alcohols, phenols & ethersalcohols, phenols & ethers 1. 1. alcohols boil at higher...

Alcohols, Phenols & Ethers

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1. Alcohols boil at higher temperature thanthe corresponding hydrocarbons due to

(A) intermolecular hydrogen bonding(B) intramolecular hydrogen bonding(C) van der Waal’s forces of attraction(D) dipole – dipole interactions

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1. Alcohols boil at higher temperature thanthe corresponding hydrocarbons due to

(A) intermolecular hydrogen bonding(B) intramolecular hydrogen bonding(C) van der Waal’s forces of attraction(D) dipole – dipole interactions

Ans: (A)

Ans: (A)

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2. Vinyl carbinol is ____________

(A)(B)(C)(D)

2 2CH CH CH OH

3CH CH CH OH

3CH CH CH OH

3 2CH C(OH) CH

2CH CH OH

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2. Vinyl carbinol is ____________

(A)(B)(C)(D) 3CH CH CH OH

Carbinol is CH3OH, which is attached tovinyl group. Therefore Ans is (C)

2CH CH OH

2 2CH CH CH OH

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2 2CH CH CH OH

3. 1-propanol and 2-propanol can be bestdistinguished by(A) Oxidation with alk. KMnO4 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 conc. H2SO4 followed by

reaction with Fehling solution.

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3. 1-propanol and 2-propanol can be bestdistinguished by(A) Oxidation with alk. KMnO4 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 conc. H2SO4 followed by

reaction with Fehling solution.

red colour.No reaction.

Ans (C)

Cu Fehling3 2 2 3 2 Soln

CH CH CH OH CH CH CHO s

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red colour.No reaction.

Ans (C)

Cu Fehling3 3 3 3 Soln

CH CH CH CH COCH|OH

4. Phenyl magnesium bromide reacts withmethanol to give

(A) a mixture of anisols and Mg(OH)Br(B) a mixture of benzene and Mg(OMe)Br(C) a mixture of toluene and Mg (OH)Br(D) a mixture of phenol and Mg(OH)Br

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4. Phenyl magnesium bromide reacts withmethanol to give

(A) a mixture of anisols and Mg(OH)Br(B) a mixture of benzene and Mg(OMe)Br(C) a mixture of toluene and Mg (OH)Br(D) a mixture of phenol and Mg(OH)Br

Ans: (B)

6 5 3 6 6C H MgBr CH OH C H Mg(OMe)Br

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Ans: (B)

5) Reduction of aldehyde, RCHO withsodium and ethanol gives

(A) 1° alcohol

(B) 2° alcohol

(C) 3° alcohol

(D) alkane

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5) Reduction of aldehyde, RCHO withsodium and ethanol gives

(A) 1° alcohol

(B) 2° alcohol

(C) 3° alcohol

(D) alkane

Ans: A) 1° alcohol

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Ans: A) 1° alcohol

6) Which of the following compound willproduce a primary alcohol on reaction withGrignard reagent followed by hydrolysis?

(A) acetone (B)methyl cyanide

(C) ethylene oxide (D) ethyl acetate

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6) Which of the following compound willproduce a primary alcohol on reaction withGrignard reagent followed by hydrolysis?

(A) acetone (B)methyl cyanide

(C) ethylene oxide (D) ethyl acetate

Grignard reagent is converted into 1° alcoholusing H−CHO or ethyleneoxide

1° alcohol containing 2 carbon atoms more thanthe Grignard reagent can be obtained by treatingwith R-Mg-X with ethylene oxide followed byacid hydrolysis,

Ans: (C) ethylene oxide

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Grignard reagent is converted into 1° alcoholusing H−CHO or ethyleneoxide

1° alcohol containing 2 carbon atoms more thanthe Grignard reagent can be obtained by treatingwith R-Mg-X with ethylene oxide followed byacid hydrolysis,

Ans: (C) ethylene oxide

7) The compound X in the reaction is

(A) (B)

(C) (CH3)2CH(OMgBr) (D)

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7) The compound X in the reaction is

(A) (B)

(C) (CH3)2CH(OMgBr) (D)

Ans:

(C) (CH3)2CH(OMgBr)

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Ans:

(C) (CH3)2CH(OMgBr)

8. In the following sequence of reaction:The compound D is

(A) 2-propanal (B) 1-propanal(C) 1-butanol (D) 2-butanal

2 2P I H OMg HCHO3 2 2 ether

CH CH CH OH A B C D

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8. In the following sequence of reaction:The compound D is

(A) 2-propanal (B) 1-propanal(C) 1-butanol (D) 2-butanal

2P/I Mg3 2 2 3 2 2 3 2 3ether

HCHO3 2 2 2

CH CH CH OH CH CH CH I CH CH CH MgI

CH CH CH CH OMgI

1-butanol +Mg(OH)I

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2P/I Mg3 2 2 3 2 2 3 2 3ether

HCHO3 2 2 2

CH CH CH OH CH CH CH I CH CH CH MgI

CH CH CH CH OMgI

1-butanol +Mg(OH)IH2O

Ans: (C)

9. Which one of the following is most acidic?

(A)CH3OH(B)CH3CH2OH(C) (CH3)2CHOH(D) (CH3)3COH

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9. Which one of the following is most acidic?

(A)CH3OH(B)CH3CH2OH(C) (CH3)2CHOH(D) (CH3)3COH

Due to the electron releasing groups in othercompounds.Ans: (a) CH3OH

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10. Which one of the following is most acidic?

(A)H2O (B) CH3CH2OH(C) CH3OCH3 (D) C6H5OH

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10. Which one of the following is most acidic?

(A)H2O (B) CH3CH2OH(C) CH3OCH3 (D) C6H5OH

C6H5OHDue the presence of more electro negativeSp2 hybridised carbon of benzene.

Ans: (D)

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C6H5OHDue the presence of more electro negativeSp2 hybridised carbon of benzene.

Ans: (D)

11)The reactivity of alcohol towardsactive metal is

(A) 3° > 2° > 1°

(B) 1° > 2° > 3°

(C) 3° > 1° > 2°

(D) 2° < 3° < 1°22

11)The reactivity of alcohol towardsactive metal is

(A) 3° > 2° > 1°

(B) 1° > 2° > 3°

(C) 3° > 1° > 2°

(D) 2° < 3° < 1°

When an alcohol reacts with a metal, forexample, sodium, bond between RO−H isbroken for which 1° alcohols are mostreactive since 1° alcohols are more acidicthan 3° alcohols which is least reactive.

Ans (B) 1° > 2° > 3°

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When an alcohol reacts with a metal, forexample, sodium, bond between RO−H isbroken for which 1° alcohols are mostreactive since 1° alcohols are more acidicthan 3° alcohols which is least reactive.

Ans (B) 1° > 2° > 3°

12) Pentan-3-ol is an example of –

(A)1 alcohol(B) 2 alcohol(C) 3 alcohol(D) aromatic alcohol

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12) Pentan-3-ol is an example of –

(A)1 alcohol(B) 2 alcohol(C) 3 alcohol(D) aromatic alcohol

Ans: (B)

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13. How many optically active isomers arepossible for butane-2, 3-diol?

(A) 1 (B) 2 (C) 3 (D) 4

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Ans: (B) There are 2 chiral carbons but due tothe presence of symmetry, the compoundshows two optically active isomers only

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Ans: (B) There are 2 chiral carbons but due tothe presence of symmetry, the compoundshows two optically active isomers only

H C OH

H C OH

CH3

CH3

H C OH

HO C H

CH3

CH3

14) The order of reactivity of a Grignardreagent with the following is

I) CH3-CO-CH3

II) CH3-CHOIII) C6H5-CO-C6H5

(A) II > III > I (B) I > III > II(C) II > I > III (D) all react with same rate

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14) The order of reactivity of a Grignardreagent with the following is

I) CH3-CO-CH3

II) CH3-CHOIII) C6H5-CO-C6H5

(A) II > III > I (B) I > III > II(C) II > I > III (D) all react with same rate

Reactivity is high when steric hindranceis the least.

C) II > I > III

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Reactivity is high when steric hindranceis the least.

C) II > I > III

15. 0.037 g of an alcohol was added to CH3MgIand the gas evolved measured 11.2 cm3 atSTP. What is the molecular formula of thealcohol?

(A)C4H10O (B) C4H8O(C) C5H12O (D) C5H10O

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15. 0.037 g of an alcohol was added to CH3MgIand the gas evolved measured 11.2 cm3 atSTP. What is the molecular formula of thealcohol?

(A)C4H10O (B) C4H8O(C) C5H12O (D) C5H10O

311.2 cm 0.037 g of alc

0.037 2240074 g

11.2

• C4H10O

• 22400 cm3 of the gas liberated by

alc

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0.037 2240074 g

11.2

• C4H10O

Ans: (A)

16. In the following sequence of reaction.

The compound A is

(A)CH3CH2CH2CH2OH(B) (CH3)2CHOH(C) (CH3)3COH(D) CH3CH2COCH2CH3

Cu HBr aq.KOH3 3573

A B C (CH ) COH

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16. In the following sequence of reaction.

The compound A is

(A)CH3CH2CH2CH2OH(B) (CH3)2CHOH(C) (CH3)3COH(D) CH3CH2COCH2CH3

Tertiary alcohols undergo dehydration togive an alkene ,2-methyl propene which onreaction with HBr gives addition productaccording to Mark Rule. That on KOHtreatment gives tertiary butyl alcoholAns: (C)

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Tertiary alcohols undergo dehydration togive an alkene ,2-methyl propene which onreaction with HBr gives addition productaccording to Mark Rule. That on KOHtreatment gives tertiary butyl alcoholAns: (C)

17. Which of the following has highestBoiling ?

(A) C4H9Cl (B) C4H9OH

(C) C4H9Br (D)

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17. Which of the following has highestBoiling ?

(A) C4H9Cl (B) C4H9OH

(C) C4H9Br (D) 3 2 2|CH CH CH CH OH

OH

Ans: (D)Dihydric alcohols have highest B.Pt due toextensive intermolecular H-bonding

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Ans: (D)Dihydric alcohols have highest B.Pt due toextensive intermolecular H-bonding

18. CH3 CH2 CH2Br

The compound Y is

(A) Propene (B) n-propylalcohol(C) propane (D) n-propyl borate

3

2 2

BHalc. KOHH O /NaOH

X Y.

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18. CH3 CH2 CH2Br

The compound Y is

(A) Propene (B) n-propylalcohol(C) propane (D) n-propyl borate

I step is de hydrohalogenation and an alkeneis obtainedII step is alkene on hydroboration oxidationgives an alcohol against to markovnikov’srule.

Ans: (B)

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I step is de hydrohalogenation and an alkeneis obtainedII step is alkene on hydroboration oxidationgives an alcohol against to markovnikov’srule.

Ans: (B)

19. Which of the following reagents is used inthe conversion of primary alcohol toaldehydes only?

(A)Corey’s reagent (B) Lucas reagent

(C) Baeyer’s reagent (D) Victor meyer’s reagent

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19. Which of the following reagents is used inthe conversion of primary alcohol toaldehydes only?

(A)Corey’s reagent (B) Lucas reagent

(C) Baeyer’s reagent (D) Victor meyer’s reagent

Ans (A): Corey’s reagent PCC

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20) The following structure onoxymercuration-reduction gives

a) b)

c) d)

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20) The following structure onoxymercuration-reduction gives

a) b)

c) d)

Mark Rule

Oxymercuration –reduction reagent is Mercuric acetate in THFand water and reduction with NaBH4 which takes placeaccording to Mark Rule

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Ans: A)

21)Which of the following functional groupcannot be reduced to alcohol usingsodium borohydride in ethanoic solution?

a) R – CHOb) R – CO – Rc) R – COOHd) RCOCl

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21)Which of the following functional groupcannot be reduced to alcohol usingsodium borohydride in ethanoic solution?

a) R – CHOb) R – CO – Rc) R – COOHd) RCOCl

NaBH4 is a mild reducing agentNaBH4 can reduce aldehyde, ketones,acid chlorides to alcohols but not acids orethers.

Ans: c) R−COOH

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NaBH4 is a mild reducing agentNaBH4 can reduce aldehyde, ketones,acid chlorides to alcohols but not acids orethers.

Ans: c) R−COOH

22) Which of the following is correct orderof solubility of alcohols in water?

A)isopropyl alcohol > n – propyl alcohol > ethylalcohol

B) isopropyl alcohol > ethyl alcohol > n – propylalcohol

C) isopropyl alcohol < n – propyl alcohol > ethylalcohol

D) n – propyl alcohol < isoporpyl alcohol < ethylalcohol

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22) Which of the following is correct orderof solubility of alcohols in water?

A)isopropyl alcohol > n – propyl alcohol > ethylalcohol

B) isopropyl alcohol > ethyl alcohol > n – propylalcohol

C) isopropyl alcohol < n – propyl alcohol > ethylalcohol

D) n – propyl alcohol < isoporpyl alcohol < ethylalcohol

Branching increases solubility, straightchain alcohols are less soluble. This isdue to the surface area of non-polarhydrocarbon part decreases and solubilityincreases.

Ans:c) Isopropyl alcohol > ethylalcohol >propyl alcohols

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Branching increases solubility, straightchain alcohols are less soluble. This isdue to the surface area of non-polarhydrocarbon part decreases and solubilityincreases.

Ans:c) Isopropyl alcohol > ethylalcohol >propyl alcohols

23) The order of reactivity of hydrogenhalide towards ROH is

a) HI > HBr > HCl

b) HI < HBr < HCl

c) HI > HBr < HCl

d) HI < HBr < HCl

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23) The order of reactivity of hydrogenhalide towards ROH is

a) HI > HBr > HCl

b) HI < HBr < HCl

c) HI > HBr < HCl

d) HI < HBr < HCl

As we move from HCl to HBr to HI, acidstrength increases and bond strengthdecreases.

Ans: a) HI > HBr > HCl

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As we move from HCl to HBr to HI, acidstrength increases and bond strengthdecreases.

Ans: a) HI > HBr > HCl

24. Which of the following reacts withsodium bicarbonate?

A) phenol B) waterC) alcohol D) picric acid.

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24. Which of the following reacts withsodium bicarbonate?

A) phenol B) waterC) alcohol D) picric acid.

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is an acid stronger than H2CO3 orHCO3

-. Hence it reacts withNaHCO3 to liberate CO2.Ans: D) picric acid

25. A trihydric phenol is –

A) catechol B) phloroglucinolC) quinol D) resorcinol

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25. A trihydric phenol is –

A) catechol B) phloroglucinolC) quinol D) resorcinol

Ans:

B)

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26.Match the acids and their pKavalues

P] p-cresol 1] 7.15Q] p-nitrophenol 2] 0.71R] phenol 3] 9.98S] picric acid 4] 10.14

A) P-4, Q-1, R-3, S-2B) P-2, Q-1, R-3, S-4C) P-3, Q-1, R-2, S-4D) P-1, Q-3,R-4, S-2

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26.Match the acids and their pKavalues

P] p-cresol 1] 7.15Q] p-nitrophenol 2] 0.71R] phenol 3] 9.98S] picric acid 4] 10.14

A) P-4, Q-1, R-3, S-2B) P-2, Q-1, R-3, S-4C) P-3, Q-1, R-2, S-4D) P-1, Q-3,R-4, S-2

Cresol is weaker acid than phenol,has higher pKa value than phenol.Nitrophenol is stronger acid thanphenol, has lower pKa value. Picricacid is the strongest acid, haslowest pKa value.Ans: A) P-4, Q-1, R-3, S-2

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Cresol is weaker acid than phenol,has higher pKa value than phenol.Nitrophenol is stronger acid thanphenol, has lower pKa value. Picricacid is the strongest acid, haslowest pKa value.Ans: A) P-4, Q-1, R-3, S-2

27.When phenol/salicylic acid isshaken with bromine water, thewhite precipitate formed is-

A) 2,4,6-trinitrotolueneB) 2,4,6-trinitrophenolC) 2,4,6-tribromophenolD) 2,4,6-tribromotoluene

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27.When phenol/salicylic acid isshaken with bromine water, thewhite precipitate formed is-

A) 2,4,6-trinitrotolueneB) 2,4,6-trinitrophenolC) 2,4,6-tribromophenolD) 2,4,6-tribromotoluene

Both phenol and salicylic acidhave ring activating –OH group.Hence both form tribromoderivativewith bromine water.Ans: C) 2, 4, 6-tribromophenol

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Both phenol and salicylic acidhave ring activating –OH group.Hence both form tribromoderivativewith bromine water.Ans: C) 2, 4, 6-tribromophenol

28.Which of the following gives atribromo derivative when treatedwith bromine water?

A) m-cresol B) o-cresolC) p-cresol D) benzyl alcohol

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28.Which of the following gives atribromo derivative when treatedwith bromine water?

A) m-cresol B) o-cresolC) p-cresol D) benzyl alcohol

m-cresol is

It has all o and p positions free forbromination. Hence forms atribromo derivative.Ans: A) m-cresol

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m-cresol is

It has all o and p positions free forbromination. Hence forms atribromo derivative.Ans: A) m-cresol

29. The number of alcoholic andethereal isomers possible forC4H10O are

A) 4 and 3 B) 3 and 2C) 3 and 4 D) 4 and 2

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29. The number of alcoholic andethereal isomers possible forC4H10O are

A) 4 and 3 B) 3 and 2C) 3 and 4 D) 4 and 2

With C4H10O – four butyl alcoholsand 3 isomeric ethers are possible.

Ans:A) 4 and 3

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With C4H10O – four butyl alcoholsand 3 isomeric ethers are possible.

Ans:A) 4 and 3

30. A compound X reacts with phthalic anhydridein presence of conc. H2SO4 forming thecompound Y which gives pink colour withNaOH solution. The compound Y is

(A)Phenol (B) Phenolphthalein(C) toluene (D) o-cresol

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30. A compound X reacts with phthalic anhydridein presence of conc. H2SO4 forming thecompound Y which gives pink colour withNaOH solution. The compound Y is

(A)Phenol (B) Phenolphthalein(C) toluene (D) o-cresol

X = phenol, Y = phenolphthalein

Ans: (B)

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X = phenol, Y = phenolphthalein

Ans: (B)

31. Identify the product ‘Y’.

A) benzyl alcoholB) anisoleC) benzoic acidD) benzyl methyl ether

OH

LiAlH4 XCH2N2 Y

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31. Identify the product ‘Y’.

A) benzyl alcoholB) anisoleC) benzoic acidD) benzyl methyl ether

For diazomethane no catalyst isrequired.Ans:D) Benzyl methyl ether

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For diazomethane no catalyst isrequired.Ans:D) Benzyl methyl ether

32. When phenol is converted to salicylaldehydeby treating it with CHCl3 and NaOH. Thereaction is called as

(A)Kolbe’s reaction(B) Friedel Crafts reaction(C) Reimer Tiemann reaction(D) Fries reaction

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32. When phenol is converted to salicylaldehydeby treating it with CHCl3 and NaOH. Thereaction is called as

(A)Kolbe’s reaction(B) Friedel Crafts reaction(C) Reimer Tiemann reaction(D) Fries reaction

Reimer Tiemann reactionAns: (C)

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Reimer Tiemann reactionAns: (C)

33. O-nitrophenol and p-nitrophenol areseparated by

(A) steam distillation (B) ordinary distillation(C) fractional distillation (D) solvent extraction

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33. O-nitrophenol and p-nitrophenol areseparated by

(A) steam distillation (B) ordinary distillation(C) fractional distillation (D) solvent extraction

Stream distillation, more volatile O-nitrophenoldue to intra molecular H-bond gets separatedeasily.Ans:(A)

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34. In the reaction3 2 2 4only AlCl O H SO

6 6 heatC H X Y Z phenol acetone

The compound Y in the above reaction is

(A) Isopropyl benzene (B) Ethyl benzene(C) Acetophenone (D) Toluene

only

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The compound Y in the above reaction is

(A) Isopropyl benzene (B) Ethyl benzene(C) Acetophenone (D) Toluene

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Ans: (A)

35. The compound C4H10O(X) is produced bythe reaction of conc. H2SO4 / H2O on alkene,and X is not resolvable into optical isomers.The X compound is

(A)2-methyl propan-2-ol(B) 2-methyl propan-1-ol(C) 2, 2 dimethyl ethan-1-ol(D) 2-methyl butan-2-ol

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35. The compound C4H10O(X) is produced bythe reaction of conc. H2SO4 / H2O on alkene,and X is not resolvable into optical isomers.The X compound is

(A)2-methyl propan-2-ol(B) 2-methyl propan-1-ol(C) 2, 2 dimethyl ethan-1-ol(D) 2-methyl butan-2-ol

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Ans: (A)

36. In the following compounds

Order of acidity is(A) (III) > IV > I > II (B) I > IV > III > II(C) II > I > III > IV (D) IV > III > I > II

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36. In the following compounds

Order of acidity is(A) (III) > IV > I > II (B) I > IV > III > II(C) II > I > III > IV (D) IV > III > I > II

Ans: (D)

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37. When ethoxy ethane is treated withexcess of HI at 373 K the product /products formed are

(A) C2H5OH + C2H5I (B) C2H5I(C) C2H6 + C2H5I (D) C4H10

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37. When ethoxy ethane is treated withexcess of HI at 373 K the product /products formed are

(A) C2H5OH + C2H5I (B) C2H5I(C) C2H6 + C2H5I (D) C4H10

Ans: (B) C2H5I

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38. Diethyl ether is not isomeric with

A) butanalB) 2-butanolC) methyl n-propyl etherD) buta-1-ol

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38. Diethyl ether is not isomeric with

A) butanalB) 2-butanolC) methyl n-propyl etherD) buta-1-ol

For C2H5OC2H5 ; CH3CH2CH2CH2OH,CH3CH(OH)CH2CH3 andCH3O-CH2CH2CH3 are all isomersbut not CH3CH2CH2CHO (butanal)

Ans: A) butanal

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For C2H5OC2H5 ; CH3CH2CH2CH2OH,CH3CH(OH)CH2CH3 andCH3O-CH2CH2CH3 are all isomersbut not CH3CH2CH2CHO (butanal)

Ans: A) butanal

39. dibenzyl ether is heated with (a)1mole HI and (b) excess HI theproducts formed are

a bA 2molC6H5CH2OH C6H5CH2OH+C6H5CH2I

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A 2molC6H5CH2OH C6H5CH2OH+C6H5CH2I

B C6H5CH2OH+C6H5CH2I 2mol C6H5CH2IC 2mol C6H5CH2I C6H5CH2OH+C6H5CH2I

D 2mol C6H5CH2I 2mol C6H5CH2OH

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Ans:B) C6H5CH2OH + C2H5CH2I,

2 mol C6H5CH2I

40. Aspirin is the acetylated product of

A) o-hydroxybenzoic acidB) o-hydroxy benzeneC) m-hydroxybenzoicacidD) o-hydroxybenzaldehyde

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40. Aspirin is the acetylated product of

A) o-hydroxybenzoic acidB) o-hydroxy benzeneC) m-hydroxybenzoicacidD) o-hydroxybenzaldehyde

is aspirin, obtained by acetylation of

o-hydroxy benzoic acidAns: A) o-hydroxybenzoic acid

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is aspirin, obtained by acetylation of

o-hydroxy benzoic acidAns: A) o-hydroxybenzoic acid

41. 2-phenylethanol is preparedusing

A) phenyl magnesium bromide andethylene oxide

B) phenyl magnesium bromide andethylene glycol

C) phenyl magnesium bromide andethyl alcohol

D) methyl magnesium bromide andbenzaldehyde

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41. 2-phenylethanol is preparedusing

A) phenyl magnesium bromide andethylene oxide

B) phenyl magnesium bromide andethylene glycol

C) phenyl magnesium bromide andethyl alcohol

D) methyl magnesium bromide andbenzaldehyde

C6H5CH2CH2OH is 2-phenylethanol(2) (1)

Ans: A) Phenyl magnesium bromideand ethylene oxide

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C6H5CH2CH2OH is 2-phenylethanol(2) (1)

Ans: A) Phenyl magnesium bromideand ethylene oxide

42. Identify the products formedwhen t-butyl methyl ether isheated with limited conc.HI

A) t-butyl alcohol & methyl iodideB) t-butyl iodide & methyl alcoholC) t-butyl iodide & methyl iodideD) t-butyl alcohol & methyl alcohol

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42. Identify the products formedwhen t-butyl methyl ether isheated with limited conc.HI

A) t-butyl alcohol & methyl iodideB) t-butyl iodide & methyl alcoholC) t-butyl iodide & methyl iodideD) t-butyl alcohol & methyl alcohol

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Ans:b) t-butyliodide and methyl alcohol

43. In the reaction

The products A and B respectively are

(A)Iodobenzene and methanol(B) Phenol and Iodomethane(C) Benzene and Methoxy iodide(D) Benzene and methanol

373 K6 5 3C H OCH HI A B

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43. In the reaction

The products A and B respectively are

(A)Iodobenzene and methanol(B) Phenol and Iodomethane(C) Benzene and Methoxy iodide(D) Benzene and methanol

The bond between -O-CH3 is weaker than-O-C6H5 because in-O-C6H5 the carbon group issp2 hybridised and oxygen attains partial doublebond character through resonance.

Ans: (B) Phenol and Iodomethane

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The bond between -O-CH3 is weaker than-O-C6H5 because in-O-C6H5 the carbon group issp2 hybridised and oxygen attains partial doublebond character through resonance.

Ans: (B) Phenol and Iodomethane

44. During the reactionThe main product A is

(A) Isobutene (B) tes butyl ether(C) Isobutane (D) ter butyl ether

3 3 3(CH ) C Cl CH ONa A

88

For the preparation of unsymmetrical ethers,the alkyl halides should be primary, whereasthe alkoxides may be 1, 2 or 3. Ether isnot formed. Elimination competes oversubstitution reaction. Hence the answer isAns: (A) Isobutene

89

For the preparation of unsymmetrical ethers,the alkyl halides should be primary, whereasthe alkoxides may be 1, 2 or 3. Ether isnot formed. Elimination competes oversubstitution reaction. Hence the answer isAns: (A) Isobutene

45. During the Friedel crafts reaction ofanisole with acetyl chloride in presence ofanhy AlCl3, the major product obtained is

(A)m-methoxy acetophenone(B) o-methoxy acetophenone(C) p-methoxy acetophenone(D) p-methylanisole

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45. During the Friedel crafts reaction ofanisole with acetyl chloride in presence ofanhy AlCl3, the major product obtained is

(A)m-methoxy acetophenone(B) o-methoxy acetophenone(C) p-methoxy acetophenone(D) p-methylanisole

Ans: (C) p-methoxy acetophenone

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Ans: (C) p-methoxy acetophenone

46. What is the major product obtained when

(A)

(B)

(C)

(D)

is heated

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46. What is the major product obtained when

(A)

(B)

(C)

(D)

C6H4 (OH)-O- bond is stronger bond than theother group. Hence the bond is C6H4 (OH)-O- isnot cleaved.

Ans: (A)

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C6H4 (OH)-O- bond is stronger bond than theother group. Hence the bond is C6H4 (OH)-O- isnot cleaved.

Ans: (A)

47. Match the structures of the compounds given inColumn I with the name of the compounds given in ColumnII. Column I

(i)

(ii)

(iii)

(iv)

(v)

Column II(a) Hydroquinone

(b) Catechol

(c) o-Cresol

(d) Quinone(e)Resorcinol(f) Anisole

(i)

(ii)

(iii)

(iv)

(v)

(a) Hydroquinone

(b) Catechol

(c) o-Cresol

(d) Quinone(e)Resorcinol(f) Anisole

48. Match the items of column I with items of column II.

Column I Column II

(i)Antifreeze used in car engine

(ii) Solvent used in perfumes

(iii) Starting material for picricacid

(iv) Wood spirit

(v) Reagent used for detectionof phenols

(vi) By product of soap industry

(a) Neutral ferric chloride

(b) Glycerol

(c) Methanol

(d) Phenol

(e) Ethleneglycol phenolicgroup

(f) Ethanol used incosmetics

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(i)Antifreeze used in car engine

(ii) Solvent used in perfumes

(iii) Starting material for picricacid

(iv) Wood spirit

(v) Reagent used for detectionof phenols

(vi) By product of soap industry

(a) Neutral ferric chloride

(b) Glycerol

(c) Methanol

(d) Phenol

(e) Ethleneglycol phenolicgroup

(f) Ethanol used incosmetics

49. The compound which is also known ascarbolic acid is

(A)Phenol (B) Benzene(C) cresol (D) Toluene

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49. The compound which is also known ascarbolic acid is

(A)Phenol (B) Benzene(C) cresol (D) Toluene

Ans: A) Phenol

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50. The IUPAC name of m-Cresol is

(A) 3-chlorophenol (B) 3-Methoxyphenol

(C) 3-methyl phenol (D) benzene -1, 3-diol

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50. The IUPAC name of m-Cresol is

(A) 3-chlorophenol (B) 3-Methoxyphenol

(C) 3-methyl phenol (D) benzene -1, 3-diol

Ans: (C) 3-methyl phenol

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51.In the following reaction:

The compound E in the reaction?

(A)Benzene (B) Phenol(C) Cyclohexanol (D) Cyclohexane

2H /NiZn Oleum NaOH HClNaOH 573 K

A B C D E

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51.In the following reaction:

The compound E in the reaction?

(A)Benzene (B) Phenol(C) Cyclohexanol (D) Cyclohexane

Benzene on fusion with Oleum and NaOH givesSod. Benzene Sulphonate

Ans: (C) Cyclohexanol

101

Benzene on fusion with Oleum and NaOH givesSod. Benzene Sulphonate

Ans: (C) Cyclohexanol

52.Phenol condenses with HCHO in thepresence of dil acid to form the polymer

(A)Bakelite (B) Buna-S(C) Teflon (D) Melamine

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52.Phenol condenses with HCHO in thepresence of dil acid to form the polymer

(A)Bakelite (B) Buna-S(C) Teflon (D) Melamine

Ans(A) Bakelite

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53. How will you distinguish between phenoland Benzyl alcohol?

(A)using neutral FeCl3(B) using acidic FeCl3(C) using neutral FeCl2(D) using acidic FeCl2

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53. How will you distinguish between phenoland Benzyl alcohol?

(A)using neutral FeCl3(B) using acidic FeCl3(C) using neutral FeCl2(D) using acidic FeCl2

All phenols give violet colour with neutralFeCl3.Fe(C6H5O)3 is violet in colour.

Ans: (A)

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All phenols give violet colour with neutralFeCl3.Fe(C6H5O)3 is violet in colour.

Ans: (A)

54. When phenol reacts with Br2 in CS2 at 0C,the major product obtained is

(A) 2-bromo phenol (B) 3-bromo phenol(C) 4-bromo phenol (D) 2, 4, 6 tribromo phenol

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54. When phenol reacts with Br2 in CS2 at 0C,the major product obtained is

(A) 2-bromo phenol (B) 3-bromo phenol(C) 4-bromo phenol (D) 2, 4, 6 tribromo phenol

Ans (C): 4-bromo phenol

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55. The reaction of CH3CH = CH OHwith HBr gives

(A)CH3CHBrCH2 OH(B) CH3 CH2CHBr OH(C) CH3CHBrCH2 Br(D) CH3CH2CHBr Br

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55. The reaction of CH3CH = CH OHwith HBr gives

(A)CH3CHBrCH2 OH(B) CH3 CH2CHBr OH(C) CH3CHBrCH2 Br(D) CH3CH2CHBr Br

Ans: (B)

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56. The IUPAC name of the etherCH3OCH(CH3)2

(A)1-methoxy propane(B) propoxy methane(C) 2-methoxy propane(D) isopropoxy methane

110

56. The IUPAC name of the etherCH3OCH(CH3)2

(A)1-methoxy propane(B) propoxy methane(C) 2-methoxy propane(D) isopropoxy methane

Ans: (C) 2-methoxy propane

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57. The reactants required for the preparationof ter-butyl ethyl ether by Williamson’sreaction are

(A) ter butyl chloride + sodium ethoxide(B) sodium ter butoxide + ethyl chloride(C) ter butyl alcohol + ethyl chloride(D) ethyl alcohol + ter. butyl chloride

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57. The reactants required for the preparationof ter-butyl ethyl ether by Williamson’sreaction are

(A) ter butyl chloride + sodium ethoxide(B) sodium ter butoxide + ethyl chloride(C) ter butyl alcohol + ethyl chloride(D) ethyl alcohol + ter. butyl chloride

Ans: (B) sodium ter butoxide + ethyl chloride

113

58) Alcohol are obtained from alkenes by

a) hydrolysis with dilute H2SO4

b) hydration with aqueous KOH

c) hydration with alkaline KMnO4

d) Hydration using conc. H2SO4 and hydrolysis

114

58) Alcohol are obtained from alkenes by

a) hydrolysis with dilute H2SO4

b) hydration with aqueous KOH

c) hydration with alkaline KMnO4

d) Hydration using conc. H2SO4 and hydrolysis

Alkenes alcohol is by hydration usingconcentrated H2SO4 and hydrolysis.

Ans: d) Hydration using conc. H2SO4 andhydrolysis

115

Alkenes alcohol is by hydration usingconcentrated H2SO4 and hydrolysis.

Ans: d) Hydration using conc. H2SO4 andhydrolysis

59) A reaction between alcohol and organicacid to form ester involves

a) the cleavage of O – H bond of acidb) the cleavage of C–O bond of alcoholc) the formation of bond between oxygen

of COO group of acid and carbon ofalcohol

d) the cleavage of C–OH bond of acid

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59) A reaction between alcohol and organicacid to form ester involves

a) the cleavage of O – H bond of acidb) the cleavage of C–O bond of alcoholc) the formation of bond between oxygen

of COO group of acid and carbon ofalcohol

d) the cleavage of C–OH bond of acid

Ans:d) Cleavage of C−OH bond of the acid

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Ans:d) Cleavage of C−OH bond of the acid

60)When phenyl magnesium bromidereacts with t-butanol the productwould be

a) benzeneb) phenolc) t-butyl benzened) t-butyl phenyl ether

118

60)When phenyl magnesium bromidereacts with t-butanol the productwould be

a) benzeneb) phenolc) t-butyl benzened) t-butyl phenyl ether

(CH3)3C−OH reacts with C6H5MgBr toform benzene, because the alcohol hasacidic H atom in its –OH group.

Ans: A) benzene

119

(CH3)3C−OH reacts with C6H5MgBr toform benzene, because the alcohol hasacidic H atom in its –OH group.

Ans: A) benzene

61) The compound which gives the moststable carbocation on dehydration is

A) B)

C) D)

120

61) The compound which gives the moststable carbocation on dehydration is

A) B)

C) D)

3° carbocations are the most stable.

Ans:B) (CH3)3C−OH

121

3° carbocations are the most stable.

Ans:B) (CH3)3C−OH

62) pent-3-en-2-ol is converted intopent-3-en-2-one when treated with

a) Jones’ reagent

b) potassium dichromate

c) potassium permanganate

d) LiAlH4

122

62) pent-3-en-2-ol is converted intopent-3-en-2-one when treated with

a) Jones’ reagent

b) potassium dichromate

c) potassium permanganate

d) LiAlH4

This reaction is done by using Jonesreagent.

Ans: a) Jones reagent

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This reaction is done by using Jonesreagent.

Ans: a) Jones reagent

63) The order of dehydration of followingalcohols is

i) ii)

iii) iv)

A) I < II < III < IV B) I > II > III > IV

C) III < II < I < IV D) II < III < IV < I

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63) The order of dehydration of followingalcohols is

i) ii)

iii) iv)

A) I < II < III < IV B) I > II > III > IV

C) III < II < I < IV D) II < III < IV < I

Allylic and 3° alcohols undergodehydration the fastest.

Ans: c) III < II < I < IV

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Allylic and 3° alcohols undergodehydration the fastest.

Ans: c) III < II < I < IV

64) Hydrogen bonding is maximum in

A) ethanol

B) diethyl ether

C) ethylchloride

D) triethylamine

126

64) Hydrogen bonding is maximum in

A) ethanol

B) diethyl ether

C) ethylchloride

D) triethylamine

Ans: a) Ethanol

127

Ans: a) Ethanol

65) The dehydration of butanol–2 gives

A. 1 – butene onlyB. 2 – butene onlyC. both 1 – butene and 2 – butene

with 1–butene as major productD. both 1 – butene and 2 – butene

with 2–butene as major product128

65) The dehydration of butanol–2 gives

A. 1 – butene onlyB. 2 – butene onlyC. both 1 – butene and 2 – butene

with 1–butene as major productD. both 1 – butene and 2 – butene

with 2–butene as major product

Ans:

d) both 1 – butene and 2 – butene with2 – butene as major product

129

Ans:

d) both 1 – butene and 2 – butene with2 – butene as major product

66) A mixture of methanol vapour and airis passed over heated copper. Theproducts are

A) carbon monoxide and hydrogenB) formaldehyde and water vapourC) formic acid and water vapourD) carbon monoxide and water vapour

130

66) A mixture of methanol vapour and airis passed over heated copper. Theproducts are

A) carbon monoxide and hydrogenB) formaldehyde and water vapourC) formic acid and water vapourD) carbon monoxide and water vapour

OHCHOHOOHCH 2Cu

23

131

Ans:

b) formaldehyde and water vapour

OHCHOHOOHCH 2Cu

23

67). Which of these is not a productof phenol?

A) bakelite B) phenolphthaleinC) paracetamol D) melamine

132

67). Which of these is not a productof phenol?

A) bakelite B) phenolphthaleinC) paracetamol D) melamine

Ans:

D) Melamine

133

Ans:

D) Melamine

68).(a) di n-propyl ether ismanufactured by heating n-propylalcohol with conc. H2SO4.(b) di isopropylether cannot beobtained in the same way becauseelimination takes place to givealkenes.A) A is true, B is wrongB) A is wrong, B is trueC) both are true D)both are wrong

134

68).(a) di n-propyl ether ismanufactured by heating n-propylalcohol with conc. H2SO4.(b) di isopropylether cannot beobtained in the same way becauseelimination takes place to givealkenes.A) A is true, B is wrongB) A is wrong, B is trueC) both are true D)both are wrong

Ans: C) both are trueBecause n-propyl alcohol is 1°alcohol. Isopropyl alcohol is 2°alcohol.

135

Ans: C) both are trueBecause n-propyl alcohol is 1°alcohol. Isopropyl alcohol is 2°alcohol.

69). To get cresol, phenol issubjected to

A) Wurtz reactionB) Fittig reactionC)Friedel-Crafts reactionD)Gatterman reaction

136

69). To get cresol, phenol issubjected to

A) Wurtz reactionB) Fittig reactionC)Friedel-Crafts reactionD)Gatterman reaction

137

Ans: C)Friedel-Craft’s reaction

70). C7H8O could be which of thefollowing?

i] cresol ii] benzyl alcoholiii] anisole iv] toluidine

A) i, ii, iii B) ii, iiiC) ii, iii, iv D) i, ii, iv

138

70). C7H8O could be which of thefollowing?

i] cresol ii] benzyl alcoholiii] anisole iv] toluidine

A) i, ii, iii B) ii, iiiC) ii, iii, iv D) i, ii, iv

C7H8O can be

Ans: a) i, ii, iii

139

C7H8O can be

Ans: a) i, ii, iii

71). A compound ‘X’ with molecular formulaC3H8O can be oxidized to a compoundwith molecular formula C3H6O2. ‘X’ ismost likely a/an

(A)primary alcohol(B)secondary alcohol(C) Aldehyde(D) ketone

140

71). A compound ‘X’ with molecular formulaC3H8O can be oxidized to a compoundwith molecular formula C3H6O2. ‘X’ ismost likely a/an

(A)primary alcohol(B)secondary alcohol(C) Aldehyde(D) ketone

Ans: (A)

141

72).Which is not a phenol –

A) aspirinB)salicylic acidC) phenyl salicylate (salol)D) naphthol

142

72).Which is not a phenol –

A) aspirinB)salicylic acidC) phenyl salicylate (salol)D) naphthol

is aspirin it is not a phenol.Ans: A) Aspirin

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is aspirin it is not a phenol.Ans: A) Aspirin

Wish you all the best

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