Chapter 16

Arihant Objective Approach to Organic Chemistry for IIT JEE and NEET all Medical Entrances Part 4 · 164 exercises

Problem 1

When aniline reacts with oil of bitter almonds \(\left(\mathrm{C}_{6} \mathrm{H}_{3} \mathrm{CHO}\right)\) condensation takes place and benzal derivative is formed? This is known as: \(\quad\) |CBSE 1995] (a) Millon base (b) Schiff's reagent (c) Schiff's base (d) Benedict's reagent

4 step solution

Problem 2

The axidation of toluene with \(\mathrm{CrO}_{3}\), in the presence of \(\left(\mathrm{CH}_{3} \mathrm{CO}\right)_{2} \mathrm{O}\) gives a product \(A\), which on treatment with aqueous \(\mathrm{NaOH}\), produces: |CBSE 1995] (a) \(\mathrm{C}_{5} \mathrm{H}_{5} \mathrm{CHO}\) (b) \(\mathrm{C}_{6} \mathrm{H}_{3} \mathrm{COONa}\) (c) 2,4 -diacetyl toluene (d) \(\left(\mathrm{C}_{6} \mathrm{H}_{3} \mathrm{CO}\right)_{2} \mathrm{O}\)

4 step solution

Problem 3

Which of the following compounds give benzoic acid on oxidation? [CHSF: 1996| (a) chlorophenol (b) chlorotoluene (c) chlorobensene (d) benzyl chloride

6 step solution

Problem 5

In case of chlorination of benzene in the presence of \(\mathrm{FeCl}_{3}\) the electrophile is: 1CHSE 1996] (a) \(\mathrm{Cl}^{+}\) (b) \(\mathrm{Cl}^{-}\) (c) \(\mathrm{Cl}\) (d) \(\mathrm{FeCl}_{3}\)

4 step solution

Problem 6

The oxidation of toluene to benzaldehyde by chromyl chloride is called: |CBSE 1996 | (a) Cannizzaro"s reaction (b) Wurtz reaction (c) Etard's reaction (d) Reimer-Tiemann reaction

3 step solution

Problem 7

Among the following compounds (I-III) the correct order of reaction with electrophile is: |CBSE 1997] COc1ccccc1 c1ccccc1 O=[N+]([O-])c1ccccc1 II 111 (a) \(11>11 I>I\) (b) III < \(I<11\) (c) \(1>11>111\) (d) \(\mathrm{I}=\| \geq \mathbb{I I}\)

4 step solution

Problem 8

1-Phenyl ethanol can be prepared by the reaction of benzaldehyde with: \(\quad\) |CBSE 1997| (a) methyl bromide (b) ethyl iodide and magnesium (c) methyl iodide and magnesium (d) methyl bromide and aluminium bromide

4 step solution

Problem 9

Replacement of \(\mathrm{Cl}\) of chlorobenzene to give phenol requires drastic conditions but chlorine of 2,4 -dinitrochlorobenzene is readily replaced. This is because: |CESE 1997| (a) NO, makes the ring electron rich at ortho and para positions (b) NO, withdraw electrons from meta position (c) NO, donates electron at meta position (d) \(\mathrm{NO}_{2}\), withdraws electrons from ortho/para positions.

4 step solution

Problem 10

Aniline is reacted with bromine water and the resulting product is treated with an aqueous solution of sodium nitrite in presence of dilute hydrochloric acid. The compound so formed is converted to a tetrafluoroborate which is subsequently heated. The final product is: 1 CBSE 1998] (a) \(1,3,5\)-tribromobenzene (b) \(p\)-bromofluorobenzene (c) \(p\)-bromoaniline (d) \(2,4,6\)-tribromofluorobengene

4 step solution

Problem 11

Aspirin is an acetylation product of: [CBSE 1998] (a) \(o\)-hydroxybenzoic acid (b) o-hydroxybenzene (c) m-hydroxybenzoic acid (d) \(p\)-dihydroxybenzene

4 step solution

Problem 12

Gammexane is: |CBSE \(1999 \mid\) (a) chlorobenzene (b) benzylchloride (c) bromobenzene (d) benzenehexachloride

6 step solution

Problem 13

Phenyl isocyanides are prepared by which of the following reaction? [CHSE 1999\(]\) (a) Rosenmund's reaction (b) Carbylamine reaction (c) Reimer-Tiemann reaction (d) Wurtz reaction

6 step solution

Problem 14

The ionization constant of phenol is higher than that of ethanol because: \(\quad\) [CBSE 2000] (a) phenoxide ion is bulkier than ethoxide (b) phenoxide ion is stronger base than ethoxide (c) phenoxide ion is stabilised through delocalization (d) phenoxide ion is less stable than ethoxide

6 step solution

Problem 15

Benzoic acid may be converted to ethyl benzoate by reaction with: |CBSE 2000] (a) sodium ethoxide (b) ethyl chloride (c) dry \(\mathrm{HCl}-\mathrm{C}_{2} \mathrm{H}_{3} \mathrm{OH}\) (d) ethanol

3 step solution

Problem 16

An organic compound \(A\) on reduction gives compound \(B\) which on reaction with chloroform and potassium hydroxide forms \(C\). The compound \(C\) on catalytic reduction gives \(N\)-methylaniline. The compound \(A\) is: \(\quad\) [CBSE 2000| (a) nitrobenzene (b) nitromethane (c) methylamine (d) aniline

4 step solution

Problem 18

When phenol is treated with \(\mathrm{CHCl}_{3}\) and \(\mathrm{NaOH}\) the product formed is: [CBSE 2002] (a) benzaldehyde (b) salicyaldehyde (c) salicylic acid (d) benzoic acid

4 step solution

Problem 23

Using anhydrous \(\mathrm{AICl}_{3}\) as catalyst, which one of the following reactions produce ethylbenzene? \(\quad\) |CBSE 2004] (a) \(\mathrm{H}_{3} \mathrm{CCH}_{2} \mathrm{OH}+\mathrm{C}_{6} \mathrm{H}_{6}\) (b) \(\mathrm{CH}_{3} \mathrm{CH}=\mathrm{CH}_{2}+\mathrm{C}_{6} \mathrm{H}_{6}\) (c) \(\mathrm{H}_{1} \mathrm{C}=\mathrm{CH}_{2}+\mathrm{C}_{6} \mathrm{H}_{6}\) (d) \(\mathrm{H}_{1} \mathrm{CCH}_{3}+\mathrm{C}_{6} \mathrm{H}_{6}\)

4 step solution

Problem 24

The molecular formula of diphenyl methane is \(\mathrm{C}_{13} \mathrm{H}_{11-}\) How many structural isomers are possible when one of the hydrogen is replaced by a chlorine atom? c1ccc(Cc2ccccc2)cc1 (a) 6 (b) 4 (c) 8 (d) \(\underline{7}\)

4 step solution

Problem 27

Electrolytic reduction of nitrobenzene in acidic medium gives: |CBSE 2005] (a) aniline (b) nitrosobenzene (c) \(N\)-phenylhydroxylamine (d) \(p\)-aminophenol

3 step solution

Problem 28

Ortho and para-nitrophenols are separated by which of the following methods? [AFMC 1995] (a) sublimation (b) crystallisation (c) steam-distillation (d) filteration

4 step solution

Problem 29

Aniline on heating with potassium hydroxide and chloroform produce: [AFMC 1995] (a) phenyl isocyanate (b) phenyl cyanide (c) phenyl isocyanide (d) phenyl thiocyanate

4 step solution

Problem 30

Hinsberg's reagent is: (a) (b) \(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{SO}_{2} \mathrm{Cl}\) (c) \(\mathrm{C}_{6} \mathrm{H}_{3} \mathrm{SO}_{2} \mathrm{NH}_{2}\) (d) \(\mathrm{CH}_{3} \mathrm{COCH}_{2} \mathrm{COOC}_{2} \mathrm{H}_{3}\)

4 step solution

Problem 31

Phenol on heating with Zn-dust produce: (a) \(\mathrm{C}_{s} \mathrm{H}_{6}\) (b) \(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{CHO}\) (c) \(\mathrm{C}_{4} \mathrm{H}_{2} \mathrm{ZnO}\) (d) \(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{CH}_{2} \mathrm{OH}\)

3 step solution

Problem 32

Acetophenone is prepared by the reaction of which of the following in presence of \(\mathrm{AICl}_{3}\) as catalyst: |AFMC 1996] (a) benzene + acetone (b) benzene + acetyl chloride (c) phenol \(+\) acetic acid (d) phenol + acetone

4 step solution

Problem 33

Phenol does not react with: (a) \(\mathrm{NaOH}\) (b) \(\mathrm{KOH}\) (c) \(\mathrm{Na}\) (d) \(\mathrm{Na}_{2} \mathrm{CO}_{3}\)

4 step solution

Problem 34

Aniline and nitrous acid react to produce (a) nitrobenzene (b) benzene diazonium salt (c) phenol (d) chlorobenzene

5 step solution

Problem 35

Coal tar is a main source of : (a) cycloalkanes (b) heterocyclic compounds (c) aromatic compounds (d) aliphatic compounds

4 step solution

Problem 37

\(\mathrm{C}_{6} \mathrm{H}_{6}+\mathrm{CH}_{3} \mathrm{Cl} \stackrel{\mathrm{A} \mathrm{Cl}_{3}}{\longrightarrow} \mathrm{C}_{6} \mathrm{H}_{3} \mathrm{CH}_{3}+\mathrm{HCl}\) is known as: (a) Kolbe's reaction (b) Friedel-Crafts reaction (c) Wurtz reaction (d) Fittig reaction

4 step solution

Problem 38

A compound on treatment with NaOH followed by addition of \(\mathrm{AgNO}_{3}\) produces white precipitate at room temperature, the precipitate is soluble in \(\mathrm{NH}_{4} \mathrm{OH}\). The compound is identified as: [AFMC 1997] (a) vinyl chloride (b) benzyl chloride (c) chlorobenzene (d) ethyl bromide

5 step solution

Problem 40

The conversion of benzaldehyde into benzyl alcohol is known as (a) Cannizzaro's reaction (b) Kolbe's reaction (c) Friedel-Craft reaction (d) Wurtz reaction

4 step solution

Problem 41

A mixture of sodium benzoate and sodalime on heating produces: (a) \(\mathrm{CH}_{4}\) |AFMC 1999] (b) \(\mathrm{C}_{6} \mathrm{H}_{6}\) (c) both (a) and (b) (d) none of these

4 step solution

Problem 42

Chromyl chloride oxidises toluene to benzaldehyde. This reaction is known as : (a) Rosenmund reaction (b) Wurtz reaction (c) Etard reaction (d) Fittig reaction

4 step solution

Problem 44

The main component of middle oil fraction of coal tar distillation is: IAFMC 2000] (a) bemnene (b) phenol (c) naphithalene (d) pyrrole

4 step solution

Problem 45

Phenol is more readily soluble in: (a) NaOll solution (b) dil. \(\mathrm{HCl}\) (c) both \(\mathrm{NaOH}\) and \(\mathrm{HCl}\) (d) \(\mathrm{NaHCO}_{3}\) solution

6 step solution

Problem 46

Bengene does not undergo addition reaction easily because; (a) it has six hydrogen atoms (b) it has a cyclic structure (c) double bonds present in benxene are strong (d) resonance stabilised system is to be preserved

5 step solution

Problem 48

Nitrobenzene on nitration produce: (a) \(o\)-dinitrobenzene (b) \(m\)-dinitrobenzene (c) \(p\)-dinitrobenzene (d) none of these

4 step solution

Problem 49

Which of the following compound can be easily sulphonated? [AFMC 2002] (a) Chlorobenzene (b) Nitrobenzene (c) Toluene (d) Benzene

4 step solution

Problem 50

Among the following groups, the ortho and para directing group is: |AFMC 2003| (a) \(-\mathrm{COCH}_{3}\) (b) \(-\mathrm{CN}\) (c) \(-\mathrm{NHCOCH}_{3}\) (d) \(-\mathrm{COOH}\)

6 step solution

Problem 51

Aniline on treatment with \(\mathrm{HNO}_{2}\) at \(0^{\circ} \mathrm{C}\) to produce which of the following compounds? [AFMC 2003| (a) diazonium salt (b) hydrozo compound (c) nhenol and \(\mathrm{N}_{3}\) (d) nitroaniline

4 step solution

Problem 52

O=C(O)c1ccc(O)cc1 \(X\) is identified as (a) \(2,4,6\)-tribromophenol (b) 2-bromo-4-hydroxylbenzene sulphonic acid (c) 3,5-dibromo-4-hydroxybenzene sulphonic acid (d) 2-bromophenol

4 step solution

Problem 53

Aniline reacts with which of these to form Schiff base? |AFMC 2004] (a) Acetic acid (b) Benzaldehyde (c) Acetone (d) \(\mathrm{NH}_{3}\)

4 step solution

Problem 54

When toluene is treated with \(\mathrm{KMnO}_{4}\), what is produced? [AFMC 2005] (a) Benzene (b) Chlorobenzene (c) Benzaldehyde (d) Benzoic acid

4 step solution

Problem 55

Carbolic acid is: (a) \(\mathrm{C}_{6} \mathrm{H}_{3} \mathrm{CHO}\) (b) \(\mathrm{C}_{6} \mathrm{H}_{6}\) (c) \(\mathrm{C}_{\mathrm{c}} \mathrm{H}_{3} \mathrm{COOH}\) (d) \(\mathrm{C}_{6} \mathrm{H}_{3} \mathrm{OH}\)

3 step solution

Problem 56

Salicylic acid is prepared from phenol by: \(\mid \mathbf{A F}\) (a) Reimer-Tiemann reaction (b) Kolbe's reaction (c) Kolbe-electrolysis reaction (d) none of the above

4 step solution

Problem 57

Reduction of nitrobenzene with \(\mathrm{Sn} / \mathrm{HCl}\) (a) aniline (b) benzene (c) axobenzene (d) azoxybenzene

4 step solution

Problem 58

The compound known as oil of winter green is: |AIIMS 1995\(]\) (a) phenyl acetate (b) phenyl salicylate (c) phenyl bengoate (d) methyl salicylate

3 step solution

Problem 59

Benzaldehyde on refluxing with aqueous alcoholic KCN produce: IAIIMS 19\%| (a) cyanobenzene (b) cyanohydrin (c) benzoyl cyanide (d) benzoin

4 step solution

Problem 60

The compound which does not produce red precipitate with Fehling's solution is: |AIIMS 1996] (a) glucose (b) benzophenone (c) formalin (d) acetaldehyde

3 step solution

Problem 61

Reduction of benzoyl chloride with Pd and \(\mathrm{BaSO}_{4}\) gives: IAIIMS 1997] (a) benzyl chloride (b) benzaldehyde (c) benzoic acid (d) benzene sulphony] chloride

4 step solution

Problem 63

\(\mathrm{BHC}\) is used as an: (a) insecticide (b) disinfectant (c) mosquito repellent (d) antiseptic

3 step solution

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