PHENOLS AND ETHERS

1) Match the correct sequence

I) Catechol A) Benzene 1, 3 diol
II) Resorcinol B) Benzene 1, 2 diol
III) Quinol C) Benzene 1, 4 diol
I II III

1) A B C

2) B A C

3) C A B

4) A C B

2) The IUPAC name of phenetole

1) Ethyl phenyl ether 2) Ethoxy benzene 3) Methoxy benzene 4)ethoxy benzene

3) Which of the following statements are correct?

A) The C-O bond length in phenol is less than in methanol due to partial double
bond character in phenol C-O bond

B) In ethers the C-O-C bond angle is greater than teterahedral bond angle due to
bulkier R groups

C) The hybridisation of oxygen in ethers is sp3 hybridised

D) methoxy benzene is known as anisole

1) A, B, D 2) A, C, D 3) B, D 4) All

4) Phenol is also known as

1) Salol 2) Carbonic acid 3) Carbolic acid 4)

phenetole

5) In hydroboration oxidation , the boron side product formed is --------------

1) Boric oxide, it is also known as boron sesquioxide

2) orthoboric acid, it is a weak monobasic acid

3) Orthoboric acid, it is a tribasic acid

4) Boric acid, it is a dibasic acid

6) The addition of water to alkenes in hydroboration oxidation follows

 1) markonikovs addition 2) antimarkonikovs addition

3) saytzeffs rule 4) Hofmanns rule

Cl

NaOH
300
atm

623k
X HCl
Y

7) X and Y respectively are

1) Phenol, , chlorobenzene 2) Phenol, sodium phenoxide

3) sodiumphenoxide, phenol 4)sodium phenoxide, chlorobenzene

Benzene X

Benzenesulphonicacid NaOH
H
Y
8) ; X and Y respectively are

1) oleum, phenol 2) sulphuric acid, sodiumphenoxide

3) oleum, sodiumphenoxide 4) sulphuric acid, phenol

9) The temperature at which diazoniumsalts are stable

1) 273-373K 2) 273-283K 3) room temperature 4) at 500K

10) Which of the following is incorrect?

1) Isopropyl benzene is known as cumene

2) cumene on aerial oxidation forms cumene hydroperoxide

3) cumene hydroperoxide on acidification forms acetone and phenol

4) isopropyl benzene is also known as anisole

O
O
CH3
O
NaBH 4

11)
OH
O O
CH3
O O CH3

1) 2)
 OH
CH3 CH3
O

3) 4)

12) The number of moles of hydrogen gas liberated on treating 1 mole of phenol with
excess of potassium

1) 1 2) 1.5 3) 0.5 4) 2

13) Which of the following reacts with aqueous sodium hydroxide?

1) phenol 2) Ethanol 3) methanol 4) isopropanol

14) Which of the following statements are correct with respect to acidity of phenols?

1) The hydroxyl group in phenol is attached to sp2 carbon atom

2) The presence of electron withdrawing group increases the acidic strength

3) The presence of electron donate g group decreases the acidic strength

4) m-cresol is more acidic than p-cresol

1) only A 2) A, B, C 3) ALL 4) A, B

15) The order of increasing order of acid strength - A) phenol B) 2, 4 dinitrophenol C)

2,4, 6 trinitrophenol D) 4-methyl propanol

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

16) Which of the following is correct?

1) The reaction of carboxylic acid with acetic anhydride in presence of

Con.H2SO4 is a reversible reaction.

2) The introduction of acetyl group on phenol is known as acetylation

3) Acetyl salicylic acid is known as aspirin

4) The reaction of acid chloride with phenol is carried out presence of base to
neutralise the formed HCl

1) A, B 2) C, D 3) A, B, C 4) ALL

17) The OH group on benzene is

1) only ortho directing 2) only meta directing

3) only para directing 4) ortho and para directing

18) Phenol on treating with dil.HNO3 at low temperature forms

1) only o-nitrophenol 2) only p-nitro phenol

3) only m-nitrophenol 4) o- and p- nitrophenol

19) Which of the following s correct?

A) o-nitrophenol is steam volatile due to intramolecular H-bonding

B) p-nitrophenol is steam volatile due to intramolecular H-bonding

C) ortho and para isomers of nitrophenol can be separated by steam distillation

D) o-nitrophenol is steam volatile due to intermolecular H-bonding

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

20) Phenol on treating with con . HNO3 forms

1) ortho and para nitro phenols 2) 2, 4, 6 trinitrophenol

3) 2, 4 dinitrophenol 4) m-nitrophenol

21) Which of the following acid donot contain carboxylic acid group?

1) picric acid 2) citric acid 3) acetic acid 4) pimelic acid

OH

Con
. H 2 SO4
X Con. HNO3

22) ; X and Y are

1) phenol-2,4 disulphonic acid, phenol

2) phenol-2, 4 disulphonic acid, 2, 4 dinitrophenol

3) phenol-2, 4 disulphonic acid, picric acid

4) phenol sulphonic acid, picric acid

Y Br2
H 2O
phenol Br2 / CS2
273k
X

23) ; X and Y respectively are

1) o-bromophenol; 2, 4, 6 tribromophenol

2) o-bromophenol; p-bromophenol

3) o-bromophenol, p-bromophenol; 2, 4, 6 tribromophenol

 4) 2, 4, 6 tribromophenol ; o-bromophenol, p-bromophenol

24) The possible major product mononitration of 3-methyl phenol produces

CH3 OH CH3
HO
CH3 O
+
N -
OH CH3 O
+ + +
- N - N - N
O O O O O O OH
1) 2) 3) 4)

25) The possible major product on dinitration of 3-methyl phenol

-
O OH CH3 O
+ +
N N -
O O

CH3 OH
+ +
- N - N
O O O O
1) 2)

CH3 O
+ -
N O CH3 O
-
O + +
N N -
-
O O O
+
N OH
O OH
3) 4)

26) The major product formed on mononitration of phenyl ethanoate

CH3

CH3 O O

O O O
+
N -
O
+
- N
O O
1) 2)
 CH3

O CH3
O O

+ O + O
N N
- -
O O
3) 4)

27) Which of the following statements is/ are correctly related to kolbes reaction?

A) It is electrophilic aromatic substitution reaction

B) The product formed is ortho hydroxyl benzoic acid

C) CO2 acts as weak electrophile

D) The product formed can be used in the preparation of Aspirin

1) A, B, C 2) A, B 3) A, C 4) All

28) The intermediate Which on hydrolysis in presence of alkali produces

salicyladehyde in Riemer tiemann reaction is

1) substituted benzylidene acetate 2) benzal chloride

3) substituted benzal chloride 4) benzylidene acetate

29) The substitution of CHO group in Riemer Tiemann reaction takes place at

1) ortho 2) para 3) both ortho and para 4) meta

A
zn dust

Benzene oleum
X NaOH
H
A
30) ; A is

1) phenol 2) nitrobenzene 3) benzene sulphonic acid 4)

Aniline

31) The conjugated diketone formed on treating phenol with chromic acid

1) Benzophenone 2) Acetophenone 3) Benzoquinone 4) Phenylbenzoate

32) Phenol on treating with chloroform in presence of aqueous NaOH and on further
acidification forms

1) Salicylicacid 2) salicylaldehyde 3) Salol 4) acetyl

salicylic acid
33) Phenol on treating with ----------- moles of bromine water forms 2,4 , 6
tribromophenol

1) 1.5 2) 3 3) 2 4) 1

B H 2 SO4
413 k

Ethanol H 2 SO4
443 k
A
34) ; A and B respectively are

1) diethyl ether, ethane 2) ethane, diethyl ether

3) ethene, diethyl ether 4) diethyl ether, ethane

35) The formation of ether on treating ethanol withH2SO4 at 413K proceeds through

SN 2 SN 1 E1 E2
1) 2) 3) 4)

36) The formation of ethers by williamsons synthesis proceeds through ---------

mechanism

SN 1 SN 2 E1 E2
1) 2) 3) 4)

37) The major product obtained on treating tert-butyl chloride withsodium ethoxide is

1) t-butyl ethyl ether 2) 2-methyl propene

3) t-butyl methyl ether 4) t-butoxy ethane

38) The major product obtained on treating sodium tert-butoxide with methyl bromide
is

1) t-butyl ethyl ether 2) 2-methyl propene

3) t-butyl methyl ether 4) t-butoxy ethane

39) The order of reactivity of hydrogen halides towards cleavage of ethers

1) HCl> HBr > HI 2) HI > HBr > HCl

3) HI > HCl > HBr 4) HBr > HCl > HI

40) Aralkyl ethers in presence of hydrogen halides, The one of the product formed is

1) Phenol 2) Benzene 3) Benzyl ether 4)

halobenzene

41) tert-butyl methyl ether on treating with HI forms

1) methanol + t-butyl iodide 2) Methyl iodide + t-butyl alcohol

 3) 2-methyl propane + methanol 4) 2-methyl propane + methyl iodide
HI /
H3C O CH3

CH3
42)

H3C OH H3C I
I OH
CH3 H3C CH3 H3C
1) + 2) +
CH3 OH
CH3
H3C H3C
OH
CH3 H3C CH3 H3C
3) + 4) +

O CH3
CH3 HI /
H3C

CH3
43)

CH3 CH3
OH H3C I H3C
I OH
H3C H3C H3C H3C
1) + 2) +
I CH3 OH CH3
H3C H3C H3C H3C
OH I
CH3 H3C CH3 H3C
3) + 4) +

44) The alkoxy group on benzene ring is ----------- directing

1) ortho 2) para 3) ortho and para 4) meta

45) Anisole on bromination in presence of Br2/ CH3COOH forms

1) 2, 4, 6 tribrom anisole 2) only p-bromoanisole

3) m-bromo anisole 4) o and p bromo anisole

46) The reagent used for the conversion of anisole to o and p nitro anisole

1) Con HNO3 2) Con. H2SO4

3) mixture of Con. HNO3 + Con HNO3 4) Oleum

47) The product obtained on williamsons synthesis of ethanol and 3-methyl pentan-2-ol
are

1) 2-methoxy 3-ethyl pentane 2) 2-ethoxy 3-ethyl pentane

3) 2-methyl pent-2-ene 3) 2-methoxy pentane

 CH 3CH 2CH 2 O CH 3 HBr
48)

CH 3CH 2CH 2OH CH 3 Br CH 3OH CH 3CH 2CH 2 Br

1) 2)

CH 3CH 3OH CH 3CH 3 Br CH 3 Br CH 3CH 2OH

3) 4)

49) Ethoxy benzene on treating with nitration mixture forms

1) o-nitro ethoxy benzene 2) m-nitro ethoxy benzene

3) o and p nitro ethoxy benzene 4) 2, 4 dinitro ethoxy benzene

H , H 2O
CH 3CH CH 2
HAlCl
3 A
3 PO4 air
catalyst ,373k
B 350 K
C D

50)

1) A = cumene B= phenol C= acetone D= phenol

2) A = ethyl benzene B = phenol C= acetone D = phenol

3) A = cumene B = cumene hydroperoxide C= acetone D= phenol

4) A = cumene B = ethyl benzene C = acetone D= phenol

51) The IUPAC name of m- cresol

1) 3-methyl phenol 2) 3-chloro phenol 3) 3-methoxy phenol 4) benzene 1, 3 diol

52) Phenol is less acidic than

1) ethanol 2) o-nitrophenol 3) o-methoxy phenol 4) o-methoxy

phenol

53) Which of the following is most acidic ?

1) Benzyl alcohol 2) cyclohexanol 3) phenol 4) m-chlorophenol

54) Phenol can be distinguished from ethanol by

A) Br2/ water B) Na C) neutral FeCl3

1) A, B, C 2) A, C 3) B, C 4) A, B

55) Match the following

Column I column-II

1) Methanol A) conversion of phenol to o-hydroxybenzoic acid

2) Kolbes reaction B) ethyl alcohol
 3) Williamsons synthesis C) conversion of phenol to salicylaldehyde
4) Conversion of 2o alcohol to ketone D) wood spirit
5) Riemer-Tiemann reaction E) Heated copper at 573K
6) Fermentation F) Reation of alkyl halide with sodium alkoxide
1) 1-D, 2-A, 3-F, 4-E, 5-C, 6-B
2) 1-D, 2-F, 3-A, 4-E, 5-C, 6-B
3) 1-D, 2-A, 3-F, 4-C, 5-E, 6-B
4) 1-D, 2-A, 3-F, 4-E, 5-B, 6-C

56) Which of the following statements are incorrect?

A) The carbon atom in CO- is sp2 is sp2 hybridised

B) Catalytic dehydrogenation of 1o alcohols forms aldehydes

C) Ketones can be prepared by using oppaneur oxidation

D) Dry distillation of calcium benzoate forms benzophenone

1) only A, B 2) only A, C 3)only C, D 4) None of these

57) Addition of water to alkynes occurs in acidic medium and in the presence of Hg +2 ion as a catalyst.
Which of the following products will be formed on addition of water to but-1-yne under these
conditions?

CH 3CH 2CH 2CHO CH 3CH 2COCH 3

1) 2)

CH 3CH 2 COOH CO2 CH 3COOH HCHO

3) 4)

58) Which of the following compounds is most reactive towards nucleophilic substitution?

CH 3CHO CH 3COCH 3 C6 H 5CHO C6 H 5COCH 3

1) 2) 3) 4)

Ph O CO Ph
59) compound can be prepared by the reaction of

1) phenol and benzoic acid in the presence of NaOH

2) phenol and benzoyl choride in presence of pyridine

3) phenol and benzoyl chloride in presence of ZnCl 2

4) phenol and benzadehyde in the presence of palladium

CH 3 C CH
40%
H 2 SO4
1% HgSO4
A Isomerisation
CH 3COCH 3
60) ; structure of A and type of
isomerism in the above reaction are respectively

1) prop-1-en-2-ol , metamerism
 2) prop-1-en-1-ol , tautomerism

3) prop-2-en-2-ol, geometrical isomerism

4) prop-1-en-2ol, tautomerism

61) Which of the following compounds gives butanone on oxidation with alkaline KMnO 4 solution?

1) Butan-1-ol 2) Butan-2-ol 3) Both of these 4) none of these

62) The IUPAC name of CHO-CHO is

1) dial 2) Ethane 1,2 diol 3) ethane 1,2 dial 4) dialdehyde

63) The reaction of phenol with benzoyl chloride in presence of pyridine is known as

1) clemmenson reaction 2) claisen reaction

3) schotten-baumen reaction 4) Michael reaction

64) Di phenyl cadmium on treating with benzoyl chloride in dry ether forms

1) Acetophenone 2) Benzophenone 3) phenyl benzoate 4) phenyl acetate

65) Benzene on treating with CO + HCl in presence of AlCl 3/CuCl forms

1) phenol 2) benzenol 3) benzaldehyde 4) benzophenone

66) Propanal and propanone are:

1) Functional isomers 2) enantiomers
3) chain isomers 4) ammonical AgNO3in the prgences of citrateion.

67) IUPAC name of C6H5-CO-CH3 is

1)acetophenone 2)methyl phenyl ketone
3) 1-phenylethanone 4) all of the above

68) The IUPAC name of valeraldehyde is

1) propanal 2)butanal 3) pentanal 4)hexanal
69) In the formation of ester from carboxylic acid and alcohol, the function of H2SO4 is to:
1) protonate alcohol
2) protonate carboxylic acid at O-atom of -OH part
O

3) protonate carboxylic acid at O-atom of C part
O

4) protonate O-atoms of -O-H and C both.

70) Correct order of decreasing reacivity of nucleophilic addition in case of HCHO,

CH3CHO, and
CH 3COOCH 3 is.
1)
CH 3COCH 3 CH 3CHO HCHO

2)
HCHO CH 3CHO CH 3COCH 3

3
CH 3CHO HCHO CH 3COCH 3

4)
CH 2COCH 3 HCHO CH 3CHO