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CHAPTER 2 ALCOHOLS, PHENOLS &ETHERS
QUESTIONS FOR DISCUSSION
1. Propanone is the product obtained by dehydrogenation of
a) 1-propanol
b) 2-propanol
c) n-propyl alcohol
d) propanal
2. On heating ethanol with excess of conc. H2SO4 to 1700C, the product obtained is
a) ethoxy ethane
b) ethane
c) ethane
d) ethyne
3. Iodoform test is not answered by:
a) CH3-CH(OH)-CH3
b) C2H5-OH
c) CH3-OH d) CH3-CH2-CH2-OH
4. The reaction C2H5ONa + C2H5I → C2H5OC2H5 + NaI is known as
a) Wurtz’s synthesis
b) Kolbe’s synthesis c) Grignard’s synthesis d) Williamson’s synthesis
6. Denaturated alcohol is
a) Ethanol + methanol
b) Rectified spirit + methanol + naphtha
c) Undistilled ethanol
d) Rectified spirit
7. Catalytic dehydrogenation of a primary alcohol given a/an
a) ketone
b) ester
c) secondary alcohol
d) aldehyde
8. The compound on dehydrogenation gives a ketone. The original compound is
a) tertiary alcohol
b) carboxylic acid c) primary alcohol d) secondary alcohol
9. Lucas test is associated with
a) Carboxylic acid
b) Alcohols
c) Aldehydes
d) Phenols
10. An oxygen containing organic compound upon oxidation forms a carboxylic acid as the only
organic product with its molecular mass higher by 14 units. The organic compound is…
a) a primary alcohol b) an aldehyde
c) a ketone
d) a secondary alcohol
11. One mole of an organic compound ‘A’ of C3H8O reacts completely with two moles of HI to form
X and Y. When ’Y’ is boiled with aqueous alkali forms Z, Z answers the iodoform test.
a) propan-1-ol
b) propan-2-ol
c) methoxyethane
d) ethoxyethane
12. The compound which gives turbidity immediately with Lucas reagent at room temperature is
a) butan-2-ol
b) butan-1-ol
c) 2-methl propan-1-ol
d) 2-methyl propan-2-ol
13. An ethers 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) inter-molecular hydrogen bonding in ethers
d) inter-molecular hydrogen bonding in alcohols
14. During dehydration of alcohols to alkenes by heating with conc. H2SO4 the initial step is
a) protonation of alcohol molecule
b) formation of carbocation
c) elimination of water
d) formation of an ester
15. Which one of the following does not have sp2 hybridised carbon?
a) Acetone
b) Acetamide
c) Acetonitrile
d) Acetic acid
16. Ozonolysis of compound gives formaldehyde as one of the products. This confirms presence of:
a) a vinyl group
b) an isopropyl group c) an acetylenic triple bond d) two ethylene double bonds
17. Propan-1-ol may be prepared by reaction of propene with:
a) CH3 – COOH
b) H3BO3
c) B2H6/NaOH – H2O2 d) H2SO4/H2O
18. Propan-2-ol may be prepared by reaction of propene with:
a) CH3 – COOH
b) H3BO3
c) B2H6/NaOH – H2O2 d) H2SO4/H2O
19. n-propyl alcohol and isopropyl alcohol can be chemically distinguished by which reagent:
a) PCl5
b) reduction
c) oxidation with potassium dichromate
d) ozonolysis
20. The –OH group of alcohol or –COOH group of a carboxylic acid can be replaced by –Cl using:
a) phosphorus pentachloride b) hypochlorous acid c) chlorine
d) hydrochloric acid
21. The major organic product in the reaction, CH3 – O – CH(CH3)2 + HI → Product is:
a) CH3OH + (CH3)2CHI
b) ICH2OCH(CH3)2
c) CH3O C(CH3)2
d) CH3I + (CH3)2CHOH
Heated
I
 ……
22.
(CH3)2CH-CH2-O-CH2-CH3
a) (CH3)2CH-CH2-I + CH3-CH2-OH
b) (CH3)2CH-CH3 + CH3-CH2-OH
c) (CH3)2CH-CH2-OH + CH3-CH3
d) (CH3)2CH-CH2-OH + CH3-CH2-I
23.Which of the following is most acidic?
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1] p-cresol 2] p–chlorophenol 3] p-nitrophenol 4] p-aminophenol
24.Basic compound present in coaltar is
1] pyridine 2] phenol
3] benzene 4] naphthalene
25.Which of the following has lowest boiling point?
1] phenol 2] o-nitrophenol 3] m - nitrophenol 4] p - nitrophenol
26.Boiling point of p - nitrophenol is more than o - nitrophenol
1] NO2 at p - position behaves differently from that at o -position
2]intermolecular H-bond in p-nitrophenol
3]intramoleuclar H-bond in p-nitrophenol 4]intermol.H-bond in o-nitrophenol
27. Which of the following compound is not a phenol?
(1)C6H5OH (2)C6H4(CH3)OH (3) C6H5CH2OH (4) C6H4(OH)2
28. An example of a trihydric phenol is
(1) picric acid(2) resorcinol (3) pyrogallol (4) o-cresol
29. 2-methyl phenol is called
(1) p-cresol
(2) o-cresol
(3) m-cresol
(4) catechol
30. With respect to functional group phenols resemble
(1) aldehydes
(2) ketones
(3) ethers
(4) alcohols
31. In the cumene process, phenol is manufactured from
(1) chlorobenzene and alkali
(2) benzene and propylene
(3) chlorobenzene and ethanol
(4) benzene and acetyl chloride
32. Phenol is completely miscible with water
(1) at all temptr (2) above 670C (3) below 180 C (4) above 1000 C
33.Coal tar contains mainly the acidic compound
1]pyridine 2]phenol
3]cresol
4]acetic acid
34.In Kolbe reaction the reacting substances are
1]phenol and CCl4 2]sodium phenate and CO2 3]sodium phenate and CCl4 4]phenol and CHCl3
35. The final product obtained by nitrating phenol is
1] Nitrophenol
2] Dinitrophenol 3] Picric acid
4] Tetranitrophenol
36. Bakelite is manufactured by heating together
1] Phenol & formaldehyde 2] Vinyl chloride & benzene3] Phenol & acetone 4] Phenol & oxalic acid
37. Order of relative strength of phenol, acetic acid, water and ethanol is
(1) water < ethanol < phenol < acetic acid
(2) phenol < water < ethanol < acetic acid
(3) ethanol < phenol < water < acetic acid
(4) ethanol < water < phenol < acetic acid
38. Which of the following reagent can be used to distinguish between phenol and benzylalcohol?
(1) FeCl3
(2) NaOH
(3) alc. AgNO3
(4) NaHCO3
39. When phenol is heated with methyl chloride in the presence of anhydrous AlCl3, we get
(1) only meta cresol (2) only para cresol (3) only ortho cresol
(4) both ortho & para cresol
40. The Hydrogen atom of the phenolic group can be displaced
1] Only by using metallic sodium
2] By using either metallic sodium or sodium hydroxide
3] By using sodium carbonate
4] By using sodium chloride
41. Phenol is 1] Basic, because it forms phenyl acetate
2] Not acidic because it does not decompose carbonates & bicarbonates
3] Acidic, because it forms sodium phenate with sodium ydroxide
4] Amphoteric, because it forms phenyl acetate & sodium phenate
42. Phenol dissolves in aqueous sodium hydroxide to form sodium phenate. But, on passing carbon
dioxide into the solution, phenol is thrown out. This shows that
1] Phenol is weakly acidic, but stronger than carbonic acid 2] Phenol is basic
3] Phenol is amphoteric
4] Phenol is weakly acidic, weaker than even carbonic acid
43. The functional group present in cresol is
1] Alcoholic - OH group
2] Aldehydic - CHO group
3] Phenolic - OH group
4] Carboxylic - COOH group
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44.Sodium phenoxide when heated with CO2 under 4 to 7 atmosphere pressure gives
1] Phenol & sodium carbonate
2] O- Hydroxy benzoic acid
3] Benzoic acid
4] Benzaldehyde
45. Reaction of phenol with alkaline CHCl3 is an example of
1] Riemer-Tiemann reaction 2] Barton’s reaction 3] Perkin reaction
4] Etard's reaction
46 Neutral FeCl3 gives purple colour with
1] Aniline 2] Phenol
3] Salicylic acid 4] Benzoic acid
47.An aromatic compound X containing Nitrogen is treated with ice coldNaNO2 & dil. HCl .The
product Y obtained is heated to get Z with carbolic soap smell. The compound X is
1] Phenol 2] BDC
3] Aniline
4] Chlorobenzene
48. Which alkene on ozonolysis gives CH3CH2CHO and CH3COCH3?
a) CH3CH2CH = C (CH3)2
b) CH3CH2CH = CHCH2CH3
c) CH3CH2CH = CHCH3
d) CH3 – C(CH3) = CHCH3
49. Picric acid is
1] Trinitrotoluene
2] Trinitrobenzene 3] 2,4,6-trinitrophenol
4] 1,3,4- trinitrophenol
50.Benzyl alcohol is isomeric with
1] Phenol
2] Resocinol 3] Toluene
4] Anisole
51.Reagent that cannot be used to distinguish phenol &alcohol is
1] n-ferric chloride 2] Na metal 3] I2 & alkali 4] oxidizing agent
52. The most convenient method to remove a phenolic group is
1] Reduce it using Sn & HCl 2] Distill with Zn dust
3] Heat it strongly with Cur
4] Reduce it using SnCl2
53. Phenol is insoluble in
(1) benzene
(2) dil. NaOH solution (3) dil. HCl
(4) ether
54.Phenol cannot be used in the preparation of
1] indicator 2] thermosetting polymer
3] antiseptic
4]tranquilliser
55. 2-methyl phenol is called
1] o - cresol
2] toluene
3] p - cresol
4] m - cresol
56.In the Cumene process phenol is manufactured from
1] benzene & oxygen
2] benzene & propene
3] chlorobenzene & sodium hydroxide
4] benzene & sulphuric acid
57.Sodium salt of benzene sulphonic acid on fusion with NaOH first gives
1] C6H5OH 2] C6H6 3] C6H5 COOH 4]C6H5 COONa
58.Phenol does not-liberate carbon dioxide from carbonates and bicarbonates, because
1] phenol is weakly acidic
2] phenol is weakly basic
3] phenol is weakly acidic and weaker than even carbonic acid
4] phenol is weakly basic but stronger than carbonic acid
59.Which of the following behaves as a weak acid?
1] C2H5OH 2] C6H5CH2OH
3] C6H5OH
4] CH3OH
60.Reaction of phenol with dilute HNO3 gives
1] meta and para nitro phenols
2] ortho and para nitro phenols
3] trinitro phenol
4] ortho and meta nitro phenols
61.Phenol reacts with bromine in carbon disulphide (or CCl4) at low temperature giving
1] m - bromophenol
2] p - bromophenol
3] 2,4,6 - tribromo phenol
4] a mixture of o & p - bromophenols
62.Phenol on hydrogenation in presence of Ni catalyst gives
1] benzene
2] cyclohexine 3] cyclohexanol 4] n - hexanol
63.Phenol is distinguished from carboxylic acids using
1] NaOH
2] NaHCO3
3] CaO 4] none
64.Phenol belongs to the solubility group…
1] II
2] III
3] IV
4] VI
65. Phenol in most easily soluble in solution of
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1] Both NaOH & dil.HCl
2] NaHCO3
3] NaOH
4] Dilute HCl
66.Which of the following is does not contain phenolic group ?
1] Phluroglucinol 2] Pyrogallol 3] Cyclohexanol 4]Picric acid
67.Rate of electrophilic substitution reactions in phenol is
1] greater than that of benzene
2] same as that of benzene
3] less than that of benzene
4] depends on the reaction
68.What explains that o-nitrophenol is more volatile than p-nitrophenol
1]Resonance
2] Hyperconjugation 3] Hydrogen bonding 4]Steric hindrance
69.Which compounds contain intramolecular hydrogen bonding
1] O-cresol 2] Salicylaldehyde 3] water 4] Ethyl alcohol
70.Which of the following does not contain a –COOH group ?
1] Picric acid 2] Carbolic acid 3] Barbituric acid 4] all these
71.The hybrid state of carbon to which –OH group is attached in phenol is
1] sp
2] sp2
3]sp3
4]dsp2
72. Phenol is obtained from Cumene which is
1] Isopropyl phenol
2] Cyclohexanol 3] Isopropyl benzene 4] Cyclohexane
73.Which of the following undergoes nitration readily ?
1] benzene 2] nitrobenzene 3] phenol 4] Toluene
74.Which compound gives Toluene when heated with zinc powder
1] phenol 2] Salicylic acid 3] Resorcinol 4] Cresol
75. Anisole is isomeric with
1] o-cresol 2] Diethyl ether 3] Aniline 4] Benzaldehyde
76.The group where all members are isomers is
1]cresol,Anisole,Benzyl alcohol
2] Methanol , formaldehyde , epoxide
3]Acetaldehyde,acetone,ethanol
4]Ethylalcohol,Diethylether ,acetaldehyde
77.Salicylic acid gives Benzoic acid when heated with
1]zinc 2] soda lime 3]Nickel and H2 4] CO2
78.Salicylic acid gives Phenol when heated with 1]zinc 2] soda lime 3]Nickel and H2 4] CO2
79.In which reaction phenol behaves similar to alcohol
1]with Na 2] Benzoylation 3] with PCl5 4]all
80.In which reaction phenol behaves different from to alcohol
1]Acetylion 2] Benzoylation 3] with PCl5 4] none
81. Which compound when dissolved in water gives a solution of pH less than 7 at 298 K
1] CH3-CO-CH3 2] C2H5-OH 3]C6H5-OH 4]CH3-NH2
82.Under suitable conditions C6H5-CH2-OH [A] , C6H5-OH[B] &C6H5-COOH [C] behave as
acids. The increasing order of acidic strengths is
1] ABC
2] BCA
3] CBA
4] BAC
83.Phenol is less soluble in water due to
1]non-polar nature of phenol
2] acidic nature of –OH
3] non-polar nature of hydrocarbon part
4] Hydrogen bond
84.Which of following can be used to separate benzene & phenol
1]dil. HCl 2] Water 3] dil. NaOH 4] dil. NaHCO3
85.Compound that liberates CO2 gas from NaHCO3 is 1]phenol 2] Pyrogallol 3] picric acid 4] none
86.p-nitro phenol is more acidic than phenol because , nitro group
is 1]electron releasing 2] electron withdrawing 3] acidic 4] basic
87.Picric acid and benzoic acid can be distinguished by
1]aqueous NaHCO3 2] aqueous NaOH 3] aqueous FeCl3 4]none
88. Phenol on standing in air develops red colour due to the formation of
1] Resorcinol 2] quinol 3] phenoquinone 4] phenoxide ion
89. Which compound cannot be prepared from phenol
1]Anisole 2]Salol 3] naphthalene 4] picric acid
90. Benzene can be converted into phenol using 1]H2SO4 2] NaOH 3] NH3 4]CCl4
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91. p-bromophenol can be obtained by treating phenol with
1] aqueous Br2
2] Alcoholic Br2 3] Br2 in CCl4
4]HBr
92.The reactive intermediate in Reimer-Tiemann reaction is
1] Carbonium ion 2]Carbene 3] Free radical
4]Carbanion
93. Dettol is
1] chlorophenol 2] Cyclohexanol 3] Hexachlorobnzene 4] Chloroxylenol
94.Phenol can be distinguished from its colour reaction with
1]FeSO4 2]BaCl2 3] Neutral FeCl3 4]Iodoform reaction
95.Phenol can be recovered from 1] Coal tar 2] middle oil 3] naphthalene 4] benzene
96. Phenol is used to manufacture Bakelite plastic. It is an example for
1] condensation homo polymer
2] condensation co-polymer
3] addition homopolymer
4] addition co-polymer
97. Which of the following statements is not true for Bakelite
1]It is a network polymer 2] It has a high molecular weight
3]It is a thermoplastic 4]It is a good thermal & electrical insulator
98. Which reagent cannot be used to differentiate phenol &ethanol?
1] Neutral FeCl3 2] Na - metal 3] bromination 4] I2 & NaOH
99.The reactants of Reimer - Tiemann reaction are
1] phenol, chloroform, carbon tetrachloride
2] phenol, chloroform, thionyl chloride
3]phenol, sodium hydroxide, chloroform
4]phenol, chloroform, phosphorus pentachloride
100. Acidic nature of phenol can be increased by fixing ….to aromatic ring
1] electron releasing groups
2]electron withdrawing roups
3] hydrogenating the ring
4]another -OH group
101. 4-Chloro –3,5-dimethyl phenol is called 1]chloramphenicol 2]barbital 3] paracetamol 4]dettol
102. A compound that undergoes bromination easily is
1] Benzene 2]Toluene
3] Phenol 4]Benzoic acid
103.An organic acid without a carboxylic acid group is
1] vinegar
2]ascorbic acid 3] picric acid 4]oxalic acid
104. Which one of the following is not an explosive ?
1] trinitrotoluene 2] trinitrobenzene 3] picric acid 4] nitrobenzene
105. Phenol is heated with Phthalic anhydride in presence of Con H2SO4. The product gives pink
colour with alkali. The product is
1] Phenolphthalein 2] Bakelite 3] Salicylic acid 4] Fluoroscein
106. Phenol is treated with Bromine water and shaken well. The precipitate formed is
1] 2,4,6-tribromo phenol
2] m-Bromophenol
3] both o- & p-bromo phenol
4] 2,4-dibromophenol
107. Phenol is strongly heated with Phthalic anhydride & Con H2SO4. Product is
1]an indicator 2]an explosive 3]a plastic 4]a drug
108. The mutual solubility of phenol and water
1]increases on heating
2] increases both on heating & cooling
3]is not affected by temperature
4] decreases on heating
109. Carbolic acid is 1] acetic acid 2] salicylic acid
3] phenol
4] Picric acid
110.Phenol does not react with
1]NaOH 2]Na 3]NaHCO3 4]Zn
111. Which of the following is least acidic
1] o-nitrophenol 2] o-bromo phenol 3] o-methyl phenol
4] phenol
112. Resorcinol is
1]1,2-Dihydroxy benzene
2] 1,3-Dihydroxy benzene
3] 1,4-Dihydroxy benzene
4] 1,2,3-Trihydroxy benzene
113. From sodium phenate solution, phenol is obtained by treating it with
(1) HCl (2) H2SO4
(3) CO2
(4) all these
114. Cumene process is the most commercial method for the mnf of phenol. Cumene is
1]1-methyl ethyl benzene
2]Ethyl benzene 3]Vinyl benzene
4]propyl benzene
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QUESTIONS FOR PRACTICE
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