NARAYANA WR) EDUCATIONAL INSTITUTIONS THE NARAYANA GROUP Alcohol, Phenol & Ether : on 1. In the given conversion, identify the suitable on. No, on No, reagents A, B and C NaHCO, wv) —a— +H0+00, CH, . CH, Cy oe Cr = (8 # 0 Choose the correct answer ~ qc ; ‘ (1) A: H,O, in aqueous NaOH, B: PCC/CH,Cl, C : Ua Becca peed (2) Only (iis possible B,H,/THP (3) Except (i) all are possible (2): B,H,/THF, B: Br,/CH,Cl,, C: PCC/CH,Cl, (4) Only (i, i possible (3) A: B,H,/THF, B: H,0,/OH,C:PCC/CH,Cl, | 4. Which order is incorrect? (4) A: Br,/CH,Cl,, B: B,H,/THF, C: H,0,/OH (1) Tendency of ester formation 2. Most stable product (P) formed in following reaction : . ae ‘OH P (2) Acidic strength : 4-Nitrophenol > 2-Nitrophenol 4 > o-cresol (3) Bond angle of CH,OH > CH,~O-CH, > C,H,OH (4) Boiling point : Pentan-1- ol Pentan-2-ol > 2,2- a (2) Dimethyl propanol (5) Boiling point : p-Nitrophenol < o-Nitrophenol ‘ (3&5 2)283 6) Cx (4) No reaction iter aaa 5. Which of the following reduction methods is not suitable for preparing an alcohol (1) CH,COOC,H, + NaBH, ——> 3 @ + Na,co, —> +NaHCO, (2) CH,COOC,H, + Na/EtOH —> (3) CH,CH,COCI* LialH, —> (4) None of these 6. Which of the following represent Williamson's ON. NO, ON NO, synthesis ? (1) G,H,ONa + CHI» (i) —— +00, (2) CH,-ONa + (CH), C-C1 : is, ONa (3) C.H,-Cl+ CH,-CH,ONa {4) (CH,), C-ONa + (CH,), C-Cl 7. Which of the, following reactions will give chiral : NaHCO; primary alcohol as major organic product? (iii — +H,0+ C0, #.0,/0H" ae ()) CH-G-cH+BH,/THF CH.CH,10. uM. 12. (2) cH-¢-cH, SPO, CH,CH, BicH-g = ¢-pHHIQCALHO, NaBH HA (4) None of these Which statements are correct {A) LiAIH, is strong reducing reagent than NaBH, (B) Carboxylic acid can not be reduced by NaBH, (C) Lucas reagent is hydrous ZnCl, & Con. HCl (D) Phenol is known as Carbolic acid MABC ABD (ABCD 4)B.CD Which of the following reaction sequence would be the best for synthesis of trimethyl carbinol ~CH,-MgBr + 0 _HO" (1) CH,-CH,-MgBr + CH,0 _ Ely ycH,-cHcH, gprs 7B, HO”, (3) CH,-MgBr + acetone Eto _H,0 (4) CH,-CH,-MgBr + CH,cHO Eto, 1,0", so propyl alcohol is heated with water in suspension of bleching powder. The products formed are: (1) ethan & propane (2) ethyne & ethene (3) Trichloro methane & calcium acetate (4) Carbon tetrachloride Which reagent is best to perform the following transformation ? T- (1) HBr, NaOH (2) HBr, R-O—O—R, hy; Me,CO*K* (3) BH,.THF, NaOH—H,O, (4) Br, NaOH When ethyl alcohol treated with cone. H,SO, at 443K and 413K then what product are formed respectively: (1) CH, = CH,, C,H,0C,H, (2) C,H,0C,H,, CH,=CH, (3) CH,=CH,, © (4) C,H,0C,H,, C,H,0C,H, 13. 14. 15. 16. 17. The isomeric alcohol which has a chiral carbon atom is: (1)n-butylalcohol_—_(2) iso-butyl alcohol (3) sec-butyl alcohol (4) tert-butyl alcohol w—to =< Structure of (A) may be: o oy 2) ay (4) Allof these Ont : Product (A) is: “CY a) ‘OF @) CY 4) Cy What is the final product of the following reaction: afar 222. a CH,CH; ist 1) fa «a t Hs a CH,CHy CH,CH, (3) nopar @) arfoa a, Product is (A) is : HO" 6. 9 ) «) Oo19. 20. 24. 2. ‘What is the major product of the following reaction CHy Chet + Her —+ ? ‘OH oCkst CH 3) Ck CHBr (4) Br Which of the following reagents can be used to oxidize 1° alcohols to aldehydes : (I)KMnO, (2)MnO;” (3)K,Cr,0, (4) PCC In oxidation of alcohols by chromic acid , the chromium is: (1) reduced from Cr’ to Cr* (2) Oxidized from Cr’* to Cr? (3) reduced from Cr” to Cr® (4) Oxidized from Cr’? to Cre Qooet ow Product (A) is ‘CHs (1) BecooH (2) Br cro eS on CH,CH,CH,OH—™=—>(A\ pean eee Structure of final product (D) is : (1) CH,-CH,-CH-NH, (2) CH, — CH —CH, NH, CHy (3)CH,-CH,CH=NH (4) om —¢ —NH, CHs 23. 24. 23. Most reactive toward acid catalysed dehydration is HH - 1H (3) (4) Ph fm mm ow 1H OH Product (A) is: Ph () mth on (2) CH, CH, Is CHs 6) bh \e ‘The best method for preparing aspirin is : COOH a or +H _— CCH, (a) or 4 + HCOOH > oo OLR" oe COOH i . (w) Or + CHy—C—NH, > oH 00H - w or + odo Le, “ ‘OH (1) Both iv & v (2) ii @) ii tay27. 28, 30. 31. 32, In Reimer-Tiemann reaction molecular weight of phenol increases by (1) 28 (2) 29 a Ce Oo iat ¥ ‘Substituion take place at the position : (yi (2)2 (3)3 (4) Both (1) and (3) Compare reactivity toward Grignard reagent : oO on 0" ) © (2)b>c>a (4) none of these So BP. products ofabove reaction are IH ok a SL CHjCHO 3) A, Aw A, A OCH one. 1 S41, x mole of HI are consumed (3)27 @)31 @ je>b>a (@)a>b>c O—CH, Sone HI, y mole of HI are consumed Sum (x+y =?): (1)2 (2)3 (3)4 as HH CIM om eee -onoh-ah 1 [ iM ‘The value of x is qa (22 (3 (a4 Compare rate of reaction with OH*/H,O VVWw @ (b) © (I)c>b>a Q)a>b>c (3)b>a>c (4)b>c>a 35. 37. Final product in the following reaction sequence is : Opcmc como, A, nor, 0 Q>eew a) O>-cxcar,cx,0cH, i) ©- (Cm=CCH,OCH,CH «w ©-e (CH,CH,OH (yr (2) (3) I (4)Iv Orns +KOH—xA) Product (A) is : OO oO ‘The reagent which will be suitable to distinguish 1-methoxy-3-methyl-2-butene from isomeric 4-methyl-3-penten- 1-ol is : (1) bromine in chloroform (2) alkaline potassium permanganate (3) ammoniacal silver nitrate (4) sodium metal suspended in hexane Qa Product obtained in above reaction is : (1) 2 CH,CHO (2)3 HCHO (3)3 HCO,H (4)3 CH,OH 18 7 Ph—O—CH, — ML, Product obtained in above reaction is : 18 (2) Ph—1, CH OH (4) Ph-OH, CH, 18 (1) Ph—OH, CH, —I (3) Ph, CH,38. 8 41. 42, HBr reacts fastest with : (1) 2-methylpropan-2-ol (2) propan-1-ol (3) propan-2-o1 (4) 2-methylpropan-1-ol ‘Among the following compounds, the correct order| of rate of oxidation towards periodic acid is : (Cos) -C-OH I (CzHs); -C-OH «ty CH,OH —CaHy~CH-OH I CH{OH = CyHs~CH-OH ( ay (1) (> (ay) > a (2) < a) < am (3) (1) > (1) = (iin) (4) () = (11) = (im) Method by which, 1-propanol and 2-propanol can be best distinguished : (1) oxidation with alkaline KMnO, followed by reaction with Febling solution (2) oxidation with acidic dichromate followed by reaction with Fehling solution (3) oxidation by heating with copper followed by reaction with Fehling solution (4) oxidation with concentrated H,SO, followed by reaction with Febling solution Which of the following statement is incorrect : (1) A secondary alcohol on oxidation generally gives a ketone (2) Ethanol reacts with cone. H,SO, at 180°C to yield ethylene (3) Methanol reacts with iodine and sodium hydroxide to give a yellow precipitate of iodoform (4) Hydrogen gas is liberated when sodium is added to alcohol Complete the following sequences with appropriate = ©, m,n CO (1) ()) is 0,/2n, H,0 ; (Il) is SeO, ; (11) is OH-/heat (2) (l) is 0,/2n, 1,0 ; (Ul) is LiAIH, ; (111) is OsO, (3) (2) is 0,/Zn; 1,0 ; (Il) is LiAIH, ; (111) is H*/heat (4) () is KMnO,/H" ; (11) is NaBH, ; (111) is H*/heat I Hq ‘The most reactive site for electrophilic aromatic substitution is : qa (2)2 (3)3 (44 When phenol is reacted with CHCl, and NaOH followed by acidification, salicaldehyde is obtained. Which of the following species are involved in the above mentioned reaction as intermediate : OH 2) on ee A a @) = 4) or 1H Which statement best explains why acidic than B » (1) The larger size of ketone group helps to stabilise the conjugate base (2) The ketone group exert a large in inductive effect in conjugate base of A (3) The ketone group allows for resonance delocalisation of the charge in conjugate base (4) The OH oxygen in A is more electronegative than the OH oxygen in B SH (1) ay, is more 46. Which of the following reactions will not yield phenol a a () NaOH (ii) H,O/H NH (2) ) NaNO3/HCL i) H,0, warning47. 49, ) Oleum ip HF NaOH, (3) O a (nzon(ag, 623K, 30020 a wore When benzene sulphonic acid and p-nitrophenol are treated with NaHCO,, the gases released respectively are : (1)80,,C0, 2)C0,,c (3) So, NO (4)80,, No, CH I (CHy—C—Br + CHyCH,OH ———++ A (major) ie criyatz0ne P = EB (major) Oy —C— Br gon 2 NO ‘CHy Possible products are : te " ea 7 cH cH, 1 u ‘Then, A and B respectively are : (Lu (2) 0,1 (3) 11 in both cases (4) 1 in both cases Consider the following reaction, >< te OX + DK ‘oH Which response contains all the correct statements about this process : () Dehydration (11) Rearrangement of carbocation (11) E, mechdnism (IV) Most stable carbocation is formed (iu (2)1, 0, ur (3)1, 0,1V (4)1, 11, 11, 1V 51, HsC. wy WEE Ais: (1) CHy CHCHOH (2) CH,CH,CH,CH,OH i (3) ie (4) No reaction Gis cry = cH HCH cH, +4, Ais: on (1) CH, = CHCOCH,CH,OH 2 Gy — at— pra GH OH (3) CH, = CHCOCH,CHO (4) CH, = CHCOCH,COOH Identify A in the given sequence of reaction : wo, wn w a) a... agytanos 8) one, y— CH=CH — CH, (4) OH Cr + CHC, + NaOH CHO ‘The electrophile involved in the above reaction is: (1) Dichloromethy! cation (CHC!) (2) Dichlofocarbene (:CCl,) (3) Trichloromethane (CHCl) ONa* (4) Formyl cation ( HO)54. 87. Phenol and ethanol are distinguished by the reaction with (1) Red litmus (2) NaHico,, (3) FeCl, (4) NaOH The product of following reaction is - Hy I CHty—C—CH— cH, HOCOACOON IO, THE (i) NaBH, CH; OH vad (2) CHy-£—CH cH OH oh ee 3) CHy-e—CH-cH On ie (4) HocH;—¢—CHy—CH CH; In the following reaction, H, CaHla gO HSC, X <= CHsCHO; Whatis x? (1) CHJCH,OH (2) CHs-O-CHy (3) CHsCH,CHO (4) CH, = CHOH Correct reaction is : 00. 10H 2S0._, a a aq NaHSO, i O-t Alkaline 10H 2) Q) KMnO, cn 61. 0) Clq ners” a. es Cae 4 Oe a0 em Inthe aay reaction the most probable product will be : Br Htc, bh _ 8H HC—+—-H 52 Hs H Hy H—+—CcH, H ‘OH (1) (2) yc—t +n ) He: H Cos Gs Cs CH; @ CH fay HO 4 H,C- H HAC: H OH Hs ‘The reaction Soe, OF G, AR +500, nd" 50, + Ha proceed by the mechanism (Sx (2) Sy2 (3) S22 Choose the incorrect statement (1) Resorcinol and catechol are structural isomers (2) Resorcinol and quinol are structural isomers (3) Quinol and catechol are structural isomers (4) Catechol, Hydroquinone and resorcinol are trihydroxy derivative of benzene Correct order of decreasing reactivity towards electrophilic aromatic substitution for following ‘compounds - 0H i Hy i) (ii) (on (ii oo (1) i >ii> iii > iv (4) Sxi (2) ii > i> iv > ii (3) iii > ii > iv >i (4) iv > iii > ii >i62. Identify end product A, B and C of the following jo CH,CH=CH, ———+A (ii) HO (H CH,CH = CH, iy pg” B go" CHACH-CH, iy pGre 1) COG a () by in allcases (2) CH,CH(OH)CH,D, CH,CH(OD)CH,, CH,CH(OD)CH,D (3) CH,~CH-CH, in all cases D (4) CH-CH-CH,D in all cases oD Supposed you carried out the hydroboration of 1-methyleyclopentene - CH o (BH; (i) Ha02, NaOH Choose the correct answer for the product formed| in the above reaction 63. HG HGH 0 Oost (a Oe Hy¢ OH CH (ii) et (iv) Xe, H Cis © Nt (1) An equal mixture of (i) and (v) (2) An equal mixture of (i) and (ii) (3) An equal mixture of (ii) and (iv) (4) An equal mixture of (iv) and (v) In the given reaction, () BH, CHs CH C=CH iy HogoH™ X will be - (1) Butanal (2) Butanone (3) 2-Butanol (4) 1-Butanol |65. Which of the following will give cis diol ? Et. Et a) wee ea Me Et aan (2) >< oo Me a@< aad Et H a@< faite 1H Propene when react with m-chloro perbenzoic acid gives as a major product : (1) Propane-1,2-diol (2) Propane-1,3-diol (3) 1,2-epoxy propane (4) 1,3-epoxy propane Which of the following alkene(s) on reaction with IH dil.H,SO, will give ee as major product ? a \67. ag (4) Allof these Ho/H? @ <4 1) Hg(OAC), HO, los. (II) NaBH/OH (1) BH,. THF a) 0,84 Select correct statement about products A, Band C (1) Ais primary alcohol (2) Bis secondary alcohol (3) Cis tertiary alcohol (4) A and C are secondary alcohol OH Major product P is OH CHO wy OH (2) (2) HO70. nm. 72. 73. 74. OH CHO (3) ow (4) None of these H/Pd Na —Na_,, “ 5 CH-C*CH ig. yp, (A) CHs Br, (B-B3s0, (O) a Cold dil. KMnO, (D) Dean be (1) Racemic mixture (2) Meso compound (3) Diastereomers (4) Cis diols How many stereoisomers are possible for Cir GG gH oH . (1)8 (24 (3)6 (4) None of these How many different structure of alcohol and ether are possible with M.F CsH,,0 (excluding stereoisomers) ? (8 (212 (3) 16 (ay14 Which of the following pairs(s) is homologs of each other 1H H,-OH HH I Sa aac H-OH 9H 8) S and Hy 1H 1H oud. H, CH, _Br, “Ho? P Major is cH, cH, Br a) OS 2) Ce 7. 76. 77. 78. (i) MeMgBr ay (ii) Hydrolysis (2) On (8), Bis Ow 9 w Con (3) oe (4) a cH (He CH ¥ oO CH, OH Seo § 12 CHa A, Band C 1. Acid catalyzed hydration (H,0/H") 11. Oxymercuration ~ Demercuration {li Hg(OAC), / H,0 (ii) NaBH, / OH"] IIL, HBO i.e. (B,H, followed by H,0,/ 8) (1) Tin all case (2) 101, 1,1 (3) 1, 1, 10 (4) 0, 1, What is the major product of the following sequence of reaction? (ca) -cucron 85 Ms, OH | (1) (CH,),-CHCHCH,CH, OH (2\(CH,),-CHCH duct 1, (3) (CH,),CHCH,CH,OH (4) (CH,),CHCH,CH,CH,OH Consider the reaction on “Ore ro Naot ,, Xand Yare respectively o om Ly +GH,OH79. 81. 82. (4) : 7 7 . or el ‘OH ‘OH Of the following alcohols, the one which is most active towards acid-catalyzed dehydration is - (1) 2-phenyl-2-propanol -propano In which of the following case configuration about chiral (*) is retained- Me (1) Ok a> Cir Et Me 2 Tr eo a, a Me Oo ee 8 Fe? Cra Et (4) In none case End product in the following sequence of reaction is, O O,/H0 CxOH)) Saft, Swot, a, NiyMi, o a[> Among the following the one that gives positive iodoform, test upon reaction with 1, and NaOH is - (1) PhCHOHCH, (2) CH,CH,CH(OH)CH,CH, (3) C,H,CH,CH,OH (4) CH,-CH,CH,OH 83. What are A and B in the following reaction? 1 Maleio |, MoLcHO Br - Weanhc . Mgcl CHOHCH, and MgBr CHOHCH, Mgci MgCl 8) CHOHCH, (4) None of these Which of the following dehydration major product is incorrect? ‘CH,OH on Oe 04 O =e cH eH —¢— cH oH cone. H3804 J CH, APE HSH, cH, aa oe cH, (3) cH cHcH cron BHO, cs, —cHtmcH—ce ‘CH; nol (CH; 4) Ces a KG ‘OH ‘CH; -on oe A PHOH (CHOC c CH,OH A,B, C, D respectively are (1) | Salicylie acid, salol, aspirin and oil of winter green. (2) Salicylic acid, aspirin, salol and oil of winter green (3) Salicylic acid, oil of winter green, salol and aspirin (4) None is correct86. When phenol is allowed to react with Br, in (i) CS, solution and (ii) in aqueous solution, the resulting compounds are| (1) (i) 2,4,6-tribromophenol and (ii) o-and p-bromophenol (2) (i) m-bromophenol and (ii) 2,3,4-tribromophenol (3) (i) o-and p-bromophenol and (ii) 2,4,6-tribromophenol (4) (i) o-and m-bromophenol and (ii) 2,3,4-tribromophenol OH 87. (Cpt ear Product 'P' is . ° Cl a) (2) f ° i a on OH ve ve 88, Sw, 8) CH,OH OCH, Product (A) and (B) respectively are OH OH TOs oO Ger ar” ‘o i on ee 6) rr & on Gye OH CHOH OCH (i) He(OAc),/H,0 89. +, (ii) NaBD, H (2) 1 (4) D BryH,O 9. cis-2-Butene —PO_, cH, cH, H OH H OH ()H —— Br (2) Br H CH CH; CHS CH; HC: OH H,c—|—.r (3) Br H (4) HO—+—H H H H | 7 eo Major product : (1) (2) (4) All of these92. 93. 94. 95. In the given reaction NO, as J -OC>H; a Br @ aHs ‘NO, NO, OCH; Br OCHs © ‘Br 3) (4) NO; Hs Ph—C == C—CH, —Hs“H22 5a. Ais - oO Pe a s a HC HC OH "I ’ 6) $ @) "yon HC HC When phe! magnesium bromide Sebcts with t- butanol, the product would be - (1) Benzene (2) Phenol (3) t-butylbenzene (4) t - butyl phenyl ether In the following reaction sequence, the correct structures of E, Fand G are 9 9 AA Heat Phi * OH elqeyrlhl+ (6) (* implies oo labelled ~“ ° () B= Ay Fe ws ‘8 Na G=cHL, 9 9 Aagren? 82 (2) B= piv ‘0 Na G=CHI, 9 i) DN Ay ° & (3) E= pr CH, F= PH ‘0 Na G=CHI, 9 ro) A. ° (4) B= pt | SCH, F= PH Na G=G os" ( ) oF CH, : am 704" [8] [A] & [B] are respectively : HoH H H3CO & QQ) OH;C —CH,OH HO CH; Hi 1H H3cO & = | HOH HO CH, HH, H Ol & (3) | HOH HCO CH, Ho Hy & (4) HCO OH HCO OH97. CH,-CH = CH, 2/200 _, A+CH,O Reduction|H,/Pd B Bis: (1) CH,CHO (2) CH,CH,OH (3) CH,CH,COOH (4) CH,COOH oO (1) Naol ot. a. 98. Product is : c—cH, G4 § 0 (1) CHI, & @e ‘CHO go (2) CHI, & ‘COOH 0 (3) CHI, & CY COOH (4) CHI, & COOH “OH Cone. HSO, A Major product is 8 (4) None CH, a) H, (3) a Find out the correct order of rate of dehydratio: for given compounds with conc. H,S0, ooaloaiol 100. Oo, @ (a ay) (1) l>> U1 > IV (2)1>1>1>1V (3)1>Uh>Iv>n (4) Il >1>I>IV 1101. Alcohols, which have two hydroxyl (-OH) groups are called: (1) Allylol (2) Diols (3) Phenol (4) (2) and (3) 1102. Primary alcohols are obtained by the reactions of Grinard reagent with: (1) CHsCOCHs (2) HCOOH (3) HCHO (4) CHsCHO 103. Ethyl alcohol containing 9.5% methyl alcohol and 0.5% pyridine is called: (1) Spirit (2) Denaturated spirit (3) Rectified spirit (4) Absolute alcohol = am N04, 2 PE A tt A828 CH, - CH, CH - CH; Zs ou (1) CHsCH2CH(OH)CHs (2) (CHs)2CH-CH20H (3) CHeCH2CH.CH20H (4) Both Land 3 105. Acetone is treated with sodium amalgam and water gives: (1) (CH,),CHOH (2) CH,CH,CH,OH (3) C,H,OH (4) CH,CH,COOH 106. The boiling point of alcohol is much more higher than alkane due to: (1) Presence of intermolecular hydrogen bonding (2) Absence of intermolecular hydrogen bonding (3) Presence of intramolecular hydrogen bonding (4) None of these 07. Most viscous among the following is: (1) Propan-1-ol (2) Propan-2-o1 (3) Propane-1,2-diol (4) Propane-1,2,3-triol ho8.In the reaction, C,H,OH > C,H,X "5 Cis: (1) Pentane (2) n-Butane (3) Isobutane (4) 2-Methyl butane 09. Ethanol when passed over ALO, at 623 K gives_ (1) diethyl ether (3) butane (2) ethane (4) ethylene