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1 221 ALCOHAL PHENOLS AND ETHERS 1. Which one is formed when sodium phenoxide is heated with ethyl iodide? [1988] Phenetole Ethyl phenyl alcohol Phenol None of these Ans: 2. Lucas reagent is [1988] Conc. HCl and anhydrous ZnCl2 Conc. HNO3 and hydrous ZnCl2 Conc. HCl and hydrous ZnCl2 Conc. HNO3 and anhydrous ZnCl2 Ans: 3. The compound which reacts fastest with Lucas reagent at room temperature is [1989] Butan-1-ol Butan-2-ol 2-Methyl propan-1-ol 2-Methylpropan-2-ol 4. Which one of the following compounds will be most readily attacked by an electrophile? [1989] Chlorobenzene Benzene Phenol Toluene 5. Propene, CH3CHCH2 can be converted into 1- propanol by oxidation. Indicate which set of reagents amongst the following is ideal to effect the above conversion? [1989] KMnO4 (alkaline) Osmium tetraoxide (OsO4 /CH2Cl2) B6H6 and alk. H2O2 O3 /Zn 6. When phenol is heated with CHCl3 and alcoholic KOH when salicyl adehyde is produced. This reaction is known as [1988, 89] Rosenmund s reaction Reimer-Tiemann reaction Friedel-Crafts reaction Sommelet reaction 7. How many isomers of C5H11 OH will be primary alcohols? [1992] Methanol is industrially prepared by [1992] Oxidation of CH4 by steam at 900 C Reduction of HCHOusing LiAIH4 Reaction HCHOwith a solution of NaOH Reduction of COusing H2 and ZnO Cr2O3. 9. HBr reacts fastest with [1992] 2-Mehtylpropan-1-ol 2-Methylpropene-2-ol propan-2-ol propan-1-ol. 10. When phenol is treated with excess bromine water. It gives [1992] m-bromophenol o-and p-bromophenols 2,4-Dibromophenol 2,4, 6-Tribomophenol. 11. Ethanol and dimethyl ether form a pair of functional isomers. The boiling point of ethanol is higher than that of dimethyl ether, due to the presence of [1993] H-bonding in ethanol H-bonding in dimethyl ether CH3 group in ethanol CH3 group in dimethyl ether Ans: 12. Increasing order of acid strength among p- methoxyphenol, p-methylphenol and p- nitrophenol is [1993] p-nitrophenol, p-methoxyphenol, p- Methylphenol p-methylphenol, p-methoxyphenol, p- Nitrophenol p-nitrophenol, p-methylphenol, p- Methoxyphenol. p-methoxyphenol, p-methylphenol, p- Nitrophenol

2 Which one of the following on oxidation gives a ketone? [1993] Primary alcohol secondary alcohol tertiary alcohol All of these 14. What is formed when a primary alcohol undergoes catalytic dehydrogenation? [1993] Aldehyde Ketone Alkene Acid Ans: 15. The stablest among the following is [1994] CH3CH(OH) 2 ClCH2CH(OH) 2 (CH3) 2 C(OH) 2 CCl3 CH(OH) Phenylethanol can be prepared by the reaction of benzaldehyde with [1997] ethyl iodide and magnesium methyl iodide and magnesium methyl bromide and aluminium bromide methyl bromide 17. [1998] RCHOHR RCHOHCH3 RCH2CH2OH CHCHOH2 18. The ionization constant of phenol is higher than that of ethanol because: [2000] phenoxide ion is bulkier than thoxide phenoxide ion is stronger base than ethoxide phenoxide ion is stabilized through delocalization phenoxide ion is less stable than ethoxide 19. Propan - 1- ol may be prepared by the reaction of propene with [2000] 20. Which of the following is correct? [2001] On reduction of any aldehyde, secondary alcohol is formed Reaction of vegetable oil with H 2 SO4 gives glycerine Sucrose on reaction with NaCl gives invert sugar Alcoholic iodine gives iodoform with NaOH 21. n-propyl alcohol and isopropyl alcohol can be chemically distinguished by which reagent? [2002] PCl5 Reduction Oxidation with potassium dichromate Ozonolysis 22. When phenol is treated with CHCl3 and NaOH, the product formed is [2002] Benzaldehyde Salicylaldehyde Salicylic acid Benzoic acid 23. Which of the following will not form a yellow precipitate on heating with an alkaline solution of iodine? [2004] CH3CH(OH) CH3 CH3CH2CH(OH) CH3 CH3OH CH3CH2OH 24. The major organic product in the reaction, CH3 O CH(CH3) 2 + HI Product is [2006] ICH2OCH(CH3) 2 CH3OC(CH3) 2 CH3I+ (CH3) 2CHOH CH3OH+ (CH3) 2CHI 25. Ethylene oxide when treated with Grignard reagent yields [2006] tertiary alcohol cyclopropyl alcohol

3 223 primary alcohol secondary alcohol [2009] benzaldehyde benzoic acid benzene toluene 30. Which one of the following compounds has the most acidic nature? [2010] 27. [2009] CH3CH2 O CH2 CH3 CH3 CH2 O SO3H CH3CH2OH CH2 = CH2 28. H2COH CH2OH on heating with periodic acid gives: [2009] 31. Among the following four compounds phenol (ii) methylphenol (iii) meta-nitrophenol (iv) para-nitrophenol the acidity order is: [2010] ii > i > iii > iv iv > iii > i > ii iii > iv > i > ii i > iv > iii > ii 32. When glycerol is treated with excess of HI, it produces: [2010] glycerol triiodide 2 iodopropane

4 224 allyl iodide propene 33. [2012] Acetone Methane Acetaldehyde Ethyl alcohol 34. Which of the following compounds can be used as antifreeze in automobile radiators? [2012 M] Methyl alcohol Glycol Nitrophenol Ethyl alcohol 35. Among the following ethers, which one will produce methyl alcohol on treatment with hot concentrated HI? [NEET2013] Phenol is distilled with Zn dust followed by Friedel Crafts alkylation with propyl chloride in the presence of AlCl3 to give a compound. is oxidised in the presence of air to form the compound. The structural formula of is [NEETKar. 2013] 4. 5.

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1. The compound which reacts fastest with Lucas reagent at room temperature is

1. The compound which reacts fastest with Lucas reagent at room temperature is 1. The compound which reacts fastest with Lucas reagent at room temperature is (a) butan-1-ol (b) butan-2-ol (c) 2-methylpropan-1-ol (d) 2-methylpropan-2-ol 2. Chlorination of toluene in the presence of

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