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    17 views10 pages

    Alco Neet

    Uploaded by

    lingarajugowda
    hi

    Copyright:

    © All Rights Reserved
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    [25 | The heating of phenyl methyl ether with produces (@) iodobenzene (©) benzene (&) phenol (@) ethyl chloride (NEET 2017) 2. Which one is the most acidic compound? MH MH J NO, on I ON NO; © @ NO, 2 CH (NEEF 2017) 3. The reaction on Bally ON O- 4. Reaction of phenol with chloroform in presence of dilute sodium hydroxide finally introduces which one of the following funetional group? 6 Alcohols, Phenols and Ethers (@ coon (© CHO 2015) Which of the following reaction(s) can be used for the preparation of alkyl halides? () CHCH,OH +He] 2 (i CH CH UID (CH) yCOH + HCI—> (@) @ and (I) only (b) GV) oaly (6) di) and (IV) only (@ @, MID and (IV) only 2015) The reaction, is CHy—C—ONa + CCH a a CH CHy~C—O-—CH)—CH; CH is called (a) Etard reaction (b) Gattermann-Koch reaction (©) Williamson synthesis (@ Williamson continuous etherification process 2015, Cancelled) Among the following sets of reactants which fone produces anisole? (@) CH,CHO ; RMgY (b) CaHOH ; NaOH, CHL (©) C¢H,OH , neutral FeCl, (@ CHCHy s CH,COCI; AIC, (2014) Which of the following will not be soluble in sodium hydrogen earbonate? (@) 2.4.6-Trinitrophenol (b) Benzoie acid (©) o-Nitrophenol (@ Benzenesulphonic acid (2014) ‘Aeckels, Phonols and Elere 9. Among the following ethers, which one will produce methyl alcohol on treatment with hot concentrated HI? CH; (@ cHy—¢—0—cH, CH & Hs“ GH CHOC cH (© CH—cH,—cH,-0-cr (©) Cy“ CH —GH—O— CH, cy (NET 2013) 10. Number of isomeric alcohols of molecular formula CHO which give positive iodoform test is @ three () four © five (@ two (Karnataka NEET 2013) 11. In the following sequence of reactions CH, BrAD 4 HOY y Li ¢ the end produet (C) is (@) acetone (© acetaldehyde (b) methane @) ethyl ateohol (2012) 12, Which of the following compounds can be used as antifreeze in automobile radiators? @ Methyl alcohol (b) Glycol (©) Nitrophenol (@) Ethyl alcohol (Mains 2012) 13. In the following reactions, I Wheat Om A+ B eye] @ Ae C eye) @ cH=t-cH,-cH, and M4 15, 16. ws i & cr,-tacn_-cry, and i © cH, =¢-CH,-cH, and es L @ CHy- ‘ =CH-CH, and t Given are cyclohexanol (D, acetie acid ID, 2,4,6-tinitrophenol (I) and pheno! (1V). In these the order of decreasing acidie character will be (@) M>M>W>T by >> 1>1V (© U>U>1V>t @) M>Iv>m>1 (2010) Which of the following compounds has the most acidic nature? Se" oS oOo" i “PO 201 208 7. 18, 19, 20. The avidity order is (@) Ge) > Gi) > > Gi) ©) Gi) > > H> Gi) (©) @> > w> Gir (@) i) > @> Gai) > GW) (2010) When glycerol is treated with excess of HI. it produces (@) 2-iodopropane (6) propene (b) ally! iodide (@) glycerol tniodide (Mains 2010) Following compounds are given @ CH.CHOH @) CH,COCH, (ii) CHy—CHOH ivy CILOTT Hy Which of the above compound(s), on being warmed with iodine solution and NaOH, will give iodoform? (@) @, Gi) and Gv) (©) @, Gand Gi) () Only Gi) @ @and Gd, (Mains 2010) Match the compounds given in List 1 with their characteristic reactions given in List I. Select the correct option List I List 1 (Compounds) (Reactions) A. CHYCH);Ni; @ Alkaline hydrolysis B CHC=SCH Gi) With KOH (alcohol) and CHCl, produces bad smell © CIKCH,COOCT, Gi) Gives white ppt ‘with ammoniacal AgNO; CH, (iv) With Lucas reagent cloudiness appears after 5 minutes (@) A-Gi), Bi), C-), Dai) (b) A-Ga),B-(9,C-0,D-09) (©) AG), BG), C49, D-0v) (@) Asiv), Boi, C-Gi), De) (Mains 2010) Consider the following reaction Ethanol "yy HEKOH, y (H,$0,, room temperature WHO, eat the product Z is (@) CHCH, ~ 0 - CH ~ CH, EAICM| Chapterwise NEET-AIPMT SOLUTIONS] (b) Cl, - CH, ~~ so,tt (©) CH,CHOH (@ CH=CH; 21, HOC gives (2009) .CHOH on heating with periodic acid CHO (@) 2HCOOH I cHo H, © 2Dc= (@ 2C0, (2009) 22. Consider the folowing reas Prenel 2885 ¢ EL y aie KM, the product Z is (@) benzaldehyde (©) benzene () benoie acid (@ toluene (2009) 23. In the reaction: cH, CH,-CH-CH,-0-CH,- CH, + Ht HS Which of the following compounds wil formed? IL be © cH -GH-cH, + cH,CHOH cH, ©) Ciel cutoH + cxcH, cH, cH, (©) CH,-CH-CH,OH + CH,CH cH, ©) CH,-CH-CH,-1 + CH,CHOH (2007) 24, The general molecular formula, which represents the homologous series of alkanols is @) CiHays0 (0) CaHasOs (©) C,H, @ Gly. (2006) 25, Ethylene oxide when treated with Grignard reagent yields ‘Aeckels, Phonols and Elere {@) primary alcohol (b) secondary alcoho! (©) tertiary alcohol {@) eycloprops! alcohol (2008) ‘The major organic product in the reaction is CH, - 0 = CH(CH,), + HI > products (@) CHsl + (CH),CHOH (b) CH,OH + (CH,),CH © ICHOCIKCH): 26. @ cHoccn), 1 (2006) 27, Which one of the following compounds is most aside? @ Cl cH, ~cH, oH on on © or © ox No, on @ 2005) cH, (2005) 28, Which one ofthe fllowing will not form a yellow precipitate on heating with an alkaline ‘olution of iodine? (@) CHACH(OH)CH, (b) CH,CH,CH(OH)CH, (©) CHOW @ CHCHOH 2004) 29. n-propyl aleohol and isopropyl aleohol can be chemically distinguished by which reagent @ PC (b) reduction (©) oxidation with potassium dichromate @ ezonolysis. (2002) ‘When phenol is treated with CHCIs and NaOH, the product formed is (@) benzaldehyde (©) salicylic acid 30. (b) saliylaldchyde (@) benzoic acid. (2002) 31. Which of the following is correct? (@ On reduction, any aldehyde gives secondary alcohol. (b) Reaction of vegetable oil with HO, gives alycerine, (©) Alcoholic iodine with NaOH gives iadoform. (@) Sucrose on reaction with NaCl gives invert sugar (2001) 32 33. 34. 38. 36. 37. 38 39. 207 - lodoform test is not given by (@) ethanal (b) ethanol () 2-pentanone (@) 3-pentanone a) CH, with RMgX leads to Reason f hog o the formation of (@) RCH,CH,O1 (b) RCHONCH, n wo "Seven (1998) Which one of the following compounds is resistant to nucleophilic attack by hydroxyl (@) Diethyl ether (©) Acetamide (©) RCHOR (b) Acetonitrile (@) Methyl acetate (1998) When 3,3-dimethyl-2-butanol is heated with H,S0g, the major product obtained is (@) 2,3-dimethyl-2-butene (b) cis and ras isomers of2,3-dimethy1-2-butene (6) 2,3-dimethyl-I-butene (@) 3.3-dimethyl-l-buteae. (1995) On heating glycerol with cone. H,8Os, a ‘compound is oblained which has bad odour, ‘The compound is (@) acrolein (b) formic acid (6) allyl sleohol (@ glycerol sulphate 994) ‘The compound which does not react with sodium is (@) CH,Coort (©) CHOW ) CHLCHoncH, (@ CHOCH, (0994) - Ethanol and dimethyl ether form a pair of functional isomers. The boiling point of ethanol is higher than that of dimethyl ether, ue to the presence of (®) H-bonding in ethanot () H-bonding in dimethyl ether © CH group in ethanol (@ CH, group in dimethyl ether (7993) Increasing order of acid strength among p-methoxyphenol, p-methylphenol and p-nitrophenol is (@) pritrophenol, p-methoxyphenol, p-metbylphenol 208 (b) p-methyiphenol, p-methoxyphenol, p-nitrophenol (©) pritrophenol, p-methylph ‘p-methoxyphenol (@) p-methoxyphenol, p-methylphenol prnitrophenol , (1993) Which one of the following on oxidation gives a ketone? (@) Primary aleohol (b) Secondary aleohol (¢) Tertiary aleohol (@) All of these. 40. (1993) 41. What is formed when a primary aleohol undergoes catalytic dehydrogenation? (@) Aldehyde (b) Ketone () Alkene @ Acid (1993) When hydrochloric acid gas is treated with, propene in presence of benzoyl peroxide, it ives (a) 2-chloropropane a2. EAICM| Chapterwise NEET-AIPMT SOLUTIONS] 46, When phenol is treated with excess bromine water. It gives (@) m-bromophenol (b) o-and p-bomophenols, (©) 2.4-dibromophenol (@) 2.4,6-tuibromophenol, The compound which reacts fast reagent at room temperature is (a) butan-L-ol (b) butan-2-o1 (©) 2-methylpropan-I-ol (@) 2-methylpropan-2-o1, Which one of the following compounds will be most readily attacked by an clectrophile? (@) Chlorobenzene _() Benzene (©) Phenol (@ Toluene (192) 47. with Lucas (1989) 48, (1989) 49. Propene, CI,CH=CII, ean be converted into |-propanol by oxidation. Indicate which set of reagents amongst the following is ideal (b) allyl chloride for the above conversion? {© no reaction (@) KMn0, (alkaline) (@) mpropyl chloride (1993) | (&) Osmium tetroxide (OsOCH,CI) 43, How many isomers of 3H, OH will be primary | (©) Balle and alk. HO, alcobols? (Oven 1989) @s os 50, Phenol is heated with CHCl, and aqueous KOH @2 (3 (1992) |” en salteylaldehyde is produced. This 44. Methanol is industrially prepared by reaction is known as {@) oxidation of CI by steam at 900°C (@) Rosenmund’s reaction {b) reduction of TICHO using LiATT (b) Reimer-Tiemann reaction {©) reaction HCHO with a solution of NaOH | (©) Friedel-Crafts reaction (a) seduction of CO using Hl, and Za0-Cr,0,, | (@) Sommelet reaction (1989.88) (1992) | 51. Lucas reagent is 45. Br reacts fastest with (@) cone. HCI and anhydrous ZnCl, (@) 2-Methylpropan-I-o (b) cone, HINO, and hydrous ZnCl (b) Methylpropan-2-o1 (©) cone. HCL and hydrous 22, (©) propan-2-01 (@) cone. HINO, and anhydrous ZnCl, (@ propan-t- LO2OR 4 6. OF HK OFX YH 1. @) 12) 1B &) ® 16 @ 1. @ ©) © HO 21.) 22. (b) 23. @ 4 (a) 26. (@) 27. 28. (©) 29. (c) 30. (b) 31 ©) 32 @) 33. @) 3h @ 36. @ 37. @) 38 @) 3. @ 4 AL @) 42 @) BD 4 &) 46. @ 47 GH ©) B © 50 SL. @) ‘Alcohol, Phonole and Ethers 208 ULUUUOALU LA EU EXPLANATIONS i UU UE 1. @):In ease of pheny rmetyl ether, methyl cay) H by protonation of ether. The O—CH, bond is weaker than O—C,H, bond as O—C,H, has partial double bond character Therefore, the attack by I ion breaks phenyl oxonium ion i formed O—CH, bond to form CHL step W — I, Cots SCH +B = CHO CH + Step I 4 I. USO ets > CibL + 61,0 2. (@ + Electron withdrawing groups intense the acidity while electron donating groups decrease the acidity of phenol 2 ©) involves the treatment of sodium alkowie with a Suva ally! halide to fom an ee 4. (©: This is Rem Williamson's ether synthesis reaction -mann reaction oH ONa oO “cure, SK or set sect on CHO CHO Saiystshyde 5. (@): I®and 2° aleohols reset with HCI in presence of anhydrous ZnCl, as catalyst while in case of 3° aleohols ZnCl, is not required 6. (©) Williamson synthesis is the best method for the preparation of ethers 7. (B): (@) CH,CHO+ RMgr > CH,-CH-OH © GOH ONE EON co c,nkocn, + Nat Methyl phenyl etbee (Willanson's ‘yates Loy vO) on Hy Aaby. AICI, A o +CH,Coct cH, cn, on , oO o-Metiy! Cocn, acelopenone we sclophonine 8. (@):The reaction is as follows ‘Acid + NaHCO, —> Sodium salt of acid + H,Ct (soluble) ‘Among all the given compounds, o-nitrophenal is weaker acid than HCO; Hence, it does not react ‘with NaHCO, Cy 34 snk, ON ct CEE eet at Ci, cH, CH; chy Hy 210 10. (b): The iodoform test is positive for aleahols with formula R — CHOH — CH. Among C,H,,0 isomers, the ones with positive iodoform test are 1 CH,—CH,—CH,—CH,— CHO —cH, 2 Hexanol 1, —CIKCH,) — Clon — cH, 3+ Methyh2-Pestanl UL (CH,),CH —CH, —CHOH—c#, 4: Metiy2-Pestanol IV. (CH),C—CHOH—CH, cH, 1. @:CrBr EX crew BOS a cu.coon S84 crcH,H1 @ © 120) 13. @): ct, cH I CH.CH~CHCH E> cH, CH-CH-CH, oH cuts ¢ SCH CHy# cH,-¢-CH,-CHy a) * in Crh CH-CH= CH, 6) ou 1-8-8 a @ cn, th I CHy-F—CH,-CH + CH,-CH- CH=CH. be br (© Mae (D) Mie 14, (@) 11> 1>1V>1 Since, phenols and carboxylic acids are more acidic than aliphatic alcohols, we find that eyclohexanol (0) is least acidic, Out of the two given phenols, IIL is ‘more acidic than IV. This is because of the presence of three highly electron withdrawing -NO, groups EAICM| Chapterwise NEET-AIPMT SOLUTIONS] fon the benzene ring which makes the O—IT bond extremely polarized, This facilitates the release of H asH Thus, 11> 1V 9 I Jeetron withdrawing —C— in the —COOHT group polarises the O—H bond and. increases the acidte strength. Acetic acd is therefore ‘more acidie than phenol or cyclohexanol The onder is I> I> 1V > 1 15. (b):Phenol is most acidic of all the given ‘compounds. In phenol, the electron withdrawing phenyl ring polarizes the O—H bond thereby facilitating the release of II as Il and hence phenol is most acidic of phenyl ring is somewhat diminished by the Cll, group and e than phenol. In (6) and (, —O1 group is attached to alkyl groups which, due to their 47 effect reduce the polarity of OH bond and so the acidie strength is low 16. (a):In phenols, the presence releasing groups decrease the acidity, whereas presence of electron withdrawing groups increase the acidity, compared to phenol. Among the meta and para-nitrophenols, the latter is more acidie as the presence of NO, group at para position slabilises the phenoxide fon fo a greater extent than ‘when itis present at meta position. Thus, correct ‘order of acidity is Parasitrophenol > meta-nitrophenol > phenol Im acetic act electron Gy) Gi) a > methy pheno @) 17. @: GHoH cit Gi CHO <3H1 ™™™> cH —> CH +1, | I | Cimon cat abt a Satiodoropane All ioide in cH, CH CH iow Ta I ca cy 2 an I i I cis Gh crt 2indapropane Prete (ata) ‘Alcohol, Phonole and Ethers 18. (©) jiodoform test. The iodoform test is exhibited by ethyl alcohol, acetaldehyde, methyl Ketones, those possess CH,CH(OH)— group, acetophenone, ‘o-hydroxypropionic acid, keto acid, 2-aminoalkanes, ete Methyl aleohol does not respond to the aleohols which 19, (9 :cH,cn,cn,cu,vn, Ss CH,CH,CH,CH,NC +3KCI+3H,0 CH,CH,COOCH, + Nao "> CH,CE DONa+CH,OH (CHyCH(OH)CH, + Cone. HC! E28, 2" Achat (CH) —CH— CH, +H,0 a loudness appear in minutes 20. Poy sis KOH cygon Py cytigpre kon, Bahan “dehyde halogenation on . caer -180, Juno eyty-0H @ 21. (6): When | ,2-diol like ethylene glycol is treated With TIIO,, each alcoholic group is oxidised to a carbonyl group by ITIO,, Since in glycol, both the ~ COI! groups are terminal, so oxidation Would yield two formaldehyde molecules. CH)=OH Ho, ies | Be acto cH,- 08 au {CH,Clanhy.A1C, . Pree emane cx) Alkylation 22. ( cH, OOH sk M10, Toluene Bensne ai (Z) 23. (¢) : The alkyl iodide produced depends on the nature of the alkyl groups. If one group is Me and the of imary or secondary alkyl group, itis methyl iodide which is produced. This can be explained on the assumption that the mechanista is Sq2, and because of the steric effect of the larger ‘group, attacks the smaller methyl group. When the substrate is a methyl alkyl ether, the products are KT and MeOH, This ean be explained by an SI mechanism, the earbonium ion produced being the FK since tertiary carbonium ion is more stable than a primary or secondary carbonium ion. 24. (a) : All alcohols follow the general formula Clg, 50. CH,OH [CHL 0) ,C,H,0H) Ha.as201 2 aS 25. (a): HCH, + CH.MeBr —> carcrcromeas ES crjcr,cr,on ey 26. (a) : With cold II, a mixture of alkyl iodide and alcohol is formed. In the ease of mixed ethers, the halogen atom altaches to a smaller and less complex. alky! group. CHOCH(CH,), +HI > CH,1+(CH),CHOH 27. (c) : Phenols are much more acidie than alcohols, due to the stabilisation of phenoxide ion by resonance 1 NO, NO) is the cleotron withdrawing group and helps in stabilizing the negative charge on the oxygen hhence equilibrium shifts in forward direction and more H" remove easily Hence itis most acidic 212 HT destabilizes the product. backward direction 28. (¢): Formation ofa yellow precipitate on heating, 4 compound with an alkaline solution of iodine is known as iodoform reaction. Methyl aleobol does not respond to this test. lodoform testis exhibited by ethyl alcohol, acetaldehyde, acetone, methyl ketones and those alcohols which possess CH,CH(OH) - group 29, (c) : n-propyl alcohol on oxidation with potassium dichromate gives an aldehyde which on farther oxidation gives an acid. Both aldehyde and acid contain the same number of C atoms as the original alcohol CHCH,CHLOH REE, cucricHio K223!8 crcr,coou Isopropyl alcobol on oxidation gives a Ketone with the same number of C atoms as the orginal sleoho a cot gt SEPALS cH -c- ou, 5 30, (b) : This reaction is called Reimer-Tiemann on " Phenol ‘CHI, ou ‘Na’ CHO : OG Ie HO Salicylaldehyde (EEC Chapterwise NEET-AIPMT SOLUTIONS] 31. © © HOH +41, +NaOH, > CHL, + Nal-+ HCOONa + 1,0 cellow solid which erystallises in ldoform is a pal hexagonal plates, 32, (d) : Ethyl sleohol, 2-alkanols, and earbonyl compounds containing CH, © group show ° iodoform test, Le, acetaldehyde and 24 So iodoform test is not given by 3-pentanone. 33. (a): R-Mg-X + CH,~C1 wy ctones ete 0: > R~CH, - CH, - OMex ‘Adis Hom AGES RCH, - CH,- OH + MgO alcool 34, (a) : Diethyl ether is a saturated compound, so it is resistant to nucleophile attack by a hydroxyl ion (1D, Other compounds have unsaturation and the unsaturated °C” atom bears partial 4ve charge, therefore they undergo easy nucleophilic attack by OIF ion 35. @): oh os CH, -CH = C= CH CH, CHC CH, on cH, OH, CH, 4.3.imehy-2ueo} cH, i Te pan, -Eu-¢ -cu, —+ cu, -¢-C cH, aie r 14 cH cH, 2. Dimetybbutne 36. (@): HOH one W804 fron SBS cH, =cHcHo +20 bron Acrolen Giycerol 37. (d) + Ethers are very inert. The chemical inertness of ethers is due to absence of acive group ‘Alcohol, Phonole and Ethers in their molecules. Since CH,- O- CH, is an inert and it does not contain active group, therefore it does not react with sodium 38, (a) : Hydrogen bonding in ethanol 39. (d) :~OCH, ~CH, are electron donating groups decreases the acidic character of phenols. NO, CN are electron withdrawing groups, tend to increase the acidic character. Thus, the order is _p-methoryphenol < p-methylphenol < p-nitrophenol 40, (b) : 2° alcohols on oxidation give ketones, 1P alcohols form aldehydes 41. (a) + Primary aleohol undergoes catalytic dehydrogenation to give aldehyde, 42, (@) +: Addition of HCL to propene even in the presence of benzoyl peroxide occurs according to ‘Markownikov's rule, HL -cu- CH CHS CH oP ia cH, 1 2-

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