Assignment on ALCOHOL, PHENOL & ETHER with answers., Assignments of Organic Chemistry

Download Assignment on ALCOHOL, PHENOL & ETHER with answers. and more Assignments Organic Chemistry in PDF only on Docsity! Alcohol, Phenol and Ethers 1217 General introduction of alcohol, Phenol & Ethers 1. Butane-2-ol is [CPMT 1977, 89] (a) Primary alcohol (b) Secondary alcohol (c) Tertiary alcohol (d) Aldehyde 2. Picric acid is [CPMT 1971, 80, 81; DPMT 1983; MP PMT 1990; BHU 1996] (a) Trinitroaniline (b) Trinitrotoluene (c) A volatile liquid (d) 2, 4, 6 trinitrophenol 3. 3- pentanol is a [RPET 2002] (a) Primary alcohol (b) Secondary alcohol (c) Tertiary alcohol (d) None of these 4. Glycerol is a [DPMT 1984, 2000; MP PET 2001; J & K 2005] (a) Primary alcohol (b) Monohydric alcohol (c) Secondary alcohol (d) Trihydric alcohol 5. Cresols are (a) Hydroxy toluenes (b) Dihydric phenols (c) Trihydric phenols (d) Trihydric alcohols 6. Carbon percentage is maximum in [BHU 1998] (a) Pyrene (b) Gammexane (c) Ethylene glycol (d) PVC 7. Ortho-dihydroxy benzene is (a) Carvacrol (b) Resorcinol (c) Catechol (d) Orcinol 8. Glycerine has [MP PMT/PET 1988; MP PMT 1989, 91; AIIMS 1997] (a) One primary and two secondary OH groups (b) One secondary and two primary OH groups (c) Three primary OH groups (d) Three secondary OH groups 9. Which of the following is tertiary alcohol[DPMT 2000] (a) OHCH OHCH OHCH    2 2 | | (b) OHCH CH CH CH CHCH 2 3 | 2 2 | | 23  (c) 3 3 | | 3 CH CH OHCCH  (d) OHCHCH  23 10. Which is primary alcohol [CPMT 1980] (a) Butane-2-ol (b) Butane-1-ol (c) Propane-2-ol (d) Isopropyl alcohol 11. Carbinol is [RPMT 2000] (a) OHHC 52 (b) OHCH 3 (c) CHOHCH 23 )( (d) 323 )( CHOHCHCHCH 12. General formula of primary alcohol is [CPMT 1975] (a) CHOH (b) OHC (c) OHCH 2 (d) OH OH C 13. Which of following is phenolic [J & K 2005] (a) Phthalic acid (b) Phosphoric acid (c) Picric acid (d) Phenylacetic acid 14. 1, 2, 3-trihydroxybenzene is also known as (a) Pyrogallol (b) Phloroglucinol (c) Resorcinol (d) Quinol 15. Butanal is an example of [MP PET 1991] (a) Primary alcohol (b) Secondary alcohol (c) Aliphatic aldehyde (d) Aliphatic ketone 16. Cyclohexanol is a (a) Primary alcohol (b) Secondary alcohol (c) Tertiary alcohol (d) Phenol 17. The characteristic grouping of secondary alcohols is [DPMT 1984] (a) OHCH 2 (b) CHOH (c) OHC | | (d) OH C OH 18. Which of the following are isomers [AFMC 2005; BCECE 2005] (a) Methyl alcohol and dimethyl ether (b) Ethyl alcohol and dimethyl ether (c) Acetone and acetaldehyde (d) Propionic acid and propanone 19. The compound OHCHHOCH 22  is (a) Ethane glycol (b) Ethylene glycol (c) Ethylidene alcohol (d) Dimethyl alcohol 20. Methylated spirit is (a) Methanol (b) Methanol + ethanol (c) Methanoic acid (d) Methanamide 21. The structural formula of cyclohexanol is[Bihar CEE 1995] (a) (b) (c) (d) CH2OH CHOH CH2 CH2 CH2 H2C H2C CHOH CH2 CH2 CH2 H2C H2C 1218 Alcohol, Phenol and Ethers 22. Molecular formula of amyl alcohol is (a) OHC 147 (b) OHC 136 (c) OHC 125 (d) OHC 105 23. Carbolic acid is [MP PET/PMT 1998; RPET 1999; KCET (Engg./Med.) 1999; BHU 2000; MP PET 2003] (a) Phenol (b) Phenyl benzoate (c) Phenyl acetate (d) Salol 24. Absolute alcohol is [RPMT 1997] (a) 100% pure ethanol (b) 95% alcohol + 5% OH 2 (c) Ethanol + water + phenol (d) 95% ethanol + 5% methanol 25. Which of the following is dihydric alcohol[DCE 2004] (a) Glycerol (b) Ethylene glycol (c) Catechol (d) Resorcinol 26. Wood spirit is known as [AFMC 2004] (a) Methanol (b) Ethanol (c) Acetone (d) Benzene 27. Oxygen atom in ether is [MP PMT/PET 1988] (a) Very active (b) Replaceable (c) Comparatively inert (d) Active 28. Which of the following is a simple ether[AFMC 1997] (a) 33OCHCH (b) 352 OCHHC (c) 356 OCHHC (d) 5256 HOCHC 29. An example of a compound with the functional group '' O is [CPMT 1983] (a) Acetic acid (b) Methyl alcohol (c) Diethyl ether (d) Acetone 30. Which of the following do not contain an acyl group (a) Acid chloride (b) Amide (c) Ester (d) Ether 31. Name of 32223 )( CHCHCHOHCCH  is [MP PMT 1992] (a) Isopropyl propyl ether (b) Dipropyl ether (c) Di-isopropyl ether (d) Isopropyl propyl ketone 32. Acetals are [BVP 2003] (a) Ketones (b) Diethers (c) Aldehyde (d) Hydroxy aldehydes 33. In ethers, the C – O – C bond angle is (a) o180 (b) o90 (c) o110 (d) o160 34. According to Lewis concept of acids and bases, ether is [CPMT 1994] (a) Acidic (b) Basic (c) Neutral (d) Amphoteric 35. The compound which is not isomeric with diethyl ether is [IIT 1981; CPMT 1989; Bihar MEE 1995; MP PET 2001] (a) n-propylmethyl ether (b) Butan-1-ol (c) 2-methylpropan-2-ol (d) Butanone 36. Structure of diethyl ether is confirmed by[DPMT 1985] (a) Kolbe's synthesis (b) Frankland's synthesis (c) Wurtz's synthesis (d) Williamson's synthesis 37. Fermentation is an [CPMT 1977; RPMT 1999] (a) Endothermic reaction (b)Exothermic reaction (c) Reversible reaction (d) None of these 38. Nitroglycerine is (a) An ester (b) An alcohol (c) A nitro compound (d) An acid 39. Which of the following are known as mercaptans [Pb. PMT 2002] (a) Thio-alcohols (b) Thio-ethers (c) Thio-acids (d) Thio-aldehydes Preparation of alcohol, Phenol and Ethers 1. Ethanol is prepared industrially by [MP PMT 1989] (a) Hydration of ethylene (b)Fermentation of sugars (c) Both the above (d) None of these 2. Ethyl alcohol is industrially prepared from ethylene by [CPMT 1985] (a) Permanganate oxidation (b) Catalytic reduction (c) Absorbing in 42SOH followed by hydrolysis (d) Fermentation 3. Propene, 23 CHCHCH  can be converted to 1- propanol by oxidation. Which set of reagents among the following is ideal to effect the conversion[CBSE PMT 1991] (a) Alkaline 4KMnO (b) 62 HB and alkaline 22OH (c) ZnO /3 dust (d) 244 ,/ ClCHOsO 4. Which one of the following will produce a primary alcohol by reacting with MgICH 3 [MP PET 1991] (a) Acetone (b) Methyl cyanide (c) Ethylene oxide (d) Ethyl acetate 5. The fermentation of starch to give alcohol occurs mainly with the help of[CPMT 1971; MH CET 1999; RPMT 2000] (a) 2O (b) Air (c) 2CO (d) Enzymes 6. Coconut oil upon alkaline hydrolysis gives [MP PET 1991; AFMC 2000; KCET 2001; BCECE 2005] (a) Glycol (b) Alcohol (c) Glycerol (d) Ethylene oxide 7. Which enzyme converts glucose and fructose both into ethanol [MP PMT 1989, 90, 96; CPMT 1983, 84, 86, 94; Alcohol, Phenol and Ethers 1221 [BVP 2003] (a) Dehydration reaction (b) Dehydrogenation reaction (c) Hydrogenation reaction (d) Heterolytic fission reaction 50. The compound formed when ethyl bromide is heated with dry silver oxide is [MP PET/PMT 1988] (a) Dimethyl ether (b) Diethyl ether (c) Methyl alcohol (d) Ethyl alcohol 51. The reagent used for the preparation of higher ether from halogenated ethers is[Tamil Nadu CET 2001] (a) conc. 42SOH (b) Sodium alkoxide (c) Dry silver oxide (d) Grignard reagent 52. Acetyl bromide reacts with excess of MgICH3 followed by treatment with a saturated solution of ClNH4 gives [AIEEE 2004] (a) 2-methyl-2-propanol (b) Acetamide (c) Acetone (d) Acetyl iodide 53. What is obtained when chlorine is passed in boiling toluene and product is hydrolysed[DCE 2004] (a) o-Cresol (b) p-Cresol (c) 2, 4-Dihydroxytoluene (d) Benzyl alcohol 54. Which of the following is formed when benzaldehyde reacts with sodium hydroxide[Pb. CET 2002] (a) Benzyl alcohol (b) Benzoic acid (c) Glucose (d) Acetic acid 55. When ethanal reacts with MgBrCH 3 and OHHC 52 /dry HCl the product formed are[DCE 2003] (a) Ethyl alcohol and 2-propanol (b) Ethane and hemi-acetal (c) 2-propanol and acetal (d) Propane and methyl acetate 56. Which of the following is industrially prepared by passing ethylene into hypochlorous acid[BHU 2004] (a) Ethylene glycol (b) Ethylene oxide (c) Ethylene dinitrate (d) Ethane 57. In which case methyl-t-butyl ether is formed [Orissa JEE 2004] (a) ClCHCONaHC 3352 )(  (b) ClCHCONaCH 333)(  (c) ClHCCONaCH 5233)(  (d) ClCHCONaCH 333)(  58. Which of the following combinations can be used to synthesize ethanol [KCET 2004] (a) MgICH3 and 33COCHCH (b) MgICH3 and OHHC 52 (c) MgICH3 and 523 HCOOCCH (d) MgICH3 and 52HHCOOC 59. OHCHCHCHHCCHCHOCHHC X 25656  . In the above sequence X can be [DCE 2004] (a) NiH /2 (b) 4NaBH (c) HOCrK /722 (d) Both (a) and (b) 60. Alkenes convert into alcohols by [MP PET 1991] (a) Hydrolysis by dil. 42SOH (b) Hydration of alkene by alkaline 4KMnO (c) Hydrolysis by water vapours and conc. 42SOH (d) Hydration of alkene by aqueous KOH 61. Acetic acid and OHCH 3 are obtained on large scale by destructive distillation of (a) Wood (b) Coal (c) Turpentine (d) Crude oil 62. Which is formed when benzalamine react with nitrous acid [KCET (Med.) 2001] (a) OHHC 56 (b) ONHC 56 (c) OHNHC 252 (d) OHCHHC 256 63. Acid catalyzed hydration of alkenes except ethene leads to the formation of [AIEEE 2005] (a) Primary alcohol (b) Secondary or tertiary alcohol (c) Mixture of primary and secondary alcohols (d) Mixture of secondary and tertiary alcohols 64. Methylphenyl ether can be obtained by reacting [J & K 2005] (a) Phenolate ions and methyl iodide (b) Methoxide ions and bromobenzene (c) Methanol and phenol (d) Bromo benzene and methyl bromide Properties of alcohol, Phenol and Ethers 1. Which compound is formed when OHCH 3 reacts with XMgCH 3 [CPMT 1977, 89] (a) Acetone (b) Alcohol (c) Methane (d) Ethane 2. A compound X of formula OHC 83 yields a compound OHC 63 , on oxidation. To which of the following classes of compounds could X being[Pb. PMT 2000] (a) Secondary alcohol (b) Alkene (c) Aldehyde (d) Tertiary alcohol 3. The boiling point of alcohol are …. than corresponding thiols [Pb. PMT 2000] (a) More (b) Same 1222 Alcohol, Phenol and Ethers (c) Either of these (d) Less 4. Methyl alcohol can be distinguished from ethyl alcohol using [KCET 1984; BHU 2000] (a) Fehling solution (b) Schiff's reagent (c) Sodium hydroxide and iodine (d) Phthalein fusion test 5. A compound X with molecular formula OHC 83 can be oxidised to a compound Y with the molecular formula 263 OHC X is most likely to be[MP PMT 1991] (a) Primary alcohol (b) Secondary alcohol (c) Aldehyde (d) Ketone 6. An alcohol on oxidation is found to give COOHCH 3 and .23 COOHCHCH The structure of the alcohol is [BIT 1990] (a) OHCHCHCH 223 (b) 3223 )()( CHCHOHCCH (c) 323 CHOHCHCHCH (d) 3223 )( CHCHCHOHCHCH 7. An organic liquid A containing HC, and O has a pleasant odour with a boiling point of Co78 On boiling A with conc. 42SOH a colourless gas is produced which decolourises bromine water and alkaline .4KMnO One mole of this gas also takes one mole of .2H The organic liquid A is [KCET 1993] (a) ClHC 52 (b) CHOHC 52 (c) 62 HC (d) OHHC 52 8. An aromatic amine (A) was treated with alcoholic potash and another compound (Y) when foul smelling gas was formed with formula .56 NCHC Y was formed by reacting a compound (Z) with 2Cl in the presence of slaked lime. The compound (Z) is [CBSE PMT 1990] (a) 256 NHHC (b) OHHC 52 (c) 33OCHCH (d) 3CHCl 9. Rectified spirit obtained by fermentation contains 4.5% of water. So in order to remove it, rectified spirit is mixed with suitable quantity of benzene and heated. Benzene helps because [KCET 1987] (a) It is dehydrating agent and so removes water (b) It forms the lower layer which retains all the water so that alcohol can be distilled off (c) It forms an azeotropic mixture having high boiling point and thus allows the alcohol to distill over (d) It forms low boiling azeotropic mixtures which distill over, leaving behind pure alcohol which can then be distilled 10. 356 aq. 356 OCOCHHCClCOCHOHHC NaOH   is an example of [BHU 1984] (a) Dow's reaction (b) Reimer-Tiemann reaction (c) Schotten-Baumann reaction (d) Kolbe's reaction 11. Ortho-nitrophenol is steam volatile whereas para- nitrophenol is not. This is due to [CBSE PMT 1989] (a) Intramolecular hydrogen bonding present in ortho-nitrophenol (b) Intermolecular hydrogen bonding (c) Intramolecular hydrogen bonding present in para-nitrophenol (d) None of these 12. Reaction of phenol with dil. 3HNO gives [KCET 1993; RPMT 1997] (a) p and m-nitrophenols (b)o- and p-nitrophenols (c) Picric acid (d) o- and m- nitrophenols 13. Phenol is less acidic than [IIT-JEE 1986; UPSEAT 2003; Orissa JEE 2004] (a) Acetic acid (b) p-nitrophenol (c) Both (a) and (b) (d) None of these 14. The strongest acid among the following aromatic compounds is [NCERT 1978] (a) ortho-nitrophenol (b) para-chlorophenol (c) para-nitrophenol (d) meta-nitrophenol 15. Diazo-coupling is useful to prepare some [CBSE PMT 1994] (a) Pesticides (b) Proteins (c) Dyes (d) Vitamins 16. Glycerol reacts with 24 IP  to form[CBSE PMT 1991] (a) Aldehyde (b) Allyl iodide (c) Allyl alcohol (d) Acetylene 17. When glycerine is added to a litre of water which of the following behaviour is observed[NCERT 1977; BHU 1979] (a) Water evaporates more easily (b) The temperature of water is increased (c) The freezing point of water is lowered (d) The viscosity of water is lowered 18. Final product formed on reduction of glycerol by hydroiodic acid is [CPMT 1987] (a) Propane (b) Propanoic acid (c) Propene (d) Propyne 19. Glycerol was distilled with oxalic acid crystals and the products were led into Fehling solution and warmed. Cuprous oxide was precipitated. It is due to [KCET 1987] (a) CO (b) HCHO (c) CHOCH 3 (d) HCOOH 20. Kolbe-Schmidt reaction is used for [CBSE PMT 1991] (a) Salicylic acid (b) Salicylaldehyde (c) Phenol (d) Hydrocarbon 21. Which of the following explains the viscous nature of glycerol [JIPMER 1997] (a) Covalent bonds (b) Hydrogen bonds (c) Vander Wall's forces (d) Ionic forces Alcohol, Phenol and Ethers 1223 22. On heating glycerol with conc. ,42SOH a compound is obtained which has a bad odour. The compound is [CPMT 1974; CBSE PMT 1994] (a) Glycerol sulphate (b) Acrolein (c) Formic acid (d) Allyl alcohol 23. Isopropyl alcohol on oxidation forms [CPMT 1971, 81, 94; RPMT 2002] (a) Acetone (b) Ether (c) Ethylene (d) Acetaldehyde 24. Benzenediazonium chloride on reaction with phenol in weakly basic medium gives[IIT-JEE 1998] (a) Diphenyl ether (b) p- hydroxyazobenzene (c) Chlorobenzene (d) Benzene 25. The alcohol that produces turbidity immediately with 2ZnCl conc. HCl at room temperature [EAMCET 1997; MP PMT 1989, 99; IIT JEE 1981, 86; CBSE PMT 1989; CPMT 1989; MP PET 1997; JIPMER 1999] (a) 1-hydroxybutane (b) 2-hydroxybutane (c) 2-hydroxy-2-methylpropane (d) 1-hydroxy-2-methylpropane 26. The reagent which easily reacts with ethanol and propanol is [MP PET 1989] (a) Fehling solution (b) Grignard reagent (c) Schiff's reagent (d) Tollen's reagent 27. Propene is the product obtained by dehydrogenation of [KCET (Engg.) 2001] (a) 2-propanol (b) 1-propanol (c) Propanal (d) n-propyl alcohol 28. Which of the following statements is correct [BHU 1997] (a) Phenol is less acidic than ethyl alcohol (b) Phenol is more acidic than ethyl alcohol (c) Phenol is more acidic than carboxylic acid (d) Phenol is more acidic than carbonic acid 29. Boiling point of alcohol is comparatively higher than that corresponding alkane due to[MH CET 2002] (a) Intermolecular hydrogen bonding (b) Intramolecular hydrogen bonding (c) Volatile nature (d) None of these 30. When Phenol is heated with phthalic anhydride in concentrated sulphuric acid and the hot reaction mixture is poured into a dilute solution of sodium hydroxide, the product formed is[MP PET 1997, 2003; RPMT 1999; KCET (Med.) 2000; CPMT 1981; CBSE PMT 1988] (a) Alizarin (b) Methyl orange (c) Fluorescein (d) Phenolphthalein 31. reagent sJon' 33 )(   CHOHCHCHCHCH X, Product X is [RPET 2000] (a) 3223 )( CHOHCHCHCHCH (b) 33 CHCOCHCHCH  (c) Both (a) and (b) are correct (d) 3223 COCHCHCHCH 32. Reaction : Ag C OOHCH   0600 23 product The product is [RPET 2000] (a) OCCH 2 (b) OCH 2 (c) 42 HC (d) 22 HC 33. Ethylene glycol, on oxidation with per-iodic acid, gives [NCERT 1983; CPMT 1983] (a) Oxalic acid (b) Glycol (c) Formaldehyde (d) Glycollic acid 34. An unknown compound ‘D’, first oxidised to aldehyde and then acitic acid by a dilute solution of 722 OCrK and 42SOH . The unknown compound ‘D’ is [BHU 2000] (a) CHOCH 3 (b) OHCHCH 32 (c) OHCHCH 23 (d) 323 CHCHCH 35. The reaction of ethylene glycol with 3PI gives [MP PMT 2000] (a) ICHICH 22 (b) 22 CHCH  (c) CHICH 2 (d) CHIICH  36. The compound ‘A’ when treated with ceric ammonium nitrate solution gives yellow ppt. The compound ‘A’ is [MP PET 2002] (a) Alcohol (b) Aldehyde (c) Acid (d) Alkane 37. Which of the following product is formed, when ether is exposed to air [AIIMS 2000; RPMT 2002] (a) Oxide (b) Alkanes (c) Alkenes (d) Peroxide of diethyl ether 38. During dehydration of alcohols to alkenes by heating with conc. 42SOH the initiation step is[AIEEE 2003] (a) Protonation of alcohol molecule (b) Formation of carbocation (c) Elimination of water (d) Formation of an ester 39. Phenol is less acidic than [MNR 1995] (a) Ethanol (b) Methanol (c) o-nitrophenol (d) p-methylphenol 40. The compound which gives the most stable carbonium on dehydration is [MNR 1995] (a) 3 | 23 CH OHCHCHCH  1226 Alcohol, Phenol and Ethers (c) (d) None of these 73. Primary alcohols on dehydration give [NCERT 1986] (a) Alkenes (b) Alkanes (c) Both (a) and (b) (d) None of these 74. Primary and secondary alcohols on action of reduced copper give [CPMT 1982; MP PMT 1985; EAMCET 1987, 93; MP PET 1995] (a) Aldehydes and ketones respectively (b) Ketones and aldehydes respectively (c) Only aldehydes (d) Only ketones 75. Methyl alcohol on oxidation with acidified 722 OCrK gives [MNR 1987] (a) 33COCHCH (b) CHOCH 3 (c) HCOOH (d) COOHCH 3 76. Ethyl alcohol on oxidation with 722 OCrK gives [MNR 1987; Bihar CEE 1995; UPSEAT 2000] (a) Acetic acid (b) Acetaldehyde (c) Formaldehyde (d) Formic acid 77. Lucas test is used for [CBSE PMT 1990; AIIMS 2002; AFMC 2005] (a) Alcohols (b) Amines (c) Diethyl ether (d) Glacial acetic acid 78. When phenol reacts with ammonia in presence of 2ZnCl at 300°C, it gives [AFMC 2001] (a) Primary amine (b) Secondary amine (c) Tertiary amine (d) Both (b) and (c) 79. Azo-dyes are prepared from [CPMT 2001] (a) Aniline (b) Benzaldehye (c) Benzoic acid (d) Phenol 80. A compound that easily undergoes bromination is [KCET (Engg.) 2002] (a) Phenol (b) Toluene (c) Benzene (d) Benzoic acid 81. Which of the following has lowest boiling point [MH CET 1999] (a) p-nitrophenol (b) m-nitrophenol (c) o-nitrophenol (d) phenol 82. In esterification, the reactivity of alcohols is[DPMT 2000] (a) 1° > 2° > 3° (b) 3° > 2° > 1° (c) Same in all cases (d) None of these 83. The role of conc. 42SOH in the esterification process is [RPMT 1999] (a) Catalyst (b) Dehydrating agent (c) Hydrolysing agent (d) Dehydrating agent and catalyst 84. Methanol and ethanol are distinguished by the [MP PET 1999] (a) Action of HCl (b) Iodoform test (c) Solubility in water (d) Sodium 85. For phenol, which of the following statements is correct [MP PMT 1995] (a) It is insoluble in water (b) It has lower melting point compared to aromatic hydrocarbons of comparable molecular weight (c) It has higher boiling point than toluene (d) It does not show acidic property 86. The reaction of Lucas reagent is fast with[MP PMT 2000] (a)   COHCH 33 (b) CHOHCH 23 )( (c) OHCHCH 223 )( (d) OHCHCH 23 87. Which of the following reagents convert the propene to 1-propanol [CBSE PMT 2000] (a) 422 , SOHOH (b) Aqueous KOH (c) OHNaBHMgSO 244 /, (d) OHOHHB ,, 2262 88. Compound ‘A’ reacts with 5PCl to give ‘B’ which on treatment with KCN followed by hydrolysis gave propanoic acid as the product. What is ‘A’[CBSE PMT 2002] (a) Ethane (b) Propane (c) Ethyl chloride (d) Ethyl alcohol 89. Which reagent can convert acetic acid into ethanol [BVP 2003] (a) Na alcohol (b) 4LiAlH ether (c) PtH 2 (d) HClSn  90. Which of the following would undergo dehydration most readily [UPSEAT 2000] (a) 1-phenyl-1butanol (b) 2-phenyl-2-butanol (c) 1-phenyl-2-butanol (d) 2-phenyl-1-butanol 91. Phenol and benzoic acid is distinguished by[BHU 2003] (a) NaOH (b) 3NaHCO (c) 32CONa (d) 42SOH 92. Electrophilic substitution reaction in phenol take place at [RPMT 2002] (a) p- position (b) m- position (c) o- position (d) o- and p- position 93. Liebermann's test is answered by [KCET 1998] 2NO 2NO NO2 OH Alcohol, Phenol and Ethers 1227 (a) Aniline (b) Methylamine (c) Ethyl benzoate (d) Phenol 94. In the sequence of the following reactions[MP PMT 2002] OHCHCH 23 dChromicAci ][ dChromicAci O][  O X COOHCH 3 X is (a) 33COCHCH (b) CHOCH 3 (c) 33OCHCH (d) COOHCHCH 23 95. The boiling point of glycerol is more than propanol because of [CPMT 1997, 2002] (a) Hydrogen bonding (b) Hybridisation (c) Resonance (d) All the above 96. Which of the following produces violet colour with 3FeCl solution (a) Enols (b) Ethanol (c) Ethanal (d) Alkyl halides 97. When heated with 3NH under pressure alone or in presence of zinc chloride phenols are converted into [RPMT 1997] (a) Aminophenols (b) Aniline (c) Nitrobenzene (d) Phenyl hydroxylamine 98. Because of resonance the oxygen atom of OH group of phenol (a) Acquires positive charge (b)Acquires negative charge (c) Remains uneffected (d) Liberates 99. When glycerol is heated with 4KHSO it gives [CPMT 1974, 85; MP PMT 1988, 90, 91, 92, 94; MP PET 1988, 92] (a) 32 CHCHCH  (b) OHCHCHCH 22  (c) CHOCHCH 2 (d) 22 CHCCH  100. An organic compound X on treatment with acidified 722 OCrK gives a compound Y which reacts with 2I and sodium carbonate to form tri- odomethane. The compound X is [KCET 1996] (a) OHCH 3 (b) 33 CHCOCH  (c) CHOCH 3 (d) 33 )( CHOHCHCH 101. The reaction of conc. 3HNO and phenol forms [MP PMT/PET 1988; BHU 1988; MP PMT 1999; Pb. PMT 2000] (a) Benzoic acid (b) Salicylic acid (c) o-and p-nitrophenol (d) Picric acid 102. Phenol is [MP PMT 1990; UPSEAT 1999] (a) A weaker base than 3NH (b) Stronger than carbonic acid (c) Weaker than carbonic acid (d) A neutral compound 103. Phenol at Co25 is (a) A white crystalline solid (b)A transparent liquid (c) A gas (d) Yellow solution 104. At low temperature phenol reacts with 2Br in 2CS to form [MP PET 1991; CPMT 1981; MP PMT 1990; IIT 1982; RPMT 2000] (a) m-bromophenol (b) o-and p-bromophenol (c) p-bromophenol (d) 2, 4, 6- tribromophenol 105. Oxidation of ethanol by chromic acid forms [MP PET 1992] (a) Ethanol (b) Methanol (c) 2-propanone (d) Ethanoic acid 106. Which of the following not gives effervescence with 3NaHCO [MP PET 1992] (a) Phenol (b) Benzoic acid (c) 2, 4-dinitrophenol (d) 2, 4, 6-trinitrophenol 107. Conc. 42SOH reacts with OHHC 52 at Co170 to form [MP PMT 1991; MP PET 1991; IIT-JEE 1981; EAMCET 1979; KCET 2001] (a) 33COCHCH (b) COOHCH 3 (c) CHOCH 3 (d) 42 HC 108. Which compound has hydrogen bonding [MP PMT 1992; MP PET 1991] (a) Toluene (b) Phenol (c) Chlorobenzene (d) Nitrobenzene 109. Which statement is true [MP PMT 1991] (a) OHHC 56 is more acidic than OHHC 52 (b) OHHC 56 is less acidic than OHHC 52 (c) OHHC 56 react with 3NaHCO (d) OHHC 56 gives oxime with OHNH 2 and HCl 110. Read the following statements carefully : (A) A secondary alcohol on oxidation gives a ketone (B) Ethanol reacts with conc. 42SOH at Co180 to yield ethylene (C) Methanol reacts with iodine and sodium hydroxide to give a yellow precipitate of iodoform (D) Hydrogen gas is liberated when sodium is added to alcohol. Select the correct statements from the above set: (a) A, B (b) C, D (c) A, B, D (d) A, C, D 111. The following reaction : 2 Anhydrous ZnCl HCNHCl   is known as [MP PET 1997] O H CHO O H 1228 Alcohol, Phenol and Ethers (a) Perkin reaction (b) Gattermann reaction (c) Kolbe reaction (d) Gattermann-Koch reaction 112. Carbylamine test is done by heating alcoholic KOH with [IIT-JEE 1984; BIT 1992; CBSE PMT 1992] (a) Chloroform and silver powder (b) Trihalogen methane and primary amine (c) Alkyl halide and primary amine (d) Alkyl cyanide and primary amine 113. Isopropyl alcohol heated at Co300 with copper catalyst to form[AFMC 1990; MP PMT 1986, 89, 92; JIPMER 2000] (a) Acetone (b) Dimethyl ether (c) Acetaldehyde (d) Ethane 114. Dehydrogenation of OH CHCHCH | 33  gives [MP PMT 2002] (a) Acetone (b) Acetaldehyde (c) Acetic acid (d) Acetylene 115. In the sequence of the following reactions   KCNHI ICHOHCH 33 YXCNCH HNO    3reduction 3 X and Y are respectively [MP PMT 2002] (a) 223 NHCHCH and OHCHCH 23 (b) 223 NHCHCH and COOHCH 3 (c) OHCHCH 23 and CHOCH 3 (d) 33OCHCH and CHOCH 3 116. Alcohols (i) ,223 OHCHCHCH (ii) 33 CHCHOHCH  and (iii) 333 ))(( CHOHCHCCH  were treated with Lucas reagent (Conc. ).2ZnClHCl  What results do you expect at room temperature (a) (ii) and (iii) react immediately and (i) in about 5 minutes (b) (iii) reacts immediately, (ii) reacts in about 5 minutes and (i) not at all (c) (i) reacts immediately, (ii) reacts in about 5 minutes and (iii) not at all (d) (i) reacts in about 5 minutes, (ii) reacts in about 15 minutes and (iii) not at all 117. Ethylene may be obtained by dehydration of which of the following with concentrated 42SOH at 160 – 170°C [DPMT 2000; MP PET 2001] (a) OHHC 52 (b) OHCH 3 (c) OHCHCHCH 223 (d) OHCHCHCH 223 )( 118. The final product of the oxidation of ethyl alcohol is [KCET (Med.) 1999 ] (a) Ethane (b) Acetone (c) Acetaldehyde (d) Acetic acid 119. The compound obtained by heating salicylic acid with phenol in the presence of phosphorus oxychloride is [KCET (Med.) 1999] (a) Salol (b) Aspirin (c) Oil of wintergreen (d) o-chlorobenzoyl chloride 120. When phenol is allowed to react with 2Br in (i) 2CS solution and (ii) in aqueous solution, the resulting compounds are (a) (i) 2, 4, 6-tribromophenol and (ii) o-and p-bromophenol (b) (i) m-bromophenol and (ii) 2, 3, 4-tribromophenol (c) (i) o-and p-bromophenol and (ii) 2, 4, 6-tribromophenol (d) (i) o- and m-bromophenol and (ii) 2, 3, 4-tribromophenol 121. Which of the following is not true in case of reaction with heated copper at Co300 [CPMT 1999] (a) Phenol  Benzyl alcohol (b) Primary alcohol  Aldehyde (c) Secondary alcohol  Ketone (d) Tertiary alcohol  Olefin 122. Which of the following is the most suitable method for removing the traces of water from ethanol [CPMT 1999] (a) Heating with Na metal (b) Passing dry HCl through it (c) Distilling it (d) Reacting with Mg 123. With oxalic acid, glycerol at Co260 gives [BHU 1996] (a) Allyl alcohol (b) Glyceryl mono- oxalate (c) Formic acid (d) Glyceraldehyde 124. Absolute alcohol cannot be prepared by fractional distillation of rectified spirit since (a) It forms azeotropic mixture (b) It is used as power alcohol (c) It is used in wines (d) None of the above 125. The reagent used for the dehydration of an alcohol is [MP PET/PMT 1998] Alcohol, Phenol and Ethers 1231 158. The vapour pressure of aqueous solution of methanal is [UPSEAT 2000] (a) Equal to water (b) Equal to methanal (c) More than water (d) Less than water 159. Glycerol reacts with conc. 3HNO and conc. 42SOH to form [CPMT 1983; MP PMT/PET 1988] (a) Glycerol mononitrate (b) Glycerol dinitrate (c) Glycerol trinitrate (d) Acrolein 160. Glycerol heated with oxalic acid at Co110 to form [CPMT 1986, 90, 91, 97; JIPMER 1997] (a) Formic acid (b) Oxalic acid (c) Allyl alcohol (d) Glycerol trioxalate 161. Dimethyl ether and ethyl alcohol are [CPMT 1986; Manipal MEE 1995] (a) Branched isomer (b) Position isomer (c) Functional isomer (d) Tautomer 162. The process of manufacture of absolute alcohol from rectified spirit is[CPMT 1986, 87; Kurukshetra CEE 2002] (a) Fractional distillation (b) Steam distillation (c) Azeotropic distillation (d)Vacuum distillation 163. When ethyl alcohol reacts with acetic acid, the products formed are [CPMT 1989] (a) Sodium ethoxide + hydrogen (b) Ethyl acetate + water (c) Ethyl acetate + soap (d) Ethyl alcohol + water 164. Picric acid is (at Co25 ) (a) A white solid (b) A colourless liquid (c) A gas (d) A bright yellow solid 165. Phenol on distillation with zinc dust gives [MP PET 1991; CPMT 1997; MP PMT 1999, 2001; Pb. PMT 2000] (a) 66 HC (b) 126 HC (c) 5656 HOCHC (d) 5656 HCHC  166. Methanol and ethanol are miscible in water due to [MP PET/PMT 1988; CPMT 1989; CBSE PMT 1991] (a) Covalent character (b) Hydrogen bonding character (c) Oxygen bonding character (d) None of these 167. By distilling glycol with fuming sulphuric acid, which of following is obtained (a) Glycerol (b) Pinacol (c) Dioxan (d) Ethylene oxide 168. The compound which gives the most stable carbonium ion on dehydration is [DCE 2000] (a) OHCH CH CHCH 2 3 | 3  (b) OH CH CH CCH  3 | 3 | 3 (c) OHCHCHCHCH 2223  (d) 32 3 3 | CHCH CH CHCH  169. In OHCHCH 23 which bond dissociates heterolytically [IIT-JEE 1988; CPMT 1996] (a) C – C (b) C – O (c) C – H (d) O – H 170. Which compound is soluble in water [IIT-JEE 1980; CPMT 1993; RPET 1999] (a) 2CS (b) OHHC 52 (c) 4CCl (d) 3CHCl 171. Which of the following is most soluble in water [MP PMT 1995] (a) Normal butyl alcohol (b) Isobutyl alcohol (c) Tertiary butyl alcohol (d)Secondary butyl alcohol 172. Which of the following gives negative iodoform test (a) OHCHCH 23 (b) OHCHCHCH 223 (c) OH CHCHHC | 356  (d) OH CHCHCH | 33  173. If ethanol dissolves in water, then which of the following would be done [MP PET 1989] (a) Absorption of heat and contraction in volume (b) Emission of heat and contraction in volume (c) Absorption of heat and increase in volume (d) Emission of heat and increase in volume 174. A migration of hydrogen with a pair of electrons is called (a) Alkyl shift (b) Hydride shift (c) Hydrogen ion formation (d) Dehydrogenation 175. When rectified spirit and benzene are distilled together, the first fraction obtained is (a) A ternary azeotrope (b) Absolute alcohol (c) A binary azeotrope (d) Denatured spirit 176. Alcohols react with Grignard reagent to form[DPMT 1986] (a) Alkanes (b) Alkenes (c) Alkynes (d) All of these 177. Action of diazomethane on phenol liberates (a) 2O (b) 2H (c) 2N (d) 2CO 178. The ring deuteration of phenol (a) Lowers the acidity (b) Increases the acidity (c) Imparts no effect 1232 Alcohol, Phenol and Ethers (d) Causes amphoteric nature 179. In esterification of an acid, the other reagent is [CPMT 1988] (a) Aldehyde (b) Alcohol (c) Amine (d) Water 180. Maximum solubility of alcohol in water is due to [MP PMT/ PET 1988; MP PMT 1989] (a) Covalent bond (b) Ionic bond (c) H-bond with OH 2 (d) None of the above 181. Alcohols can be distinguished from alkenes by (a) Dissolving in cold concentrated 42SOH (b) Decolourizing with bromine in 4CCl (c) Oxidizing with neutral permanganate solution (d) None of the above 182. At Co25 Ethylene glycol is a (a) Solid compound (b) Liquid (c) Gas (d) Brown solid 183. When primary alcohol is oxidised with chlorine, it produces [AFMC 1999] (a) HCHO (b) CHOCH 3 (c) CHOCCl 3 (d) CHOHC 73 184. Alcohols combine with acetylene in the presence of mercury compounds as catalyst to form (a) Acetals (b) Xanthates (c) Vinyl ethers (d) None of the above 185. The compound which will give negative iodoform test is [CPMT 1993, 99] (a) CHOCH 3 (b) OHCHCH 23 (c) Isopropyl alcohol (d) Benzyl alcohol 186. Which of the following is most acidic [CPMT 1999] (a) Phenol (b) Benzyl alcohol (c) m-chlorophenol (d) Cyclohexanol 187. Number of metamers represented by molecular formula OHC 104 is [Tamil Nadu CET 2001] (a) 4 (b) 3 (c) 2 (d) 1 188. When ether is exposed in air for sometime an explosive substance produced is [RPMT 2002] (a) Peroxide (b) TNT (c) Oxide (d) Superoxide 189. Ether which is liquid at room temperature is[BVP 2002] (a) 352 OCHHC (b) 33OCHCH (c) 5252 HOCHC (d) None of these 190. In the following reaction ,2][4 2 HIP Red 5252 OHXHHOCHC    X is [MP PMT 2002] (a) Ethane (b) Ethylene (c) Butane (d) Propane 191. Diethyl ether absorbs oxygen to form [DPMT 1984] (a) Red coloured sweet smelling compound (b) Acetic acid (c) Ether suboxide (d) Ether peroxide 192. Diethyl ether can be decomposed by heating with [CPMT 1980, 81, 89] (a) HI (b) NaOH (c) Water (d) 4KMnO 193. On boiling with concentrated hydrobromic acid, phenyl ethyl ether will yield [AIIMS 1992] (a) Phenol and ethyl bromide (b) Phenol and ethane (c) Bromobenzene and ethanol (d) Bromobenzene and ethane 194. Ether is formed when ethyl alcohol is heated with conc. .42SOH The conditions are [KCET 1984] (a) Excess of 42SOH and Co170 (b) Excess of OHHC 52 and Co140 (c) Excess of OHHC 52 and Co180 (d) Excess of conc. 42SOH and Co100 195. The ether when treated with HI produces [IIT-JEE 1999] (a) (b) (c) (d) 196. Addition of alcohols to aldehydes in presence of anhydrous acids yield [CET Pune 1998] (a) Carboxylic acids (b) Ethers (c) Cyclic ethers (d) Acetals 197. In which of the following reaction, phenol or sodium phenoxide is not formed [CPMT 1996] (a)  KOHalcoClNHC .256 (b)  NaOHOClHC 56 (c)  NaOHaqClNHC .256 (d)    OH NNClHC 2 56 198. Dimethyl ether when heated with excess HI gives [CPMT 1996] (a) ICH 3 and OHCH 3 (b) ICH 3 and OH 2 (c) ICHHC 362  and OHCH 3 (d) ICH 3 and HCHO O CH2 ICH2 OHCH 2 I OH Alcohol, Phenol and Ethers 1233 199. The ether that undergoes electrophilic substitution reactions is [JIPMER 2001] (a) 523 HOCCH (b) 356 OCHHC (c) 33OCHCH (d) 5252 HOCHC 200. Acetyl chloride does not react with [MNR 1995] (a) Diethyl ether (b) Aniline (c) Phenol (d) Ethanol 201. The products formed in the following reaction   heat 356 HICHOHC are [IIT 1995] (a) IHC 56 and OHCH 3 (b) OHHC 56 and ICH 3 (c) 356 CHHC  and HOI (d) 66 HC and OICH 3 202. Etherates are (a) Ethers (b) Solution in ether (c) Complexes of ethers with Lewis acid (d) Complexes of ethers with Lewis base 203. An ether is more volatile than an alcohol having the same molecular formula. This is due to[AIEEE 2003] (a) Dipolar character of ethers (b) Alcohols having resonance structures (c) Inter-molecular hydrogen bonding in ethers (d) Inter-molecular hydrogen bonding in alcohols 204. When ether is reacted with ,2O it undergoes explosion due to [CPMT 1996] (a) Peroxide (b) Acid (c) Ketone (d) TNT 205. The compound which does not react with sodium is [CBSE PMT 1994] (a) OHHC 52 (b) 33 CHOCH  (c) COOHCH 3 (d) 33 CHCHOHCH  206. Methyl-terbutyl ether on heating with HI of one molar concentration gives [MP PET 1997] (a) COHCHICH 333 )( (b) ClCHOHCH 333 )( (c) ClCHICH 333 )( (d) None of the above 207. A substance OHC 104 yields on oxidation a compound OHC 84 which gives an oxime and a positive iodoform test. The original substance on treatment with conc. 42SOH gives 84 HC . The structure of the compound is [SCRA 2000] (a) OHCHCHCHCH 2223 (b) 323 )( CHCHOHCHCH (c) COHCH 33)( (d) 3223 CHCHOCHCH  208. Ethylene glycol reacts with excess of 5PCl to give [Kerala PMT 2004] (a) 1, 1-dichloroethane (b) 1, 2-dicholoroethane (c) 1, 1, 1-trichloroethane (d) 1, 1, 2, 2-tetrachloroethane (e) 2, 2-dichloroethane 209. Which of the following will not react with NaOH [CPMT 2004] (a) (b) OHHC 52 (c) 23CONHCH (d) 3)(CNCH 210. The boiling point of methanol is greater than that of methyl thiol because [Kerala PMT 2004] (a) There is intramolecular hydrogen bonding in methanol and intermolecular hydrogen bonding in methyl thiol (b) There is intermolecular hydrogen bonding in methanol and no hydrogen bonding in methyl thiol (c) There is no hydrogen bonding in methanol and intermolecular hydrogen bonding in methyl thiol (d) There is intramolecular hydrogen bonding in methanol and no hydrogen bonding in methyl thiol (e) There is no hydrogen bonding in methanol and intramolecular hydrogen bonding in methyl thiol 211. In the reaction )( 110 | 2 2 | | A COOH COOH OHCH OHCH HOHC C    product (A) will be [Pb . CET 2001] (a) Glycerol monoformate (b) Allyl alcohol (c) Formaldehyde (d) Acetic acid 212. Which of the following will not form a yellow precipitate on heating with an alkaline solution of iodine [CBSE PMT 2004] (a) OHCH 3 (b) OHCHCH 23 (c) 33 )( CHOHCHCH (d) 323 )( CHOHCHCHCH 213. In Friedal-Crafts acylation, besides 3AlCl , the other reactants are [DPMT 2004] 2NO 2NO NO2 OH OH OH 1236 Alcohol, Phenol and Ethers 5. Substances used in bringing down the temperature in high fevers are called [DPMT 1983] (a) Pyretics (b) Antipyretics (c) Antibiotics (d) Antiseptics 6. When glycol is heated with dicarboxylic acid, the products are (a) Polyesters (b) Polyethers (c) Polyethylene (d) No reaction at all 7. Cresol is [BHU 1996] (a) A mixture of three cresols with little phenol (b) Used as dye for wood (c) A soapy solution of cresols (d) Having an aldehyde group 8. Phenol is used in the manufacture of [AIIMS 1996] (a) Bakelite (b) Polystyrene (c) Nylon (d) PVC 9. In cold countries ethylene glycol is added to water in the radiators to[CPMT 1971; NCERT 1971; MP PMT 1993] (a) Bring down the specific heat of water (b) Lower the viscosity (c) Reduce the viscosity (d) Make water a better lubricant 10. Power alcohol is [KCET 1990] (a) An alcohol of 95% purity (b) A mixture of petrol hydrocarbons and ethanol (c) Rectified spirit (d) A mixture of methanol and ethanol 11. 4-chloro-3, 5-dimethyl phenol is called[KCET 2003] (a) Chloramphenicol (b) Paracetamol (c) Barbital (d) Dettol 12. Alcoholic fermentation is brought about by the action of [CPMT 1977, 79, 88; DPMT 1983] (a) 2CO (b) 2O (c) Invertase (d) Yeast 13. Rectified spirit is a mixture of [DPMT 1982; MP PMT 1976, 77, 96; CPMT 1976, 77, 90; KCET 1990] (a) 95% ethyl alcohol + 5% water (b) 94% ethyl alcohol + 4.53% water (c) 94.4% ethyl alcohol + 5.43 % water (d) 95.57% ethyl alcohol + 4.43% water 14. Methyl alcohol is toxic. The reason assigned is[RPET 2000] (a) It stops respiratory track (b) It reacts with nitrogen and forms CN in the lungs (c) It increases 2CO content in the blood (d) It is a reduction product of formaldehyde 15. Glycerol is used [Kurukshetra CET 2002] (a) As a sweetening agent (b) In the manufacture of good quality soap (c) In the manufacture of nitro glycerine (d) In all of these 16. Glycerol is not used in which of following cases (a) Explosive making (b) Shaving soap making (c) As an antifreeze for water (d) As an antiseptic agent 17. Liquor poisoning is due to [CPMT 1971] (a) Presence of bad compound in liquor (b) Presence of methyl alcohol (c) Presence of ethyl alcohol (d) Presence of carbonic acid 18. In order to make alcohol undrinkable pyridine and methanol are added to it. The resulting alcohol is called (a) Power alcohol (b) Proof spirit (c) Denatured spirit (d) Poison alcohol 19. Denatured spirit is mainly used as a [MNR 1995; MP PET 2002] (a) Good fuel (b) Drug (c) Solvent in preparing varnishes (d) Material in the preparation of oil 20. Main constituent of dynamite is [MP PET 1992; BHU 1979] (a) Nitrobenzene (b) Nitroglycerine (c) Picric acid (d) TNT 21. Wine (alcoholic beverages) contains [CPMT 1972, 77; BHU 1996; AFMC 2001] (a) OHCH 3 (b) Glycerol (c) OHHC 52 (d) 2-propanol 22. Tonics in general contain [MNR 1995] (a) Ether (b) Methanol (c) Ethanol (d) Rectified spirit 23. Widespread deaths due to liquor poisoning occurs due to [DPMT 2001] (a) Presence of carbonic acid in liquor (b) Presence of ethyl alcohol in liquor (c) Presence of methyl alcohol in liquor (d) Presence of lead compounds in liquor 24. Diethyl ether finds use in medicine as [KCET 1989] (a) A pain killer (b) A hypnotic (c) An antiseptic (d) An anaesthetic 25. Washing soap can be prepared by saponification with alkali of the oil [CPMT 1986] (a) Rose oil (b) Paraffin oil (c) Groundnut oil (d) Kerosene 26. Ether can be used [CPMT 1982] (a) As a general anaesthetic (b) As a refrigerant (c) In perfumery (d) All of these 27. The Bouveault-Blanc reduction involves[MP PET 1991] (a) NaOHHC /52 (b) 4LiAlH (c) MgXHC 52 (d) HClZn / 28. Which is used as an antifreeze [AFMC 1992] (a) Glycol (b) Ethyl alcohol (c) Water (d) Methanol Alcohol, Phenol and Ethers 1237 1. Which will undergo a Friedel-Craft's alkylation reaction [Pb. PMT 1998] (a) 1, 2 and 4 (b) 1 and 3 (c) 2 and 4 (d) 1 and 2 2. The product ‘A’ in the following reaction is A O CHCH RMgI   22 — [MP PMT 2003] (a) RCHOHR (b) 3CHRCHOH  (c) OHCHCHR  22 (d) OHCHCH R R 2 3. Glycerol boils at Co290 with slight decomposition. Impure glycerine can be purified by [CPMT 1983, 94] (a) Steam distillation (b) Simple distillation (c) Vacuum distillation (d) Extraction with a solvent 4. Phenol DCB NaOHOHSOHNaNO     2422 / Name of the above reaction is [KCET 2003] (a) Liebermann’s reaction (b) Phthalein fusion test (c) Reimer-Tiemann reaction (d) Schottenf-Baumann reaction 5. The correct order of boiling point for primary ),1( o secondary )2( o and tertiary )3( o alcohols is [CPMT 1999; RPMT 2002] (a) ooo 321  (b) ooo 123  (c) ooo 312  (d) ooo 132  6. What will be the products of reaction if methoxybenzene reacts with HI (a) Methyl alcohol (methanol) + iodobenzene (b) Methyl iodide (iodomethane) + benzene (c) Methyle iodide + phenol (d) Methyl iodide + iodobenzene 7. Ethylene reacts with Baeyer's reagent to give[CPMT 1988] (a) Ethane (b) Ethyl alcohol (c) Ethylene glycol (d) None of these 8. Which of the following statements is correct regarding case of dehydration in alcohols [CPMT 1980, 85; MP PMT 2001; BHU 2002] (a) Primary > Secondary (b) Secondary > Tertiary (c) Tertiary > Primary (d) None of these 9. Oxiran is (a) Ethylene oxide (b) Diethyl ether (c) Ethyl glycolate (d) Glycolic ester 10. Propan-1-ol can be prepared from propene by alcohol [AIIMS 2003] (a) 422 / SOHOH (b) OHOAcHg 22 /)( followed by 4NaBH (c) 62HB followed by 22OH (d) 4223 / SOHHCOCH 11. Distinction between primary, secondary and tertiary alcohol is done by[MP PMT/PET 1988; RPMT 2000] (a) Oxidation method (b) Lucas test (c) Victor Meyer method (d) All of these 12. Oxidation of which of the following by air in presence of vanadium pentoxide gives phenol (a) Toluene (b) Benzene (c) Benzaldehyde (d) Phenyl acetic acid 13. The most suitable method of the separation of a 1 : 1 mixture of ortho and para nitrophenols is [CBSE PMT 1994, 99; CPMT 1997] (a) Distillation (b) Sublimation (c) Crystallization (d) Chromatography 14. Which of the following does not form phenol or phenoxide [AFMC 2000] (a) ClHC 56 (b) COOHHC 56 (c) ClNHC 256 (d) NaSOHC 356 15. Which of the following will be obtained by keeping ether in contact with air for a long time[RPMT 2003] (a) OHOCHCHOHC  )( 352 (b) OHOCHHC  252 (c) OHHCOHC 5252  (d) OHOCHCHOCH  )( 33 16. When a mixture of ethanol and methanol is heated in the presence of concentrated 42SOH the resulting organic product or products is/are[Manipal MEE 1995] (a) 523 HOCCH (b) 33OCHCH and 5252 HOCHC (c) 523 HOCCH and 33OCHCH (d) ,523 HOCCH 33OCHCH and 5252 HOCHC 17. In the following groups I OAc II OMe III 2MeOSO IV 32CFOSO The order of leaving group ability is [IIT 1997] (a) I > II > III > IV (b) IV > III > I > II (c) III > II > I > IV (d) II > III > IV > I 18. Epoxides are (a) Cyclic ethers (b) Not ethers (c) Aryl-alkyl ethers (d) Ethers with another functional group 2NO CH3 1 CH2CH3 2 COOH 3 OH 4 1238 Alcohol, Phenol and Ethers 19. The reaction of CHCHCH 3 OH with HBr gives [IIT-JEE 1998] (a) 23CHBrCHCH OH (b) CHBrCHCH 23 OH (c) 23CHBrCHCH Br (d) CHBrCHCH 23 Br 20. Which of the following compounds on boiling with 4KMnO (alk.) and subsequent acidification will not give benzoic acid [KCET 2001] (a) Benzyl alcohol (b) Acetophenone (c) Anisole (d) Toluene 21. The best reagent to convert pent-3-en-2-ol into pent-3-in-2-one is [AIEEE 2005] (a) Acidic permanganate (b) Acidic dichromate (c) Chromic anhydride in glacial acetic acid (d) Pyridinium chloro-chromate 22. When alcohol reacts with concentrated 42SOH intermediate compound formed is [AFMC 2005] (a) Carbonium ion (b) Alkoxy ion (c) Alkyl hydrogen sulphate (d) None of these Read the assertion and reason carefully to mark the correct option out of the options given below: (a) If both assertion and reason are true and the reason is the correct explanation of the assertion. (b) If both assertion and reason are true but reason is not the correct explanation of the assertion. (c) If assertion is true but reason is false. (d) If the assertion and reason both are false. (e) If assertion is false but reason is true. 1. Assertion : A triester of glycerol and palmitic acid on boiling with aqueous NaOH gives a solid cake having soapy touch Reason : Free glycerol is liberated which is a greasy solid [AIIMS 1996] 2. Assertion : Phenol is a weak acid than etnanol Reason : Groups with + M effect and – I effect decrease acidity at p-position[AIIMS 2002] 3. Assertion : Phenol is more reactive than benzene towards electrophilic substitution reaction Reason : In the case of phenol, the intermediate carbocation is more resonance stabilized [IIT-JEE (Screening) 2000] 4. Assertion : Phenol undergo Kolbe reaction, ethanol does not. Reason : Phenoxide ion is more basic than ethoxide ion. [AIIMS 1994] 5. Assertion : Lucas reagent is a mixture of anhydrous 2ZnCl and concentrate HCl Reason : Primary alcohol produce ppt. with Lucas reagents. [AIIMS 1995] 6. Assertion : Resorcinol turns 2FeCl solution purple. Reason : Resorcinol have phenolic group.[AIIMS 2000] 7. Assertion : Glycerol is purified by distillation under reduced pressure. Reason : Glycerol is a trihydric alcohol. 8. Assertion : Alcohol and phenol can be distinguished by sodium hydroxide. Reason : Phenol is acidic while alcohol is neutral. 9. Assertion : Alcohols are dehydrated to hydrocarbons in the presence of acidic zeolites. Reason : Zeolites are porous catalysts. 10. Assertion : The major products formed by heating 3256 OCHCHHC with HI are ICHHC ,56 and OHCH3 . Reason : Benzyl cation is more stable than methyl cation. [AIIMS 2004] 11. Assertion : The pka of acetic acid is lower than that of phenol. Reason : Phenoxide ion is more resonance stabilized. [AIIMS 2004] 12. Assertion : Alcoholic fermentation involves conversion of sugar into ethyl alcohol by yeast. Reason : Fermentation involves the slow decomposition of complex organic 13. Assertion : The water solubility of the alcohols follow the order t-butyl > s-butyl alcohol > n-butyl alcohol. Reason : Alcohols form H-bonding with water to show soluble nature. 14. Assertion : Absolute ethanol can be obtained by simple fractional distillation of a mixture of alcohol and water. Reason : The absolute alcohol boils at 78.3°C. 15. Assertion : Acid catalysed dehydration of t- butanol is slower than n-butanol. Reason : Dehydration involves formation of the protonated alcohol,  2ROH . 16. Assertion : Tertiary alcohols give turbidity immediately with Lucas reagent. Reason : A mixture of conc.HI + anhydrous 2ZnCl is called Lucas reagent. Alcohol, Phenol and Ethers 1241 16 c 17 e 18 b 19 b 20 e 21 c 22 b 23 c 24 b 25 c 26 a 27 a 28 b 29 b 30 c 31 d 32 c 33 b Alcohol, Phenol and Ethers 1239 General introduction of alcohol, Phenol & Ethers 2. (d) 2, 4, 6-trinitrophenol or picric acid 4. (d) OH CH OH CH OH CH ||| 22  Glycerol is trihydric alcohols. 5. (a) 6. (c) % of 100 substanceofMass ofMass  C C %79.7100 154 12 4 CCl %74.24100 291 72 666 ClHC %70.38100 62 24 22  OHCHOHCH . 7. (c) o-dihydroxy benzene or catechol. 8. (b) OHCH OHCH OHCH    2 2 | | one secondary and two primary alcoholic groups. 11. (b) Carbinol is OHCH3 (Methanol). 12. (c) – OH group is attached to primary carbon. 13. (c) Picric acid is phenolic whileothers are non phenolic. 15. (c) Butanal CHOCHCHCH  223 , an aliphatic aldehyde. 16. (b) Cyclohexanol is a secondary alcohol because OH group is linked to o2 carbon. 18. (b) OHHC 52 and 33 CHOCH  are isomers. 20. (b) 5-10 % methyl and remaining ethanol is called methylated spirit. It is also known as denatured alcohol because it is unfit for drinking. 21. (a) or 23. (a) 5% aqueous solution of phenol at room temperature is called as carbolic acid. 25. (b) Glycols are dihydric alcohols (having two hydroxyl groups). Ethylene glycol is the first member of this series. glycol) (Ethy lene 2 2 | OHCH OHHC 26. (a) Methanol is also referred as wood alcohol or wood spirit or wood naphtha as the earliest method for its preparation was by destructive distillation of wood. 34. (b) Ether is basic because lone pairs of electrons are present on oxygen atom, ROR    . 39. (a) Thio alcohol is known as mercaptans. Preparation of alcohol, Phenol and Ethers 1. (c) Hydration of alkenes 423422 HSOCHCHOHSHCHCH    4223423 2 SOHOHCHCHHSOCHCH Boil OH   Fermentation of sugars: Fructose 6126 Glucose 6126 Invertase 2112212 OHCOHCOHOHC   252 Zymase FructoseorGlucose 6126 22 COOHHCOHC   2. (c)    Hydrolysis 42322 42 HSOCHCHCHCH SOH 4223 SOHOHCHCH  3. (b) Hydroboration oxidation (Industrial preparation of alcohol) BCHCHCHHBCHCHCH 3323 ether Dry 6223 )( 2 1 3   OHCHCHCHBCHCHCH OH   2233323 3)( 22 4. (c)  OMgI CH CH CHMgICH O CHCH | 2 | 2322 3 OH OH OH 2NO 2NO NO2 (Picric acid) or 2, 4, 6- trinitrophenol OH CH 2 CH 2 2CH cyclohexanol CH–OH 2CH 2CH OH N2O 2NO 2NO OH OH 3CH Hydroxy toluene 1240 Alcohol, Phenol and Ethers OH I MgOHCHCHCH  alcoholPropy l 223 5. (d) AlcoholStarch Enzymes   6. (c) Coconut oil + Alkali  Soap + Glycerol It is a saponification reaction. 7. (c) 2 alcoholEthyl 52 Zymase FructoseorGlucose 6126 22 COOHHCOHC   8. (d) chlorideBenzy l 2 heat/Light 3 2 ClCHCH Cl   NaCl OHCH NaOHaq     alcoholBenzy l 2 . 9. (a) Maltose 112212 barley )germinated(from Diastase 2 Starch 5106 )()(2 OHCnOnHOHC n   Glucose 6126 yeast)(from Maltase 2112212 2 OHCOHOHC   252 yeast)(from Zymase 6126 22 COOHHCOHC   10. (b) 11. (c) +   OH 2 + HClN 2 12. (c) OHOHCHCHHCOOHCH LiAlH 2233 44   13. (b)    Hydrolysis 3 | 2 3 MgIO CH CHOC H H MgICH OH I MgOHCHCH  23 14. (b) + NaOH   conc. + 15. (d) + 42 dil. 2 SOH OH  HClN  2 16. (c) NaIHOCHCHICONaHC  52525252 17. (b)  NaOHCHCl 33 OHNaCl 223  18. (c) formate PotassiumalcoholMethyl 3 Conc. HCOOKOHCHHCHOHCHO KOH   It is cannizzaro’s reaction. 19. (d) SolubleBenzeneAlcohol (dry )  (Alcohol) 2HONaRNaOHR  21. (c) OHCHHHCO atmK ZnOOCr 3 200,672 / 2 gaswater 2 22    23. (c) 42 .Conc || || SOH O O O C C   + OH 2 24. (c) Glucose 6126 yeast)(from Maltase 2 Maltose 112212 2 OHCOHOHC   . 26. (d) Grignard reagent reacts with compounds containing multiple bonds like NCSCOC  ,, . 28. (d) Acetone reacts with Grignard’s reagent to give tertiary alcohol. alcoholbutyl -ter 33323 )()( 2 OHCCHMgBrCHOCCH OH   29. (b)   OH O CHCHMgBrHC 2 2252 )( alcoholbuty l- )( 2252 OHMgBrOHCHCHHC n A  30. (a) OHH NaOH 2/    31. (b)   Boil 2OH HClN  2 32. (b) MgIO HC CHMgIHCOC H H  52 | 252 OHCHHC   252 Hydrolysis or OH I MgOHH 73C 35. (d) OH Br MgOHROMgBrRORMgBr   Alcohol hydrolysis 2 reagent Grignard 39. (b) 252 Zymase Glucose 6126 22 COOHHCOHC   During fermentation 2CO gas is eliminated. 40. (c) OHNOHHCHNONHHC 22522252  ClNN  OH CHO CHO OHCH 2 COONa ClNN  OH OH OH C O C || O OH OH Phenolphthalei n H OH H OH SO3Na OH Phenol N = N – Cl OH Phenol CHO Benzyldehyde OHCH 2 Benzyl alcohol Alcohol, Phenol and Ethers 1243 33. (c) OHHIOHCHOHIO OHCH OHCH 234 2 2 2|  35. (b) 22 2 2 | 3 2 2 | 2 CHCH ICH IHC PI OHCH OHHC I    36. (a) 3963 nitrateamm.Cerric 6324 142 .yellow )()()()( alcohol NON ppt ROHNOCeNOCeNHOHR  37. (d) 523 25 25252 )( HCOOOHCHCHOHCOHC C hv o  38. (a)   442 HSOHSOH alcohol Protonated 52 alcoholof nProtonatio 52 H H OHCHOHHC       39. (c) 43. (d) OHCHCHOHCHCH C COAl o X 222 350 23 32 )(  44. (a) atm KCO 73 400,2      Rearr. 45. (c) 46. (b) ion Carbonium Methy l 3233 3 | | 3 3 123 HCHCCHHCCH CH C CH CH oo o    47. (c) Alcohols having less number of carbon atoms are more soluble in water. 48. (a) ONaHCNaOHHC 5252  OHHCOHCOHHC SOH 25252 Conc. 52 42 2   50. (a) 51. (d) HClPOClClHCPClOHHC  352552 (B)(A) KClCNHCKCNClHC  5252 (B) 52. (c) 53. (b) Higher alcohols are stronger and have bitter taste. 54. (c) Order of reactivity with alkali metal (e.g.- Sodium) follows the order ooo 321  . 56. (c) mole molemole HONaCHNaOHCH gms 2/1 2 11 33 2 1 )23(  57. (d)  322233 PBrOHCHCHCHCH 3322233 POHBrCHCHCHCH  58. (a) reactionNo23  ClOHCH OHClCHHClOHCH ZnCl 233 2   33333 33 POHClCHPClOHCH  HClPOClClCHPClOHCH  3353 59. (d) 3 || 3 ][ 3 | 3 CH O CCHCH OH CHCH O  60. (c)   water2Br 61. (d) Due to hydrogen bonding. 62. (a) CHOCHOHHC Pt 3 air 52  63. (c) OHCHCHOHCHCH C SOH o 222 170 Conc. 23 42   66. (b) Tertiary alcohol readily reacts with halogen acid 3 | 3 | 3 3 3 3 CH CH OHCCH CH CH OHCCH      Nitro group is electron with-drawing. Hence, increases acidic nature. OH 2NO OH ONa NaOCO2 COONa OH etheriethyl Perchlorod 3223 CClCClOCClCCl  Dar k Ligh t Cl2 3 || 3 CH Cl CHO Cl CHCH  --dichlorodiethyl ether 5252 HCOHC  Hydrolys is COOHHC 52 CH3 OH OH OH 2NO 2NO OH OH Phenol Br Br Br OH 2,4,6 tribromophenol or white ppt. C o 110 C o 137 C o 170 OHHSOHC 2 sulphate hydrogenEthyl 452  OHHCOHC 2 EtherDiethyl 5252  OHHC 2 Ethene 42  OHHC 52 H2SO4 1244 Alcohol, Phenol and Ethers Presence of 3 alkyl group increases electron density on o3 carbon atom. Hence OH group is easily removed. After the removal of OH group o3 carbonium ion is formed which is most stable 67. (d) 23 180160 conc. 223 42 CHCHCHOHCHCHCH C o SOH    Propyne 3 .Alc | 2 | 3 2 CHCCH Br CH Br CHCH KOHBr    68. (b) Lower alcohols are soluble in all solvents. 69. (c) 32 || 3 ][ 32 | 3 CHCH O CCHCHCH OH HCCH O  70. (b) Due to the resonance stabilisation of phenoxide ion. 73. (a) C SOH oo OHCHCHR 170 Conc. alcohol1 22 42   OHCHCHR 2 Alkene 2  74. (a) 2 alcohol1 2- HCHOROHCHR Cu o  2 || alcohol2 | HR O CRR OH CHR Cu o  75. (c) HCOOHOHCH SOH OCrK 42 722 3   76. (a) COOHCHOHCHCH OCrK 323 722   77. (a) Lucas test is used for the distinction of primary secondary and tertiary alcohols. 78. (a) + C ZnCl o NH 300 3 2  + OH 2 80. (a) A compound that undergoes bromination easily is phenol. Due to presence of – OH group the ring becomes much more active in substitution reactions. The bromination occurs due to availability of electrons on ortho and para position. 81. (c) o-Nitrophenol has intramolecular H-bonding. 84. (b) OHHC 52 gives iodoform test having - hydrogen atom while OHCH3 does not give due to the absence of -hydrogen atom. 85. (c) Phenol has higher boiling point than toluene because of hydrogen bonding. 87. (b) 1Propanol . 1Propene 22323     OHCHCHCHKOHaqCHCHCH 88. (d) CNHCClHCPClOHHC KCN 5252552   89. (b) 4LiAlH + ether, is reducing agent. 97. (b)   2 3 ZnCl NH OH 2 98. (a) Oxygen atom of OH group acquires positive charge. 99. (c)         Unstable | || | || Glycerol | | | | 4 H CH OH HC C OH H CH OH HCH HCHO KHSO H CH H O C HC | || || ||    or Acrolein || | 2 CH CHO CH 100. (d) 3 || 33 | 3 42 722 CH O CCHCH OH CHCH SOH OCrK   COONaCHCHI pptI NaOH 3 Yellow 3 2   101. (d) (conc.) 3 42 conc.   SOH HNO 102. (c) Phenol is weaker acid than carbonic acid OHHC Ka 56 108 1010   , 32 710 COH Ka  , COOHCH Ka 3 510 103. (a) 104. (b)   2 2 CS Br + In presence of non-polar solvent )( 2CS the ionization of phenol is suppressed. The ring is slightly activated and hence mono substitution occurs. On the other hand with 2Br water phenol forms 2,4,6-tribromo phenol. OH 2NH HCl / H2O COOHHC 56 OH 2NH Aniline . . HO   HO   HO   . . . . HO  : OH o - bromophenol OH Br p -bromophonol OH Br Br Br Br OH OH OH OH 2NO 2NO NO2 Picric a id Alcohol, Phenol and Ethers 1245   water 23Br HBr3 In aqueous solution phenol ionizes to give phenoxide ion. Due to the presence of negative charge on oxygen the benzene ring is highly activated and hence trisubstituted product is obtained. 105. (d) acidAcetic 3 alcoholEthyl 52 3 COOHCHOHHC CrO   107. (d) OHHCOHHC C SOHConc o 2 Ethane 42 170 . Ethanol 52 42   108. (b) 109. (a)  + H 110. (c) (a) 3 || 3 Oxidation 3 | 3 CH O CCHCH OH CHCH   (b) OHCHCHOHCHCH C SOH o 222 180 .Conc 23 42   (d) 22323 222 HONaCHCHNaOHCHCH  112. (b) Carbylamine reaction OHKClCNCHKOHNHCHCHCl 2 isocyanide Methyl 3 alc. 233 333   113. (a) Secondary alcohol on dehydrogenation gives acetone 23 || 3 300 3 | 3 0 HCH O CCHCH OH CHCH C Cu  114. (a) 3 || 3 ][ 3 | 3 CH O CCHCH OH HCCH O   118. (d) COOHCHCHOCHOOHHC 3352 ][  . 119. (a) + OH POCl 2 3    120. (c) (i)   2 2 CS Br + (ii)  )( 23 aq Br + 3HBr In aq. solution phenol ionize to give phenoxide in which highly activates benzene ring and give trisubstituted product while in presence of 2CS an inert solvent phenol is unable to ionize due to which benzene ring is slightly activated. Hence, monosubstituted product is obtained. 122. (d) Traces of water from ethanol is removed by reacting with Mg metal. 123. (a) alcoholAlly l 22 260 | Gly cerol 2 | | 2 OHCHCHCH OOHC COOH OHCH OHHC OHCH Co      125. (c) 126. (b) OHCHCH 3 pptI NaOH CHI Yellow 3 2   Iodoform test is given by compounds in which  OH CHCH | 3 or  O CHCH || 3 group is present. 127. (c) 23Br HBr3 1 mole 3 moles 1 mole 94 grams of phenol reacts with 480 gms. of 2Br . 2 gm. of phenol — 22.102 94 480  gms. 128. (b) 25252 222 HONaHCNaOHHC  130. (a) tionEsterifica 23333 OHCOOCHCHOHCHCOOHCH  131. (b) OHCH3 has highest boiling point because of hydrogen bonding. 132. (b) HC OHO OHO CH        HOHOHO OH Phenol O Phenoxide ion Salicylic acid OH COOH OH Phenol 56HCOOC OH Salol Phenyl salicylate OH Phenol Br Br OH Br 2, 4, 6-tribromophenol OH Phenol OH Br o- and p- bromophenol OH Br OHHOCHC 25252  Diethyl ether 32OAl Co250 32OAl Co250 OHHC 242  Ethene OHHC 52 1-phenyl ethanol OH Br OH Br 1248 Alcohol, Phenol and Ethers 209. (b) OHHC 52 (ethanol) is a very weak acid hence it does not react with NaOH. However it reacts with metallic sodium. 210. (b) Methanol has high boiling point than methyl thiol because there us intermolecular hydrogen bonding in methanol and no hydrogen bonding in methyl thiol. 211. (a) oxalate acidGlycerol |||| 2 2 | | 110 acidoxalic | Glycerol 2 2 | | OH O C O COCH OHCH HOHC COOH COOH OHCH OHCH HOHC C     emonoformatGlycerol || 2 2 | | 2 H O COCH OHCH HOHC CO     212. (a) Formation of a yellow precipitate on heating a compound with an alkaline solution of iodine is known as iodoform reaction. Methyl alcohol does not respond to this test. Iodoform test is exhibited by ethyl alcohol, acetaldehyde, acetone, methyl ketone and those alcohols which possess )(3 OHCHCH group. 213. (b) In friedal craft acylation, aromatic compounds such as benzene, phenol etc. undergo acylation with COClCH3 in the presence of anhydrous 3AlCl and gives ortho and para derivatives. Intermediate is OCCH  3 (acylium ion) of this reaction. In fact denotes friedel craft alkylation. 214. (a) This reaction is known as Reimer Tiemann reaction. 215. (a)   2 acidFormic 380 Glycerol 2 2 | | acidoxalic | COHCOOH OHCH OHCH HOHC COOH COOH K alcoholAlly l 2 2 || | 2 Dioxalin 2 2 || | Glycerol 2 2 | | acidoxalic | 2 CH OHCH HC OCOCH OHCH OCHOC OHCH OHCH HOHC COOH COOH CO    Thus at 530 K allyl alcohol is formed. 216. (c) deAcetaldehy 3 2 2 | 2 2 anh. CHOCH OHCH OHCH OH ZnCl    217. (d) Ethyl alcohol give positive iodoform test (i.e. yellow ppt. with 2I and NaOH)  NaOHIOHCHCH 64 223 OHCOONaCHNaICHI 23 ppt.yellow 3 35  218. (d) Tertiary alcohols react fastest with hydrogen halides 2 methyl propan-2-ol is a tertiary alcohol. 219. (a) When benzoic acid reacts with ethyl alcohol in the presence of sulphuric acid ethyl benzoate is formed. This is known as esterification.   42 alcoholEthyl 52 acidBenzoic 56 SOH OHHCCOOHHC water 2 oateEthyl benz 5256 OHHCOOCHC  220. (a)   3 3 3 omide br magnesiumPhenyl CH CH CH COHBrMgPh  OMgBrC CH CH CH HPh  3 3 3 221. (b) MgICHICHMg 3 ether Dry 3   222. (a) Ethyl alcohol on dehydration with conc. 42SOH at 170°C gives ethylene. OHCHCHOHCHCH SOH C 2 Ethylene 22 conc. 170 alcoholEthyl 23 42    223. (d)   nDehydratio butanol2 3 | 23 CH OH HCCHCH butene2 33 duct)(Major pro butene1 223 CHCHCHCHCHCHCHCH  224. (b) Fats are esters of higher fatty acids with glycerol, hence on alkaline hydrolysis they give back glycerol and sodium or potassium salt of acid (this is called soap). (Soap) 2 2 | | Fat 2 2 | | 33 RCOONa OHCH OHCH HOHCNaOH OCORCH OCORCH HOCORC  225. (c) 3 | 223 300 3 3 | | 3 0 CH OHCHCCHCH OH CH CCH C Cu  OH + CH3Cl and + CH3Cl OH Pheno l + CH3COCl    3AlCl OH o-acetyl phenol COCH3 + OH COCH3 p- acetyl phenol Acetyl chlorid e O– Na+ CHO  H OH Salicylaldehy de CHO OH Pheno l    NaOHCHCl aq.3 O– Na+ Intermediate CHCl2   NaOH Alcohol, Phenol and Ethers 1249 227. (c) OHOH O CCH OH OH OH CCH 2 || 33  If two or more OH groups are present on carbon atom then it immediately looses water molecule and forms acid or aldehyde. Two OH groups on the same carbon aldehyde is formed Aldehyde Unstable |2 O H CR OH OH CHR OH    Three OH groups on the same carbon acid is formed. acid 2 O OH CR OH OH OH CR OH    228. (d) 3242 , OAlSOH and 43POH all can act as dehydrating agent. 229. (b) iodideAlly l 2 2 | || 2 2 | |3 Gly cerol 2 2 | | 22 3 ICH CH HC ICH ICH IHCHI OHCH OHCH HOHC IOH                  230. (a) ndehydratio Conc. anolMethy l but 2 2 3 | 23 42   SOH OHCH CH HCCHCH uctMajor prod eneMethy l but-2 2 3 | 23 CH CH CCHCH  233. (c) 22233 32 CHCHOHCHCHCHOCH OAlCu    234. (b)   4 neAcetopheno 3 || 56 LiAlH CH O CHC alcohol2 3 || 56 o CH O CHHC  235. (d) OHHCOHHC C SOHConc o 242 170 52 42   236. (b) Because conc. H3PO4 acts as a dehydrating agent. 238. (c) 352 2 CHIOHHC I NaOH   yellow ppt. 2 3 I NaOH OHCH   No reaction 239. (d) It is not acetaldehyde or acetone as does not react with hydrazine. It is not OHCH 3 as does not react with Na. 240. (a) The ether molecule gets protonated by the hydrogen of the acid to form protonated ether or oxonium salt. HBr  Br The protonated ether undergoes nucleophilic attack by halide ion )( X and forms alkyl alcohol and alkyl halide 241. (a) chloridebuty l 3 | | 3 3 . alcoholbuty l 3 | | 3 3 2    t ZnCl HClconc t CH ClCCH CH CH OHCCH CH 242. (a) HClN  2 OH   base NN  OH This is an example of coupling reaction 243. (b) Reimer-Tiemann reaction involves the carbon carbon bond formation.   KNaOH CHCl 340, 3 NaCl HCldil    . 244. (a) This is Reimer-Tiemann reaction where the electrophile is dichlorocarbene )(: 2CCl generated from chloroform by the action of a base. 3CHClOH  ⇌ 22 :: CClClCClHOH   245. (a) Phenols are much more acidic than alcohols but less so than carboxylic acids or even carbonic acid. This is indicated by the values of ionisation constants. The relative acidity follows the order: ROHHOHOHHCCOHRCOOH Ka 1814 56 10 32 75 1010101010   OH + H2O   43. POHConc CH3 OCH3 CH3 O CH3 H Protonated ether +: H3C O CH3 H + +Br–  transition state H3C O CH3 .... Br H + H3C OH +CH3Br  p-hydroxy azobenzene (orange dye) OH OH CHO OH CHO salicylaldehyde 1250 Alcohol, Phenol and Ethers Uses of alcohol, Phenol and Ethers 1. (a) Dynamite dinitrateGlyceryl trinitrateGlycerylGlycerol Kieselguhr onAbsorbed3      HNO 3. (d) COOHCHOHHC 3 air racetiiAcetobacto52   4. (b) Aspirin or Acetyl salicylic acid. 6. (a) n (HOOC COOH ) + glycolEthy lene 2 2 |               OHCH OHCH n     C O || Polyster 22 || n OCHCHOC O       9. (a) Ethylene glycol is added to lowering down the freezing point of water so that it does not freeze. 10. (b) Power alcohol 80% petrol and 20% ethyl alcohol 12. (d) 252 yeast)(From Zymase 22Glucose COOHHC   16. (d) Glycerol is not used as an antiseptic agent. 18. (c) Denaturing can also be done by adding 0.5% pyridine, petroleum naptha, 4CuSO etc. 20. (b) A mixture of glyceryl trinitrate and glyceryl dinitrate when absorbed on kieselgurh is called dynamite. 22. (c) Tonics have generally contains ethyl alcohol. 23. (c) Due to presence of methyl alcohol in liquor. 24. (d) An anaesthetic. 25. (c) Groundnut oil. 27. (a) alcoholButyl 273 / butyrateEthyl 5273 52 OHCHHCHCOOCHC OHHCNa   28. (a) Glycol is used as an antifreeze for automobile radiators because it lowers down the melting point of water. Critical Thinking Questions 1. (c) or will undergoes a Friedel Craft’s alkylation on ortho or para position because of more electron density. 2. (c)   HOH RCH OMgI HCRMgICHCH 22 | 22 OHCHCHROHMgI  22)( 3. (c) The liquids which decompose at its boiling point can be purified by vacuum distillation. Glycerol which decomposes at its boiling point (–563K) can be distilled without decomposition at 453K under 12mm Hg pressure. 4. (a) Liebermann’s reaction. 5. (a) o1 alcohol o2 alcohol o3 alcohol Boiling point of alcohols decreases as the number of branches increases. 6. (c) ICHHI 3 7. (c)  OHKMnOCHCH 2422 423 KOHKMnO OHCH OHCH 223 2 Glycol | 2 2    8. (c) Correct order of dehydration in alcohols 3° > 2° > 1°. 9. (a) Oxiran is ethylene oxide, O CHCH 22  10. (c)   22 62236 OH HBCHCHCH OHCHCHCH 223  11. (d) Distinction between primary, secondary and tertiary alcohol is done by all three methods : oxidation, Victormeyer and Lucas test. 12. (b) 52 2 air, OV O   13. (a) o- and p-nitrophenols are separated by steam distillation because o-nitrophenol is steam volatile while p-isomer is not. 14. (b) Benzoic acid. 15. (a)   light/2' O ROR OHOCHCHOHC  )( 352 16. (d) 33 )( 33 42 OCHCHOHCHOHCH ConcSOH   523 )( 523 42 HOCCHOHHCOHCH ConcSOH   5252 )( 5252 42 HOCHCOHHCOHHC ConcSOH   17. (b) IV > III > I > II. 18. (a) Cyclic ethers are called epoxides. O CHCH 22  19. (b) CHCHCH 3   HBr 3OCOCH COOH Terephthallic acid OH O-CH3 OH OH CH2CH3 OH OH