel{\mathrm{NaOH}}{\longrightarrow}\) phenyl benzoate (d) phenol + chloroform \(\frac{\mathrm{NaOH}}{\text { salicyladehyde }}\)

An organic compound of molecular formula \(\mathrm{C}_{4} \mathrm{H}_{10} \mathrm{O}\) does not react with sodium. With excess of HI, it gives only one type of alkyl halide. The compound is (a) 1-butanol (b) ethoxyethane (c) 1 -methoxypropane (d) 2 -methoxypropane

A compound of the formula \(\mathrm{C}_{4} \mathrm{H}_{10} \mathrm{O}\) reacts with sodium and undergoes oxidation to give a carbonyl compound which does not reduce Tollen's reagent, the original compound is (a) sec-butyl alcohol (b) \(n\)-butyl alcohol (c) isobutyl alcohol (d) diethyl ether

Which of the following is correct? (a) Reduction of any aldehyde gives secondary alcohols (b) Reduction of vegetable oil with \(\mathrm{H}_{2} \mathrm{SO}_{4}\) gives glycerine (c) Reaction of ethanolic iodine with \(\mathrm{NaOH}\) gives iodoform (d) Sucrose on reaction with \(\mathrm{NaOH}\) gives invert sugar

Ethanol, on reacting with \(\mathrm{PCl}_{s}\) gives ' \(\mathrm{A}\) ', \(\mathrm{POCl}_{3}\) and HCl. 'A' reacts with silver nitrate to form 'B' (major product) and \(\mathrm{AgCl}\). 'A' and ' \(\mathrm{B}\) ' respectively are (a) \(\mathrm{C}_{2} \mathrm{H}_{5} \mathrm{Cl}\) and \(\mathrm{C}_{2} \mathrm{H}_{5} \mathrm{NO}_{2}\) (b) \(\mathrm{C}_{2} \mathrm{H}_{6}\) and \(\mathrm{C}_{2} \mathrm{H}_{3} \mathrm{NO}_{2}\) (c) \(\mathrm{C}_{2} \mathrm{H}_{5} \mathrm{Cl}\) and \(\mathrm{C}_{2} \mathrm{H}_{5} \mathrm{OC}_{2} \mathrm{H}_{5}\) (d) \(\mathrm{C}_{2} \mathrm{H}_{6}\) and \(\mathrm{C}_{2} \mathrm{H}_{5} \mathrm{OC}_{2} \mathrm{H}_{5}\)

The compound 'A' when treated with methyl alcohol and few drops of \(\mathrm{H}_{2} \mathrm{SO}_{4}\) gave smell of winter green. The compound 'A' is (a) oxalic acid (b) tartaric acid (c) salicylic acid (d) succinic acid

An organic compound 'A' reacts with methyl magnesium iodide, to form an addition product which on hydrolysis forms the compound 'B'. Compound 'B' gives blue colour salt in Victor Meyer's test. The compounds 'A' and 'B' are respectively (a) acetaldehyde and isopropyl alcohol (b) acetone and isopropyl alcohol (c) acetaldehyde and tertiary butyl alcohol (d) acetaldehyde and ethyl alcohol

In the following reaction, \(\mathrm{X}\) is and \(\mathrm{C}_{2} \mathrm{H}_{5} \mathrm{OC}_{2} \mathrm{H}_{5}+4 \mathrm{H} \stackrel{\text { Red } \mathrm{P}+\mathrm{HI}}{\longrightarrow} 2 \mathrm{X}+\mathrm{H}_{2} \mathrm{O}\) (a) ethylene (b) propane (c) ethane (d) butane

The reagent required to convert propene to 1 -propanol is (a) \(\mathrm{B}_{2} \mathrm{H}_{6}\) followed by \(\mathrm{H}_{2} \mathrm{O}_{2} / \mathrm{NaOH}\) (b) concentrated \(\mathrm{H}_{2} \mathrm{SO}_{4}\) followed by hydrolysis with boiling water (c) HBr followed by hydrolysis with aqueous KOH (d) \(\mathrm{Hg}\left(\mathrm{OCOCH}_{3}\right)_{2}\) followed by reduction with \(\mathrm{NaBH}_{4}\) -

A compound 'A' has a molecular formula \(\mathrm{C}_{2} \mathrm{Cl}_{3} \mathrm{OH}\). It reduces Fehling's solution and on oxidation, gives a monocarboxylic acid 'B'. 'A' can be obtained by the action of chlorine on ethyl alcohol. 'A' is (a) chloroform (b) chloral (c) methyl chloride (d) monochloroacetic acid

Among the following, the most stable compound is (a) cis-1, 2-cyclohexanediol (b) trans- 1,2 -cyclohexanediol (c) cis-1, 3-cyclohexenediol (d) trans- 1,3 -cyclohexanediol

(I) 1,2 -dihydroxy benzene (II) 1,3 -dihydroxy benzene (III) 1,4 -dihydroxy benzene (IV) Hydroxy benzene The increasing order of boiling points of above mentioned alcohols is (a) \(\mathrm{I}<\mathrm{II}<\mathrm{III}<\mathrm{IV}\) (b) \(\mathrm{I}<\mathrm{II}<\mathrm{IV}<\mathrm{III}\) (c) IV \(<\mathrm{I}<\mathrm{II}<\mathrm{III}\) (d) \(\mathrm{IV}<\mathrm{II}<\mathrm{I}<\mathrm{III}\)