MCQ ON ALCOHOL,PHENAOL & ETHER

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 The product ‘A’ in the following reaction is [MP PMT 2003] (a) (b) (c) (d) Glycerol boils at 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 Phenol Name of the above reaction is [KCET 2003] (a) Liebermann’s reaction (b) Phthalein fusion test (c) Reimer-Tiemann reaction (d) Schottenf-Baumann reaction The correct order of boiling point for primary secondary and tertiary alcohols is [CPMT 1999; RPMT 2002] (a) (b) (c) (d) 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 Ethylene reacts with Baeyer's reagent to give [CPMT 1988] (a) Ethane (b) Ethyl alcohol (c) Ethylene glycol (d) None of these 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 Oxiran is (a) Ethylene oxide (b) Diethyl ether (c) Ethyl glycolate (d) Glycolic ester Propan-1-ol can be prepared from propene by alcohol [AIIMS 2003] (a) (b) followed by (c) followed by (d) 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 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 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 Which of the following does not form phenol or phenoxide [AFMC 2000] (a) (b) (c) (d) Which of the following will be obtained by keeping ether in contact with air for a long time [RPMT 2003] (a) (b) (c) (d) When a mixture of ethanol and methanol is heated in the presence of concentrated the resulting organic product or products is/are [Manipal MEE 1995] (a) (b) and (c) and (d) and In the following groups 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 Epoxides are (a) Cyclic ethers (b) Not ethers (c) Aryl-alkyl ethers (d) Ethers with another functional group The reaction of with HBr gives [IIT-JEE 1998] (a) (b) (c) (d) Which of the following compounds on boiling with (alk.) and subsequent acidification will not give benzoic acid [KCET 2001] (a) Benzyl alcohol (b) Acetophenone (c) Anisole (d) Toluene 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 When alcohol reacts with concentrated intermediate compound formed is [AFMC 2005] (a) Carbonium ion (b) Alkoxy ion (c) Alkyl hydrogen sulphate (d) None of these Here, D is [BVP 2004] (a) (b) (c) (d) Phenol is more acidic than [Pb. CET 2003] (a) (b) (c) (d) Both (a) and (c) In the reaction, product (A) is [Pb. CET 2000] (a) Acetaldehyde (b) Cinnamic acid (c) (-nephthol (d) Phenol The correct order of ease of dehydration of following is [CPMT 2004] (a) I > II > III (b) III > II > I (c) I > III > II (d) III > I > II reacts with a compound containing [Pb. CET 2002] (a) group (b) – OH group (c) group (d) – NO group Cumene process is the most important commercial method for the manufacture of phenol. Cumene is [KCET 2004] (a) 1-methyl ethyl benzene (b) Ethyl benzene (c) Vinyl benzene (d) Propyl benzene The compound X in the reaction [Roorkee 1999] is (a) (b) (c) (d) Reaction is called [MP PET 2003] (a) Lederer Manasse reaction (b) Claisen condensation (c) Benzoin condensation (d) Etard reaction When phenol is reacted withand followed by acidification, salicyldehyde is obtained. Which of the following species are involved in the above mentioned reaction as inter mediate [DCE 2000] (a) (b) (c) (d) All of these The order of solubility of alkanols in water is (a) Propanol < Butanol > Pentanol (b) Propanol > Butanol > Pentanol (c) Propanol > Butanol < Pentanol (d) Propanol = Butanol = Pentanol In the following compounds The order of acidity is [IIT-JEE 1996] (a) (b) (c) (d) Butanal with dilute NaOH gives [UPSEAT 2000] (a) (b) (c) (d) The correct order of the solubility of the different alcohols in water is [Pune CET 1998] (a) n-propyl alcohol > ethyl alcohol > n-butyl alcohol (b) Ethyl alcohol > n-butyl alcohol > n-propyl alcohol (c) n-butyl alcohol > n-propyl alcohol > ethyl alcohol (d) Ethanol > n-propanol > n-butyl alcohol Which one of the following will most readily be dehydrated in acidic condition [IIT-JEE (Screening) 2000] (a) (b) (c) (d) Which of the following compounds will be most easily attacked by an electrophile [CBSE PMT 1998, 99] (a) (b) (c) (d) Fittig's reaction produces (a) Alkane (b) Alcohol (c) Diphenyl (d) Diethyl ether p-cresol reacts with chloroform in alkaline medium to give the compound A which adds hydrogen cyanide to form, the compound B. The latter on acidic hydrolysis gives chiral carboxylic acid. The structure of the carboxylic acid is [AIEEE 2005] (a) (b) (c) (d) 1. (c) or will undergoes a Friedel Craft’s alkylation on ortho or para position because of more electron density. 2. (c) 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) alcohol alcohol alcohol Boiling point of alcohols decreases as the number of branches increases. 6. (c) 7. (c) 8. (c) Correct order of dehydration in alcohols 3° > 2° > 1°. 9. (a) Oxiran is ethylene oxide, 10. (c) 11. (d) Distinction between primary, secondary and tertiary alcohol is done by all three methods : oxidation, Victormeyer and Lucas test. 12. (b) 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) 16. (d) 17. (b) IV > III > I > II. 18. (a) Cyclic ethers are called epoxides. 19. (b) 20. (c) on oxidation does not give benzoic acid. 21. (c) Chromic anhydride in glacial acetic acid is the best reagent to convert pen-3-en-2-ol into pent-3-in-2-one. 22. (a) In all cases intermediate is carbonium ion, and there may be 1, 2-hydride or 1, 2-methyl shift to form more stable carbonium ion. 23. (c) The reaction sequence is as follows 24. (d) Methoxy group due to +I effect increase electron density on OH – group, thus making it less acidic. Thus o-methoxy phenol and acetylene are less acidic than phenol, p-nitrophenol is more acidic than phenol 25. (b) Perkin reaction is the condensation reaction in which an aromatic aldehyde is heated with an aromatic aldehyde is heated with an anhydride of an aliphatic acid in presence of sodium salt of same acid to form (, ( unsaturated acid. 26. (b) The correct order of stability of carbocation is as follows 27. (b) is used in organic chemistry to replace the –OH group by –Cl and carbonylic oxygen by . 28. (a) 29. (b) + It is Kolbe’s reaction. 30. (a) It is Lederer Manasse reaction. 31. (b) 32. (b) Propanol > Butanol> Pentanol The solubility of alcohols in water decreases as the molecular mass increases. As the size of alkyl group increases, hydrophobic character increases, Hence solubility decreases. 33. (d) IV > III > I > II. group is electron withdrawing group while group is electron releasing group. 34. (d) 35. (d) Ethanol > n-propanol > n-butyl alcohol Solubility of alcohols in water decreases as the size of alkyl group increases because tendency to form hydrogen bonding decreases. 36. (a) Aldols ((-hydroxy aldehydes or (-hydroxy ketones) readily undergo dehydration to form (, (-unsaturated aldehydes or ketones. 37. (c) Phenol is most easily attacked by an electrophile because presence of –OH group increases electron density at o- and p- positions. 38. (c) 39. (b) ALCOHOL , PHENOL & ETHER Mrs. SHALLU JINDAL AGGARWAL (M): 9878608983 Mrs. SHALLU JINDAL AGGARWAL : (M)9878608983 OH (IV) OH NO2 (III) OH (II) OH CH3 (I) OH H O O H O OCOONa COOH ONa COONa ONa COONa + CO2X COOH OH ONa OH III OH II OH I OCH3 OH OH NO2 carbonium ion OH OH OH O-CH3 OH 4 OH 3 COOH 2 CH2CH3 1 CH3 OH O OH O OH OH Cl CH3 OH OH CH3 CH(OH)COOH OH CH3 CH(OH)COOH OH CH3 CH2COOH OH CH3 CH2COOH OH III OH II OH I CH O – OH | C – (CH3)2 CH3 CH3 Cumene or 1, methyl ethyl benzene CH + CH3 CH3 CO Phenol Acetone ONa COOH ONa COOH OH O OH O H H OH2 + H+ –H+, –H2O O (-Hydroxy ketone OH CH3 O CH3 CHCl2 ( O CH3 CHO ( A OH CH3 CH(OH)COOH OH CH3 CH(OH)CN