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ETHERS, , JEE-MAIN-SR-CHEM-VOL-III, , 10. The IUPAC name of C2 H 5 − O − CH (CH 3 )2 15. Among the following compounds, the one, which does not react with sodium is, 1) Ethoxy propane, 2) 1,1-dimethyl ether, 1) CH3CHOHCH3, 2) CH 3OCH 3, 3) 2-Ethoxy isopropane 4) 2-Ethoxy propane, 11. ‘A’ reacts with C2H5I giving ‘B’ and NaI. Here, 3) CH 3COOH, 4) C2 H 5OH, ‘A’ and ‘B’ respectively are, 16. Which of the following halogen acids is most, 1) CH 3COONa, CH 3OCH 3, reactive towards the given reaction ?, 2) C2 H 5OC2 H 5 , C2 H 5COOC2 H 5, 3) C2 H 5ONa, C2 H 5OC2 H 5, 4) C2 H 5OH , C2 H 5OC2 H 5, 12. Which of the following compounds when, heated with CO at 1500C and 500 atm. pressure in presence of BF3, forms ethyl propionate ?, 1) C2 H 5OH, , 2) CH 3OCH 3, , HX, R − O − R →, 1) HCl 2) HI 3) HBr 4) Equally reactive, 17. Which of the following compounds is produced when this reaction takes place ?, , CH 3, |, HI, H 3C − C − O − CH 3 →, cold, |, CH 3, , H, |, 2) H − C − OH, |, 1) 1 Mole of C2 H 5 I and 1 mole of C2 H 5OH, H, 2) 2 Moles of iodoethane, 3) Both of these, 4) None of these, 3) 2 Moles of ethanol, 18. Alcohols can be distinguished from ethers by, 4) Iodoethane and ethanol but not in a 1:1 mole, 1) Sodium metal, 2) Ester formation, ratio, 3) Iodoform test, 4) All the above, 14. The major product obtained on the, Dry Ag 2O, HCl, , → X , → Y The, 19. CH 3CH = CH 2 , Heat, monobromination (with Br2 / FeBr3 ) of the, product Y in the above sequence is, following compound is, 1) Di isopropyl ether, 2) Di n - propyl ether, , 3) C2 H 5OC2 H 5, 4) CH 3OC2 H 5, 13. One mole of diethyl ether on heating with, conc.HI gives, , CH3, |, 1) H3C − C − OH, |, CH3, , 3) 2 - Propanol, 4) 1, 2 - Epoxypropane, 20. A mixture of ether and ......... gives temperature as low as 163 K, 1) NaCl, , 80, , 1), , 2), , 3), , 4), , 2) Ice 3) Solid CO2 4) C2 H 5OH, , 1) Both A and R are true and R is the correct, explanation to A, 2) Both A and R are true and R is not the correct, explanation to A, 3) A is true but R is false, 4) A is false but R is true, 21. Assertion (A) : Ethers behave as Lewis base, in the presence of mineral acids., Reason (R) : Oxygen atom in ether is having, lone pair electrons., 22. Assertion (A) : Diethyl ether is used as general, anaesthesia., Reason (R) : Diethyl ether produces, unconsciousness without effecting lungs., NARAYANAGROUP

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ETHERS, , JEE-MAIN-SR-CHEM-VOL-III, 23. Assertion (A): Ethers are relatively inert, when compared to C2 H 5OH, Reason (R): The hybridization of C and O in, CH 3 − O − CH 3 is SP3, 24. Assertion(A): Diethyl ether reacts with hot, Conc H 2 SO4 and gives ethyl hydrogen, sulphate, Reason (R) : The reaction involves cleavage, of C-O bond in diethyl ether., 25. Assertion (A): Ethers behave as base in, presence of mineral acids, Reason (R): Oxygen atom in ether is having, lonepair, 26. Assertion (A): Alkyl aryl ethers on reacton with, HI give alkyl iodide, phenols, Reason (R): Aryl - oxygen bond is weaker than, alkyl oxygen bond., , LEVEL-I (C.W) - KEY, 1) 1, 8) 3, 15) 2, 22) 1, , 2) 2, 9) 2, 16) 2, 23) 2, , 3) 2, 10) 4, 17) 2, 24) 1, , 4) 2, 11) 3, 18) 4, 25) 1, , 5) 3 6) 4 7) 4, 12) 3 13) 2 14) 4, 19) 1 20) 3 21) 1, 26) 1, , 14. Methoxy group is strong ring activating group, the methyl group, 15. Due to absence of acidic hydrogen ether has no, reaction with sodium metal., 16. Order of reactivity HI > HBr > HCl, 17. Reaction proceeds by SN1 mechanism, 19. X = CH 3 − CH − CH 3 ;, |, Cl, , 20. Acts as freezing mixture, , LEVEL-I (H.W), NOMENCLATURE, 1., 2., 3., , 4., , LEVEL-I (C.W) - HINTS, , Alcohols and ethers are functional group 5., isomers., CH 2 − CH 2 − O − CH 2 − CH 3 ,, , 1., 2., , CH 3 − O − CH 2 − CH 2 − CH 3 and, , CH 3 − O − CH (CH 3 )2, 3., , CH 3 − CH 2 − O − CH 2 − CH 3 is ethoxy ethane, , 4., , NaOH, C6 H 5OH , → C6 H 5 − O − C2 H 5, C2 H 5Cl, , 5., , 2 RX + Ag 2O → ROR + 2 AgX, , 6., 7., , ( ), C2 H 5 − O − C2 H 5 →, C2 H 5 − O − O − C2 H 5, , In ethers H-bond is absent, , 8., , C2 H 5 − O − O − C2 H 5, , 9., 10., 11., 12., 13., , 2C2 H 5OH , conc.H 2 SO4 ,1400 C, Nomenclature, , .., , .., , .., , C2 H 5ONa, C2 H 5OC2 H 5, chemical reactions of ether, C 2 H 5 − O − C 2 H 5 + 2HI→ 2C 2 H 5 I + H 2 O, , NARAYANAGROUP, , The following represents ether, 1) (RCO)2 O 2) RCOOR 3) RCOR 4) ROR, The dialkyl derivative of H2O is, 1) Alcohol 2) Ether 3) Ester, 4) Ketone, Which of the following is a simple ether?, 2) CH3OC2H5, 1) CH3 OCH3, 3) CH3CH2OCH(CH3)2 4) C2H5OC3H7, Ethers are isomeric with, 1) Aldehydes, 2) Acids, 3) Alcohols, 4) Ketones, CnH2n+2O is the general formula of ethers. To, exhibit the functional group isomerism 'n', must be minimum, 1) 1, 2) 2, 3) 3, 4) 4, , PREPARATION METHODS, 6., , 7., , O, , .., , Y = CH 3 − CH − O − CH − CH 3, |, |, CH 3, CH 3, , 8., , Heating together sodium ethoxide and ethyl, chloride will give, 1) ether, 2) ethyl alcohol, 3) acetaldehyde, 4) acetic acid, Williamsons synthesis is used to prepare, 1) Diethyl ether, 2) PVC, 3) Bakelite, 4) Ethyl alcohol, Which of the following is not an isomer of diethyl ether ?, 1) 2-methyl - 2- propanol 2) 2-Methoxypropane, 3) 2-Methyl-1-propanol 4) Ethoxyethane, , PROPERTIES AND USES OF ETHERS, 9., , The compound in which hydrogen bonding, is not possible is, 1) C6 H 5OCH 3, 3) H2O, , 2) CH3CH2OH, 4) CH3COOH, 81

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ETHERS, 10. Diethyl ether is used as, 1) Anaesthetic 2) Solvent 3) Refrigerant 4) All, 11. The safest general anaesthesia used at present, is, 1) chloroform, 2)diethyl ether, 3) acetylene, 4) halothane, 12. Formula of halothane is, 1) CF2Cl2, 2) CF3Cl, 4) (C2F4)n, 3) CF3-CHClBr, 13. The IUPAC name of an unsymmetrical ether, with the molecular formula C4 H10O, 1) Ethoxypropane, 2) Methoxyethane, 3) Ethoxyethane, 4) Methoxypropane, 14. Consider the following reaction, ∆, C2 H 5 I , → (Pleasant smelling liquid), X is, X, 1) Sodium, 2) Dry silver oxide, 3) Ethyl chloride, 4) Dry silver powder, ∆, HI , 15. C2 H 5 − O − C2 H 5 + excess, ( hot )→ X + Y , here, X and Y are, 1) C2 H 5 I and C2 H 5OH 2) C2 H 5 I and H 2O, , JEE-MAIN-SR-CHEM-VOL-III, 10., 11., 12., 13., 14., 15., , All are uses of diethyl ether., Halothane does not cause side effects., CF3CHClBr, methoxypropane, Dry silver oxide, C2 H 5 I and H 2O, , 5OC2 H 5, 16. C6 H 5ONa + C2 H 5 I → C6 HPhenetole, 17. Alkoxy group is ortho, para directing group, , LEVEL-II (C.W), METHODS OF PREPARATION, 1., , 2., , Which of the following pairs of reagents will, not form ether, 1) C2H5Br + C2H5ONa 2) C2H5Br + CH3ONa, 3) CH3Br + C2H5ONa 4) C2H5Br + HCOONa, What is Y in the following reactions, C2 H 5 I + NaOC2 H 5 → X + NaI, , X + 2 HI → 2Y + H 2O, , 3) C2 H 5OH + H 2O, 4) C2 H 4 + H 2O, 16. Which one of these is formed on heating so- 3., dium phenoxide with ethyl iodide ?, 1) Phenetole, 2) Ethyl phenyl alcohol, 3) Phenone, 4) None of these, 17. Anisole with conc. HNO3 and conc. H 2 SO4 4., gives, 1) Phenol, 2) Nitrobenzene, 3) O- and - P-Nitroanisole 4) O- Nitroanisole, 18. Oxygen atom in ether is, 1) Very active, 2) Replaceable, 5., 3) Active, 4) Relatively inert, , 1) C2 H 6 2) C2 H 5 I 3) C2 H 4 4) C2 H 5OC2 H 5, Which of the following cannot be prepared, by using Williamson synthesis ?, 1) Methoxybenzene 2) Benzyl-p-nitrophenol ether, 3) Methyl tert-butyl ether 4) Ditertiary butyl ether, , Methoxy benzene is called anisole., , How many more structures can be, drawn for the same formula ?, 1) 5, 2) 4, 3) 3, 4) 2, Which of the following types of ethers cannot be synthesized by Williamson synthesis?, , LEVEL-I (H.W) - KEY, 1) 4 2) 2 3) 1 4) 3 5) 2 6) 1 7)1, 8) 4 9) 1 10) 4 11) 4 12) 3 13) 4 14) 2, 15) 2 16) 1 17) 3 18) 4, , LEVEL-I (H.W) - HINTS, 1., 2., 3., 4., 5., 6., 7., 9., 82, , General formula is R-O-R, R-O-R is ether, Same type of alkyl groups are attached to, oxygen atom., Alcohols are isomeric with ethers, Two, C2 H 5Cl + C2 H 5ONa → C2 H 5OC2 H 5 + NaCl, , Ethers, In ethers H-bond is absent, , 1), , 6., , CH 3, CH 3, |, |, H 3C − C −− O −−C −− CH 3, |, |, CH 3, CH 3, , 2), , CH 3, CH 3, |, |, H 3C − C −− O −−C −− H, |, |, CH 3, CH 3, , 3) C6 H 5 − O − C6 H 5, 4) None of these, Which alkyl halide would be preferred for, the synthesis of the following ether by, Williamson synthesis ?, CH 3, |, H5C2 − O − C − H, |, CH 3, , 1) n-Propyl chloride, 3) Ethyl chloride, , 2) Isopropyl chloride, 4) Methyl chloride, NARAYANAGROUP

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ETHERS, , JEE-MAIN-SR-CHEM-VOL-III, , PROPERTIES AND USES OF ETHERS, 7., 8., , Which of the following does not react with, diethyl ether, 3) BF3, 4) HCl, 1) C2H5ONa 2) AlCl3, C − O − C bond in ethers can be cleaved by, 1) KMnO4 2) LiAlH 4 3) KOH 4) HI, , LEVEL-II (C.W) - HINTS, 1., , C2 H 5 Br + HCOONa, , 2., 3., 5., 6., 7., 8., 9., 10., 11., 12., 13., 14., , ∆, → 2C2 H 5 I + H 2O, (C2 H 5 )2 O + 2 HI , , HI, → X +Y ., A + B → CH 3 − O − C (CH 3 )2 , Correct statement among the following is, 1) A and B are CH3ONa and (CH3)3CBr, 2) X and Y are CH3I and (CH3)3COH, 3) X and Y are CH3OH and (CH3)3CI, 4) A and B are CH3OH and (CH3)3COH, HI, 10. P + Q → Anisole , → R + S., Correct statement among the following is, 1) P and Q are C6H5ONa and C2H5Cl, 2) R and S are C6H5I and CH3OH, 3) R and S are C6H5OH and CH3I, 4) P and Q are C6H5Cl and CH3ONa, + HI, → (CH 3 )3 CI + CH 3OH, 11. (CH 3 )3 COCH 3 , 1., It follows which mechanism ?, 2) SN2, 3) E1, 4) E2, 1) SN1, 12. Which of the following reagents can distinguish ethyl methyl ether from isopropyl al2., cohol ?, 2) AgNO3 / NH 4+ OH −, 1) Br2CCl4, , 9., , 3) I 2 and NaOH, 4) CuCl / NH 4+ OH −, 13. Which of the following compounds is produced with this reaction takes place ?, HI, C6 H5 − O − CH 2C6 H5 →, cold, , 3., 1), , 2), , 4., 3) Both of these, 4) None of these, 14. Which of the following compounds is produced when this reaction takes place ?, , Tertiary alkyl halides do not gives ethers., Williamson’s synthesis follows SN2 mechanism, Williamson’s synthesis follows SN2 mechanism, C2 H 5ONa, , HI, X and Y are CH3OH and (CH3)3CI, R and S are C6H5OH and CH3I, SN 1, Ethers do not gives Iodo form test, Phenoxide ion is stabilized by resonance, Nucleophile attacks on less hindered carbon, , LEVEL-II (H.W), METHODS OF PREPARATION, The reaction, sodium alkoxide + alkyl halide, → ether is called, 1) Wurtz reaction, 2) Kolbe’s reaction, 3) Williamson’s synthesis 4) Perkin’s reaction, In which of the following reactions, the, product is an ether?, 1) C6 H 6 + CH3COCl / anhydrous AlCl3, 2) C2 H5Cl + aq.KOH, 3) C6 H 6 + C6 H5COCl / anhydrousAlCl3, 4) C2 H5Cl + C2 H5ONa, Williamson’s synthesis is an example of, 1) Nucleophillic addition, 2) Electrophillic addition, 3) Electrophillic substitution, 4) Nucleophillic substitution reaction, Ethoxy benzene is called PHENETOLE., , How many more ethers can be, , HI, CH 3 − CH − OCH 3 →, cold, |, CH 3, , drawn for the same formula ?, 1) 5, , 2) 4, , 3) 3, , 4) 2, , CH3, |, 1), CH3 − CH − OH, , 2) CH 3 − OH, , PROPERTIES AND USES OF ETHERS, , 3) Both of these, , 4) None of these, , 5., , LEVEL-II (C.W) - KEY, 1) 4, 8) 4, , 2) 2, 9) 3, , 3) 4 4) 2 5) 4 6) 3 7) 1, 10) 3 11) 1 12) 3 13) 2 14) 1, , NARAYANAGROUP, , 6., , Diethyl ether reacts with cold. HI to give, 1) Ethyl iodide, 2) Ethyl alcohol, 3) Both 1 and 2, 4) Ethylene, Hybridisation of oxygen in diethyl ether is, 1) sp, 2) sp 2, 3) sp3, 4) sp 3 d, 83

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ETHERS, 7., , JEE-MAIN-SR-CHEM-VOL-III, , In the reaction, , heat, → the, (CH3 )3 C − O − CH 2CH3 + (1HI, mole), , LEVEL-III, 1., , product(s) formed is (are), 1) (CH3 )3 C − OH and CH 3CH 2 I, 2) (CH3 )3 C − I and CH3CH 2OH, 3) (CH3 )3 C − I and CH 3CH 2 I, 4) C ( H3C )3 − O + − CH 2CH3I−, , 2., , |, H, , 8., , HI, →, CH 3 − CH − OCH 3 , excess, ∆, |, CH 3, , 3., Which of the following is not formed in the, above reaction ?, 1) Methyl iodide, 2) Isopropyl iodide, 3) Isopropyl alcohol, 4) All of these, 4., HI, 9. C6 H 5 − O − CH 2 CH 3 , → which of the following is not formed in this reaction ?, 2) C6 H 5 − OH, 1) C6 H 5 − I, 3) Both of these, 4) None of these, 5., 10. Ethyl phenyl ether on reaction with excess, HI yields, 1) Ethyl iodide and iodobenzene, 2) Ethyl iodide and phenol, 3) Ethyl alcohol and phenol, 4) Ethyl alcohol and iodobezene, 6., , LEVEL-II (H.W) - KEY, 1) 3, 8) 3, , 2) 4, 9) 1, , 3) 4 4) 2, 10) 2, , 5) 3, , 6) 3, , 7) 2, 7., , LEVEL-II (H.W) - HINTS, 1., 2., 3., 5., 6., 7., 8., , Williamson’s synthesis, , (C2 H 5 )2 O + HI → C2 H 5 I + C2 H 5OH, sp hybridisation, Nucleophile attacks on tertiary carbonium ion, 8., which proceeds by SN1 mechanism, , CH 3 − CH − I, |, CH 3, , HI, 9. C6 H 5 − O − C6 H 5 , → C6 H 5OH + C 2 H 5 I, 10. In phenol C - O bond not cleaved by HI, 84, , Al2 O3, , → C. Then ‘C’ is, 3600 C, , 1) Ethyne, 2) Ethene, 3) Ethoxy ethane, 4) Ethyl alcohol, In the sequence of reactions (A) is :, 2 5, (A) → (B) , → (C) , → C2H5I, , Na, , C H I / heat, , HI / heat, , 1) Acetic acid, 2) Methyl alcohol, 3) Ethyl alcohol, 4) Propionic acid, HBr reacts with CH 2 = CH − OCH 3 under, anhydrous conditions at room temperature, to give, 1) H 3C − CHBr − OCH 3 2) CH 3CHO and CH 3 Br, 3) BrCH 2 CHO and CH 3OH 4) BrCH 2 − CH 2 − OCH 3, The major product obtained when tert-butyl, bromide is heated with sodium ethoxide is, 1) 2 - Methyl - 1 - propene 2) Ehene, 3) tert - Butyl methyl ether 4) Diethyl ether, , A + B → CH 3 − OC (CH 3 )3 , X +Y ., HI, →, Correct statement among the following is, 2) X and Y are CH 3 I and (CH 3 )3 COH, , Nucleophillic substitution reaction, , HI, CH 3 − CH − O − CH 3 , → CH 3 − I + CH 3 − CH − OH, |, |, CH 3, CH 3, ↓HI, , conc. H 2 SO4, , → C, 'C' is, 1400 C, 1)Ethoxy ethane, 2) Ethanol, 3) Ethanal, 4)Acetone, conc. H 2 SO4, Aq . KOH, B, CH3-CH2 Cl , → A →, 1400 C, , 1) A and B are CH 3 ONa and (CH 3 )3 CBr, , C2 H 5Cl + C2 H 5ONa → Nacl + (C2 H 5 ) 2 O, , 3, , A compound X of the formula C2H6O, on, reaction with Na metal gave Y, X also reacts, with PCl5 to give Z. The product obtained in, the reaction between Y and Z is, 2) CH3COCH3, 1) CH3CHO, 3) CH3COOC2H5, 4) C2H5OC2H5, Aq . KOH, AlCl, 3, CH2=CH2 + Hl →, A , → B, , 3) X and Y are CH 3 OH and (CH 3 )3 CI, , 4) A and B are CH 3 OH and (CH 3 )3 COH, IUPAC name of methyl isopropyl ether is, 1) 2-methoxy propane 2) 3-methoxy propane, 3) Ethoxy ethane, 4) Methoxy ethane, + HI, → (CH 3 )3 CI + CH 3OH It, 9. (CH 3 )3 COCH 3 , follows which mechanism?, 2) S N 2, 3) E1, 4) E2, 1) S N 1, 10. Which of the following is strongest Lewis, Base, 1) H 2 O 2) CH 3OH 3) CH 3OCH 3 4) C6 H5OH, NARAYANAGROUP

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ETHERS, , JEE-MAIN-SR-CHEM-VOL-III, 11. CH 3CH 2 CH 2 OH + PBr3 → A ,, CH 3CH 2 CH 2 OH + Na → B , A + B → C ., Product ‘C’ is, , 1) (CH3CH 2 CH 2 )2 O, , 2) CH 3 − CH = CH 2, , 3) Both (1) & (2), , 4) (CH 3CH 2 )2 O, , LEVEL-IV, 1., , Which of the follwoing ether cannot be, prepared by Williamson’s synthesis, , 1), , 2), , 12. C2 H5 − O − C2 H5 + HI(excess ) →, 1) C2 H 5OH and C 2 H 5 I 2) 2 moles of C 2 H 5 I, 3) 2 moles of C2 H 5OH 4) C2 H 4, 13. C6 H5 − O − CH3 + HI(excess ) →, , 3), 2., , 1) CH 3OH and C6 H 5 I 2) CH 3 I and C6 H5OH, 3) CH 3 I and C6 H 5 I, , 4) C6 H 6 and CH 4, , 4) All, 1.68 mg of an organic compound (A) with, molecular formula (C9 H12O3 ) on Zeisel, estimation produces an yellow precipitate of, wt 4.7 mg the compound (A) is, , LEVEL-III - KEY, 1) 4, 8) 1, , 2) 1, 9) 1, , 3) 2 4) 3 5) 1 6) 1 7) 3, 10) 3 11) 1 12) 2 13) 2, , 1), , 2), , 3), , 4), , LEVEL-III - HINTS, 1., , X = C2 H 5OH , Y = C2 H 5ONa; Z = C2 H 5Cl, , 2., , A = C2 H 5 I , B = C2 H 5OH , C = C2 H 5OC2 H 5, , 3., 4., 6., , A = C2 H 5OH , B = C2 H 5OC2 H 5 , C = C2 H 4, A = C2 H 5OH , B = C2 H 5ONa, C = C2 H 5OC2 H 5, , 3., , It proceeds by elemination instead of, nucleophillic substitution reaction., , HBr, , (Cs2 )→ B ( halogen compound ), , CH 3 Br + NaOC (CH 3 )3 → CH 3 − O − C (CH 3 )3, , A & B respectively are, , ↓ HI, CH 3 − OH + (CH 3 )3 C − I, , 7., , 1) CH 3 − Br , CH 3 − Br, , 2) CH 3 − Br ,, , 11. A = CH 3CH 2CH 2 Br ; B = CH 3CH 2CH 2ONa, , C = (CH 3CH 2CH 2 )2 O, , 3), , C2 H 5 − O − C2 H 5 + HI (excess ), , LEVEL-IV - KEY : 1) 3 2) 3 3) 1, , , CH 3 − Br, , 4), , 12., ↓, C2 H 5 I + C2 H 5OH, , LEVEL-IV - HINTS, 2., , ↓ HI, C2 H 5 I, , 1.68 ×10−3 grams of given, , ↓ HI, No reaction, , NARAYANAGROUP, , 4.7 × 10−3, = 2 × 10−5, 235, , compound, , forms, , −5, , C6 H 5OCH 3 + HI → CH 3 I + C6 H 5OH, , 13., , Number of moles of AgI=, , 2 × 10 moles of AgI, Number of moles of AgI given by 168 grams of, , given compound is, , 168 × 2 ×10−5, =2, 1.68 ×10−3, , Number of moles of AgI is equal to number of, moles of alkoxy groups in 1 mole of ether, 85