EXERCISE #1 IH 06H +e Lene SOL, Major product: “ + 6) =< >. (D) None of these Correct order of dehydration of following alcohols will be : Con ©) -on (S-0n Con \ 2 3 4 (A)1<2<3<4 — (B)4>3>1>2 (4>2>1>3 (D)1>3>4>2 Dehydration of the isomeric alcohols le . rT © a ay ™ What will be the order of rate of reaction ? (A) IV>I>I>1 (B)I>I>MI>IV (C)IV>II>IN>1 (D)M>IV>1>I1 Find out major product of following reaction. CH, CH, Ph pp £00 14804 OH OH Q Ph f HH 3 1H, 3 h (A) Ph tn, BPI Ph (C) CH—C—+-Pn (py CH, Ph cH, cH, Ph on H, H, "—CH = CH, —>H,C—C—CH—CH, , This interconversion can be achieved by : Hy 1H,OH (A) Acid catalysed hydration (B) Oxymercuration-demercuration (©) Hydroboration - oxidation (D) Any method mentioned above ‘4 fi. He (OAc), HOH (ii) NaBH, O1F (A) O (B) O © O (D) (A) or (B) 1-Methylcyclohexanol. Here A is :1. 10. nu. 12. He, cucu, Rees” a cus ccH,08 Cen ty Select schemes A, B, C out of () Acid catalysed hydration (I) HBO (II) Oxymercuration-demercuration (A) Linall cases, (B) 1,0, (OU, M1 (D) 11, 1,11 HBO, oxymercuration-demercuration and acid catalysed hydration will give same product in ay oC © O ©) oy Which of the fotlowing ethers is least reactive to cleavage with cone. HBr ? (A) Ph—CH,—O—CH, (B) Ph-O-Ph_ ANAND) -0-L Consider the reaction of HI with the following: Which forms di-iodide on reaction with HI (excess)? (A) Land II both (B) Honly (C)lonly (D) none Find out major product of following reaction. OH Je aes oO “ Od @) © ©) On In the given reaction Hc. OMe OMe (A) u,c—¢—cH,—cH, (B) me CH; Hy (© H,C—CH—CH,—CH, (D) H,C—CH—CH,—CH, Hy Hy14, 15. 16. 17. In the following reaction S ne > Product ‘The major product is : HH HH HH a) B) Cy © @) on CH;OH CH.OH CHy Qe le Qa 0 ‘CH CH cH CH; on om on (CH,),C=C(CH,), >A —O, B, Product'B'is 10” " timitedamount (A) (CH3)2C-C(CH3)y @) (CH).¢—CH), \f OH Cl (© (CH,),C—C(CH,), (D) None. | OH OH Find out correct product of reaction : OO Br, (A) (B) © OO »OCweCQu. eGQkn + HI —> Product, Product is : (x ce) (A) k @) k © K ) H I Io" on” I~ on™18. 19. 20. 21. Pcl, dil HO, Sn SO 7 x Ahoy @ ; Fis: CH, (A) CH,-CH,-CH,-OH (B) H,C-CH-CH, (C) oon ~ CH, - OH (p) CH, - CH = CH, 7 cH, When 2-chloroethanol is warmed slightly with dilute NaOH, the major product formed is : (A) CH,~CH,-CH,-O-CH,-CH,-Cl_—_(B) HO-CH,-CH,-CH,-CH,-OH (©) HO-CH,-CH,-OH () WV How many total alcohols are form by acidic hydrolysis of following ether. ao (ays B)6 ©7 (D8 Which of the following test can be used to differentiate methyl alcohol and iso-propyl alcohol. (A) Litmus paper test (B) Bromine water test (©) Lucas test (D) All of these (On reaction of ether with BF,, ether acts as : (A) Electrophile (B) Nucleeophile (C)Ambiphile (D) None Give suitable major product for following reaction Cl, (AH, -R eo, (® ]+R-cH,-0n ef) 1H, - 0; * no So“ © oe +R-CH,OH ) Woh CHHOH, ()-cu- cr, Seen CH,CH, (A) (B) CH,CH, (C) oO H-CH, ‘OCH,CH, CH,CH, 'OCH,CH, H.-CH,21, 29, ° Hom" oo" CH, Product 'X' will be : (a) ST » £¥a © ae () All of these Ho’ Hy uy Ho Wye ot QE SEN? reduc, Product is : (A) H,C—CH-CH,—CH=CH,—CH,_(B) HyC—CH—CH,—-C=C—cH, Me OMe © ace =c—cH, @) Hee Si C=ee— CH, The product of the reaction is : WA] ae LkH =r aon a ay acy (© HS-CH,))-O-Bt_(D) HS-(CH))-CH OH Identify the major product of reaction : Ts, _KStL ) SHB) AZé0 RE No reaction a oH 4 cose or PBs KEN, Final product is ? St a cH, 7 (A) CH,CHy ct xe (© cHcHy Diethyl ether on eat exposure to air gives (A) Ethanol (B) Diethyl peroxide (C) Diethyl hydroxy peroxide (D) Bthanoic acid WN Ais Be ee cr cu,EXERCISE # 2 chiex Cre AMES Product What is the product ? (A) Enantiomer (B)Diastereisomer (C) Meso (D) Achiral (@ cueN RMsx 0 CHEN, B) : RMX ar” A) aer> (B) CB) will be: (A) 1° ROH (B) 2 ROH (©) 8 ROH (D) Alkene Br "Gy ME, (a) 002, =r) (B) AHS) gas, product Cis: anny (a) co (B) Co, (Co, (D) Aminxture “CO, and CO, oe (vs same? a0: te Product Product of reaction is : OCH, 1 Ch’ ese ‘CH, HI 1H © : D) hen, L enon © no“n con, CH, CH; OH MeBr + > X+Y Soi (lea) X and Y are respectively : co8mger ) © only @) and oO sf Co) O and oO (D) None of these¢ elles PMB (excess) (X) ; Product (X) is: H,0' 9 a ee 6) ph_t_ph OH © Ph—C—Ph (D) Ph—C—O—Ph Ph 7. PhMgBr+H,C—C=n "2 5 product : ee A cea (A) Ph—C—cit, (B) PPh (Q)HjC7~ “CH; (D)Ph~ ~CH, Ph 2CHMeBr 8. — wy ano > Méjorproduet IH IH (a) B) Woy OH © Ay (D) Noreaction x RM 9. el. oe, 3° Alcohol. Find out value of X’. (A)2 (B)3 (4 @)1 SH SH Hs yay. (0) CH MB A WAP HN WK (Hn,0 HO’ (A)2 (B)3 «4 (@)5i 12, 13. 14, 15. s MgBr Identify (X): 1H (D) ° Qa oman Qe oo HO’ HO’ 1H If phenyl magnesium bromide and acetaldehyde are the reactants, the product formed after hydrolysis. would be : (A) Benzyl alcohol (B) 1-Phenylethanol_(C)2-Phenylethanol (1D) Acetone °, : + CHMgbr 2ALO, p Br, 9 ME» R HCHO, s, sis: HHA0 1H ‘OH 2 ne) ol oa CH,MgBr + Hol, 4, y Malate, ¢ 1 pM ¥ Product E is ols 9 QQ T oT G5 dios, on, oe Which of the following reagents (A to D) would you not select to convert C,H,COCH, (acetophenone) to the following alcohol ? 1H, CH, CHC — Sen OH (A) CH,CH,CH,MgBr and hydrolysis (B) CH,MgBr and acid hydrolysis (C)(CH,),CHMgBr and acid hydrolysis (D) PhMgBr and acid hydrolysisHy 1 KCI 2 HE OH S22 5 4 KON CHaMess 16. HOHM® °° Et the final product C is : Et Et Et Et : Hi : j ve OH (a) H, B) n, Ocuy ©) cuy 0 0 0 oO 17. Which combination of reagents will not bring about the following conversion ? oy (A) MeMgB1/H®, H,SO,/A, HB1/H,0,, hv (B) MeMgBr/H®, H,SO,/A, HBr (C) MeMgBr/H®, HBr/CCl, (D) MeMgBr, NH,Cl Paragraph for Q.No. 18 to 19 Alcohols are converted to tosylates by treatment with p-toluene sulfonyl chloride (TsCl) in presence of pyridine. This overall process converts a poor leaving group (OH) into better one (OTs). A tosylate is a better leaving group because its conjugated acid p-toluene sulfonic acid is strong acid. Because alkyl tosylates have better leaving tendency they undergo both nucleophilic substitution and elimination, ar i] c,cH,-+6H ro -{)- cH, —Putsine pooreaving Tayler co wish t — CH,CH,—O-S. cH + J +i § an h Or CH,CH,-LOTs| 1 Better leaving group os Nn. 8 ee NaOCH; + CH,CH,+OTs —"—> CHjCH,-OCH; + NaOTs Bohs Gen, sts —2—+ 4,0 = CH, + ROT (Alcoholic) Banat enone18. 19. 20. Find the major product of following reaction : HC, 9 a tl ridine : sonra + Vcr dine_, KCN, CH,CH, § wy YSc_en (B) CH,;—CH= CH,-CH,-CH,-OH > CH,-CH,-CH,-CH,-OH (Solubility in 1,0) (B) CH,-CH,-OH > CH,-O-CH, > CH,-CH,-CH, Boiling point) (© Pentan-1-ol > Pentanal > Ethoxy ethane (Boiling point) (D) CH,-OH > CH,-CH,-OH > CH,-CH,-CH,-OH (Boiling point)EXERCISE # 3 Bryhy ConcH,S0, o, Abe Ale KOH 1804 5 ayaa" 2? arte (Major product) Find out the structure of ‘A’: ‘Hy (A) a oO © a () A Predict the reducing agents in foflowing reaction. Ont, 1H (A) LialH, (B) NaBH, (C)H,/ Pt, A (D) Both (A) and (B) Find out the product when the following compound react with NaBH, : ‘OCH; A) aon ®) “Cn Qo omer © aCe ‘Compound whieh does not give alcohol on reduction by LiAIH, is/are ? Me-CH-CH,, f g anergy’ Mop N ONS? (@)Me-C-0-C-Me Choose the incorrect option ? (A) Boiling point increases with increase in carbon due to increase in vander wall forces (B) Branching in carbon decreases the boiling point (©) High boiling point of alcohols are mainly due to pressure of intermolecular H-bonding (D) Methoxymethane has higher boiling point than ethanol & propane Ethoxyethane & butan-1-ol are miscible to almost same extent (7.5 & 9 gm per 100 ml water respectively because of : (A) Same molecular mass (B) They are isomers (©) Both can form hydrogen bond with water (D) Wateris universal solventHy 7 a) Find out ‘A’ of the reaction H 1H H HOH HO CH,OH ) ®) © 00C,H,, 8 —tultL, ; Products of the reaction are : (A) Racemic (B)Diastereomers _(C) Meso 9. Reduction of R—CH,OH —> RCH, can be carried out by : (A) LiAlH, (B) H,/ Ni (C) Red P + HI H,co__ocn, 10. O SEL, (x), Product (X) is : Aa HO, IH H,CO._OCH, (B) 0 © HH ‘OH H 11. Select the correct synthesis Ul H(OAe) NaBH, NaOH er ame CT ©) (Os: +(CH),CONa => uscoXO) ae) (D) Optically pure (D) NaBH, / AICI, @)12. 4, Identify the final product of following sequence of reactions : Cron Fl» HE KOHL, 030 Gi) HIO, @) a @) Pry ° hy © ) Che and its enantiomer HH Which of the following reaction is not possible ? (A) CjH,OH + HBr —> C,H,Br + H,0 (B) (CH,),CCI + NaOCH, —> (CH,),COCH, + NaCl no . ows 1+ CHONa SO, AY : VK aust 2 energy, OH ‘Which of the following reactions proceeds with inversion of configuration ? Me (A) Hon Na SEB, Et Me (@) HL on G1, 1L0N Et Me © Lon Fey St0N Et : Ph (D) Hy} -0H Sh, KCN, cH,15. CH,-CH-CH=CH, _ Reagent cH, Alcohol which is true about alcohol and Reagent ? List-I (Alcohol) (A) CH, -CH-CH, ~CH,OH CH, (B) CH, ne iaeh med CH, OH i (©) CH, -C-CH,CH, H; I (D) CH -CH-C-CH, CH, List-IT (Reagent) (P) BH, , H,O, / NaOH (Q Hg(OAc), , H,O / NaBH, followed by P.C.C. (R) Hg(Ac), H,0 / NaBH, (S) dil. H,SO,EXERCISE [AIN) ds In the following sequence of reactions CH,CH,OH ——2-> AME» p HCHO, ¢_Ih®, p then compound 'D' is - [AIEEE-2007] (1) Butanal @)n-Butyl alcohol (3)n-Propyl alcohol (4) Propanal A liquid was mixed with ethanol and a drop of concentrated H,SO, was added, A compound with a fruity smell was formed. The liquid was : [ATEEE-2009] (1) CH,COCH, = @) CH,COOH_—@3) CH,OH (4) HCHO From amongst the following alcohols the one that would react fastest with conc. HCl and anhydrous ZnCl is: [AIEEE-2010] (1) 1-Butanol (2)2-Butanol (3)2-Methylpropan-2-ol (4)2-Methylpropanol Consider the following reaction : [ATERE-2011] C,H,OH + H,S0, > Produce Among the following, which one cannot be formed as a product under any conditions ? (1) Ethyl-hydrogen sulphate (2) Ethylene (3) Acetylene (4) Diethyl ether An unknown alcohol is treated with the "Lucas reagent’ to determine whether the alcohol is primary, secondary or tertiary. Which alcohol reacts fastest and by what mechanism :-_ [AIEEE-2013] (J) secondary alcohol by SN! (2) tertiary alcohol by SN" G) secondary alcohol by SN? (4) tertiary alcohol by SN? Allyl phenyl ether can be prepared by heating: (JEE-MAIN-2014) (1) CH,=CH-CH,-Br + C,H,ONa (2) CgHs-CH=CH-Br + CHy-ONa (3) CoHsBr + CH;=CH-CH,-ONa (4) CH,=CH-Br + CgH,-CH,-ONa In the Victor-Meyer’s test, the colour given by 1°, 2° and 3° alcohols are respectively :- (1) Red, blue, colourless (2) Colourless, red, blue (JEE-MAIN-2014) (3) Red, blue, violet (4) Red, colourless, blue Williamson synthesis of ether is an example of (JEE-MAIN-2014) (1) Nucleophilic addition (2) Electrophilic substitution (3) Nucleophilic substitution (4) Electrophilic addition ‘The gas evolved on heating CH;MgBr in methanol is : [JEE-MAIN-On- () Ethane (2) Propane (3) Methane (4) HBr10. i. 12. 14. Bouveault-Blanc reduction reaction involves: (JEE-MAIN-On-line-2016] (1) Reduction of an ester with Na/C,H,OH (2) Reduction of an ester with H/Pd (3) Reduction of a carbonyl compound with Na/Hg and HCI (4) Reduction of an anhydride with LiALHy ‘The major product the following reaction is [JEE-MAIN-On-line-(Jan)-2019] —, (ii) EtOH OEt OEFt Br OEt OEt OEt Br a @ LC 3) a) ‘The major product obtained in the following conversion is :- [JEE-MAIN-On-line-(Jan)-2019] Br,(1 equ) \f_Meou CH,. CH, CH,. Br ae cue Me rr 1 | (2) 3) 4) y (a) Q) _ a ‘The major product in the following conversion is : [JEE-MAIN-On-line-(Jan)-2019] cuo-<_Y-cr-ci-cu, Hes 2 a Ho-{O)~cit-Chi-chy, @) Ho-{O)-cH-cH-cH, Br Br (3) croX{O)-ct ee (4) cno{ genet, jr © ‘The major product of the following reactions: OCH, om econ) CH=CH, OH ee Br OH CH,CH,Br (CH,CH,Br Br-CHCH, Br-CHCH,15. The mojor product of the following reaction [JEE-MAIN-On-line-(April)-2019] 6 ; 16. ‘The major product of the following reaction is : ON sess) [JEE-MAIN-On-line-(April)-2019] noo om 1 . oe > ov NC“™I Nc~SOH ‘OH 1 oS S Nc“ ~OH NC“™1 17. Consider the following reactions : [JEE-MAIN.On-line-(April)-2019] —A80 opt A ear Turbidity He" iH", , NaBH, ZnCl, Wn Zone. HCP 5 Minutes ‘Ais: (1) CH=CH (2)CH;-C=CH 3) CH=CH, (4) CH,-C=C-CH, 18. Heating of 2-chloro-1-phenylbutane with E(OK/EtOH gives X as the major product. Reaction of X with Hg(OAc),/H,0 followed by NaBH, gives ¥ as the major product. Y is : [JEE-MAIN-On-line-(April)-2019] ou a ao pp70N OH oa OIA OH19. In the following reaction squence, structures of A and B, respectively will be : [JEE-MAIN-(Jan)-2020] ‘OH ® nn §O3 OH OH oOo" GO °CH,Br 20. _I-methyl ethylene oxide when treated with an excess of HBr produces [JEE-MAIN-(Jan)-2020] be Br Br Br = 2>3 (B)3>1>2 (C)1>3>2 (D)3>2>1 Oy Ons Cyr Stoo) [JEE 2003] C,H,0H tyro) “ (Oy-ocat, B) (On (©) CHjOC,H, (D) C,H,OC,H, Reaction of entainomerically pure acid with 1 chiral carbon and racemic alcohol with 1 chiral carbon gives an ester which is: [JEE 2003] (A) Meso (B) Optically active mixture (©) Racemie mixture (D) Enantionmerically pure Onacid catalysed hydration, 2-phenyl propene gives: LJEE 2004] (A) 3-phenyl-2-propanol (B)2-phenyl-1-propanol (C) L-phenyl-3-propanol (D) 2-phenyl-2-propanol Phenyl magnesium bromide reacting with t-Butyl alcohol gives UJEE 2005] CH Alls (A) Ph- OH (B) Ph-H (C) Ph-O-C-CH, (D) Ph-C-CH; Nei Neu: b 3 In the reaction € poo HBr, the products are [JEE 2010] (A) proc, and H, @) Cpr tent cHBr © Cris naction ) Cpe and CH,Br10. ‘The major product in the following reaction is c. 1. CH.MgBrr, dy ether, °C LCHMeBr dry ether, 7G I, 2 ag acid HC. R a ay tt nay (B) H. Nn Hy . CHy? © () CH; 07 SCH, 0” CH; The acidic hydrolysis of ether (X) shown below is fastest when [JEE 2014] (Non (VL ont + non O QO (A) one phenyl group is replaced by a methyl group (B) one phenyl group is replaced by a para-methoxyphenyl group (C) two phenyl groups are replaced by two para-methoxyphenyl group (D) no structural change is made to X The correct combination of names for isomeric alcohols with molecular formula C,H,,0 is/are- [JEE 2014] (A) tert-butanol and 2-methylpropan-2-ol _(B) tert-butanol and 1, 1-dimethylethan-1-ol (©) n-butanol and butan-1-ol (D) isobutyl alcohol and 2-methylpropan-1-ol13. 17. peer Sol. Sol. ‘Ans. (B) Ans. (B) Ans. (B) Ans. (B) Ans. (A) Ans. (C) Ans, (A) Ans, (C) ‘Ans. (A) Ans. (C) Ans. (B) Ans. (B) Ans. (B,C.D) Ans. (B) Ans. (D) Ans. (C) Ans. (A,B,C) Ans.(3) Ans, (1) ANSWER KEY EXERCISE # 1 CHONa+ CH-CH-CH.{Br—> ‘Ans. (1) Vietor Meyer's Test TPAlcohol Conc. HI Red P+ C\H,0-CH,-CH=CH, Allyl phenyl ether AgNO, enon SS, Rent AO R-C-NO, ul Now Ni ed |ssott Blood Red colour 8. Ans. (3) BEBRBS A) “Ans. (©) Ans. (C) Ans. (A) Ans. (B) Ans. (D) Ans. (A) Ans. (B) ‘Ans. (D) Ans. (A) Ans. (B) Ans. (A) Ans. (D) ‘Ans. (B) Ans.(B) Ans. (B) 2 Ans.(C) 3 Ans.(@) 6. Ans. (D) 7. Ans. (©) 10. Ans. (C) 11. Ans. (B) 14. Ans. (B) 15. Ans. (A) 18. Ans. (B) 19. Ans.(D) 22. Ans.(B) 23. Ans.(C) 26, Ans. (B) 27. Ans. (A) 30, Ans.(C) EXERCISE #2 2. Ans. (C) Ans. (C) 6 Ans. (C) 7. Ans. (D) 10. Ans. (C) 11. Ans. (A) 14. Ans.(D) 15, Ans.(A,B,D) 18. Ans. (C) 19. Ans. (A) EXERCISE # 3 2. Ans. C) 3. Ans. (BY 6. Ans (C) 7. Ans. (C) 10 Ans. (C) 11. Ans. (A,B,C) 12. 14. Ans. (B,C,D) 15. Ans.(A)->P; (B)>R; (C)S; D)>Q EXERCISE # 4 (J-MAIN) 2. Ans. (2) 3. Ans. (3) 5. Ans. (2)2Alcohol ection C28 HL, pcp ABNOS Red} wctho,— (ano, 41180) so, RENO, ho Peruri [sso Ble our $°Alehal acon EE ey BNO, ed, neo, (avo, #1180) No, Txsott cole 8. Ans.(3) Sol. Nucleophilic substitution RB Na+ R’-X—+RO-R’ Ke 9. Ans.) 10. Ans.(1) 11, Ams(4) 12. 14. Ans.(4) 15. Ans(4) 16. Ans.(1) 17. 19. Ans.(4) oH Sol. & . H,-Br nee eo) [pseter OH Ans. (2) Ans. (2) 13. Ans. (2) 18. Ans. (4)Sol. ae Sol. Sol. Ans.(4) Br CH, QI SH, > CH,— Gps Hip? CH,- du CH, 2 ? Br iH EXERCISE-5 (J-ADVANCE) Ans. (A) 2. Ans.(B) Ans.(D) 4. Ans.(B) ‘Ans. (D) 6 Ans. (B) 7. Ans.(D) Ans. (D) ch . t oe r-bond give nucleophilic addition reaction] eaving group) give substitution (® Grignard prefer to give nucleophilic addition on polar n-bond and form anion intermediate. cre Se Mg cl—+ ch - (ii) In next step anion give intramolecular nucleophilic substitution reaction & form 5 membered ring. h Phow HO'+ mon —— ph- ce h 7 Ph ©, no 1f2Ph groups are substituted by 2MeO—{©)— groups then carbocation formed in above sequence is more stable and rate of above hydrolysis increases10. Ans. (A,C,D) ‘The combination of names for isomeric alcohols with molecular formula C,H,,0 is/are Hd Formula Names CH,CH,CH,CH,OH n-butyl alcohol /_ n-butanol / butan-1-ol CH,-GH-CH-OH isobutyl alcohol / 2-methyl propan-I-ol cH, CH,-CH,-CH-OH CH, Secondary butyl alcohol / butan-2-ol CH, cui-t-on CH, Tertiary butyl alcohol / tert butanol / 2-methyl propan-2-ol, /1,1-dimethy! ethan-1-ol