ceNII Bala M.S. Chouhan WE REL ORGANIC CHEMISTRY _ JEEo gogaao0 SHR! BAN ee aTHGUTORSI FEDUGATIONAL PUGLISHERS & DISTRIBUTORS) | 6, Gulshan Vinar, | Opp. Mahalaxmi Enclave, \ Jansath Road, Muzaffarnagar (U.P.) | Phone : 0131-2660440 (0), 2600503 (R) | website : www.shribalajibooks.com i NL Published by: ' SHRI BALAJI PUBLICATIONS - ‘email : sbjpub@gmail.com First edition: 2008 " Second edition : April 2008 : Third edition: April 2009 Seventh edition: April 2013 Eighth edition: April 2014 ©All Right Reserved with Author Price : = 480.00 Typeset by : Sun Creation Muzaffarnagar All the right reserved. No part of this publication may be reproduced, stored in 2 retrieval system cr transmitted, in any form or by any means, electronic, mechanical, photocopying, recording of otherwise, without the prior permission of the ‘authors and publisher. Any violationfbreach shall be taken into legal action.Dedicated to the Lotus feet of Revered Guruji SHRI KESARAM JI MAHARAJAdvanced Problems in ORGANIC CHEMISTRYIt is a matter of great pleasure for me to present the eighth edition of “Advanced Problems in Organic Chemistry for JEE” before JEE aspirants. During my teaching experience, I felt that the facts may be made more and more clear to the students through problematic approach. Although an ‘ocean of material in Organic Chemistry is available with the students, yet the approach to design the problems has been changed in recent years and if one tries to swim in this ocean, it will be a very difficult task. To make the students more familiar with trends and tricks how to solve problems, the present problem book has been presented. In the current scenario of stiff competition especially for JEE, one must be clear that almost all the sincere applicants are well equipped with the facts of subject, yet the winner is one who knows how to use these equipments with accuracy and efficiency. AS an experienced teacher, I would like to suggest students three golden rules toscore high in OrganicChemistry: 1. Don'tgetbehind 2, Workoutanumber ofproblems of differenttypes 3. Revise through short notes / learning chart. Thope that the present book will cater to the needs of JE aspirants & as, a matter of fact, they will enjoy the present venture and I would feel rewarded if this book is found helpful to the students and teachers in real terms. All attempts have been made to make the book error free however a few misprints may inadvertently creep. J acknowledge the blessing and support of my mother Smt. Raj Kanwar, father Shri B.S. Chouhan, brother Dr. VS. Chouhan, my wife and daughter, They inspired meal the time during the preparation of this book. The support and valuable suggestions from my colleagues especially Mr. N. Avasthi, Mr. VX. Jaiswal, Mr. Nitin Jain, Mr. N.K. Sethia, Mr. Vikash Gupta, Mr. Pankaj Joshi, Dr. S. Kothari, Mr. Vineet Khatri, Mr. Ashish Mishra, Mr. Manish Arora, Mr. Govind Khandelwal, Mr. Rahul Pareek, Mr. Rahul Malav, Mr. Akshay Choudhary, Mr. Hanuman Sahay, Mrs. Neha Joshi, Mrs, Neetu Jha, Mr. Kamlesh Gupta, Mr. Kumud Ranjan and Mr. KD. Tiwari are highly acknowledged. I also pay my sincere thanks to all the esteemed members of M/s Shri Balaji Publications in bringing out this book in such anice form. In the last, constructive criticism and valuable suggestions from the readersaremost welcometo make the bookmore useful. M.S, CHOUHAN email: mahen_chouhan@yahoo.com Mob.(Only for SMS) : 09828025625A few words to the JEE Aspi Dear JEE aspirants, | hope that this collection of problems will surely help you during your preparation for JEE. In this book, each chapter consists of two levels : Level 1 - includes the problems having only one option correct. ‘These problems are based on different facts and their twists. Level 2 - includes unique approach which may be used to solve the problems altogether different from the prevailing trend followed by JEE, These approaches will undoubtedly help you in the quick revision of the key facts and their applications. 1 wish all of you a grand success in the ensuing Joint Entrance Examination. Your valuable suggestions and constructive criticism for the betterment of the book are welcome. M.S, Chouhan e-mail : mahen_chouhan@yahoo.comeneral Organic Chemistry ~~ Isomerism (Structural & Stereoisomerism) [547 TAllo Hatides (substitution Reaction) Alkyl Halides (Elimination Reaction) ——————[—[—_———— Alkyt Halides itheir Derivatives’ ‘| S05] —— awa] CEN Practical Organic Chemistry "ear [Ga Taoneeais [is JuuracNames ss O™OC~—SSHow many 2° Hydrogen atoms are present in the given following compound ? Son @2 5 oO7 @s Identify which functional group are Not present in the given following compound ? 9 NH oO (a) Ketone (b) Ester (¢) Amide (@) Ether Correct energy profile for amine inversion and hybridization of nitrogen in transition state is: tt = wh b T= WUT (a) ®)@ 0) @) “o ®B @ L____, L_____, 4 s A se © @ /\ ® ) a ® L___, L___, o Gio Gi Compare the heats of combustion of above compounds: @ O >> Gi) ©) @>G)>G © G>@> Gi @ Gi) > Gi) > 0 Which of the following is not a resonance structure of the others ? 9 9 9 Z . = @ © o @ Rank the hydrogen atoms (Hq, Hy, H) in the following molecule according to their acidic strength. HH @a>b>c (b)b>a>c © b>e>a @c>b>a ° I CHy —C—0-— CH; ‘Compare the bond lengths a and b. (@a=b @) b>a @b © cf @) Dun Diacone lactone frlactone Sclactam ‘The functional groups present in Cortisone are : HOH, ©. is och, 9 Cortisone (a) Ether, alkene, alcohol (b) Alcohol, ketone, alkene, ether © Alcohol, ketone, amine (© Ether, amine, ketone Select the acid with the highest K, ((e., lowest pK). Oo Oo Oo (@) W367 “OH py Cl ©, Oa Most stable carbocation among the given example is : CH @ @ L—F © ANY e © CO-% (@ cH, Set the following in increasing order of their pK values. ° ° I II @) Cs 0-H @) CH; —C—O—H — @) CH; —OH oO @y 99 a}xdst0 racine rofsssilig os “0 fir om msl < Td) vo 19. Circle represents most tbat, atoms,in these molecule. Which of. che llowine 5} correct Gree anne i ft 27. Se ted bond angl hevcarteo ase! urd: to their ok trot the lowest ee (3 Sa “B: a 4 beat) ¢ Bites oc a KO) “ ie) ia oy N @ oe at f < Ay tig Qxeons nojeorh)s cod wash ko ayameo = aad2>4>310'° * ()3>%4>2>1 ese oD ©2>4>1>3 2 meres LPR I> 24 ov, cosy 33. Which of the following has lowest pK, value ? 1m {78 OME oh Onno @) @) CH ? sow Ye . me * chon Farene ins saetusb oA +35. 36. 37. 38. Arrange the following (w, x,y, 2) in decreasing order of their boiling points: ODO 1H ow) oo) ” @ @w>x>2>y Owox>y>z Ow>z>y>x @wos>x>y Arrange the following in increasing order of their acidic strength. QO ‘OCH; o a O am a c $ ‘Oo ‘O” @mx>y>z (b)w>z>x>y (z>w>x>y Warx>wry Arrange the following alcohols in decreasing order of the ease of ionization under acidic conditions. TP OLD OLD am (a) 1>M>1 . wisnem @ U>M>T @u>i>m ‘Among the isomeric amines select the one with the lowest boiling point. H | CHy N i NH, N, @ O o ‘o © O @ O CHy Which one of the compounds shown below, is not an isomer of the others ? @ C) O) o-~ Arrange the anions (p) CH3, (q) NHg, (r) OH™, (s) F”, in decreasing order of their basic strength, (@p>q>r>s (@)q>p>r>s ©r>q>p>s Wr>p>q>s One among the following compounds will not give effervescence with sodium carbonate: 1H OH NOz, NO. (@) CeHsCOgH = (b) {© CeHsOH @ NOg The carboxylic acid which has maximum solubility in water is: (a) phthalic acid (b) succinic acid (© malonic acid (@) salicylic acid46. 47. 49. 50. 51. 52. 53. Among the following compounds, the most basic compound is : me) 0) { * ol 3S wh) H oO H aa H Arrange the (C-H) bonds x, y and z in decreasing order of their bond dissociation energies in homolysis. @y>x>2 (b) > x>y (@ z>y>x @y>z>x 23 g of sodium will react with methyl alcohol to give : (a) one mole of oxygen (b) 22.4 dm? of hydrogen gas at NTP © 1 mole of Hy (@) 11.2 L of hydrogen gas at NIP Which of the following is most polar? O © © fa) (b) (©) d) . ° o < NH; < N-H: € ™N; © The correct order of decreasing basic strengths of x, y and 2 is : @x>y>n (b) x>2>y © y>x>e @y>z>x Which of the following is the strongest Bronsted acid ? NH, NH, Which of he following i the strongest Bronsted base ? NH, H # | k N. @ o AV o¢ 7 @¢0 > H H Which of the following is polar aprotic solvent ? (@) DMSO (b) Crownether —() DMG (d) Alllof these OH55. 56. 57. 58. 59. 60. ‘Some pairs of acids are given below. Select the pair in which second acid! (@) CH,CO3H and CHFCOjH (b) CH FCO 7H and CH,CICO2H (©) CHyCICOH and CHyBrCO2H (@) CHCH,CHFCO 2H and CHyCHFCH2CO 7H stronger than first H—cCmctc=aclcny; ‘Compare the bond lengths a and b: (@a=b ()a>b (Ob>a @a>>>b Which (isomeric) amine has lowest boiling point ? (@) 1° amine (b) 2° amine (© 3° amine (@) cannot predict cl ‘ed 280, P ; Pwill be: i @ (b) 2sbel? © OC (4) mixture of (a) and (b) Which of the following substances is not an isomer of 3-ethyl 2-methyl pentane ? @ ~~~ ) © (d) All are isomers Which of the following is an isomer of compound 1 ? oO CH3CH2CHO CH3 —tocay CH, —CH=CH—OH CH,—CH—CH, a) @ @ NoZ% w (a) 2 0) 4 (c) 2and3 (d) all are isomers Br Which statement is incorrect in respect of the above reaction ? (a) Product is aromatic (b) Product has high dipole moment (©) Product has less resonance energy (d) Product is soluble in polar solvent61. 62. 63. 66. 67. Some pairs of ions are given below. In which pair, first ion is more stable than second? @ ® (a) CHy —CH—CHg and CH; — CH—OCH, 8 ® () CH3 — CH — CH CHy and Cy = CH—CHy —CHp Cay CH, (Oo a CH, CH, —N —CH, @ and | Hy —by- cr, cH, —c®—cH, Among the given pairs in which pair, first compound has higher boiling point than second ? (@) CHy —CH,OCH, and CH, — oH —CH3 OH (0) CHy —CHy —CH2 —CHg andCHy —CH, —CHy 3 3 2 Si cH, (c) CH3 —CHz —CH2 —CH2 —CH3 and CH; — CH —CH,—OH (@) CHs —CHy ~-CHy — CH and CH, —CH, —CH, —Cl Which of the following alcohols is the least soluble in water ? (@) Ethanol (b) 1-Propanol (© 1-Butanol (@) 1-Pentanol Which of the following alcohols is expected to have a lowest pK value ? (@) Ethanol (b) 1-propanol (© 2,2, 2-trifluorethanol (@) 2-chloroethanol Which of the following alkenes is the most stable ? (a) G o me © “U @ L Bond X is made by the overlap of which type of hybridized orbitals ? (a) spand sp? (b) sp and sp? (©) sp? and sp* (@ none of these Increasing order of acidic strength of given compounds is : ea Co Oe" HCO a70. nn. 72. ‘@m1>3 (b) 1 >2>3 () 2>3>1 @)3>2>1 Decreasing order of acidic strengths of following compounds is : A ‘N @ QO oy oO @ (@x>y>e )y>x>z (z>y>x (djz>x>y Among the given pairs, in which pair second compound is more acidic than first ? t i I (a) BrCH,NO» and CH3CH3 (b) CH3 —CCH,CN and CH, —C—CHg OH 1H H H o O & @ & cH,—C =0 CH75. 76. 77. 78. 79. ‘Which of the underlined atoms in the molecules shown below have sp-hybridization ? (u) CHCHCH; ——_(v) CH CCHC! (w) CHy CH @ H-C=Cc—H (y) CH3CN (2) (CH3)2CNNH2 (a) xandz (b) x, y, and 2 (© uwandx (d) v, xand y Which of the following, is the product of the reaction between AICI; and CH OCH ? a a a A CH 1, __ CH, @ ad—Al—o () C1—AI— |” SCH | “cH; a a cl ca a ae os a ls © (@ Cl—aAl— CH;OCH, on | a a Which of the following compounds contain atleast one secondary alcohol? 2 HO” “4 HO “on HOY ‘4H HO* oe H a a) aD yy wo @ LILW,V @) Lm (© LI t,v “eo 1,0,V Which of the following has the most negative heat of hydrogenation ? S @ Cr ) CY © co @ Cr Which of the following options is the correct order of relative stabilities of cations I, II and III as written below (most stable first) ? cu, Ts + + oO cr (ID H2C == CH —CH, —CH—CH3, ap Hye C— CHa CHg @i>m>m (b) 1 >>I (© Wl>1>0 @i>m>u What is the decreasing order of stability (most stable —> least stable) of the following carbocations ? AAAKA OC 1 @3>2>1>4>55 () 3>2>5>4>1 © 1x4>2%5>3 (@) 3>124>2=580. 81. 85. the hydrogen indicated by arrow will be easily removed as : (@ Ht (b) H® @H (@ H? Rank the bond dissociation energies of the bonds indicated with the arrows. (from smallest to largest). @1<2<3 (b) 3<2<1 @2<3<1 (d)3<1<2 Rank the following compounds in order of decreasing acid strength (most acidic > least acidic) . OH OH OH OH On, O QO O NO 3 4 1 2 (@2>4>1>3 (b)1>3>4>2 ()3>1>2>4 @3>1>4>2 Rank the following compounds in order of increasing acidity (weakest acid first). 1 fH 10 ly NO, (a) 2<3<1 @) 3<1<2 (1<2<3 @2<1<3 Which of the following phenols has the largest pk, value ((.e., is least acidic) ? @ a_\-or ©) on Lyn (© HC ) WB WA (©) SA SB (@) SB SA (©) WA WA The hydrogen bonding is strongest in which one of the following set ? (a) F—H---F (b) O—H---S (©) S—H---F (d) F—H---O Intermolecular hydrogen bonding is strongest in : (a) methylamine (b) phenol (c) formaldehyde (d) methanol A _H a H ‘SH iH sS ‘ A OH © b Identify most acidic hydrogen in given compound. @a (b) b Oc @d Which of the following compounds would you expect to be strongest carbon acid ? ° ce o&) 0 (©) CH,(CO,Et) (d@) CHyCOCH{COOC,H, 5-Bromo-; 2-eyclopropy cyclohex-2-enol have correct structure is: OH Br’ Br (dd) ‘OH93. 94, 95. 97. + Rearrange the following in the increasing order of acidic strength: + @ benzoic acid (ii) pmethoxybenzoic acid ii) o-methyoxybenzoic acid @ i-04 = () K+ EtOH == 08 © Mech? + 1,0 == @ O® +CHOH === Which compound posses highest dipole moment ? (a) naphthalene (b) phenanthrene (c) anthracene (d) azulene GFO+O%O (E = activation energy) Relation between activation energies of above reactions is : (@)E_>E,>E3 (0) Es > Ey > Ep =) Eg>By> By (A) Ey > By > Ey Rank the following solvents in decreasing order of ability to dissolve given compound. Solvent Et,0 me | EcOH Solute (a) Bt,0 > H,0 > EtOH (b) H,0 > EtOH > Et,0 (©) H,0 > Bt,0 > EtOH (@) Et,0 > E1OH > H,0 MeN: :NMe2 OD) 1, 8-Bis (dimethylamino) naphthalene is after referred 30 a8 (Proton sponge) Its basic strength is 10° more than 1-dimethyl amino naphthalene. Reason for high basic strength is : (@) resonance (b) steric inhibitation of resonance (© ortho effect (@ hypereonjugation99. 100. 101. 102. In the given pair of compounds, in which pair second compound has higher boiling point than first compound ? @ on and Co ) =o and > (©) HO— CH, —CH, —OHand CH, —CH, —CH, —OH Dipole moments of given compound will be ; Me’ "Me NO, NO, “ © (@) (A) = 6.87D, (@B) = 4.11D (b) (A) = 4.11, (8) = 6.87D © @ =411D, @) =4.11D (@) (A) = 6.87 D, (8) = 6.87D Order of decreasing basic strengths of halides is : @ Fo >Cr s1 > Br (&) F >clr > Br or (©) > Bro >Cl >F> (d) 1 >CP >Br >F™ Among the xylenes, which is thermodynamically most stable ? (@) @) © @) Allare equally stable Heat of combustion of two isomer x and y are 17 kJ/mol and 12 kJ/mol respectively. From this information it may be concluded that : (a) isomer x is 5 kJ/mol more stable (b) isomer y is 5 kJ/mol less stable © isomer y has 5 kJ/mol more potential energy (@) isomer x is 5 kJ/mol less stable103. 104. 105. 106. 107. 108. Rank the following substances in decreasing order of heat of combystion (most exothermi — least exothermic) LIN AKA wo @) © (a) B>A>C (b) A>B>C (0 C>A>B @C>B>A o 2 o cy Choose the statement that best describes given compounds, (a) 1, 3,4 represent same compound (b) 1 and 3 are isomer of 2 and 4 (©) 1,4 are isomer of 2 and 3 (@) All the structure represent the same compound Decreasing order of acid strengths is : ® Ph—OH, Ph—CH,—OH, Ph—CO,H, Ph —CH, —NH3 wy (a) © (0) (@B>A>C>D @)C>A>B>D ()C>A>D>B (@)C>B>A>D Rank the following in decreasing order of basic strength is : (A) CH, —CH, —C = (B) CH, —CH, —$” - (©) CHs —CH, —CO3 (D) CH; —CH, —O7 (@B>A>D>C (b)D>A>B>C (A>D>B>C WA>D>C>B ‘Among the given compound choose the two that yield same carbocation on ionization, ‘Br Br @ac () B,D AB (@) B,C Oxalic acid pK; Malonic acid PK Heptanedioic acid PK, where pK;, pK, PK are first ionization constants. Incorrect order is : (a) pK, > pK, > pK3 (b) pK, < pK, PK > PK, @ PK > pK; > PK109. 110. 111. 112. In sets a - d) oly onie of the'set is incorrect regarding basic strength. Seléct it NH (a) Ph —NH — Ph, < Ph— NH, < (strong base) H a ol < oO O H 'N’ J} N, ot > 4 > L> $-6.§ Dipole moment of which ketone is maximum ? fel oO @ ch o) GO © A @ CL ° ‘Oo Correct order of basic strengths of given amines is : (@) MegNH> MeNH, > MeN > NH (Proticsolvend) ° (b) PeaNH > Begtt> BIN 12 >NH3_ (Protic solvent) eS (©) MesN > Me,NH > Me~ NH, > NH; (Gas phase) (@) All are correct NH, CHS, Order of basic strength Ph—NH», Ph—-NH—Me, Ph—N—Me, ic) @) i Me © ) @A>B>C>D (b)B>A>C>D ()C>B>A>D ()C>B>D>A113. 114. 115. 116. 117. 118. Carbon-carbon double bond length will be maximum in which of the following compounds ? (@) CH, —CH = CH, (b) CH, —CH =CH—CH, (© CH —G =¢—CHy (@) CH; = CH CH; CH3 Which has maximum dipole moment ? @ BQN «i A Git) cA Compare the basic strengths of compounds given: @ @ > @ > Gd () Gi) > @ > Gd © Gi) > Gd > O @) Gi) > G) > @ For the following two reactions, which statement is true ? a a Ae Tactonk Tecion 8 (@) Reaction A is faster and less exergonic than B (b) Reaction Bis faster and more exergonic than A (©) Reaction A is faster and less endergonic than B (@ Reaction Bis faster and more endergonic than A Identify the site, where attack of H* is most favourable. @a (b) b Wc @d Rank the following alkenes on order of increasing Amex. (a) 1<2<3 (b) 1<3<2 @ 2<1<3 @2<3<1120. 121. 122. 123. 124. 119. Which of the following cyclic amine has lowest AG* for inversion ? @ Dw ~ CHy-Me o Dy -nBu © [Dy-eau @f>n-Ph Rank in the order of increasing acidic strength: 9 CO,Et Et0,C. CO.Et OgEt °. "COEt (A) (@) © @A propane (®) cyclobutane +H, + butane (© eyclopentane +H, —> pentane (@) cyclohexane +H, —> hexane oO 8 Compare basic strengths of the above compounds: (@A>B>C @)B>A>C (C>A>B (@C>B>A On reaction with acid, 4-pyrone gives a very stable cationic product. Which of the following structures shows the protonation site in that product ? 4-Pyrone A H @ Hwa © @ 48 0" H 0" bh125. 126. 127. 128. 129. 130. 131. Which of the following is the most stabilized carbocation ? OMe OMe te OMe © SN oe ote o Ae oo Ae Which carbocation is the most stable ? ak © ares © AK : @ Ak Consider a positively charged C,H; species in which the positively charged carbon is sp- hybridized, the uncharged carbon is sp’-hybridized and an empty p-orbital is perpendicular to the x system. What it the best description of this cation ? (@) vinyl (b) allenyl © alkyl @) allyl Which of the following reactions is not exothermic ? (a) CH —Cl + CH, —CHy — > CHy + CH, —CH, —Cl (b) CH; —Cl+ (CHs)3C—H = —+ CH, + (CH,),C—Cl (©) CH,;—Cl + CH, =CH—CH, —> CH, + CHy =CH— CH, — Cl (d) CH, —Cl + CH, = CHy — + CH, + CH= CHC) List the following carbocations in order of decreasing stabilization energies. + ' o ay on ay CK m™ oO (@) LLY (b) MTV, U1 © ULV, 40 (@ 1, 0,1, For the following two acid-base reactions, which statement is true ? (DCH,CH; + CH;NH, = <2 — CH,CH, + CH,NH™ pk =35 ke =80 apr + HO = HF + HO" pK, 715.7 PK 32 (@) Lis favoured to the right, IT is favoured to the left (b) Lis favoured to the left, 11 is favoured to the right (©) Tis favoured to the right, ITis favoured to the right @) Tis favoured to the lef, Il is favoured to the left Rank the hydrogen atoms (H,, Hy, H,) in the following molecules according to their acidic strengths: Ss TFS f@a>b>c ()b>arc @b>c>a @a>c>b133. 134, 135. 136. In which of the following reactions, backward reaction is favoured ? (a) HC =C—H + Lit-cH.CH, == H—CmC:9Li* +Hj,C—CH, 9 A = ©) pyc Son + “OCHaCHs = ae A, + HOCH,CH, + _s 2 (© CH,CH, SH, +CHyCH,OH = cH,CH,SH + CHyCH, 0-H H + rs NH, OH NH OH, Which carbocation is the most stabilized ? “CO “OO © CO: oD ~ % ‘Taking into account of hybridization and resonance effects, rank the following bonds in order of decreasing bond length. oO wae ay (@) I> =m @) > m>1 (© 1>m>0 (@ U=m=1 Which one among the following carbocations has the longest half-life ? @ bic 06 OHO) © CK) @ iy Ech, cH, Rank the following alkenes in order of decreasing heats of hydrogenation (largest first) AZ “yr NYO 1 2 3 4 (a) 2>3>4>1 (bl) 2>4>3>1 (© 1>3>4>2 @1>4>3>2137. 138. 139. 140. 141. 142. Which of the following reactions is most exothermic ? (a) » + chs ya + HC! o> + Bags ar + HBr © Ye cl, séa +Ha = @) ws Br, For 4+ HBr Which energy diagram best represents the given reaction ? Cty f—~ & = Hy SHC ‘CH; E E E E @ ) © @ Br H, HH @ 1 Which one of the following is most stable ? Which of the following is strongest acid ? a Si Kd Compare ee stability of the following resonating structure. ao i i ~ ai Il t (a) G) > Gi) > Gid (b) Gi) > @ > Gi) (©) @) > id > Gi) @) Gi) > Gi) > © Compare relative stability of the following resonating structure. wow ah oe tl I144. 185. 145. 155, a 147. 153. 148. 159. Which of the fi\ lowing orders pr beat Which of the following has thé lowesr barrie to'rota wo oes sa ay @ pot $ raxorbydaibjs eam aerizhauoamon gniwollais cdi? OBL ON Re in Spt aniwollets ~o { i Cfo ( Sto Use al Fe As ‘answer ai question below. L-o~ a as an Which of the 2 Ges} = =28. 6keal molt) > there cau Cee BON > (© We Maly cH, & noe oy Ny ‘OOO a wns Sones is pracnea sor monn A FUe2keal ml) 4. + “Anger w «Calculate the resonapce:eneray of anthracene!) hg ast 1a09, HO) .bive sitsoA .FeL iis or(@) 84 ‘kcal/mét pbs gb) }200 )Kéal/ rho 2i(o) 1 ¥110 ke cal/ mol 9jos (a) 216) amok How many double bond equivalents does a compound gh, pojectan ‘ria Geis posseis?'gHO,HO Bar “OgHie HD ie cat. cry HQGQPEHO bas Hc03,HD (6 (a) 0 HO,HO,HO bas .OD,HO (b) " (b)‘1 =O, Ho bac Hy 09,HO (9) ©2 ama 3 tates Js 0 wont Su Hows a nest be bend al Niosd amonellin Gi (asin below) possess 2 .H.. -S2E les 6 NH, oi H y Agate! Xo levinonss older r20rn oft 3 0” pe fasta” 7 pat O order of 12? Oxy 32 the given ca()163 Hacuares rs % ZG ut 33) 8 >) @ IG) ) ‘WMiat is thé oxidation stat€ of d$mium in 7B aifd:7C}) ppoetively? 7 CP we y ee sear 358 patie corn Safin Sang US arw-ae i ‘onesie Tame con meee eed) all are equally sta tSo nin einen cp anitinst & (6) 160. Zi Za Zi. ono, ox “sane & (8) tity 149. For the sive ‘compounds the correct order efesonance energy is : (a) I> 1>0 st Lo) > 1 > wo BEL ©! aitan I o(@) M>1>1, F ebapogras seaeit to 35; 180d ral toenian 2 29/oq priwollo odo rit aa 2? mig ati A EAP ey One Cine <1 (4) 161. Gi, by fi'cH, - CN" © ‘city -¢ =NC fred Cs tg como hesYCHs acidic hydraren ? “CHs HO. The Fonds stability order ofthe givetr canonical structifes is ]_$ zat G@) 1S M5 mH a Ones _ . @ism>n Yo a @ usm 3 s w $ sbavo P igo sand to nobanazerby 0 sth pene abo wot adi to dist IL ety (b) Nhs Ml< 1 (0) ay < a ae i o § sbytah pr) wl aurertteleniaan rbd § abuiahreap aie compe HN ee Si 0 WvSilabie Tor the aataeck OF CHO" AY 153, (a) 1: acid, (CA, CONIC); 2 aad if 4.8. Et(c)13 (CHyCH,O1, b@): ated 0 What 163. CH; CHit HCHO Zone Ci ge cao! HA CH COE! eS HCAS NSE aduusct'to J07 (2) ©),60,H and QO a DY Clay yO wht DH-CH{OH Which of the following ofdefs'of otation Barrie¥ abGut the C'= C bond; as indicated, is correct ? (a) a2, @ 15> 10 | $ swouwe Esoitonso E(b)‘I11 >I > Tutsurte sesd Yo dain TONE Seo MO), @ urd % . \ () i 164. 50 in. OrstieaO’, ~ a Oxkso- oe o raw, + Wore Ipe, whic of the following orders of BR barrier about ae CC. bond, NS i indicated, is 153. correct? Nentitl energy diagrem to the (@)1>1>m fone) | (© M>I>0 f *\ \@.N> 1 > I eer 165. Which of the follo fesenomal isnot etonan ge sabned 8 tai bunee Fans snaibe of apa 'soinonn to olden ay Qronte @ Drove Cee @ C2 fsre so as ot . : oe 4167. 168. 169. 170. 171. 172. Homologous compound have same: (a) General formula (b) Emperical formula (© Structural formula (@) Molecular formula Most acidic is: OH OH OH OH @ O ) QO © Qh, @ QO CH, NO, Which of the following substituents will decrease the acidic strength of phenol? (@) —NO, (b) —CN (© —CH, (@) —CHO Which of the following structures possesses a cross-conjugated system? (a) CH, =CH—CH =CH—CH, (b) CH, =CH—C =CH, | CH,CH, (©) CH, =CH—CH—CH =CH, (@) CH, =CH—C =CH, | | CH= CH, CH=CH, Examine the following resonating structures of formic acid for their individual stability and then answer the question given below. { - - r H—C—OHe—sH—C= 64 —5 HC 0 ot + I u uw Vv Which of the following arrangements gives the correct order of decreasing stability of the above-mentioned resonance contributors? @ I>I>m>V ) I> 1>m>1V (© Weil>I>n @ W>il>t> Which of the following is not resonating structure of each other? (@ CH, —N=C =SandCH, —S—C =N (6) CH, —G =OandcH, —C =O ° - (© CH; at omanace, —c @ CH, =CH—C = NandCH,—CH =C =N- OH 6-H In the molecule CH,! linearly is: @) 2 () 3 @4 @s5 =CCH =CH,, the maximum number of carbon atoms arranged173. 174. 175. The stability order of the following carbocations is: + + : + ARAB 4 I I I WV (a) I>IV >>I (b) IV >> D> © U>m>1>v (@) I> tl>n>1V Total number of a-hydrogen in given compound is: @)4 ©) 5 © 6 @7 In which pair second ion is more stable than first? VV OO Oo co or a wa Gi) (iv) (a) G@ and (ii) (b) (ii) and (iii) © Gi) and Gv) (@) Gii) and (iv)|GENERAL ORGANIC CHEMISTRY ANSWERS — LEVEL 1 49. | cb) | 50. | () | 52. | (a) | 52. | (a) | 53. | @ | 54. | @ 1 55-] © | 56.| © 41.] © [42] @ | 43-| @ | 44-| © | 45-| © | 46-| @ | 47-] o | 48.| @ 57. & {58. @) | 59.| @ | 60.| (©) | 61.| ) | 62] o | 63.| w | 64.] © | 73. | (a) | 74. | @) | 75-| @ | 76- | (a) | 77-| @ | 78-| @ | 79-| & | 80-| @ @) | 84. | | 85-] @) | 86 | (a) | 87-| (@ | 88. | O) 97. | (b) | 98. | (d) | 9% | (a) |100.| 205.| (<) |106.| () |107-| ) |108.| @) 113] «© [114] |245-| (@ 116. (a) -| @_|103.| (@) 104. (a) | f112.| @ |122,] (@ [229.] (@ _[220.| () .| (b)_|127.] (a) |228.] (a) 135.| (a) |136.} (a) 129.| (b) |130.] (ay |132.| (<) |132.| (@) |133.| () ]134, 1—T 137, [ise (d) |139.] (©) |140.) (c) [141.] (a) [142. 145.| (a) |146.| () |147-| (a) {148.| &) |249.| (a) |150.| 144, (©) 151.1 (a) |152.] (b) 156.| (¢) [157-| @ |158-| @) |2159.] « |160.| (0) 164,| (a = a a je 166.| (a) |167.] (a) |168.] (c) 172.| (a) |173.| « |174.| @ |175:| (){34 —_ : ORGANIC Chemistry for IIT-JEE — | Tay HN newer 2 of 1, Rank in order of radical stability (1 = most stable). © Oo »O oY? oa Oo 2, Predict the acidity order for the three phenols shown below : Acidity order : 1 (most) to 3 (least) NO, NO, CH OL HAN. NH NO2 EN.|GENERAL ORGANIC CHEMISTRY A. Which of the phenol derivatives above is the strongest acid ? Compound A © Compound B © Compound ¢ © Compound D © Compound E Compound F B. Which of the phenol derivatives above is the weakest acid ? CO Compound A CO Compound B CO Compound c CO Compound D Gi Compound E © Compound F C. Which of the mono-nitrophenol derivatives above is the strongest acid ? O Compound A O Compound D D. Which of the carbon-substituted phenol derivatives above is the strongest acid ? © Compound c © Compound F 4: The following questions refer to the twelve compounds given below. You may enter as many as six choices in each answer box. 1 OD pl eae td) HF () Oe: oO L\ 0 @ or 5) CO, @ Co 6 oO” a “et ® Co Oo A. Which compound may serve only as H-bond acceptors?» [______] B. Which may serve both as H-bond donors and acceptors? = ("____] €. Which compounds will not participate in H-bonding? = [1] 5. Consider the following compounds and answer A and B. i) ( a OA, ao Ch av) ' A. Which of the compounds is the strongest Bronsted acid ? @1 o) 0 © m @iVv10. In the two questions below, you are asked to rank the relative strengths of illustrated acids and bases. Use your knowledge of resonance and inductive to.answer this. ‘A. For the series of bases shown below, rank the set from strongest to weakest. com TOES N loolacls N N’ N H H @ ) © @ Weakest ~ Ay Strongest a 'N Me N’ N’ x7 le Me, {sd} @ ) © @ 1 Weakest B. For the series of acids shown below, rank the set from strongest to weakest. Stronges ® ine} "Che. “oH a ai @ mol 1096 ; Own ) : eS HO,C, HO,C. NO, ol Oo a oy © @ Weakest Strongest (ey © @ Weakest 11. In each of the following sections four compounds are listed. (Decreasing order of acidic strength, 1 is strongest & 4 is weakest). (ay | SSOLatise | crycocHcoeati | (CHsCo)y Cte RC ea CH wo RCH2NOz RSOLHs (CelHs)3CH RCOCHs (9 LS CHa(NO2)2 HC aN RCHLOL HsGENERAL ORGANIC CHEMISTRY H; @ oO 2 “pd Oy SO o?¢ A [ QD () w © ‘ | ° ¢ eg H HH HN H H H ? Nn? nw 3 c. I i i} é i OL > © Ly DS H)N “NH, HN “CH, HIN’ OH HjC CHs 13. Compare acidic strength of the following (Write your answer in box). ANZA IAA LAO o @) {b) © OH OH OH . FC @) ©ORGANIC Chemistry for IIT.JEE Q @) F wr Br o) © QO oO QO E. 0 0 @ © H H HOH eels @ | @) © 14, Arrange the hydrogens in increasing order of their acidic strengths. 9 0, FOF HY A. BH Ha i o. Hy H H’ Ib, ib Nie Ong H15. The compounds whose structures are shown below, incorporate a variety of functional groups. The question on the right ask you to identify which compounds have a specific functional group. For each compound that has the designed group, enter the appropriate number. The aromatic rings should not be counted as double bonds. SosO8 Se OH ‘toners 2, munconn A. alcotine 4. ibuprofen 5. camphor ° HC. ote 4 Oe ‘O Heo HyC7 SCH 7.aspirin 8. geraniot 9. acetaminophenol O—CHy a Which have carbon-carbon double bonds ? Which have a ketone carbonyl group ? Which have an aldehyde carbonyl group ? Which have aromatic rings ? Which have a hydroxy group ? Which have ether groups ? G._| Which have an ester group ? f H._| Which have an amide group? I,_| Which have a carboxylic acid group ?[[Probtem ‘A = £ 0 ona oe CY Cy ‘O. OR OH OCH, OH Sr O _— N—-H | ew | Om] Cit [Oe ‘0 oO H i I H Cl Cc C. ScoH Cc. 4 CX Peon Cy oot Cy 2 FS conH ca ‘cl ‘A. Which is the strongest acid in 1? @a (b) B ac @)D B. Which is weakest acid in 1? @a ) B amc @D C. Which is the strongest acid in 2? (aa )B @c (@)D D. Which is weakest acid in 2? @a (b) B @c ()D E. Which is the strongest acid in 3? @aA (b) B @c @D F. Which is weakest acid in 3? (aa (b) B @c (4) D G. Which is the strongest acid in 4? @A (b) B @c @p HH. Which is weakest acid in 4? @a ©) B @c @D}GENERAL ORGANIC CHEMISTRY 17. For each of the six structural formulae (A through F), shown below, five questions are posed. The answer to each is a number that should be entered in the appropriate answer box. CH, O-sc~c03 " N . (i) Number of sp? carbons : B. Number of sp? C. Number of sp? “ . carbons : carbons : (ii) Number of sp? carbons: Number of sp? carbons: Number of sp? carbons : (iii) Number of sp carbons : Number of sp carbons : Number of sp carbons : (iv) Number of carbon-carbon Number of carbon-carbon Number of carbon-carbon o-bonds : o-bonds : g-bonds : aesonse (v) Number of m-bonds to Number of xbonds to Number of r-bonds to carbon : carbon carbon D. (i) Number of sp? carbons: E. Number of sp? F. Number of sp? carbons : carbons (ii) Number of sp? carbons: Number of sp’ Number of sp? carbons : carbons = Gi)Number of spearbons: Number of spearbons: Number of p carbons : (iv} Number of carbon-carbon Number of carbon-carbon Number of carbon-carbon o-bonds : o -bonds : o-bonds = (v) Number of zt bonds to Number of bonds to Number of x-bonds to carbon : carbon + carbon :....oO ~~ ORGANIC Chemistry for ITT-JEE , 18. Match the column (1) and (11). (Matrix) Molecule Property TL @ @®) cis-compound PL ) PF @ trans-compound © CO @ Highest heat of combustion _ I san — 19. Match the column (1) and (II). Molecule pKa of Conjugate acid Ch @ wo ©) os H @) G3 @ 5.33 Gy oy © o 10.65 N. @ N © 1095 220. joGENERAL ORGANIC CHEMISTRY : 45 20. The junctures centred on atoms A, B and C on the given structure. | ‘A. Which juncture has the greatest deviation from planarity ? A ) B oc (@) Cannot be predicted B. Of the carbon-carbon bonds, (shown above) numbered from 1 to 4, which represent the most favourable site for Ha addition ? @1 @)2 ©3 @4 21,_ Select the most stable structure in each of the following Part (A) 4 “GO PO FO fO Part (B) O@AZT- jorRy |onw le ANF Part (C) (@) H& = CH—CH = CH—CHy (b) HE. = C = CH—CHy—CHy (©) HyC—CH = C = CH—CHy @HE =CH—CH,—CH = cH, 22._Match the column I and II. (Matrix) @)_f=no: Kp) __|-meffect [07 q)__|+metfect [=o — cH, ie) | reffece @ [-con te) [-vefiect 23,_Match the column I and 1. (Matrix) (@)_ [HC —CH = CH—CHy (6) _ [HC —CH = CH—CN Dipole (trans > cis) © _|ry¢—cH = cH [Melting point ((erans > cis) ce ae __ [Boiling point (cis > trans) |24. Identify the most stable structure in each of the following : [[rare A) CH, CH3~ + @ > t—H < a (b) cH, ©) Part (B) HY + N Oy" Nome HO “a Cy 4. c. OG Nox ch, Ho [rare © Fe (d) Part (D) x + @) ie ) aa © “T @ aa Part (E) CH, CH, os aK 0 > =cO . o = HZ Nau H H —- CH — CH. H oS aco _ @ Neel ua Nu Hy Nu Part (F) + + CH CH, CH @) Cow © cr o Or +p oo a7} Part (G) 1 HOH ‘ H HoH H H & SeK' | fF + £ ot # lo Hu lot or ° 4 H H ° ° i. HOH a H a HoH Hou | HOH 25, Identify the most basic compound in the following. = Part (A) 0 oO NH NA (b) " ‘NH NH A NH @ Ko) @ ‘° Part (B) NH NH, NH — CHy @ © o) ca) ‘N Part (C) (a) NaOH (b) NaQOCCHy (©) NaOcHy (a) NaNHy fo | Part (D) | NH NH NH, NH, @ ©) © @ O NO3 OCH, a — ail48 a a ORGANIC Chemistry for IIT-JEE 26. Identify the most acidic hydrogen containing compound from the following. Part (A) —— @ @ ) 6) » QO QO) O 1S in, [OO Part (B) ° ° ° ©, CO,Bt @ © © i ° C—O—E ° —____L Part (©) OH OH OH on @ “© © @ NO, CH,CHg NO, NH — CHg Part (0) ° ° Oo 9° 9 0 eA JU fe |@ RA Part (2) a) ° oH CH, — NH| CH,OH or ao © @ or o @|GENERAL ORGANIC CHEMISTRY Part (F) —_ (a) CHyCHOH (b) CHyCHNH2 (c) CH3—C == CH | (4) CH3 —CH = CH, Part (G) + NH ts (0) CHy —COgHt NHS (a) CH —COH ay 6 () wo L Part (H) OH OH OH OH No, Jo ) a) @ : NO, No, NO, NO, No, Part (1) or alSno ys @ @ o o =: been ee ard zoo e I Na,—C—H Nu Give the type of hybridization present at each atom. @ No (iv), — Gi)e2 — Wi)C3 —.fo ORGANIC Chemistry for IIT-JEE 28. Predict the direction of the following equilibrium. Write your answer in the box given below. : x a> @ Phy CBr = 4 BIT oe + Ph3CH oO . & (@) © @) ; _ °. oJ co = OD. te Hm KF H H 29, Match the column J and IL. (Matrix) 0. ‘OH (a) | NaHCO, will react with | oO ‘OH (b) | Na will react with Squaric acid | o @ Cc—O—H (c) | NaOH will react with (4) | Nant will react with Oj {s) S—O-H 30, Match the column I and I. Acid PKa (a) | CHs Coat @) 5.69 + (b) (CHla):NCHLOH @ 4.27 {o) (CH), N(GH)4O3H @) 1.83 ~ —T [ © |Sac—cx,—coz ®) 4.80[GENERAL ORGANIC CHEMISTRY 31._Match the column I oO I (a) Opes 0- 1+ nat (s) Ha & _ i CO2H | | $03 te 32.) COO) —REESOD 5 (A) + (B) MEO (C) 4 (D) : on * = } CH—OH | tl | : CH . Sum of molecular mass of gas (A + ©) is: (@) 88 (b) 90 (© 92 @ 40 i Oo 33. ph—C 9 — 400s 54) gas | Ph —C = CH—*2_(B) gas Ph —OH—N2MH2_4(C) gas 1 R—O—H—‘#_,(D) gas | ‘Sum of molecular mass of gas A +B+C +Dis :34, Match the column I and M1. ORGANIC Chemistry for IIT-JEE o co @ He Molecule Rotational free energy barrier ° Ph (a) | Ph @ 180 kJ/mol ° Ph__Ph I (b) I @ 88.3 ki/mol I Ph7 Ph Ph Ph l a Ui cl © cl ci o) 21 ki/mol I Ph~ Ph | © vi ¢ ~) Negative barrier|GENERAL ORGANIC CHEMISTRY 35. Consider the following reaction of boron trifluoride (BF,) and acetone : i a i CHy~ cH, i A. What is the critical HOMO (nucleophile) of this reaction ? (2) non-bonding orbital on boron (b) c-orbital of acetone (©) morbital of acetone (d) non-bonding electron pair orbital on oxygen B. What is the critical LUMO (electrophile) of the reaction ? (a) porbital of BF, (b) o-orbital of BF, (© * orbital of acetone (d) non-bonding electron pair orbital on oxygen C. Which of the following is the correct product of this reaction ? (Lone electron pairs are not shown explicitly). Br. fod Sqr BFs eg BFs °, 1 BF A ) pe 3) oO @ CHg ‘CH A BF, 36. Rank the following carbocations according to stability (1 = most stable, 5 = least stable). fl | AK AA Ee] E] Put the answer in the boxes, OOOOO‘ORGANIC Chemistry for 11T-JEE 37. Among the given molecules, identify aromatic, anti-aromatic and non-aromatic molecules. > : a A @ Lv @ AA oly : of} of) | al J ay B’ e’ A of oo 7 s i i of] aa lf J ass oo) i NY Oo t oll © Q o Cl (10) a3) [~~ (4) “9 x) | H 2 | Ss \ ev J a2 @3) eal Lo! = el J 26) {| a oo 0" N nA H 1) OD OOADT 9) a ol 3) MEN ~N-8 34) (De @s) uve \ D H (36) ‘ iSGENERAL ORGANIC CHEMISTRY j | % nd, oat SO @7 C1 38) || Q J 40) || | ‘NN’ A — N=N (4) aa | 43; \ 3 oo ApBe. re ee ORGANIC Chemistry for UT-JEE 38. Among the given pairs, which is more reactive towards AgNO (or) toward hydrolysis. Compound (A) Put the Compound (B) | Answer here Br JQ bv D-l a +1 O- CHg -CH2 ~CHp -Cl Br Hy-Br {6 | —t Br Br 6 O L e & O a|GENERAL ORGANIC CHEMISTRY 10. 1 CHy-Cl 39. Put the answer in boxes given as directed. [ Name of force Correet | responsi S.No. | Property Molecules Answer | ble for the property ‘a, _ {highest boiling NCI, CINH, —NH,CI NH. Ipoint . B ighes boting — C3 OH HH Ht c, |mestsoluble ee on * lin water x ‘OH ‘SH highest D. solubility in Oo» we benzene 40. Circle any conjugated portions of these molecules. w ~ A CH, = C = CH-CH = CH) | | | 0° ~ 4 aoe an.) © OfORGANIC Chemistry for IIT-JEE 41. Arrange in the order as directed - ‘A. The given alkenes in the order of their stability (1- most stable, 3-least stable). ces C Arrange the following in the order of their acidic strength (1-most aci OH = “YY Mmm “S~ “of ©. Arrange the following molecules in order of expected boiling point. (1=highest bpt ; 4=lowest bpt.) ae Ae Ae oe D> Oo oOo D. Arrange the following alkenes in order of their stability. (1 = most stable ; 5 = least stable). x n g > i CJ COGENERAL ORGANIC CHEMISTRY 42, Match the column. (Matrix) Coluran (1) Compounds fete) Number of Benzylic hydrogen 43. Identify (+M) mesomeric & (-M) group of following. +M = eee 0 O Oh ©Hy He Ha (A) Identify the type (1°, 2° or 3° alkyl, vinyl, allyl etc.) of these H-atoms. (B) Arrange them in the decreasing order of their case of abstraction (easiest first) 51. Consider the molecule shown below and answer with respect toHy=—> Her wtb He r Ha Hg He Hy 1° (A) Identify the type of Hratom (1°, 2°, 3° alkyl, vinyl orally" tT viuaeion x, sabrevad 2b (B) Arrange them in decreasing order of their bond én wolfe? 52. Rank the following carbocations in order of Stability ‘(1 = ze ° 3° So CO 2 : Oo ‘most stable) 53. Rank the following alkenes according to energy (1. = lowest energy). DogeGENERAL ORGANIC CHEMISTRY 54, Match the column: Peo mete) {Double bond equivalent value) @ @) abs ) @ 12 ro} @ 13 (@) (s) 14 | L @ 1s64 ORGANIC Chemistry for IT-JEE = “SUBJ! 1, How many 2° carbon in the following ? 2. Find out the double bond equivalent (DBE) value of the given following compound: | 9 NH, =N ° L 3. Total number of functional groups present in the given following compound : | 9° | So 4. Total number of a-hydrogen in the given following compound is:GENERAL ORGANIC CHEMISTRY L Total number of DBE value in : | Com ) | j | | | i 7. How many isomers of CqHyoO reacts with Na metal to evolve Hy gas 7 (excluding stereoisomer) 8. [x}-crown-[y]-ether. value of 2¥ =? 3 9. Which of the given following compound will react with NaHCO; or soluble in NaHCO ? ° i | OH OH oon i (@) 0b) © i (© CHs —‘ORGANIC Chemistry for IT-JEE 10. How many compound are stable after deprotonation ? @ ' @ oh © QO @ oO : © Q o QO11. 12. 13. 14. 15. 16. 17. 18. 19. 20. 21. 22. A-b;B-e;C-a;D-b A-a,cf,g,k,1;B-b,d,h,j;C-e,i A-d;B-a C ii > i> iii; b-ili> iv >i> ii a—4, 2,3,1;b-3,1,4,2;¢-2, 1,3, 4; -2,3,4,1 A@-d>b>c>a;— (i)-e >a>b>d B(i)-c>d>b>a; (iJ -b>d>c>a (3214 )2143; ©3124 @3412 A-cHy > Hy >He Ac Hy =1° alkyl; Hy = 2°alkyl; H, =2° allyl; Hy =vinyl; H, =3°allyl B- Easiest to abstract: H, >H, > Hy >H, > Hg Hardest to abstract A> Hi, =2° alkyl; Hy =2° allyl; H, =vinyl; Hy =3° allyl; Hg =1° alkyl BUH, > He >Hy >Hy >Hq A-2; B-1; C-3; D-4 53. A-1; B-4; C-3; D-2 ax; b-t; ct; ds Subjective Solutions: 4210 211 3.3 4.6 5.4 613 7.4 8.7 9.2 (c,d) 10. 3a, f)wm Relation between (X) and (¥) is : (a) enantiomers (b) diastereomers (© E and Z isomer (@) constitutional isomer 2. Which of the following cyclopentane derivative is optically inactive ? oH H CH CH, (a) b) © H (OH i oOOn # H H CH; $e @ Ky © A, OH H cH,4 Which is the most stable conformer along the 2, 3 C~ C bond axis of the compound ? HC. F wy HC ‘CH F E CHg H H. cH, CH, H. H HC. (@) cH, © CH, ©) F @ HAC H CH, H Hy CH CH3 HC Assign double bond configurations to the following : COOH NG, ‘cH,OH HN-H,¢ XN @E Wz OBE O22 Allegra, 2 common prescription drug with the structure shown below, is given for the treatment of seasonal allergies. How many stereogenic carbon does Allegra possess ? “COOH ‘CHg OH @1 (b) 2 Os @4 How many meso isomers of C,H,Cl, will be ? fo (b)1 @2 (d) 3 The stable form of trans-1, 4-dimethylcyclohexane is represented as: CH, CH, © 27 ® CHs CH CHs (© BF ety @10. 11. 12, 13, Which of the following compound is non-resovable (meso) compounds ? OH Br e Me OH Br H od) © of 1 () Allof these ( n Br HO ~CH,-CH,-F me Which conformer of above compound is most stable across C —C3? (@) staggered (b) eclipsed (partially) (© gauche (@) fully eclipsed The following molecule is fluorometholone, a steroidal anti-inflammatory agent. How many stereogenic centers does it contain ? fluorometholone f@)5 &) 6 ©7 @s How many chiral carbons are there in Reserpine (an antipsychotic drug) ? - y “ N’ ON H PX @9 (b) 8 7 @6 How many chiral centers are in the following compound ? @ 4 @) 5 ©6 @7 Among the following, the optically inactive compound is: i N SN @ HCH, E ©) or Mo . HcoO oH 4. ‘Saco ofbase (4) ; Unknown compound (A) is : 4 (C=C) 9° HH HH 9° o oO OH @ (b) © @ 15. Which of the following compounds might be useful to the chemist trying to increase the optical purity of the (d) sample ? HOC CO, @ Sr ©) HO COnH .COQH @ Cy 16. Which of the following molecules is (are) chiral ? .CH3 H Cy, A S 2 Hf x, \CH(CHs)2 H % o a ap m AC, 4H HG, Lo S ™) wD (@) land (b) Ml and IV (© i, Vand VE @ 1, I, Wand Vi ©17. The structure of (S)-2-fluorobutane is best represented by : . F @ Cty GHCH,CHy a C-F RY © nc CH,CH; 18. How are the following compounds related ? HC, Br i OS Br HBr H (a) Diastereomers (b) Enantiomers (©) Meso compounds (@ Identical 19. Which one of the following is chiral ? (@) 1, 1-Dibromo-1-chloropropane (b) 1, 3-Dibromo-1-chloropropane (© 1, 1-Dibromo-3-chloropropane @ 1, 3-Dibromo-2-chloropropane 20. Among the following, the Newmann projections of meso-2, 3-butanediol are : Me Me Me Me H. OH 4. OH HO. Me Me. H HO: HOH HHO. HoH OH Me Me H OH P Q R s @ PQ @) PRR ORS @os 21. The binaphthol (Bnp) is: CU... Cs (a) an optically active compound having chiral centre (b) an optically inactive compound (© ameso compound (A) an optically active compound without having chiral centre22. 24. 25. 26. 27. 28. re OS or cey a a a a ‘The maximum number of stereoisomers that could exist for the compound below ? Br Br Br Br @6 @) 8 © 10 @ 16 The following pair of compounds is best described as : Ag {a) identical (b) diastereomers (©) enantiomers (d) none of the above Determine the absolute configurations of the labeled carbons (a and b) a b Which of the structures (a - d) will be produced if a “ring flip” occurs in the following ‘compound in chair form ? GT @ Lk ® FA © ey ww ) L~Ty Which of the following compounds is most stable ? opz7 » ky © Eo @ Which is the most stable chair form of this compound ? e29. 30, 31. @ tA. © XA o ZA oA Which pairs of the salts would have identical solubilities in methanol ? Ph Ph H @ nar, cut -cog cy -c00 NHg H Ph Ph Ph (In NI sro, war, cH; H H cop coo" (@ 1&1V (b) 1&0 © 1&l (@ Wav ‘The following compounds differ in respect of : OH OH in On oh oS HO” Hot "0H HO’ 1H OH OH (a) their chemical and physical properties (b) nothing. (©) the direction in which they rotate plane of polarized light (@) their interactions with molecules Indicate whether each of the foltowing pairs are identical, or ? Br wo H H an cig H H cH, Br Br T I mi (a) enantiomers diastereomers enantiomers (b) identical enantiomers enantiomers (c) enantiomers diastereomers identical (d) enantiomers identical identical Which of the following is achiral ? @ o WY© (d) a molecule of 3-methylheptane 33. Which of the following compounds are meso forms ? CH CHy CH oH H—a oH ca—-+H ‘CH, CH,CHy CHy 1 2 3 (@) 1only () 3 only (©) land2 (a) 2and3 34, The separation of a racemic mixture into pure enantiomers is termed as : (a) Racemization _(b) Isomerization _(c) Resolution (4) Equilibration 35. Rank of the following groups in order of R, $ precedence (IV is highest) : - CH(CH,), — CH,CH,Br ~ CHBr -C(CH,), 1 2 3 4 I 0 m1 v I 0 m Vv @3 2 4 1 @)1 4 2 3 @3 4 1 2 @ 3 4 2 1 36, Which of the following is a meso compound ? Ho ow, g Qo cer, Clay. : HyCus fi, Hg @ Cu) cl (Bo HyC 1 H ‘CHyCH HC C1 mC gl Zoo Hing. = @ Ge wm (rn cti,cl ‘CH cl 37. Among the following structures, select E isomers (arrows indicate the bonds to be considered) ? Br cH, Cl CH, 8 H WA Lar HG HR F yc So YC \ CH: 3 HyC7 $ H CH, @ Q @ « (a) land2 (b) Land 3. (©) land4 (@) 2and 338. 39, 40. 41. 42, ‘Which of the following compounds has a zero dipole moment ? fol a cl wo” © CK, © On Pluto, where everything is frozen, astronauts ) HL, 1, V (©) 0 Ir (@) Lm49. 50. 51. 52. 53. Which of the following carboxylic acids could be resolved by reaction with an enantiomerically pure chiral amine ? CO, NO2 ON CO,H f@) (b) ON NO, 2 Cot HO,C 2 Cost co,H © (d) HO,C NO, NOQ What is the relationship between the molecules in the following pairs ? CHO. CH,OH H ‘OH HO HH H-4—OH H OH HO H and HO H H ‘OH HO H ‘CH,OH CHO Fischer projections) (a) enantiomers _(b) diastereomers (¢) identical (@) structural isomers What are the correct designations for the structure below ? “Or, 10,4 @EE ©) ZE OBZ (@) No geometrical isomers are possible Which of the following molecules are chiral ? o AU a A ay ode ou KI (@) Tand 0 (®) TandV © Mand mt @ 0, mV Which one of the following isomeric structures has the lowest energy ? @) ion 0) Cx © Cx qd) 3>1 ()'1>3>2 (© 3>1>2 @2>153 Compare the stabilities of the following two compounds : A: cis-1-Ethyl-3-methylcyclohexane B : trans-1-Ethyl-3-methylcyclohexane (a) Ais more stable (b) Aand B are of equal stability (c) Bis more stable (d) No comparison can be made What, if anything, can be said about the magnitude of the equilibrium constant K for the following equilibrium ? 2 a H H. H CH, CH(CHs)2 @K=1 ) K<1 © K>1 (A) No estimate of K can be made93. 9s. 96. 97. What is the relationship between the two structures shown ? cH, Gl 1H: aL (@) Constitutional isomers (b) Stereoisomers (©) Different drawing of the same conformation of the same compound (4) Different conformation of the same compound Which of the following statements is true ? (@ van der Waals’ strain in cis-1, 2-dimethyleyclopropane is the principal reason for its decreased stability relative to the trans isomer (b) Cyclohexane gives off more heat per CH, group on being burned in air than any other cycloalkane (© The principal source of strain in the boat conformation of cyclohexane is angle strain (@) The principal source of strain in the gauche conformation of butane is torsional strain Ph—CH = NO,H—SES 5 (x) _, Isomer (x) is: is (50°08) (a) Ph —NO—CH,OH (b) Ph —CH, — NO, (©) Ph—NH—CO,H @ None Which of the following will not show geometrical isomerism ? @) CH, —€ = CH— cH, —CHl, (0) City ~GH—CH — CH— CH, — CH, CH; CH; (©) CH, —CH —CH—CH, (@) CH, —CH, —CH = CH—CH, —CH, ‘The two compounds shown below are : and (a) diastereomers (b) eriantiomers_—_—_(c) epimers (@) regiomers ‘The molecular formula of diphenylmethane, How many structural isomers are possible when one of the hydrogen is replaced by a chlorine atom ? (@) 6 ) 4 @s @7 Correct configuration of the following molecule is : Hy H——0H CHy—j—0n H (a) 28, 35 (b) 2S, 3R (© 2R, 38 (d) 2B, 3R99. 100. 101. 116. 102. 103. 104. 105. gin which ofthe following keto forms more dominating than enol fo 28.8+ Yo neipayer aflneg? basélusico seed siohslizlb fa bayogatar ny a6 fu ex Sho [its 303 to Hon 9g 106. 199. 107. 108. Saram 19x cue ae) @ om oA hide Which’ of ihe following will have One of the s 98. Maxiimuni én enol content ig in ub er 4pn 7 OE aeOE Cy ‘Or (a) 3o uisq insea: Pn ving gaiwollol as oPaic®! 20K CEbhW bios indy pH ome? méio ? 44,3 All of unese (a) 2-chlorobutane Gto1f, _~ & 2,3 orobutate (© 2,3-dichloropentéhe ~(@ Diviéroxypiopanoic seid aThe correct decreasing order in the enol ‘content of following molecules is :O11 (2) o @ QO Q Which conformer of abl cn Jlound is rllan de (cansider conformer i : CS “ (a) Staggered © NO y @ Do, (a) 1> nsmodl fo fea > - Ob () >a Sip wasn +1 Total number of stereoisomiéts 6 ore Impound 1-broftio-: schloféeyelobutane is: @0—f 4 Oi ——-H 2a cH,(@) 3 Total number of stereoisomers of the 1,3-dichlorocyclohexane is: aad, 911A (l) @ 0 ®1 Gg ..03 a &) ;aaSutslom Milo wiRinsnsuntor sIT OFT Total number of stereoisomers of the compound 1, Ay -dichlorocyelohexane is : (@) OLD ODL p-O2tL,, 1@4D,b sTotal number of stereoisomers of the compound 2-4-dichloroheptane is: ‘(@) Og 2r (b) ) 2e ar (0) © 3: at @ id) fly eclipse sally eclipsed ha “Ue SO Co § noisizoqmnos och sug Boy 189 16H1W zootgob Ay eee (2) & oursio '0 2 Q ORGS Sa Selmemd Sts oN 1 ‘Amiig the Following Compounds, which will give | aii feel contéht in solution : (a) ©" Which of the 9 owing ahh tune gepres orapou 2. Me n (a) Ces “CL cH, —C—Cgh, (by: Clg on, —C—CH, Me~ Ie 9 pir 6 cH, Chl, CHC @& ch, cen, = co0csH5(0) Which of ie folowing Hee hadbiSbnol form ? od ae (0) baviogmoo gniwotlal 104 sition asmoziomar woreda lost EEE ms OHO = ome cp OH OH £ ws BE Th RGR oC. excees:of mixture Sry! of (+) 2-butanol and '4g of © -2-butanol.COnH 120. oH CHg How many representations of lactic acid are possible in Fischer projection (4 & I) ? (a) 8 (b) 12 © 24 (@) 36 121. Total number of stereoisomer formed by the given compound i (a2 @) 3 4 @s 122. The number of stereoisomers formed by the given compound is : ¥ ee - h (a) 2 () 3 4 ds 123. Which of the following compound does not undergo base - catalyzed exchange in DO even though it has an o-hydrogen? OL “A X (4) both (b) & () 124, oon — Bele Product Identify the product formed in the above reaction:125. 126. 127. Os @» ®) ». D D OH DR © ». (2) None of these 5 H In 3-methyl-2-cyclohexenone which hydrogen cannot undergo deuterium exchange when it reacts with CH,0°/CH,OD? ° @ @) ol fae @) (@ HH, @) Hy (c)_H,,H. (d) Hs,H. tHe oy D Hs,Hs oO a uy ‘The tautomer of II is : fa) I ) Wh (c) both I and Ill (d) none of these oO Ha HB ly In the enolization of the given molecule, the H-atom involved is : @ oH ) BH © yH (@) cannot be enolized128. 129. 130. 131. 132. 133. 9 Oo oO @ ay Among the given structure which can exhibit tautomerism ? (@) Lonly (b) Honly © Mlonly (d) none of these 0 9 9 5 CHy CH, 3 CH; CH. 3 is oO ain ay Identify the which can exhibit tautomerism ? (a) Tonly (b) Monly (© Monly (@) all of these CH,-CH = OS CH, = CH-OH @ a Between the two tautomers which is more stable ? @ (b) () 1=1 (d) none of these OH ° OH C>-O=-& = = —= o @ a Correct stability order of the given tautomers is : @I>n>m (>) >>I (© W>i>m @m>m>1 OH HH Oo-C-C0 = = =— 0 a ay Correct stability order of the given tautomers is : (a) 1> > ) > U>1 (© w>i>m @0>m>1 o ou o- 1H = @ x%; —_— | y% - ‘oO 4 = | 5% Sou The correct order of enol contents x, y, 2 is :134. 135. 136. 137. 138. @x>y>e (by z>y>x Oyrx>z @x>z>y OH = [/ = CS x% ; L Y= y% oN ' AD), snes mpm Hi The correct order of x, y, zis : (@x>y>2 (b) s>y>x @y>xre @x>2>y CES Among the given ketones, theo one which does not enolize is : @I @) 0 om (d) none of these CH i H Pol ove Product ‘The product of this reaction should be : Ps CH CH; Oo mous OTL wmarine © an assong the given compounds, the correct order of enol content is : @) 1>m>11 Om>m>1 | @ u>1>m @ u>m>1 % ‘ : 5 ° oO © a a, Among the given compounds, the correct order of enol content is : @I>m>m (b) I> a> @ U>1>m @u>m>1139. 140. 141. 142. 143. 144. ct : oO an a Among the given compounds, the correct order of enol content is : (@) >> (o) > 1 >1 (© W>t>t @ U>1> mr How many geometrical isomers are possible for the above compound ? (a) 3 b)4 (6 (d) 8 Which of the following compound will not show, geometrical isomerism across the n-bond ? Mei H 2 @ Tt < o Mei CH a Br Br 1 cd FE FE 1 Br Br [—— |}|—— 4H HO Ng——."“H Choose the correct relation between h and l, ? @h=b WO hob Oh» @ ® H CHY Hy a 374. Gy How many atoms will be bisect during plane of symmetry ? (@) 2 @) 4 @6 @s175. 176. 177. 178. 179. 180. 181. The number of all types of isomers of chlorobutane is : (@) 2 (b) 4 6 @5 Which of the fotowing pairs of cemonis are not positional isomers ? OI ob Do," De (CH,OH © oY * (d) All of these cH, and oy Which of the following pairs of compounds are functional isomers ? and “\of oO oO @ Ns wo AJjm ly oO © ASB ana AP @ he ana “\ The isomeric alcohol which has a chiral carbon atom is: (a) n-butyl aleohol (6) iso-butyl alcohol (c) sec-butyl alcohol (4) tert-butyl alcohol The pair of enantiomers among the following compound is: CH CHy an om mts “i a (@) and IV @ 0 and W (© Mand I @) Land It Which of the following is chiral? (a) Cell phone (b) Spiral staircase (¢) Scissor (d) All of these In which of the following compound, possess plane of symmetry as well as centre of symmetry? H: a cl CH, cH, (@) (b) © @ cl ‘CHy CHS182. Which of the following compound has one of the stereoisomers as a meso compound? vw. wer aS 183. For the following Newman projection i H H, rt Cl. H H. ch (b) (d) @ 4% © aX © Ae @ Ae uy i aa cr 184. Which of the following is correct for the given compound? (a) It possess centre of symmetry (b) It possess C, axis of symmetry (©) It possess plane of symmetry (a) Compound is chiral 185. Which of the following molecules has axis of symmetry and a coaxial plane of symmetry? ee A oO @ ¥ “ore © oN “COO (©) All of these@) | 2. | ©) ) © @) | 6 |] 7 1 © (d) ey (d@) © | 24] @ © | 32.] @, (b) © | 48.} @ (@ | 56. | ( © | 64] @ (a) | 72. | (a) © | 80. | (b) 81. | (a | 82.| (a | 83-| @ | 84. | ~@ | 85-| c@ | 86. | @ | 87.| @ | 88. | @ 89. | (a) | 90. | () | 91. 97.| (a) | 98. | @ | 9% 105.| (a) |106.| (a) {107.| 113.] (a) {114.| (@ [115.| 121.| (a |122.| @) [123 129.| (a) |130.| (a) |131.| 137.| (c) |138.| (a) [139 145.| @) [146.| @) |147. 183.| () wee] @ |155. 161. (vy |162.| (ay |163, 169.| (b) |270.] (c) |172. 177.| (by |278.| (©) |179. 185. ©.|ISOMERISM oa 1. Match the Column (1) and (11). (©) | CH, —CH = CH—CH = CH—CH =CH—CH, lo 2. Match the Column (1) and (IN. CH; —CH = CH—CH = CH CH =CH-Ph | cd Equilibrium Constant @) R=—H @) 38 (b) R=—CH; () 23 © R=—Et @ 18 Re==— CH—CHy ‘Hs © 1 eelORGANIC Chemistry for IIT-JEI 3. Match the Column (1) and (II). (Matrix) Molecule Nature CO,CH,CH,OH ®) Chiral fa) COzH ¥_CO,CH,CH,0,C (b) 4 4 (@) i E> co,cH,cH,0,¢72 4 Achiral H H oH HO co, © wo Meso CO,H HOH H COH H @ (=) | Compound containing even number of chiral centers(Matrix) qa ‘Compound Isomerism | CHy, H @ @) Geometrical isomerism H Et CH, Et (b) @ Optical isomerism H H D CH, Et © () | Compound containing plane of symmetry H H CH CH, CH, (a) (s) | Compound containing center of symmetry H H112 & 5.__ Match the Column (1) and (11). ORGANIC Chemistry for IIT-JEE Molecules Relationship (a) . ca cl and Cr ©) Identical Hy Aut CH cl o| CE hat CHly stl CH, © Cz mY CH w Diastereomer CH, Leitch @ Enantiomer and cl (4) (s) ‘Structural Isomerism ak Mn, Q 2 £ ig 6.__Match the Column (I) and (1). (Matrix) Compound Nature CHs Br OHCH, @ OOP)» | ciscompound HO’ Br Br OHGH, ) D592 (| trans-compound CH3HO Br su CH © : Cre pil aie Hts snacts CES (8)] optically inactiveJISOMERISM ae 7,__Match the Column (1) and (11). (Matrix) 113 Property Chiral centers containing compound @ Presence of stereocenter ©) Optically active compound —] (dd) (s) 8,__Match the Column (1) and (11). (Matrix) Compound containing plane of symmetry Property fa) (P) Polar molecule | (b) @ Optically active (c) F oC» tl E w Optically inactive H A. F @) ) Plane of symmetry H H14 i ee ee ORGANIC Chemistry for IT-JEE. 9. Match the Column (I) and (1). (Matrix) Molecule Property Me wl ® , ® Meso compound Me jv ) (@) Achiral Cory Me Me 0H ° wt o Chiral compound Me o (8) | Compound will show geometrical isomerism[pomertso, eo 8} 10. Match the Column (1) and (11). Modified Newmann Projection Conformers CH3CH3 (a) Ton (p) Fully eclipsed Ht HH H CHy (b) QO (@) Partially eclipsed cH “WH —~T CH3 H H () () Gauche H HH CH —| Hs H CH @ ®) Staggered H H H116 ORGANIC Chemistry for IIT-JEE 11, Match the Column (1) and (11). cor mee) cert mele Newmann Projection Name of the Compound CHs H. CHy {a) @) 3-methy] pentane H H CHg — CH CH3 ®) H @ n-butane H H H | CHs H © ®) Methyl-cyclopentane H H CH H H H (d@) (s) 1,2,4-trimethyl cyclohexane H H CHy CHISOMERISM _ ee : 117 1 itch the Column (1) and (1). (Matrix) Cree Molecule (a) AG (©) Rotates plane polarized light a (b) (@) | Cannot rotate plane polarized light Br Me Plane of symmetry | —_—_ CHy (d) c=C (s) Centre of symmetry CHy bt = 13.__Match the Column () and (1). Molecule Stereocenters CH; —CH = CH —CH— CH f) Br ®) 1 H—C =C—CH =CH—CH—CH—CH, b) @) br br @ 2 I ©) Ph— S— CH = CH —FH—CHy ®) 3 CHs Ph—CH—Et (a) 1 (s) | 4718 14. Match the Column (1) and (11). ORGANIC Chemistry for IT-JEE Molecule Stereoisomers H Zo come fa) ) 2 H Fo SCOMe ) @ ° H Zo cOMe © CY @ 4 ce cH ~COMe (@) 8ISOMERISM 1S. Match the Column (1) and (I). (Matrix) 119 Molecule Property i Me .C—~Me @) ae ©) Meso Compound 0 MeN. Me OH w C= C—Me (q | Compound having even no. of 0) chiral centres ° oO H © a ° () | optically active compound oO 'N’ H COOH | @ i 1— OH {s) | Compound having odd no. of H—}— 0H chiral centres. COOH \? ©)220 ahs at ah gt” ORGANIC Chemi 16._ Match the Column (1), (11) and (111). (Matrix) eran On) ion) Cro R OL) 1 ITJEE. j Molecule No. of Chiral Center ,-¥ (P)| optically active |(w) 0 H H CHy cH (q) | Optically inactive | 60 1 5 - ° ° Hs ON Her (2) [Plane of symmetry] 2 Et Mn yw (s) Centreof | ¢y 3 cl cl symmetry, From the above compounds select : (A) wo of which are chiral and contain chiral centre + es two of which are achiral and contains chiral centre : lo two of which are chiral and does not contain chiral centre Lo ‘two of which are achiral and does not contain chiral centre :ISOMERISM 121 a a I, cl ca) A cl Cl, A cl a ‘cl al ‘cl a @) a a 2 ad ql, cl cl, cl a a a ! (c) wm Ww) Consider the given structures and answer A, B & C. A. Which of the compound is optically active ? (@P O)R Os @T B, Which of the isomer is most stable ? @R (b) S @OT @u 19, _ Identify relationship between following pairs : COnH COnH on u H on cl, Br Br, g ca a ‘OH Hi cl & E CO,H COgH H () Sc—catF HC’ F ENG SH H CHg If they are enantiomer answer will be 1, if they are diastereomers answer will be 2, ifthey are constitutional isomers answer will be 3 and if they are identical present 4as the answer. Sum of answer of each parta +b +c + dis20. _Ineach of the following three questions a hydrocarbon is named. For each select from among the sixteen conformational structures (a through p) all structures that represent possible conformers of that compound. Write letters (a through p), corresponding to your selections, in each answer box. A. _| 2-methylbutane 2,3-dimethylpentane, Lethyl-1, 3-dimethyl cyclohexane Ho gh cathy cH HC H (a) ye CH doy y © CHEN aC Cas C2Hs AAC H CH, CH Bon Hs H htt ney [eo © A a CH, Hs ° CH * HCW CH Ci H H ows CoHs CH 9) o HC CoH cH; “ cH ‘CHR WOT Yoon, HCH Cate cH " sockets Jaalneg~ ren] wba ‘CH; oe 2H HCH CH ,C bod ) Chee cof Lee a CH CH H C2Hs : CH. H H 8 L—21. Examine structures a through j, shown below, with respect to their symmetry or lack of it. Assume that the five-membered rings and the ring in compound g are planar. The wedge-hatched bonds in b, ¢, d & e designate specific configurations. Also, for the acyclic compounds assume stable anti conformations. Answer each of the following questions by writing letters (a through j), corresponding to your selections, in each answer box. If there is no structure that fits the description enter an x in the answer box. A. [Which structures are chiral ? | B. | Which structures have a plane of symmetry? C._|Which structures havea center of symmetry ? | HL oH Hg Br Br @ | Cy jo OH Br, Br br, or @ Co eo Sy je CO @) @)] cH,CHCI, |] CHSCHCIGH, o C,HsCHCICH, | | 22. @ 1,2-dichlorocyclopropane = w Gi) 1,3-dimethyl-cyclobutane = x Gil) 2-bromo-3-chlorobutane Gv)1,3-dimethyl cyclohexane Calculate total number of stereoisomer of the above compounds. Sum ofw+x+y422.....126 4 Ss ‘ORGANIC Chemistry for ITJEE “27. _‘The configuration of eight compounds, a through h are shown below, using various kind of ~seéreo representations. To answer the quéétion given below, write (a through h) indicating ; your choice. v H —#H (a) cH, ~ Cro (b) x =Pl ‘ Z (Oper Gone -he © A CHy CH, + Hes) hy { cH=Cr ( I CH. ° CH ls ‘ = | Which of these configuration are achiral? B. | Which configuration has no stereogenic center? C. | Which configuration has more than one stereogenic center? | | Which of these configuration are meso compound? +28. The structural formula of ten compounds, (I) through (X) are drawn below, you may select any one of these structure. ~ . __ Answer the following question about that fo toy a7 Wd .ISOMERISM. cH CH, St CHyq cy wv OD v ‘DO vI 2 ct - oH CHa CHg, VIL OD ji] x cH” OH $ OH CH x cH OH A. How many chiral centre are present in this compound ? (@) 0 () 1 ©2 @ 3 () 4 os B. _Isthis compound chiral or achiral ? (a) Chiral (b) Achiral C. What symmetry element are present in this compound ? (@) None (b) Plane of symmetry —_(€) Center of symmetry 29. The structure of one of the enantiomers of the amino acid cysteine is shown below. coon Rfara)e CHS! Classify this structure as: @)Ror $ (®) DorkORGANIC Chemistry for IITJBE 30. Identify the following double bonds either E, Z or None (N) in the compounds given below either. A = — oO. B. (a) Bongkrekic acid is a toxic compound produced by Pseudomonas cocovenenans, and isolated from a mold that rows on bongkrek, a fermented Indonesian coconut dish. (a) Label each double bond as E, Z or neither (N) cron ti [eu (b) How many total stereoisomers (including all types) are possible for bongkrekic acid ? (© How many sites of unsaturation are present in bongkrekic acid ?ISOMERISM 31. Designate the following double bonds as E, Z or none (N) configuration in the boxes provided below. Ss O 1 CI 1 of S 32. The following compounds may exist as two or more stereoisomers. ‘These may be classified as enantiomer pairs or meso compounds. CoH 02H (a) CoH” CO, truxinic acid iQ} ‘COjH (e) C(CH3CHC), ch cs) Oeeeonn ct Celis CO ® o,e Cots eruxilic acid "go “> COR ro} “= = CHCO,H co ‘Answer the following question about the above structure. (A) Total number of stereoisomers : (B) Number of enantiomeric pairs : (©) Number of meso compounds :130 ‘ORGANIC Chemistry for IIT-JEE 33. Identify axis of symmetry in the given compound. Mea__cl 1 Me Ep Es Et @ if Et Er a ow cl cad oN Mec / ~cMes © iv: / Mes CA ®) oy. 4 ao)34, ay (12) Ab (13) Lon al For each of the following pharmaceutical compounds, identify all stereogenic (ie., all asymmetric carbon atoms) and label the configuration of each as being either (R) or (8). amoxicillin Q s—080,NH, ow" Q © 7ORGANIC Chemistry for IIT JEE 35. Find relationship between given pair : 7. Teath Constitutional. Identical] Enantiomer | Diastereomer | °"V eo nerStructural formula of compound (A) is following: HO,C. oH A. The correct statement(s) about the compound (A) is/are: (a) The total number of stereoisomers possible for (A) is 3 (b) The total number of mesoisomer possible for (A) is 1 (c) The total number of pair of enantiomer possible for (A) is 1 @) All of these B. Number of plane of symmetry in cis-form of compound (A) is: (ao @) 1 (2 @) 3 ‘37. Match the column. (Matrix) DOT EE Cath Ys CsHi2 Cota Q Cre aORGANIC Chemistry for IIT-JEE 38. Match the column. (Matrix) rrr ro peter) way: % of enol content o 9 i It o City -C-cly-C-CHy @ se o o I it 4 il [ (d) CHy -C-CHy C0 Et (s) Keto-Enol is not possible 39. Draw a most stable conformation (N ~ C) bond in the following compound. 40. Find total number of stereoisomers for each compound given below : 9 { (Q) Ph - 8 -CH =CH -CH2 -CH =C =C =CH-CH =CH -CHy, oss cect a H Br ORD WIS ‘NO, CI .N-OH, (4) Ph- GH -GH-NH- CH, me OH CH N-H q (6) H-0-C-GH-GH-C-H acs OH OH OHISOMERISM a. ® o XX =ot-cn = CH-CH, (40) CH; -CH = CHG -CHy an Ho o © CH MgBr + Ph lage? (@) EtmgBr + Ph =C-CHy -CHs ag17. In which of the following reaction an acid-base reaction takes place ? MgCl hee doy = 2 K, ry — , wo OF tem Li uv Mgcl D . - tat Heo +9 19 OF © CO @ Allof these t boa, Fe ve “uo So HO 18. OSs eu fm Product (8) inthis ean is HO 8 - ve or ak ox “OL CQL, © eg “Oe Ph Ph , 19. All of the following compounds react with ethylmagnesium bromide, Aicnols are reformed from three of the compounds. Which one does not give an alcohol? *” tHe os wed one Ot MO) IL fa) CH coe eT) htt Oo . . if . © C\-,0te, . a 20. A student was carrying out a Grignard reaction between PhMgBr and ethyl benzoate. She ran out of anhydrous ether just after the Grignard feagent was made. Which of the following 1-¢, Solvents can still be used to dissolve the ethyl benzoate for its reaction with already formed ~ PhMgBr ? o a rina ao {a}acetone No) extytaceate 0) absolute alcohol @) béndene OH H 0 Me0,C. rh ma y > NN Bu BUN, a. o) xohnigne_, HO ; HOP dou Fr HO’ HO" oe Number of equivalents of Grignard reagent (x) used in reaction (1) is : “(@).S equivalent —(b) 4 equivalent, (¢) 5 equivalent «,>,32(4)-6 equivalent seb SO earn wr, Fat Boao sea .4) 8 mo22. 25. 26. oH Br CH - Ph a) Mgsetier Cy SS TD n-cHo * amor y H H The given product can not be obtained in the above reaction. Identify the correct product obtained. qt g CH - Ph CH - Ph of ol) of ol Tyg Sy 7 7 H OH CH -Ph Which of the following give two isomers of 3° alcohol, when treated with phenyl magnesium bromide ? DD "O -O "OO ° ° Me fH —He¥s8:_, product of the reaction is H Ph Me le Me H Mey LH @ o (© Both (a) and (6) (4) None of these HO H H ‘OH Ph Ph —AM#8!_, Product; The product of the reaction is : G~ ob (a) HSO, —CH, —CH, —CH, —CH, —R (b)H—SO,(CH,)3 —R © Mee: (d) H—SO,(CH)3 —R ‘sj, MBPT When carboxylic acid reacts with organolithium reagents to give ketones, side reaction sometimes occur. For example,27. 28. 29. 30. CH; | Il HOCH,CH,CHCH,CH,COH —@)GHsl_, Nia ‘tetrahydrofuran Hy CH, HOCH,CH,LHCHCH,-C —CH, + compound (8) Compound A 63% 37% Value of (x) in above reaction is : (a) 2 (b) 3 O4 @ 5 Which of the following alcohol can not be prepared by the reaction of acid chloride with excess of Grignard reagent followed by acidification ? OH OH OH OH @ mm b) pe @r ps @ cure oe CHy Ph Gi) NHAC ensioo" Product (B) of the above reaction is : The reaction of elemental sulphur with Grignard reagent followed by acidification leads to the formation of (a) mercaptan (b) sulphoxide (© thioether (@) sulphonic acid + MgBrCH,CH,CH ,CH,MgBr “ane” HE, product; Product of the reaction is : (CH CH CH)! wouor ‘ I (@) HO — (CHa); — C — CH, — CH, —CH3(b) (CHy)3 — OH 10" (c) HO’ e — CH, —CH3 (d) C3 on HOT ‘CH, — CH, — CH32, 33. 34. 35. OH a x x CHyMaBr | ‘- CHy Gg . aA Cy Me~~OH Me Number of moles of CHgMgBr consumed in above reaction is (a) 2 ) 4 os @s End product of the given reaction is : C1 we, (4) as0 Cy eo? OES ® OH oC) oC HH oO~ oO ‘Which of the following compound is not a suitable solvent for Grignard reaction ? 0. fa) (b) C J ‘0 ‘0 rae) , 4-dfoxane) (©) CH; —O—CH,—CH,—O—CH; (d) Br A X7™ —®, predict major product of the reaction : (2 mole) i @ AN OA ZF OA @nn~w ‘Which of the following reaction sequences would be the best for synthesis of t-butyl alcohol ? 0, K Sa, 0, 08 (@) CH3CH,MgBr + CH, ~ CH, —B20_, 1,0" _, ) CH CH,CH)Mgbr > ne, 9 I () CHyMgBr +CH, —C—CH, 22° , #0? _, I (d) CH,CHMgBr + CH; —C—H—220_, _Hs0?36. What is the major product of the following reaction ? CH; —C=N. ee #308 i H 4 Z . 1 ) @ CHs —CH, —NH—CHy (b) Clly - C-CHy i i (0 CHy —C—CHy (d@) CHy —CH, —C—OH BY UCHs 37. — ee Products; Product obtained in this reaction are : (@) diastereomers (b) racemic (©) pure enantiomer (4) meso 38. CH3CO2Et + (CH2)5(MgBr)2 Gq GyHy40 5 compound (A) will be : a Hi OH (a) b) ‘OH e (© CHy —C—(CH2), —CHs @) 9 Il C-Ph 39. eo Fhagnr/ouel_» (4); A will be : DH GsHtwo dp» i hh © Oe or" MeO. OMe o n-tu,us 40. I ___, product of the reaction will be : (a-Buanbuwyl group) ‘Br41. 42, 45. MeO, OMe Meo. OMe @ 0) Bu nBu OMe. Bu OH, OH © (d) Br ‘Br 1 8 i OY stats 0 moter: O,Me “YY oO -D «D Ethyl acetoacetate when reacts with one mole methyl magnesium iodide then product of reaction wil] be : 7 of gener Il (a) CH, —C—CH, —C—cH, ®) Cy — € — City — 6 — CH, HH: g f° . © CHy — C— CH — COEt (d@) CH; —C—CH, — CO, Ft MaBr, I! CH MgBr + Et—O—C—O—Et => (A); Product A i (excess) “om oh yt @a7~ ow © ow For the sequence of reactions, A—‘#isM#l_, g_M20/H* . tort-Pentyl alcohol. The ‘compound A in the sequence is : (a) 2-Butanone () Acetaldehyde | (c) Acetone (4) Propanal (excess CHy-ti_, (4 I PhMgBr + CH, ~CN——5~> (A) Ph -C-O-H. Om Same product (A) will form in both reactions. A is: e i @ Ph—G—CHy (0) Ph—CHO (© Ph—C—CHg (4) Ph—CH, —COH CH,46. 47. 49. 50. 51. Which of the following Grignard reagent can be prepared ? (a) Br —Mg — CH, —CH, — CH, —O— H (b) Br — Mg —CH, —CH, —SH (© BrMg —CH, —CH, — NH @ Brig — CH, — CH, —N—CHy In the reaction sequence CH (9 CHM /CuCd abe: — 2 EMERIOS + (9, Product (0 will be : CH3,_,0H 9 OH CH3 H CH @ (b) © @ Ha HH ‘CH; (CH,0),co— SO A, A (alcohol) can also be obtained by : i CH3MgBr(2mol)_ (CH 3MgBr(2 mol) (@) CHcH,cHO SS (b) CHC OC3Hs, a l Cigna mod) (©) CH3CCH; ee @ asin (b) and (c) ‘The principal product of the reaction between methyl butanoate and 2 moles of CH3MgBr after hydrolysis is : (a) C3H,;COCHs (b) C3H7C(OH)(CH3)2 (©) CgH,CHOHCH (d) CgH,COCH(CH3)2 Which of the following compounds will form hydrocarbon on reaction with Grignard reagent ? (@) CH,CH,OH (b) CH{CHO (© CHsCOCH, (@) CH3CO;CHs What is the product (B) of the following reaction sequence ? Br Ae At bn, WW Fn0_, B "CHy Ha 0 : Ss A 0H 5 CH ~ HH CH "S © “OH (4) CHs ‘OH re}53. 55. 56. Which, if any, of the following pairs of reagents could be used to prepare 2-phenyl-2-butanol? Oo Oo I I (@) CH,CH,Mgar + Ph —C—CH () CHgCH )MgBr +C,H5CH,CH i i © CHjMgl+CgH5CH,CCH, (d) CoHsMgCl + CH, CCH,CH,CH, ‘What is the product of the following reaction? Ch + 2CHgMgBr —Ldiethvlether_, product ‘o7S0. 2. HO" @ HO-FHCH,CH,Cti,¢H -OH (b) CH,OCH,CH,CH,CH, prem CHy CHg IH CHs I © HOCH;CH,CH CHa ¢—Ol © HOCH,CH,CH,CH,HOCH CHy CH3 Ph Mg. 4 1 HCHO, ; Product (B) is : pr ether 2H Ph @) =< CH, — On (b) Ph—C mC —CH, —CH, —CH, — OH © Ph—C =C—CH, —CH, —OH (d) Ph—CH, —C = C—CH, —CH, —OH ‘What sequence of steps represents the best synthesis of 4-heptanol (CH3CH ,CH,),CHOH? (@) CHjCH,CH ,MgBr(2moles) +- formaldehyde (HC =O) in diethyl ether followed by H,0+ (b) CHjCH,CH .MgBr + butanol (CH,CH CH,CH =0) in diethyl ether followed by H,0+ (© CHCH,CH,CH,MgBr + acetone (CH) ,C =O] in diethy! ether followed by Hj0+ (@) (CHCH,CH,),CHMgBr + formaldehyde (HC =O) in diethyl ether followed by H,0+ Oo Et oN aati comment on stereochemisty of products : H "Me (a) diastereomers (b) racemic (©) single stereoisomer (@) meso57. 59, CH,—OH | CH —OH +CH,MgBr—> xCH, Exces Hy— SH ° What is the value of x in the above reaction ? @ ) 2 ©3 @4 0.40 g of an organic compound (A), (M.F.- CsH,0) reacts with x mole of CHaMgBr to liberate 224 mL of a gas at STP. With excess of Hz, (4) gives pentan-1-ol. The correct structure of (A) is: (a) CH, —C = C —CH, —CH, —OH (b) CH, —CH, —C = C—CH, —OH (©) H—C = C—CH, — CH, — CH, —OH @ H=C m¢—cH, — CH—CH; H g Bre Mg atc —cH = cH, > > 8, tt Hs —CH = CHa Dayar NEG > 2, {ow ne) End product (X) of the above reaction is : CH il (@) CH, =CH—CH, —C—CH3 (b) HC =CH —CH =¢ —CH Hs OH (c) HC = CH—CH,+C—CH3 ~ Hs @ H,C-= CH cH, —CH—CH, —OH CHg Re ae gh? WL (B); Product (B) is CHy — CH — CH, — CH, CH; —O—CH, —CH, —CH. @) NO 2 Is (b) CHs 2 12 3 (© H,C = CH— CH, —O—CHy @ HC — GH — CHs ‘061. Compound A was treated with a large excess of CHsMgBr. The resulting product was exposed to POCL; /pyridine to give compound B, as one of many products: B Which of the following compounds can be A? oO oO @ “or oO oO NX oO - “wT fe) or @ 62. Identify product Z in the following reaction sequence : Oo oO “or 0 Oo Oo o So’ oO "corte HC —CHCH,br_—MOL, yee”, » 2 Ho" i i (@) H,C =CHCH,CC,Hs (b) H,C = CHCH,NHCCgHs OH NH, i | (©) HC =CHCH,CHC,Hs (d) H2C = CHCH,CH C,HsGrignard Reagent _ 161 emt Grignard reagent is usually prepared by R-X+Mg—222 5 RMgx Grignard reagent Ar -X 4 Mg —2° 5 arMex. Grignard reagent ' Grignard reagent acts as a strong base. Grignard reagent carry out nucleophilic attack in | absence of acidic hydrogen. Grignard reagent form compiex with its ether solvent. | Complex formation with molecule of ether is an important factor in the formation and stability of Grignard reagent. | A. What is the correct order of reactivity of halides with magnesium ? (a) R-Cl>R-Br>R-1 (b) R-Br>R-Cl>R-1 () R-I>R-Br>R-Cl (@) R-I=R-Br=R-Cl B. Which of the following will undergo acid-base reaction with Grignard reagent ? (@) HC =CH (b) R-OH (© R-CO,H @) All of these ©. Which of the following reactants give primary alcohol as a major product when reacts with RMgx followed by acidification ? 7 ll @ CH, — CH Gi) H-C-H Ocha eH — CH3 oO i (CHa -C-H wi Ca (@) i,ii,v (b) i, ii, v, vi (0) ii, iv, vi (@) vy, iv, iii, vi ql D. Cl-C-0 - Bt —WARMEX_, 3° alcohol, Value of x is : (@) Witcl @2 @) 3 o4 @5 i is EB. H-O-CH, -CH, — -0- Br Oe HO -CH, -CH2 -C—Ph, Value of x is : bn @2 (b) 3 oO @s162 a ORGANIC Chemistry for I1T-JEE F. Which of the following Grignard reagents is not possible ? (a) HS ~CH, ~CH, —CH)MgBr (0) HO-CH, ~CH, ~CH,MgBr (©) NH, -CH, -CH -CH.MgBr @) Allof these G. How many different Grignard reagents when react with EtOH, give n-butane as product (excluding stereoisomerism). @) 1 @) 2 ©3 dd) 4 2. Match the column I and II. (Matrix c Tome) Cnet Reactant Product i ©) | phuigpr+cl-C-0-Bt a> @) Ph -CH ~OH fexcess) ° T Ph—CH-Ph ©) | phwigpr+ H-C-O-Bt—s—> @ 1H exces) + i (© | phuigprs H-C-H > © (exces) i @ | pavgbr+ CH, -C-0-Bt a> ) cones LL 3. Match the column I and Il. i Reaction Reactant PhM; @ alcohol t i rey) IgBr + (A) —{5— 1°alcohol q we ) CHy =o =C-CHy | ‘by | PhMgBr + (B) ———> 2°alcohol il by a @ oni, cy oO 3ealcohol {i PhMgBr + (C) —;5~ 3°alcohol (r) © 2 * G cH, --H Oo (a) | PhMgBr + () —O (s) it ia H-C-H Match the missing reactant A, B, C, D4. Match the column I and il. (Matrix) Moles of PhMgBr used i PhMgBr + Et ~O-C-O ~ Et —--—»3°alcohol ——_—___H? i PhMgBr + HO-CH, ~C @) (@) , | ~CHy —z5~> 3" alcohol 9 i PhMgBr + CH, -C-CH, ——» 3ealeohol PhMgBr + 5. When 20 g of a compound (A) (M.F. = C,H, 0,) reacts with excess of CHyMgBr, 14.6 L of ‘CH, is obtained at STP. What is structural formula of (A) ? CH,—OH CH,0H (a) (CH—OH), b) no—cHt, —4—cx,on u,—on OH HO, OH © CI () Both (a) & (b) HO’ ‘OHORGANIC Chemistry for IIT-JEE SUBJECTIVE PROBLEMS ' H AMebr | Or Neo itt an | How many geometrical isomer of (X) is possible ? 2. How many isomer of C,HgO when reacts with CH; MgBr followed by acidification to give 2° alcohol (only consider carbonyl isomers)? (including stereoisomer) 3. — "otal number of RMgX are consumed in the following reaction a CoN A, 4. How many isomers of C4Hj 0 reacts with CH,MgBr to evolve CH, gas ? ( Excluding stereoisomer) 1. A-cGB- |; C~ a; D-b; Eb; F-d;G-b 2. a-r,b-q;e-pid-s 3. a-s;b-re-qd-p 4, a-rb-q;c-pid-s 5. (d) Subjective Problems L422 °° 37 444Aba "HYDROCARBONS (ALKANES) 1 On halogenation, an alkane gives only one monohalogenated product. The alkane may @ 2-methyl butane (b) 2, 2-dimethyl propane (©) cyclopentane (d) both (b) and (¢) Which of the following compounds can be best prepared by Wurtz-reaction ? (@) Iso-butane (®) n-butane (©) n-pentane (@) Iso-pentane A hydrocarbon A (V.D. = 36) forms only one monochloro substitution product, A will be : (@) iso-pentane (b) neo-pentane (© cyclohexane (4) methyl-cyclohexane Ethyl iodide and n-propyl iodide are allowed to undergo Wurtz reaction. The alkane which will not be obtained in this reaction is : (a) butane (b) propane (©) pentane (d) hexane Hy— CH —CH,—CH, —G2_5 CH Number of chiral centers generated during monochlorination in the above reaction : f@1 ) 2 ©@3 (d) 46. a % 10. 11. CH,Cl— CH, Above conversion can be achieved by : @ mn/H* (b) LiAlH, (© Mg / (ether) then H,0 (@) all of these n-Butane Sa, Give the total number of monochloro products(including stereoisomers), which are possible in the above reaction. @) 2 b) 3 @4 @5 CH, +Cl, —™>CH,Cl+ HCl To obtain high yields of CH,CI, the ratio of CH, to Cl, must be : (a) high (b) low (c) equal (d) can't be predicted Double bond equivalent of cubane is : Cubane @4 (b) 5 @6 @)7 How many bond cleavages are required to convert cubane into non-cyclic skeleton ? do Cubane Non-cyclic skeleton (a2 (b) 3 4 (@5 Draw an energy profile diagram for a three step reaction in which first step is slowest and last step is fastest. (Assume that reaction is exothermic) PEI PE @ © ‘progress of reaction progress of reaction PE © (@) None of these13, 14. 15. 16. 17. stereoisomers. (a4 ) 5 © 6 @7 NDNDa py H,02 Product (P) is : » D wit D (a) (b) D () D (d) both (b) & (c) (4 ain Double bond equivalent (degree of Unsaturation) of (A) is : @1 (b) 2 ©3 mw Arrange the following alkanes in decreasing order of thei heats of combustion. 5s I @ CHy~¢— CH Gi) CH;— fe —CH, —CH, CH, CH, (Neo-pentane) (Gso-pentane) Gi) Gii)CH, —CH, —CH, —CH, —CH, (pentane) (a) @ > Gi) > Gi) (b) Gi) > @ > Gi) © Gi) > Gd > @ @ @ > Gi > Gi) Gh +h, BL ‘CH, CH; Product of the above reaction will be : (a) Racemic mixture (b) Diastereomers (© Meso (@) Constitutional isomers CH; fo. 300% r + Br ——> CH) —CH, Which of the following compound will not be obtained as a product in the above reaction ?18. 19. 20. 21. 22. 23. H————3r H—————Br @ (>) Br—}—— Hq} CH.—CH; CH,—CH; CH; CHs H—}———r Br——————H o CH @ H——}——Br a Br CH CH, —CHy Following are the structures of four isomer of hexane. Among the names given below, which correctly identifies the fifth isomer ? CH,CH,,CH,CH,CH,CH, (CH,)3CCH,CHy (CH,),CHCH,CH,CH, (CH ),CHCH(CH) (a) 2-Methyl pentane (b) 2-Ethyl butane (© 2,3-Dimethyi butane (@) 3-Methyl pentane Which of the following describes the best relationship between the methyl groups in the chair conformation of the substance shown below ? CH; CH; (a) Trans (b) Anti (© Gauche (@ Edlipsed Compare the stabilities of the following two compounds (A) and (B): A: cis-L-ethyl-3-methyl cyclohexane B: trans-1-ethyl-3-methyl cyclohexane (a) Ais more stable (b) Bis more stable (©) Aand Bare of equal stability (4) No comparison can be made Which conformation of ethane has the lowest potential energy ? (@) Eclipsed (b) Skew (©) Staggered (d) All will have equal potential energy Ethane is subjected to combustion process. During the combustion the hybrid state of carbon changes from : (a) sp? to sp® (b) sp* to sp (©) spto sp* @ sp? to sp? CH, —CH, —CH, —CHy cH, — CH—cH, CH, Above reaction is an example of:25. 26. 27. 28. 29. 30. (a) isomerization (b) polymerization (©) cracking (@) dehydrogenation Which of the following has highest chlorine content ? (a) Pyrene (b) DoT (© Chloral (@) Gammaxene Pure methane can be prepared by : (a) Wurtz reaction (b) Kolbe electrolysis method (©) soda-lime de-carboxylation (@) reduction with H, Calcium carbide + heavy water —> ? The product of the above reaction is : (a) CH, (b) Cab, (© Ca(OD), @ , CH, — c,—<_ | CH, —c,—< > cH, —cH, Ethyl cyclopentane Ethyl cyclohexane Ethyl cycloheptane o a ap Arrange the compounds I, Il and III in decreasing order of their heats of combustion: (@) U>1> Ul (b) I> > m1 () M>0>1 (@) W>t> Analkane (mol. wt. = 86) on bromination gives only two monobromo derivatives (excluding stereoisomers). The alkane is : Hs (@) CHy— CH —CH, — CH, — CH () cH, —CH, CHy CH CHa © cH, — HH CH, @ ofa CH; CH3 CH; Order of the bond strength of C—H bonds involving sp, sp? and sp* hybridized carbon atoms is : (@) sp>sp? >sp® (b) sp? >sp” >sp ©) sp? > sp? >sp (@) sp? >sp>sp* HOO cH, oH HCH, o ay am Among the structures given , select the enantiomers : (@) Land (b) Tand mr (©) Mand HT (@) | Mandi32. 33. 34. 35. 36. 37. oO aD ap ‘The correct order of reactivity of I, Il & I towards addition reactions is : (a) 1> > 0 ®i>u>m © W>n>1 @m>1>0 a Br —NeOorether_, (ay < » om Product (A) of above reaction is : XO +O 2 wD Which of the following reactants is suitable for preparation of methane and ethane by using one step only ? (@) H,C = CH, (b) CH,OH (©) CH, —Br (@ CH —CH, —OH How many carbon atoms does an alkane (not a cycloalkane) need before itis capable to exist in enantiomeric form ? @4 ) 5 6 (7 Among the following free radical bromination reactions, select those in which 2° halide is the major product — CH) —CH, tit, eye o> ° @\ 2m, Bev (R) “Ss fh Brgy oye CL) SAK 225 @ P,QRS (b) WRU © P,RS,T @P,OR8,T (A) + Cl, —2-s monochloro product ‘To maximise the yield of monochloro product in the above reaction ? (a) Cl, must be added in excess (b) Reactant (A) must be added in excess (© Reaction must be carried out in dark (4) Reaction must be carried out with equimolar mixture of Cly and A Hy — CH, —CH, —cH, 22 Major product in the above reaction is : (a) Racemic mixture (b) Meso (©) Diastereomers (@ Constitutional isomers38. 39. 40. 41. 42. Select the chain propagation steps in the free-radical chlorination of methane. (1) cl, —> 2cl* (2) Cl’ +CH,—> CH,Cl+H* (3) Cl’ +CH, —> CH} +HCL @) HY +Cl,— Hel+cl" () CH} +Cl,—> CH,Cl+cl* (@) 2,35 (b) 1, 3,6 © 35 ) 2,3,4 CHy Bry/by —+—> Monobromo derivatives ‘The number of possible monobromo products is (excluding stereoisomers): @4 ) 5 Os (d@) 10 CH, et st +Be ——> He ‘OH CH, —H* Br* will abstract which of the hydrogen most readily ? fa ()b @c @d Arrange the following compounds in decreasing order of their heats of combustion : Ae a. ae ca, ots BS tre CH, CH, o wo Gin @ Gi) > G > @ ©) Gi) > @ > Gi) © Gi) > > W @ @ > G > Gi CH,—CH,—CH,—CH,—F a db c d Arrange the hydrogens a,b, ¢,d, in decreasing order of their reactivities towards chlorination: @a>b>c>d b) b>c>d>a © b>c>ard @c>b>a>d On catalytic reduction (H, /Pt) how many alkenes will give n-butane ? @1 (b) 2 o3 @4 On catalytic reduction (H,/Pt) how many alkenes will give 2-methylbutane ? f@1 (b) 2 ©3 @4.46. 47. 49. OQ ly (excess) Ear How many dichloro products are formed in the above reaction (including stereoisomers)? (a) 5 (b) 6 7 Wo CHy—CH sn pw Np Product of the above reaction will be : (@) Racemic mixture (b) Diastereomers (©) Meso (@ Constitutional isomers Ph—CH, — GH CH, Bu/hv D Product of the above reaction will be : (a) Diastereomers (b) Racemic mixture (© Meso (@) Constitutional isomers CH, —cl 3 cH,— dl Products obtained in above Wurtz reaction is : © S&S Hy cHy (a) al ‘CH © (d) Both (a) and (6) cHy CH Rank the transition states that occur during the following reaction steps in order of increasing stability (least > most stable) : Ome 1 HC -OH,—> CHS +H,0 2. (CH,)sC-OH,—> (CHy)9C* + H,0 3. (CHy))CH-OH, —> (CH4),CH" +H,0 (a)1<2<3 b)2<3<1 (1<3<2 @2<1<3HYDROCARBONS (ALKANES) 50. Which of the following does not represent major product of that reaction ? 2-0 . Nee et ws @ <> ame? > 9. | @) | 10.] @ | 11-] © | 12] © | 13. | @ }14-] © |15-| © 16. ) 17.| @ | 18. | @ |19.| © | 20. | (a | 21.] (© | 22. |) | 23.| @ 24, fa) 25-| ©) | 26. | @ | 27-] @ | 28.| © | 29.| @ | 30. | @ | 31.| 32. ) 33. (©) | 34.| @ | 35.| w | 36.| w) | 37-| @ [38.| © 40. (a) 41.| @ | 42.| © [43.] © | 44] © | 45-] © | 46. | @ 49. | | 50. | @ 48. (d)ORGANIC Chemistry for IIT-JEE For the given question (1, 2, 3), consider the following reaction. ia +X, + monohalogenation product A. Light is involved in which step of the reaction : (a) Initiation only (b) Termination only (©) Propagation only (d) Propagation and Termination B. Which halogen will give the best yield of a single monohalogenation product ? (@) Fe ) cl, © Br @l How many monohalo derivatives are possible (excluding stereoisomers) ? @ 3 4 ©s @6 1 j Halogenation is a substitution reaction, where halogen replaces one or more hydrogens of hydrocarbon. | R—H+X,—™4R—X+HX | Jess than 1 keal about 1.5 keal I difference of Ey 4a) difference in Ey | 3 Pree radical | alkane g g i ° jz: Free radical { ce alkane + Br* | Progress of the reaction Progress of the reaction | Chlorination is exothermic and Bromination is endothermic and transition state resembles with products transition state resembles with products Chlorine free radical make 1°, 2°, 3° radicals with almost equal ease, whereas bromine free radicals have a clear preference for the formation of tertiary free radicals. So, bromine is less reactive, and more selective whereas chlorine is less selective and more reactive. The relative rate of abstraction of hydrogen by Br* is o> 2 '> 1° (4600) (82) (1) The relative rate of abstraction of hydrogen by Cl* 3°> 2 > 1° (5) (3.8) ()AL c Fr Consider the above argument and answer A to G Lhalo-2,3-dimethyl butane will be obtained in better yields, if halogen is : @) Br, (b) Clp OL (@ Can't be predicted Above product will obtained in better yield if X is @ a, ) ly © Bry (@) Can't be predicted CH; I (CH,— CH—CH, —S24"_, Product Major product in the above reaction is : CH, CH, | I (a) CH, — CH—CH, —Cl ) cH, GH— Chie a (©) CH, —CH, —CH, —Cl @ CA,—FH— CH, ~ Gis a Which of the following will give five monochloro products, when allowed to react with Cl, in presence of sun light (excluding stereoisomers) ? (@) n-pentane (b) Iso-pentane _—_(c)_2-methyl-pentane (4) 3-methyl pentane cH; CH, CHy CH, I I Bryfhw | I GHa— ¢—GHly— GH —CHly ————> ity— ¢ et — Ga — ¢ CHa CH CH, Br 2, Bromo-2, 5,5 trimethyl hexane (9) What is the value of x (% yield of product)? (@) 18% (b) 82% © 90% (@) 60% What would be the product ratio x/y in the chlorination of propane if all the hydrogen were abstracted at equal rate ? CH, —CH, —CH, CH —CH, —CH,—Cl+ CH, — GH Cs cl (cs) @ 1 3 9 1 i pb) 2 2 @ 2 f@ 3 ©) 7 © i () 3 How many dichloro products (including stereoisomers) will be formed when R-2-chloropentane reacts with Cl, in presence of UV radiation ? @s5 (b) 6 7 @s176 ORGANIC Chemistry for IT-JEE Sars? (A); Product (A) is : 14 14 14 (a) ) oO @ 14 14 rz oe? (COzCHs +H, (1 mole) 4. a (A); Product (A)is : ‘CO,CH, (a) Meso compound (b) Racemic mixture (c) Diastereomers _(d) Optically active ° NAOH, CaO, 6 I Ph—CH, —C—OH ~S (A) Product (A) is : (@) Ph—CO,H (b) Ph—CH,—OH = (c) Ph—CH @ Oo Match the column I with column Il and with column II. Monochloro products Mono-chloro products (excluding (including stereoisomerism) stereoisomerism) |__L City ~ GH —CH, CH, ®) bs, @ 2 © 3 CH, CHy lod | ©) cH —c—c—cH, fy 3 o 5 CH, CHy (@)| CHs CHa CHa —CHs | (5) 4 ® 6[zxprocarsons (ALKANES) 2 177] A. | B-2-chloropentane te Optically active di-chloro products (P) B. om Optically active dichloro products (Q) c, |R-2-chlorobutane a Optically active di-chloroproducts (R) Sum P+Q+Ris: 8. Match the column I and II. Column (1) rerouD me) Reaction ‘Type of Reaction (@) C oe. ®) Meso compound CHg ) 7 Sa @ Diastereomers CH Hg CH, © OO wa, | Racemic rs CH,0° 4 Optically inactive due to absence @ =a ©) of chiral center | r lL.[a6 + ORGANIC Chemistry for IIT-JEE 9. Match the column : . TT mee Column (II) Reaction Product CH; M5, (a) (p) T (2) CH3CO,T 3 CH. ©) @ b (2) BT, ‘4 H (2) CHCO,D CHg SH © BD THE ® D “ecco 'CH3CO,H- @ © > angie, patton? 10. How many distinct monochlorinated products, (including stereoisomers) may be obtained when the alkane shown below is heated in the presence of Cl, ? @1 2 © 3 @4 @6 11. How many distinct monochlorinated products, (including stereoisomers) may be obtained ‘when the alkane shown below is heated in the presence of Cl, ? (a) 2 @)4 (5 @o ©s| HYDROCARBONS (ALKANES) 12. Match the column : —St_, CH ~Cl ‘dry ether ICH, ~Cl+CH, -CH, Coo) -d— > CNR) dimerization product (@) ay eter ~Cl+CH, -CH, ~ +CH, ~CH, -CH, }+CH ~CH, ~ % -a—_M_ H.C =CH-CH =CH-CH, ~Cl Ne J iry ether wo yet CH Cl (CHy—CH,—CH,—CHy 13, S-2-chloro hexane 224 (0). (9) = total number of di-chloro product10. co 12, 13. A-a;B-GC-b A-b; B-¢ Ca; D-c E-c; F-b;G-c abe a c a-q-%b-s-2c-p-w;d-q-x P+Q+R=10 a-qb-pye-nd-s a-pjb-s;c-q3d-r a e a-sb-1c-p;d-q 91. (R)-3-bromocyclopentene (shown below) reacts with Br, /CCl, to form two products, Y and 2, ¥ is not optically active (does not rotate plane-polarized light). What is the structure of Y? © co, (d) All of these HO’Which of the following products cannot be obtained in ozonolysis of o-xylene? CHO i @ | (b) CH; —-C—C—H CHO 9 9 0 I t tot (©) CH, —C—C—CcH, (@cH, —C—C—cHO [ X= O—4*_, major product of the reaction is : OH . HO @ (b) oOo CH, —CO,K OH ——Seaulwsis_, (A) (Kolbe electrolysis method) CH, —CO.K «gon Product (A) of the reaction is : (@) CH —CHy () CH, —cH, (©) CH3 —CH =CH) @) none of these x Sis Atami 5 BA (©); Product (C) of the reaction i HL 9 @ AN © O of of10. 1. 12. ‘The reaction of propene with H0* will proceed with which of the following intermediates ? Son, OH | e | (@) CH, —CH,—CH, (>) CH; —CH—CH, Por, OH | I (©) CH, —CH—CH; @ CH, —CH—CH, Which of the following bromides is the major product of the reaction shown below, assuming that there are no carbocation rearrangement ? + HBr —+C,3H,yBr (equivalent) Br Br, @) &) YY © A @ Oe Which of the following reactions results in the formation of a pair of diastereomers ? HAC. H HgCy CH: HBr = HBr G) HaCg Sista, ) s i, Oe S WG Bg, a a © My mnt © Se Tare What is a likely product of the reaction shown ? HC, 4H ACH, Cy suvenaHC on HC, Br H3C, OCH. a Hy CH. SCH, br CH OCH, d ‘Br " (a) “OCHs (b) “CHs (6) @ 1 os jr Br 13. Which of the following, when undergoing addition of HBr, will form ONLY a pair of diastereomers ? 14. How many transition states and intermediates will be formed during the course of following reaction ? OH (a) 3 transition states and 3 intermediates (b) 4 transition states and 3 intermediates (© 3 transition states and 2 intermediates (d) 5 transition states and 4 intermediates 15. Product of which of the following reactions, is racemic mixture ? CH @ he ) Q = HC’ ‘CH " CH, 3 CHy x, ,CH3, Be © =P (@) Hac a CH 16. The product(s) of the following reaction can best be described as : oy = (a) a racemic mixture (b) a single enantiomer (©) a pair of diasteriomers @ an achiral molecule 17. Taking into account the stability of various carbocations and, as well as the rules governing mechanisms of carbocation rearrangements, which reaction is most likely to occur during the given reaction ? PAT?18, 19. 21. go a © my — OY B® ao, (d) None Consider the following reaction in which the intermediate carbocation loses H* to give the final product ? neo A Which of the following energy profiles best represents the overall reaction ? ° ls Vr . lw] ° A] Methyl vinyl ether, HC = CH —OCH,, reacts with Br, /CH,OH. If methanol is reacting as water would, and if this reaction follows a typical mechanism of electrophilic addition, what ‘would be the expected product ? Br, och Br _,OCH3 OCH; Br OO @ gco wo < Se a ~« ‘OCH; ‘OCH, ‘OCH, 2, 4-hexadiyne (CoH) is allowed to react with Li in NH,(liq). The product obtained is treated with 1 equivalent of Cl, in CCl,. Which of the following constitutional isomers are possible products ? a 1 q o a a4 a & & & ° ow on 0 o (a) land IT (b) Wand Ir (© landV (d) Land IT Which of the following is the best stereochemical representation when reaction between 1L-methyleyclohexene and NBS react in aqueous dimethyl sulfoxide ? OH OH Caowsnew (a) (b) © (d) None of these . Br “Br Br22, 23. 24, 25. 26. Which of the following is among the major products of the reaction of (E)-3-methyl-2-pentene with BH, in THF followed by the addition of H,0,/HO™? OH OH H Me Et. Me. Me, OH H. H @) (b) © @ H ‘Me H ‘Me iH ‘Me Et ‘OH Me Et Et Me Compare rate of dehydration of (i), (ii) and (il) by cone. H_S0,. OH (@ @ > Gi) > G ©) @ > Gi) > Gi) © Gi) > @ > Gi @ Gi) > Gd > @ How many products will be formed in this reaction ? ” “" 1.0304 EE 7 NaHs0, (a) 10 (b) 2 @3 @4 H H ~ a Poa O=CR ZO @). Product (A) of the reaction is: cHy ‘C(GH,),CH,OH T+ Br Br cH, HDA cH. «MR or EK CHS Oo cHY ©: (CH Br © Ht of YCHs Br CH, 1 CH )—GH +H, = CH, —HE-> (A); @) is: CH oy >< oO (d) CH, +H —CH, —CH =CH, aX a4 2 2 CH,HYDROCARBONS (ALKENES) Rae he 187 27. Predict the product (A) of the following reaction HO. Yr. g~ A wy -d LB Ailw Y FR ea “g os at) noe nite? 28. Ce oF whey i ition product ani hue \ ps 1 SK i 4 ne ort Nea = by, Si bE () @ atu my CaN Se 2 ai 30. OS ye (B) —&H2._5 (6) HO f End product of the reaction is : @ CY e Q e © QO ea ° (a) OS «OSSD(ORGANIC,Chemistry fori VEE] 41. 42. 44. a7. The major product of the following reaction sequence is ast Sa ae? ¢ AHO? > og OE GH oyX w >< © XK ro y Which one ofthe following compounds gives acetone (CH), = 625 dne of the product of its ozonolysis ? Heeb foe, oY OY OSS, § WO, Addition of HCI to'3, 3-dimethyl-1-butene ylelds wo products oiie of which has alebnanged carbon skeleton. Among the following carbocations, select the possible intermediates in that reaction? Lege 4 : (Cig) ,COHCH,CI, (CH,),CCHCH, , (CH), CC(CHs)2 {Cina GcHicH)s i Dot ren . 3 wok toon. , @i2° - * w)1,3 (14 HO (@y'233 (6).2,4° z Conversion of cyclohexene to cyclohexanol can be conveniently achiéved by : (@) NaOH+H,O ,/ \ (>) Br, —H,0 ow (© hyéroboration, oxidation (@) hydroboration hydrolysis, Trans-cyelohexane-1,2-diol can be obtained by the reaction of cyclohexene with : (@) Kno, ©) 050, (©) peroxy formic acid /H;0° ‘nvissaix tue (4) SEO. + re = - be Bromination of (E)-2-butenedioic acid gives oS US tbs Hud HO. ALC? (@) QR, 3S)-2, 3-dibromosuccinic acid () (2R, 3R)-2, 3:dibromosuccinic acid (© amixture’of (2R, 3R) and (28! 38)-2, 3-dibromosuecinic acid @) (28, 38)-2, 3-dibromosuccinie acid _ 3mN ‘The major product formed during the reaction of 1-methyl €yclopentene with CH ,CO3H i is CH CHg soto OY gts CE 20S OS gr en cH—co, 2H electrolysis S MoH, AT Bs Product (B) ofthe reaction is? CH —CO;H (womele) roe HO Jo (a) CH, —CH, - () HC =CH, (© H-C=C—H (@) CH, =CH—CH =CH,49. oO. WE») Hs, CHLCHOK , (py | Product (P) is : (@) NaBH, HO™ 2004) OH OCH,CH OH Ort @ oCY b) CY 0X, @ CK 1H Et 50. What is the major O expected from the following reaction ? 4tn0, HO" ead SL. CH, —CH =CH, 5 (A); Product (A) of the reaction is : (@) Cli, —FH—CH, — Br (b) H,C =CH—CH, — Br © cH, —G-—=cH, @ Br—cH, —CH, —CH, —Br Br ° ° i IL Et-CH-~C~ Et-CH-C~ 52. bs, cw Ay bay a” ; Reagent (A) in the reaction is : | c=ch, Hy” (a) 03/Zn(H,0) —(b) HIO, (c) CrO3 (d) Cold dil. KMno,54, 57. 58. 59. 60. 61. Which compound is a possible product from addition of Br, to 1-butene ? wr p) Br @ aN » od © 9A YN Addition of Br to cis-2-butene would give a product whichis: (a) achiral (b) racemic (©) meso (@) optically active Addition of Br, to trans-2-butene would give a product which is: (a) achiral (b) racemic (© meso (@) optically active Addition of 030, to cyclopentene would give a product which is: (@) achiral (®) racemic (© meso (@) optically active Addition of BH, followed by HO, to trans-2-butene would give a product which is: (a) achiral (®) racemic (©) meso @ optically active CH,CHCH = CH) CHyCH - CHCH, 4 bu 3 Reagent A may be : (a) H,0/H* (b) BH. THF/H,0, ~OH™ (© Hg(OCOCH,),.THF/NaBH,.NaOH (4) All are possible ‘The major product of the following reaction is : CHy —CH = CH, + HBr, _, (@) CH, —CH, —CH, — Br (b) CH,CH@N—CH, (©) BCH, —CH = CH, @ Do HO; a® Rw 3.) Identify (B) :62. 0. (a) Lt b) 0, O LO, HO- (CH), — COgH (CHy)3 — CO,H Which of the following is a major product of the reaction shown below? HO: (CH,)5 —CO,H % Br, ho CH, GOH o) wuBr H In methyl alcohol solution, bromine reacts with ethylene (ethene) to yield BrCH ,CH,OCH, in addition to 1, 2-dibromoethane because (@) the methyl alcohol solvates the bromine () the ion formed initially may react with Br~ or CH,OH (c) this is a free radical reaction (@) the reaction follows Markovnikov's rule Which of the following compound was the starting material for the oxidation shown below ? @ . HO, Kind, /i4 H 1H (@) “CY &) Cer Which series of reactions will achieve the following transformation ? Br Ne ts Ko 1 2 a 1 @ Ci, /CCl, Br, (b) HBr ai, /cd, © a, /ccl, NBS/hy (@) NBS/hv cl, /cal, 2 + 0,66. 67. 68. 69. Taking into account the stability of various cycloalkanes and carbocations, as well as the rules governing mechanisms of carbocation rearrangements, what is the most likely product, of this reaction ? ia} HAT NA —? {a) (co) wc A triene is treated with ozone followed by zinc in acetic acid to give the following three products. What is the structure of the triene ? An ay Wa, Oo 0 “~O O ~O “O Which of the following compound would yield trialkylborane shown below when treated with BH, /THF? RSS. Products = © L ow (a) 2-methylbut-1-ene (b) 2-methylbut-2-ene (©) 3-methylbut--ene (@) 3-methylbut-1-yne If the following compound is treated with Pd/C in excess of hydrogen gas, how many stereoisomers of the product will be obtained ?70. 71. 73. 74. @1 (b) 2 @3 wm4 Which is the most precise designation of stereochemistry for the products formed in the electrophilic addition of DBr to 1-methylcyclohexene ? (D = 7H, an isotope of hydrogen) Br AH fa) hap Br E2CHy © Cx (@ both (a) and (b) H Consider the addition of HBr to 3,3-Dimethyl-1-butene shown below. What is the best mechanistic explanation for the formation of the observed product ? CH, | HBr A CH; — C —CH = CH,— > Hac I / CHy HC (a) Protonation of the alkene followed by a hydride shift and addition of bromide to the carbocation (b) Double bond shift in the alkene following by the protonation and addition of bromide to the carbocation (©) Addition of bromide to the alkene followed by a double bond shift and protonation (@ Protonation of the alkene followed by a methyl shift and addition of bromide to the carbocation Propene CH ,CH = CH, can be converted into 1-propanol by oxidation. Indicate which sets of reagents amongst the following is ideal to effect the above conversion ? (@) KMn0, (alkaline) (b) Osmium tetroxide (O50, /CH,Clp) (©) BH, and alk. H30, (@ 0,/2n Which is the most suitable reagent among the following distinguish compound (3) from the others ? (1) CH;C m= C —CHy (2) CH,CH, — CH, —CH, (3) CH,CH,C = CH (4) CH,CH = CH, (a) Bromine in carbon tetrachloride (b) Bromine in acetic acid solution © Alk. KMnO, (@) Ammonical silver nitrate ‘The principal organic product formed in the reaction given below is : CH, = CH(CH,) COOH + HBr —2esmide_, (@) CH, —CHBr(CH,),COOH (b) CH, =CH(CH,),COBr (©) CH,BrCH, (CH) ,COOH (d) CH, =CH(CH, ),CHBrcOOH77. 78. 79. 80. 81. When 2-butyne is treated with Pd - BaSO,; the product formed will be (a) cis-2-butene (b) trans-2-butene — (¢) 1-butene (@) 2-hydroxy butane ox A == C—CH; aay Cy tre In the reaction, CH,’ (@) HNO, (b) 0, © 05 (@) KMn0, Which of the following alkene on catalytic hydrogenation given cis and trans-isomer ? @ HC =), ©) act) CH CHy i. © cHy ‘I (d) all of these CH3 In the reaction of hydrogen bromide with an alkene (in the absence of peroxides), the first step of the reaction is the ..... to the alkene, (a) fast addition of an electrophilic () slow addition of an electrophile (©) fast addition of a nucleophilic (@ slow addition of a nucleophile Which of the following alcohols cannot be prepared from hydration of an alkene ? OH @ AVY" @) Yo © AAn @ ou Which of the species shown below is the most stable form of the intermediate in the electrophilic addition of Cl, in water to cyclohexene to form a halohydrin ? H @ Che 0 CL H f ) 0X “Ce ‘cl ‘n The reaction, (CHy),€ = CH, + Br’ —> (CH), ¢ -CH,Br is an example of a/an .. .. step in a radical chain reaction. (a) initiation (b) termination (©) propagation (@) heterolytic cleavage| HYDROCARBONS (ALKENES) 82. 83. 85. Which of the following most accurately describes the first step in the reaction of hydrogen chloride with 1-butene ? aANGQHne a AA‘ OAH AV te OA nvAASo + @ IAA tr Which of the following best describes the flow of electrons in the acid-catalyzed dimerization of (CH3)3C =CH, ? H, Hg @ KK HG ) SoLou, ™ Snore L Hc” ‘CH HC ‘CH, Hae Ce CH, 7 HAC pots @ HC—C4, ‘cH, HC Hydroboration of 1-methyleyclopentene using B Dg, followed by treatment with alkaline hydrogen peroxide, gives Me Me Me Me -alll D vali D ail OH hatt| OH @) stor Ob) WEL © oD @ ull HL H COOH te OH H D Vl ai HOOCCH(Br)CH(Br)COOH HOOC © w HOOG COOH —32+ HOOCCH(BN)CH(Br)COOH @ wm ‘The correct statements with respect to the above pair of reactions are that (1) the reactions are stereospecific (ID) (is erythro and (¥) is threoisomer (HID C9) is threo and (¥) is erythro isomer () each of (P) and (Q) gives a mixture of (X) and (¥) (@) Land (b) Tand I (© Jand v (@) Hand Iv86. The products P and Q in the following sequence of reactions, are MeO. 1, 0H osCeauie) L __oytensie) No >? apres, Merifiteys > 2 OMe MeO, Meo, Me o#c CHO olnctmot ot onc ‘OMe le Me 87. 4:Pentenoic acd when reaed with Iy and NOHCO, gives: (a) 4, S-diiodopentanoie acid (b) 5-iodomethyl-dihydrofuran-2-one (© S-iodo-tetrahydropyran-2-one (@) 4-pentenolyiodide 88. Co, —2280n0S 5 (4) 5+ (B) Product (B) ofthe reaction is: le, CH=CH, By @alcxon Conant : 89. ao A nee? ® paar? ©)» Product (C) is: (styrene) (a) Ph—C=CNa (b) Ph—CH, —C=CH (©) Ph—C =C—CH, (@) Ph—CH=C =CH, 90. Which of the following will give a mixture of cis and trans-1,4-dimethyl cyclohexane, when undergo catalytic hydrogenation ? chy (a) (b) 0 () Q (d) both (a) & (b) CH; cis 3-6 dimethy] cyclohexene 91. An optically active compound A with molecular formula Cyt, undergoes catalytic hydrogenation to give meso compound, the structure of (A) is : CH; CHy (CHz ~ CH @ ) © Ax, @ oS CH’ da,92. 95. 97. CHs— Ci CHa CH Cc + HBr —_>—> Products “ Rat cHy “cy ee08eey How many products will be formed in above reaction ? @)2 (b) 4 ©3 @6 Clay D = #25 Product of the reacion is : D CH3 (@) Racemic (b) Diastereomers (©) Meso (@) Pure enantiomers ‘i He : ion is : cis-2-butene 2» product ; Product of the reaction is : (@) Racemic (b) Diastereomer (©) Meso @ E and z isomer CHy LH = CHy (a) ) Rate of reaction towards reduction using (H2/P1) : (a) a>b b)a=b (©) b>a (2) Reduction of given molecule is not possible 0. RL AN UR S 2 . I HP FSR SOs , product + CH —S —CHs bb 8 cine sae Product A of the above reaction is : fa) n—ter (b) R’— CHO (©) R—CO,H (@) both (a) and (b) C —O—O—-H aucrany A a C=C. ——_— > Produet; Product is : HO Ng ona, MCPBA —> Metachloroperbenzoic acid98. 99. 100. 101. 102. 103. ‘ORGANIC Chemistry for HTJEE) Cy CH CHS @ OK oO OOK H7 Ny 3 HONS “H HL Sls HL Alig © Sees @ See? CHS ‘of ~CHs H@ \of SCHg CHs, H OD Ba THE, (A); Product of the reaction is : (2) HzO), HO™ CHg CH; CH3, CH H * on H H @ (b) © Cony (d) OH H H CH Hg —CH = CH, —OTHE:#s_, (4) ; Product (A) of the above reaction is: (2)cHi,C037 (a) CH —CHD—CH,D (b) CH, —CHT—CH,T (©) CH3 — CHD—CH,T (d) CH, —CHT—CH,D Optically active isomer (A) of (CHCl) on treatment with one mole of H, gives an optically inactive compound (B) compound (A) will be : (a) CH, —CH—CH = CH, (&) CL—cH—cH =CH—CHy bat bay (© Cy —G—Gii, — cH = CH, @ CH, ~CH,— CH—CH = cH, An organic StnpoundC,, on ezonalysis give HCHO, C0,,CH,CHO. Compound willbe: (a) H,C = CH—CH=CH, (») CH, —CH =C = CH, (© CHy —C =C—CH, oC] OH (@ Che © OH © Chere @ Che CHjOH HH | OH Gs — CH ee wt @) Re oO CHs, Product (C) in the above reactions is :104. 105. 106. 107. CHy CHs CH, | (© CH; —CH—H (@) CH, — CH I Ha-Br CH, -Br CH, I (CHy —C=CHp + (CHg )gCHCH 25> Cala (A) Unknown (A) in the above reaction is : (a) 2, 2, 3-trimethyl pentane (b) 2, 2, 4-trimethy! pentane (© 2, 2-dimethy! hexane (@) noctane Ao HBr + (Pp) —M&OH_, (Q) ; Product (Q) is: Oo cl @) (b) Br. CHAO AL AA ome ? ° (©) CHy -C-OMe © oy Am is soe (ay —2sit_, ay —82 5 (CE) a KMn0, Product . of the reaction is: learleqreqres What is the major product expected from the following reaction ? CH; —2=9, product CHg CHy D D (a) ) © @ a a CH, cH. H H a H108. Choose the correct product of this reaction : 1.Be ee, 21,0 I He CH Sapr 0H @) ary sl Br CH 109. Oo —LBA/THE_, 4; product A is: 2. H,0,/0H" CH, @ in oO © Cho @ fis ws en Oo” He(0A0,. 11,0 110. ~ Product; Product is : 2.Naltl oe CH3 uns ,H @) st CX, © Che @ 3 111. Choose the correct product of the following reactions 112. How many stereoisomeric tetrabromides will be formed in the following reaction ? OSSF 2, caiy fa) 2 ®) 3 o4 (d) 6114, 115. 116. 117. How many stereoisomeric pentabromides will be formed in the following reaction ? Br an a 4 ay (a2 (b) 3 4 {d) None of these NA a? EES © (majo Identify (Z) in the above sequence of reactions : @ AZ 0 AY ©. CH, © C A (@ “or CH, —CH—CO,K —tesmebst_, (4) (Major) CH, —CH—CO,K Major product (A) of the above reaction : @ Ag od Oon-Z @ I Lven = oy DAA +O, (only one enantiomer is taken) Which of the following statement is correct about A and B? (@) Aand B are mixture of diastereomers (b) A and B are mixture of enantiomers (©) Aand Bare optically active (@) Bis racemic mixture CH; CH;0" —NsBHa_, gO, p20, () (one of the product) H HO O Identify the product (C):118. 119. 120. 121. 20 CH, —OH Ii | (@) CHy —C—C—O—CH, () cH —OH | CH, —OH Ho Guo (© CH—OH @ qHoH | CH, —OH CHO CHO ° “ 2 CL HO", gy acc Phat”, yy ‘OH Product (¥) of the above reaction is : @ Oy o) O ; o H = CH—CH, CH = CH—CH,— OH “OC “OC HH 3 Na/ianls , p_B2_ ¢@); then Qis: In the reaction Me — =C—Et (a) A pure compound which is optically inactive due to internal compensation (b) A binary mixture which is optically inactive due to external compensation (©) A binary mixture which is optically active (@) A pure compound which is optically inactive due to absence of chiral centre (a), ©) @ © Which (x-bond) will reduce first, when above compound undergoes catalytic hydrogenation ? @a (b)b @e @d Compound A, which is a degradation product of the antibiotic vermiculine has following structure 9 i g ox Na nN = cH Nan (a) SB) SS ©). Unknown © is: Gated, PHC” Gh Bae Gata122. 123. 124. 125. Z (a) CHY i “ i C CH. CH CH, Cy b) cH cu Nou NeW cu ‘OCH, CH, CH) ° I Il c CH, CH, ALAN, © on Na Nc NA Nou“ Socts CH (d) None of these J : ‘O Reagent (A) and (B) in above reaction are : (a) A=RCO3H, B= H,02 (b) A=RCO3H, B= HIO, (©) A=RCO3H,B=05 (d) A =03,B = RCO3H Rank the following in the increasing order of rate of reaction with HBr . od) ae) @un ) (@) R>P>Q (b) R>Q>P (© P>R>S @P>S>R Select the reaction(s) that would result in the formation of 2-bromopropane. (D CH,CH = CH, + HBr—Pemside_, (I) CH,CH = CH, + HBr—Se_, (UD CHCH,CH, + Br, —Y > (IV) CH3CH = CH, + Br, (a) Land I (b) Wand I (c) 1H, and I (d) I, and Which of the following reactions generates the major product ? Ignore stereoisomerism. o CY += CX, ©126. 127. (2) Halon, Hy0,TH oC) sane IH aya om _, Or 110, 84504, Chou © Cy fe Ce ‘Br In the given selective hydrogenation which combination is incorrect ? “Ow “OC (W.C. = Wilkinsons catalyst) wo AWAY os =A (W.C. = Wilkinsons catalyst) @ gi (CH, —CH = CH—CH,; 1. NaNH, 2. BO: ¢ \—= >) 8, EG C0. Compound (C) in above sequence of reaction is : 2 HOH i 0 DYO Galo128. 129. 130. 131. OC one? 45 CH. 202/ 5 Major product (A) is : Coe b @ cH, © Br 10=@ oC In the reaction given below, the product would be : OH I Hy —CH =CH —CH, 2 5H, —CH, —CH —CHy (@) a mixture of diastereomers (b) optically active © optically pure enantiomer (@) a racemic mixture Surprisingly, the reaction shown below goes through classical carbocation. What is the major product of this reaction ? Br + HBr —> (a) trans-1, 3-dibromocyclohexane () cis-1, 3-dibromocyctohexane (©) trans-1, 2-dibromocyclohexane (@) cis-1, 2-dibromocyclohexane The major product of the reaction given below is : Aro i? OH QH © Br, Lon © Br ALA_on Br Br Gi) xo, Jon @) HO AA _on o # a Oo, Sher wo Cee wi (@) (@ and Gd (©) ii) and civ) (©) (v) and (vi) (d) none of these132. 133. 134, 135. 136. 137. Which reaction will occur at the fastest rate ? Br Oe G ov =e : Br CORO eve 6 a . O Above reaction is known as : (a) Wurtz reaction (b) Wurtz fittig reaction. (© Fittig reaction (d) Kolbe electrolysis i chy —cHy C4 BAP, Product is : (a) propane (b) propanol (© prapanoie acid (@ propene Which of the following compound give diastereomers when treated with Br, in CCl? »~H o> © Ow O s $ CH, CH, HY "CH HS Neu, ‘Methylcyclopentane ‘LMethyicyclopentene _3-Methyleyclopentene _—_4-Methylcyclopentene A mixture of CjH, CH, and C,H, is bubbled through alkaline solution of copper (D) chloride, contained in Woulf’s bottle. ‘The gas coming out is : (@) original mixture (®) CoH (© CaHg and CoH, mixture (@ Calg and Coil “AY #1, Possible products 2/4, (y) products oH @ ‘The number of possible products for x and y is (@ 2,4 @) 3,5 © 3,6 @ 3.4139. 140. 141. 142. 143. 144. Select the incorrect statement : (@) Bromine is more selective and less reactive (b) Chlorine is less selective and more reactive (c) Benzyl free radical is more stable than 2° free radical (@) Vinyl free radical more stable than allyl free radical Which of the following compound does not evolve CO, gas, when undergo oxidative ozonolysis ? SS (@) (b) (©) Hy = CH—CH = CH, oD cis-3-hexene —© + meso 3,4-hexanediol trans-3-hexene —_» meso 3,4-hexanediol. Choose pair of reagent (a, 5) for above conversions. (a) Cold KMn0 4,050, (b) Cold KMn0 4, RCO3H/Hj0° (© RCO3H/H,0%, cold KMn04 (d) None of these oO lt (4) 22-9 (@) Bates (cy Tia. NE Product (C) of the above reaction is : (a) 1,3-hexadiene (b) 1,4-pentadiene (©) 1,3-butadiene (@) 1,3-heptadiene How many carbon-hydrogen bond orbitals are available for overlap with the vacant p-orbital in ethyl carbocation ? @o (b) 3 Os m6 O-O-0 To achieve above conversion, the reagents used will be : (a) 03/H0,, HO-/a (b) HBr, ale. KOH, 03, LiAIH,,H*/A (©) HBr, t-BuOK, 03, KMn0O,, A (@) HCl, KMnO, (cold), H*/A. ° HE Qt 2» X (major); Product (X) is: ZA145. 146. 148. ABO 8 Desessng vont of heat evolved upon catalytic hydrogenation of given reactants with a H (Pd/C) is : nae @ 0) (a)b>c>a>d (b)d>a>c>b “pacman @c>b>c>d The correct order of heat of hydrogenation of given molecules is : (a) d>c>a>b ()) d>c>b>a (© b>a>c>d @d>a>c>b AA 1. Hg(OADa — a OH yaa, A Product (A) of the above reaction is : 0; 70: ‘0. 0. i C= CH, CT wae fajon) Product (4) is : ar Br Br @) UT Br ) ty © @150. 151. 152. we. [Oe Product; Comment upon optical activity of the product. (@) Racemic mixture (b) Diastereomers (c) Meso (4) Optically inactive due to absence of chiral center Fs CHs — C =CH —CH, —Hix0t0,/B10H1_, (4) 0080) Product (A) of the above reaction is : Hs Hs @ CHy—¢ — GH—CH, (b) CHly—C —GH— Git, HgOAcOEt OEt HgOAc Gls GH © GHs— — CH —CHs @ CHa—§ — CH— Chis OH HgOAc HgOAcOH _ 103 Ou MezCH — CH— Me sry) “ay acon? BD HH Product (B) of above reaction : {a) Me,C(OH)GHMe (b) MesCH — CH— Me 1H () Me— a Mes (d) HO —CH, —(CH,)Me 1H In which of the following reaction, Markownikoffs rule is violated ? (a) CH, —O—CH =CH, > () CH, —NH—cH =cH, 3, yi (©) CH, —s—cH = cH, > (@ 0,N—CH =CHy a Decreasing order of rate of reaction of molecules towards electrophilic addition reaction is : CH = CH = CH, CH = CH, CH = CH eee154. 155. 156. 157. fa>b>c>d (b) b>c>a>d © d>b>c>a @b>d>c>a 2CH; —C =CHy BAGH) _, (4) ajo Ph Product (A) is : Ph Ph Ph Ph ‘CHy : Product (B) of the above reaction is : OR @ cy ) OL O° 0" OR © cy @ CL ‘O° 0" ‘O—OR Which of the following compounds gives the same carbocation on ionization ? a ee (a) 1 and 3 (b) 2 and 4 (© land2 (@) Land 4 For the following reactions the major products are shown HC ~ CH —CH = cH, 8% 51,6 = cH—CH— cH, ***S.cH,cH! =CHCH, | Br Br These provide an example of control at low temperature and control at higher temperature, 1 2 1 2 (a) kinetic thermodynamic (b) thermodynamic —_—ikinetic (© kinetic kinetic (@ thermodynamic _ thermodynamic159. 160. 161. 162. 163. CHs, HH o> _Xon Dehydration of the above compound will give : (2) meso product (b) racemic mixture (©) diastereomer (A) optically pure enantiomer CH, ~ CHy H cl HBr. ~eai, > CH = CH, What is stereochemistry of product ? (a) Racemic mixture (b) Optically inactive (©) Diastereomers (@) Meso product aN hy Ss oe) CHy End product formed in the above reaction is : (a) Optically active (b) Racemic (©) Meso (@) Diastereomer How many moles of BH, are needed to react completely with 2 mole of 1-pentene in ‘hydroboration-oxidation reaction ? (@) 2mole (b) 3 mole © 33mole (@) 3/2mole OCH u 1,0" a? 4 8 Product (B) in the above reaction is : ° 9 OCH f@) ) © or @ OH OH OCH164. 165. 166. 167. ue low cone of Bt (9 HC =CH —CH, Ore oBh_4(7) Product of the above reaction is : “ (@) H,¢ =cH —cH, —Br (b) H.C = CH—CH, —Br 4 © CHa Tic, (4) both (a) and (b) Br Br In which of the following reactions 1,3-butadiene will be obtained as a major product ? (CH)COK(2mole) (@) Br—CH, —CH, —CH, —CH, — Br ERE > (b) HO—CH, —CH, —CH, —CH, —OH—S#s8% _, © Hc =cH—c =cH— Me) Nie (@) Allof these cl, 1.H,0 HT " be x ; A. oa sco? a A; Identify @ CHa GH b) CHy- FH -CHO CH ™ Il (© CH, —C—CcH, —CH, (@ CH, —C =CH, HS0, a A; Hi Product (A) is : @ o) eon © © £1[HYDROCARBONS (ALKENES) 4.3.5 168. 169. 170. avi. 172. CHE (©) Iso-butene > trans-2-butene > I-butene (d) n-Hexane < n-Heptane < n-Octane Predict the major product of the reaction. a i cH, ~E= 6G = Ch, ae S00 — SOO (Product) CH; Cty Ce t (@) CH, —C = ¢ —cH, —cH—CH, 45 Gis cy Gi Hy (© CHy—C = C —CH,—CH—CH, (@) CHy —C—C—CH, —CH = CH, j if OH OH bu bn — sold ai XM94_, Product of the reaction is: (a) Meso compound (b) Enantiomeric pair (©) Diastereomers (@) Optically pure enantiomer 9 H H H Home YUH ' YH c C: c. croc oO Nose > a | i i | o# i i HOH H 0 (dichloromethane) (Cig), @ + @) Optically active Optically inactive173. 174. 175. Product (A) of above reaction is: (a) CH,O—CH—CH, —CH, —CHO OH cons | (b) CHO —CH, —CH —CH —CO,H (© CHjO—GH—CHt, — CH, —COoH COjH @ clo GH —CH, —CH, —CH, —CHO CoH 9 C7 Product (mote) Addition of a mineral acid to an olefin bond leads to major product, Identify it: Q ° Br @ © LOY Br ° Br QO © @ Br (one ml FO: "Product In polyenes that contain differently substituted (C=C) double bonds, it is possible to hydrogenate chemeselectively one (C=C) double bond. Product is :176. 177. 178. mcrna loom Product (MCPBA —> meta-chloro perbenzoic acid) Stereochemistry of the product of above reaction is : (@) Meso (b) Racemic (© Diastereomers (@) Optically inactive due to absence of chiral center. Ce cen, atid Identify product (P). 0 l SS a ox (A) + POPhs Hite Me najos) Me H Product (A) is (a) trans-2-butane _(b) cis-2-butene (©) 1-butene (@ Iso-butene In which of the following reactions, two products will be formed other than phosphonium ylide (POPh, ) ° @) + Ph3P =CH,—> (b) CHyCHO + PhsP —=¢—CHy—> CH; ° i I (©) Ph—C—H+Ph3P =CH—Ph—> (d) H—C—H+Ph3P =CH—CH, —>196. 197. 198. 199. To carry out the given conversions, select the correct optio ll a7 R;—C—R,+R,COLH Ry o—o H a“ i No No te RC, + R,—CHO Ry NG 7 ‘ oe — R, —CH — Ry + Ry —CH) — OH (a) a=Ag,0, b=Zn/CH3COzH, c= LiAlHy () a@=H,0., b=CHg -S-CH, ¢=NaBHy (©) Both (a) and (b) (d) None of these The product (A) of given alkoxymercuration de-mercuration is : CH; CWHe(O_CCH)n CHAOH_, (ay NaBH, HO (aj00 oc OCH, OH on @ (b) © @ ONa HC=CH Ht Ha AN,Oy CH —C =CH, HSI, Bg a End product of the reaction is : (@) Hye = cH—¢ =cH, () CHy —CH =CH—cH =cH, CHy (© H,C =CH—CH =cH, (@) jC = CH—CH, —CH = CH, Major product of the given reaction is : HC = CH — CH, IS» (a) CH — GA, (b) CH3 — FH —CHs rod I (© CHy —CH, —CH, —1 @ 1—CH, —CaH, —CH, —1{HYDROCARBONS (ALKENES) 200. 201, 202. 203. ‘The rate constant for a reaction can be increased by a the stability of the reactant or by b the stability of the transition state. Select the correct choice for a and b. (a) decreasing, decreasing (b) increasing, decreasing (©) decreasing, increasing (d) increasing, increasing Major product of the given reaction is : HC = CH, + >= CH, E+ Product ° an ok ue © x (d) H.C =C-CH, -CH, -CH3 Oo +PhgP=CH,—> (A) ‘Major Major product (A) is : OH @ O ) O io) O @ QO In the given reaction, only one alkene undergo preferential oxidation by electrophilic ozone. Identify product (P) of the given reaction: OMe os or Mes, FHC thes ane, > P) [ co2Me S02Me f) © CHO ‘OH 1) (©) CHy —C—CH, —CH=C—CH, —CHO OMe ou (@) CH; —CH—CH, — CH= ¢ —CHy — CH, —OH Me204. CH,—CH,—CH = CH, "5 (p) ; Product (P) is: (major) On a a cl 205. Cee ate (A) ; Major product of the reaction is or Chi fa) (b) Oo 0 ° 1 I °Co “OD 0 ‘0 ° 0 OH o~2 ca Ho 206. OMe A)» (B) Product (B) is: et , (@) Ph-CH-CH =CH -CH, -C-H (b) PhCH =CH-CHO (© Ph-(CH=CH)2-CHO (@) Ph-(CH =CH), -CHO 207. Isobutene, in the presence of H,SO,, forms a mixture of two isomeric alkene (Cg Hy). The major alkene is : CHy CHy CHs CH, | | I I (a) CH3 —C—CH = C—CHy (b) CH, —C—CH, —C =CH | | CHs CH; CHy CH; CH CHy I I | I (© CH; —CH—CH =CH-—CH—CH, (4) CH, =-C—CH, —CH, —CH—CH,209. 210. An unknown alkene (A) reacts with 3 mole of H gas in presence of platinum catalyst to form L-isopropyl-4-methyl cyclohexane. When unknown alkene (A) is ozonized and reduced, following product are obtained i Ry tot H-C—H, H—C—CH,—C—C— CH, CHy —C—CH,—C—H ‘The alkene (A) is : @ ©) 0 © 0 @ 3 ° i nocion Hs O aie? OO BOC) (2) Mg/ether (CH3—CH2—Br Product (C) is OEt OEt H OH @ oH ©) OH OH OEt H © on (d) Both (a) and (b) iil OH The following reaction take place in high yields. COxCH3 T EEL, Product Use your knowledge of alkene chemistry to predict a product even though you have never seen this reaction before CO,CHs 1 S025 fa) (b) HgOAc211. 212. 213. CO,CH, CO,CH; © (d) oH ‘OH °° 0 0 ° 9 0 54 bd ecHty bb cay scHty -t bin Qin Glyoxal 2,3-Butanedione Pyrualdehyde What is the ratio of glyoxal to pyrualdehyde obtained in the above reaction ? (a) 1:3 (b) 3:1 (© 3:2 @ 2:3 CH, Which of the following product cannot be obtained in above reaction ? i i 5 e (@ H—C —cH,—C—H (b) CH; —C—cH, —C—# ° i (©) CH FR cA (d) None of these CHO CH: CH: + a )4(10~* mole) Ng eT + CHy)gN —O4 8,0 22 4 4 CH,)N 2om Ny cHy Clg coast notes) 2, 3-imety-2butane (0.028 mol) (TMAO ~ trimethyl amine —N — oxide) Product (A) is : CH CH3 a See won, dba (a = is —C—C—CHy cay No/ cts I | OH OH I (© CH, —C—CH, (@) CH; —C— C(CHy),214, 215. 216. HO, Product (A) of the reaction is on OH @ ) “OO (@) None of these OH wt HS A) 2 (majo Product (A) is: (a) ) Cx S © @ CHa Cy Do = CH CHa > 7 Hy CHOCHY © © © Arrange the above in the decreasing order of reactivity towards HBr : @a>b>c () b>a>c @b>c>a @a>c>b217. Which reaction has the lowest AG* or (Activation-Energy)? HBr. r ole els Br Br a Ha ol La Br 218. Which of the following will rearrange ? oa + a @ @ @ yt + f@1 (b) Land3 © all @) 1,2,4, 219. Which of the following is most likely to undergo a favorable hydride shift ? @ TL 0) he OSS @ OU ¥ 220. Energy profile diagram for dehydration of 2-butanol using conc. H,SO, is given below : Reaction co-ordinate Product (b) of above reaction is : (@) L-butene (b) cis-2-butene (©) trans-2-butene (d) iso-butene222. 223, 224, 225. How many alkene on catalytic hydrogenation given isopentane as a product ? (a2 )3 4 @)s5 Which of the following would not rearrange to a more stable form ? @ G + 6) Ho o>~ a Consider the following reaction, _ BrCHCHF + SbR; —“22_, CHp — CHa + SDFG 60°C Ng LJ " In this reaction SbF; acts as: (a) anacid (b) a base (©) a nucleophile (d) an electrophile oO Bult. Major (x) —AésHolis_, Major(y) —H-B_5 Major(Z): KOH/S Peroxide Product (2) is: Br @ CY ) Bi Br Br © @ asi ®) 7 NaN» Cit CHC CH SN SE (A) oO) Relation between (B) and (C) is: (a) Enantiomer (b) Diastereomer (©) Geometrical isomer (d) Meso226. The reaction of HBr with the following compound would produce : oro Br, ‘OH (a) OD ® OO Br Br, ‘Br © OK " @ Ot) Br Br 227. Oo +Br, 2% cy is an example of: (a) Nucleophilic addition (b) Nucleophilic substitution (© Hlectrophilic addition (@) Elecrophilic substitution (©) Free radical substitutionHYDROCARBONS (ALKENES) ta fo gos 231 - | © a (d) ) (b) 89.| (© | 90. | @ | 93. | ca) | 96. | (a) | 97. | @) | 98.| @ | 99. (b)_|103.| (a) |204.] 105.| (b) 107.| (b) |108.| cb) |109.| ca) ]120.| ca |111.] @ [112.4 113.| (a) '115.| (c)_|116.| (ay {117.| co) [128.| @) [119.| @) |220-| @ 121.| ©) 123.| (ay |124.| (by |125-| (a) |126.| (a) |127-| (by |128.] co) 129,| (4) '134.| (c) [132.| ca) [133.| (©) [134.| cay [135-1 (a) |[136.] © 137.| &) '139.| (4) {140.| (oy {141.| oy |142.] @y [243.| wy |244.] 145.| ©) '147.| (b) |148.| (ay |149.| (a) |150.| @y |152.| (a |152.] (a 153.| (©) 155.| (b) |156.| () |157-| (@ |158.| (@ |159.| @) |160.{ (- 161.| (b) 163| @) [164.| (a) |165.| (a) [166.| @) |167-] @) |168.] (a 169.| (c) 171.| ) |172.| @ |173.| @) |174-| @ |175.| @) |176.{ 177.| (b) 179.| (b) |280.| ()_|182.| bo) |182.| o |183.| (¢ |184.| 185.| (c) 187.| (a) |188.| (by |189.| co) [190.| wy |193.| (@_|292.| @ 193.| (c) 195] (c)_[196.| ()_|197. '199.| (b) |200.] (c) [203.1 () 1203.| (6) |204.| (a) |205. 207. 208. 209.| (b) 244.1 (c) |212.| ( |213.| @) |224.| (a) |215. 217.| (a) 219.| (a) |220.| (vy |221.| () |222.| «@ 223. }225.1(b,c) }227.| (©)ORGANIC Chemistry for IT-JEE AHCI! [B. Bry CC. Hg(OAd)y in H,0 | D.ByHg(BH,)in ether E. H,0)_|F.KMn0, in H,0 [G. HoBr H. NaBHy In each reagent box write a letter designating the best reagent and condition selected from the above list of reagents. erechig (CH, ).CHCH = CH, evens Sead |(CH ),CHCH(CI)CH 2.Chioro-3-methyl butane (CH, ),CHCHBrCH Br 1, 2ibromo-3-methy! butane (CH ),CHCHOHCHBr 1 brom0-3-methy?2-butanol (CHg),CHCH(OH)CH, ‘Somethyl-2butanot (CH ),CHCH(OH)CH OH ‘3-methyl, 2butanediol Propene (CH, — CH = CH) can be transformed to compounds (a to j) listed in the left-hand column. Write letter designating the reagent, you believe will achieve desired transformation. In the case of a multi step sequence write the reagent in the order they are to be used. one Hig(OAc), in H20 Bol in THFHYDROCARBONS (ALKENES) = vole 233 ¢. | CHyCH,CH,OH two €. | NaBH, in alcohol d.} CHCOCH, three Dz | Br, inCHCl e.| CH3CH{CHO three E. | H,0, in aqueous base pt £.| CHyCH(OH)CH2Br | one F. | HOBr (NBS in aqueous acetone) pp &:| (CH)2CHBr one G. | HBr in CHCl tJ po pop h,| CHjCH(OH)CH,OH | two H. | 050, in ether i. | CHy -CH -CH, -cl jos 1. | Thionyl chloride (SOCI2) js | CHy -C =CH two J. | NaHSOs in aqueous acetone K. | NaOH in alcohol and reflux j++ L, | NaNHz (strong base)234 ‘ORGANIC Chemistry for HT-JEE 3. In each reaction box write a single letter designating the best reagent and condition selected from the list at bottom of the page. «&. > first step, ~ second ste; T. |. > third step) fonts o aa oo oP O A. NaBH,/alcohol | B. Ph—-COgH/ CHCl, | G. PCC D. CHjONa/CH30H E. Bye in THF =| F. H,0,/aq.NaOH | G. HPO, &heat_ | H. AICI3/CoH, I. 0 inCH,Cl, | J. Brin CHCl, K. 20% KOH &heat | L. Ph —Li/etherHYDROCARBONS (ALKENES) 4, Match the reagents a-j with products A-J. There is one best product for each reaction. 235 L_ (9. The molecule (x) is the starting material forall reactions in problem. Do the ones you know first and then tackle the rest by deductive reasoning H,0 heat, pH_7 oO ne *BUOK, polar aprotic solvent (2) 0g, ether (2) H,0, NaOH, H0 Brp,CCly NBS, hy, CCl, () H30C+) (2) NaOH, H,0 (1) BH, ether (Q)H02 @ (1) 0504 (2) NaOH, H,0 H2/Pd/C(EtOH)[ese Zev gtab. 5. Match the column: Cran) (a) | cH, —c =C—cH, ORGANIC Chemistry for HT-JEE forse Ct) cis-product with H2/Pd- BaSO, CH,—CH,—C=CH CH,—C ==CH Trans-product with Na/lig. NH White with amm. AgNO3 (@) | cH; —c=c—er H, gas with NaHYDROCARBONS (ALKENES) 237 6. Match the column I with column II and with column ITI (Matrix). Column-t Reaction eo es Nature of product formed See Number of chiral center present in _ product. (Consider only one isomer in case of racemic mixture or Diastereomer) fa) "4 Br, @) ie mi (w) Ka a (P) | Racemic mixture (w) oO CH C J Bry (b) i Cla (@) | Meso Go 1 CH, 2 ed? © * {#) | Diastereomer 2) 2 (a) (8) | Vicinal dihalide @ 3238 7. Match the column I and II. ‘ORGANIC Chemistry for HT-JEE Reaction Product 080, ®) (@Ns0H, 130 OC) gamer, @ D0, NaOH, 0 a oH HO ;—OH a (A) (2) OH a! @ f Jo as Le 2 Sum of molecular mass of A, B, C, D (i.e. A+ B + C+D) is equal to :HYDROCARBONS (ALKENES) 9. (all isomers) Ni (1) C,FCIBr aw) (exclude stereoisomer) Qc, 4Hq alkene) —"2>(B) (exclude stereoisomer) (all isomers) 239 Total number of products A and B (i.e. A + B) is equal to:_| Reaction 1 Reaction 2 CH CH, H Br H—}-~>- Br cH cH | (cis) 2s br, a. = | Gerans) 2+ (Q) cH H——Br H—l|-o.23 CHs CHy Reaction 3 Reaction 4 os CHy H—-—Br H Br r ( = R e (cis) ® I Geransy eo CH CH CH City Sum of products P,Q, R, S (ie. P+Q+R+5) is equal to:‘ORGANIC Chemistry for HIT-JEE i Viadimir Markovnikov rule : Alkenes undergo electrophilic addition reactions. Itis triggered by the acid acting as’ a electrophile toward n-electrons of the double bond. Markovnikov’s rule states that when an unsymmetrically substituted alkene reacts’ with a hydrogen halide, the hydrogen atom adds to the carbon that has the greater number of hydrogen, e.g., CH [ S-a+ H-cl —2o5 Cx Tamethyl cyclopentene 1.chloro-1-methyl cyelopentane Mechanism : i 2 Step -1 [seu Ca =a Cy ge cH, ae . 3 Step- 2 Hs ae = Cx A. c. Which o} the following is most reactive toward Markovnikov addition ? 0. “Oo CX What is the energy profile for the given reaction ? @ > I © Reaction co-ordinate Reaction co-ordinate © I @ | E E Reaction co-ordinate Reaction co-ordinate In which of following reactions carbocation rearrangement is possible ? (a) (CHy),CH — CH = CH, HS > (b) (CHs)3C —CH =CH, 5 OC/Cly (©) Ph—CH, —CH = CH, (@) All of theseD. FE Identify the major products r,, r, and r, in the given reactions. Hb oO _ Har HBr po? "3 OH oD CH CHy CH, Hy @ , , OH 3 oD CH CH, CH (b) > > Br CH oO in all the reactions In which of the following reactions, product is racemic mixture ? 1H 5 @ in all the reactions (a) CH, -CH, ~CH =CH, > (b) NG = vt HBr 1s ~ CH ~CH = CH, a HZ Nc, Ole CH 7s - HBr oF on a (@) All of these In which of the following reactions, diastereomers will be formed ? Hy @ a b) a CHy r © (d) All of these‘ORGANIC Chemistry for I1T-JEE eMac CH, —CH, —CH —CH, +CH,OH —" CH, —CH, —CH—CHy OcH, Consider the above reaction and answer A to E. What is electrophile in first step ? ® (@ CH, e (© CH —CH, —CH—CH, What is nucleophile in first step ? (a) CHJOH () H,0 What is electrophile in second step ? a) cH 3 (0 CH —CH, —CH—CHy What is nucleophile in second step ? (a) CH, —CH, —CH = CH, (©) HO Which step is rate determining step ? (a) attack of nucleophile CH,0H (© attack of nucleophile HzO () He @ HO® (b) 1-butene (@) CH -O-CH, (b) He @ (@) CH, —CH, —CH, —CH, () CH,OH (4) CH —O—CH, (b) attack of electrophile H® e (d) attack of electrophile CHHYDROCARBONS (ALKENES) _ fo 13. Match the column I and II; Conversion Reagent Hg Br @) OQ} ®) S0,Cl,/ hv (2 equivalent) — CH3 CH,- Cl ®) cl @ NBS (2 equivalent) : — CH Br © OQ}. w NBS then SO,Cl,/hv 3 — CH3 CH,-Cl @ 2 ) SO, Cl, / hv then NBS 3 — _!@ -A; Gi) - B; Gill) - G; (iv) —C; () -F a-D;b-A,C;c-B,E; d~A, C Fye-B, E,F; fF; g-G; h-1, Ki-B, E, 1 j-D,L Reaction 1 : B, D; Reaction 2:E,F,C Reaction 3:1, Reaction 4: L,G Reaction 5 : BL, C a-C;b-D;c-A;d-F;e-I; f-J; gE; h-H;i-Byj-G -nse-4sd-pq a-p.g a-1,s-2;b-p,s—yse-p,s-ysd-as-y a-1b-pic-qd-s 8 AFB+C+D=312 At+tB=5 10. P+Q+R+S=8 A-b;B-GC-d;D-b;E-d;F-d 12, A-b;B-b;C-c; D-b;E-b ag; b-p; c-s; der° dcr, ci 0) 0m, 1. oy (ay Beall” og) 5 Product (B) is: 70-80% @ue 46% CH=CH Cm CH cH, oY oF 2 NAN fe ae (A); Produce (4) i: (a) H,C =CH—CH =CH, (©) CH; —CH, —C =CH ‘0 Nats 3. CHCH,C == CH OPT Ls af Product (K) of the above reaction is : Cm C—Et (a) (b) CH, —C = C—CH, (@ CH, —CH=C =H, JP) OH Cm C—Et )4 7 OH C= C—CH, —CH; © CH, — CH, —CH, —C = CH+LiNH, —> (a) G2 (6) vicina amide ‘ Give the structural formula of compound (8) : (a) CH3 — (CH), —C —SO;H (b) CH, — (CH), —C == C—CHg I (© CH; —(CH,), —C =C—CHy ~oy @ CH, —CH, —C =C—CH, CH - CH, ~ CH 4S — S ; This conversion can be acheived by : (@) NaNH,, CH;CHO (b) NaNH, CH;—CH,—CH)—Br (©) KOH, CH, CH, — Br @ KOH, CH.— CH, Brrr ‘Which alkyne will give 3-ethylhexane on catalytic hydrogenation ? NN 0d @ &) S © (d) Alll of these Reactant P gives products Q or R. HH ‘The possible reagents are : @ 2Na/lia. NH ()_H,/Pd/CacO (quinoline) (UD 2H,/Pd/C ‘The correct statement with respect to the above conversion is/are : (a) Qis obtained on treatment with reagent (1) (b) R and Q are obtained on treatment with reagent (iI) (© Ris obtained on treatment with reagent (1)10. 11. 12. (d) Ris obtained on treatment with reagent (U1) Br— (CHp)12 —C == CHM, (4) 22" (B) ; Product (B) is: H ° <> ° a> H H © (@ Br—(CH,)—CH = CH, Ph—C=CH —“2, Major product of the reaction is : MeOH Ph. H Ph OMe “Ns a a @ c= ® Sc=c aN H Nu (© Ph—C=C—OMe @ th-g—cH, q OMe Ph—C—CH, “2, (4) ; Product (A) is : i Prot cl eo (@) Ph--CH=CH, (b) Ph—-C=CH —() Ph—CH, CH, (d) Ph—C=CNa Which combination is best for preparation of the compound (A) shown below ? CHy ‘C — CH,CH,CH,C = CH CH,CHs (a) Bs (@ Hse “p — CH,CH,CH,Br MEH qy yy “ — CH,CH,CH,Br SECA) CH,CH, CHyCH H Hs Hy me 1. Nav, Wm% 1. Nail Ny (© Hem cpr 4) @ Yc—sr a 2, BrCH;CH,CH c= cr 7 72. BrCH,CH,GH,C=eH CHSCH, CHACH), Which one of the following is the intermediate in the preparation of a ketone by hydration of an alkyne in the presence of sulfuric acid and mercury ({1) sulphate ?13. 14, 15. 16. a7. 18. Ch "oO. — CH, —C= CH 0” “O — CH, —C = C—CH, — CH, — CH, — Br To carry out above conversion, (A) and (B) respectively, are : (@) NaNH,,Cl—CH, —CH, —CH, —Br (b) NaNH,, F—CH, —CH, —CH, — Br (©) NaNH,, I—CH, — CH, —CH, — Br (@ NaNH,, I—CH, —CH) —CH, —I i H—C=:C—Ph ———+——> Product; Product obtained in this reaction is : H-N (a) Ph—G=CH—I (>) Ph—¢H— CHa —I 1 I (© Ph—C=C—I @I—C=c—H o HON a (4) P=» (8); Produc (B)is City I Lack “ort i Is Oe Li 0 Which of the following alkyne on treatment with H,(2 mole)/ cy gives an optically inactive ‘compound ? (a) 3-Methyl-1-pentyne (b) 4-Methyl-1-hexyne (© 3-Methyl-1-heptyne (d) None of the above Cac, 2205 (a) —Resttoncutube_, (B), Product (B) of the reaction is : (Calcium carbide) (a) Toluene (b) Ethyl-benzene (©) Benzene (d) Butyne What is the final product, C, of the following reaction sequence ? \ 1.NaNlty =H ‘2. CH3CHBr A a —enetiad 5 Bane Br Br Br Br oye ok ory oy Br NH Br19. 20. 21. 22. 23. 24. sty Compound (p> <> CH) — CH, — CH — CH, AgNO en Looe, Precipitate ° 9° il 9 90 ° 05 iol itt I CHO. H—C—CH,— CH, —C—C—H +H—C—C_O-H+H-—C-—O-H+]| Meas cHO Compound (X) will be : @ ~ Sm = cH—c=cH (by cn, c= ot © © econ, c= cn @ Cc § Choose the sequence of steps that describes the best synthesis of 1-butene from ethanol : (@) @) NaC = CH ; (2) Hp, Lindlar Pd (b) GQ) NaC ==CH ; (2) Na, NHy (©) (1) HBr, heat ; (2)NaC=CH ; (3) Hp, Lindlar Pd (q) (1) HBr, heat ; (2) KOC(CH,); , DMSO ; (3) NaC m= CH ; (4) Hp, Lindlar catalyst Which alkyne yields butanoic acid (CHjCH,CH,COH) as the only organic product on treatment with ozone followed by the hydrolysis ? CH—C= CH (a) 1-Butyne (b) 4-Octyne (c) 1-Pentyne (d) 2-Hexyne E> Cvan—o-coo LI Carlina oxide Unit of unsaturation in compound (A) ? (a) 7 bs 9 (d) 10 Oo D> suo, ¢4) MOL py Habe (cy Prodiict (C) of above reaction is: (@ H.C =cH, (b) CH; —C =C—cH, (c) HC = CH (d) CH, —CI 1H —CH, To convert 1-butyne to 1-D-butanal, one would carry out the following steps : (@ Sodium amide, then D,O (iD) Disiamy Iborane, then hydrogen peroxide/sodium hydroxide (I) The transformation can not be carried out with the indicated reagents, {a) I, followed by II (b) II, followed by1 (c) III (@) 1ORGANIC Chemistry for IT-JEE 26. 27. 28. ‘An unknown compound (AYhas a molecular formulaC,H.. When (A) is treated with excess of Bry a new substance (B) with formula C,H Br, is formed. (A) forms a white ppt. with ammonical silver nitrate solution. (A) may be : (a) But-L-yne (b) But-2-yne (©) But-L-ene (d) But-2-ene One mole of 1,2-dibromopropane on treatment with X moles of NaNH, followed by treatment with ethyl bromide gave a pentyne. The value of Xis : (a) One (b) Two. (©) Three (d) Four CHy CHy~CH-CasCH = __excessHBr ‘The product of the above reaction is : Hy Br Br CHg Br (@) CHy~CH-CH-CHy (b) CHy ~ CH-C = CHa e Br Hy, Br © Gis CH-G-CHs @ CH, ~CH-CH)-CH Br f CH, —C = C—CH, — MO _4(4) Product (A) is: 09 @ cu—cr,—l_t ig (b) CHy—C—C—CH, IH OH (©) CHy—CH—CH—CH (@) 0 = CH—CH, —CH,CH = 0. 9. | w) | 10.| @ | 12. ] @ | 22-| @ | 13-] © | 14-| c@ 4] 15-| © | 16] @ 17.| ( | 18-| (@ | 19-| G@ | 20-| © | 21-] ©) | 22-] © | 23-| © | 24] © 28. | (a) | 26. | ( | 27-| © | 28-| oBA ALKYL HALIDES Substitution Reactions (S,;,S,,.,S,,) ne? 1. Which of the following is not expected to be intermediate of the following reaction ? OH To = + ou, + Oo 0 ao CH Br. H jon j 2. +Nal— > product; $2 product of the reaction is : H: CH3, ‘Acetone CH, ~ CH4 5. CH, CH; CH CH i H i 1 I CH H yy cH, Ow cH, © # ct, oy A CH,- CH; CH, ~ CH CH) ~ CH CH, ~ CH Rate of S nN? will be negligible in : Br Br Br Br OO 9 eA QO ‘What is the major product obtained in the following reaction ? CH)-Br Cx product ‘Br CH,-NH, CH,-Br CHy-NHy, CHy-NHy (@) Ch ©) © CK @ cr ‘Br ‘NH NH CH. is 1 (C1-CHy -G—CHl, ~CHtz ~ Cl +1" — pyr product; Major product of this reaction is: CH, OH CH; 1 @) ICH, -C -Clty ~CH, -Ch (b) Gl-Chty -C CH, ~CH, =1 CH; CH, CH As (0 H,C=C~ CH, -CHy =Cl (@) Gl-CHy ~G CH, = CH, cH, Which of the following expressions is representative of the rate law for aS ,2 reaction ? (@) Rate = k [electrophile] (b) Rate =k [electrophile} [nucleophile] (© Rate =k [nucleophile]? (@) Rate =k{electrophile}? wk Nal (1 mole) 42°» (A) ; Major product of this reaction is : Br’ (anajor) @ whe ©) Lt © WL Nt @ BLO8. 10. wa. 12. 13. Which of the following alkyl halide undergo rearrangement in S, reaction ? rae cl (a) CHy - C- CH- CH, (b) Ch © (A) All of these [ f ‘CHg CH; I Arrange the following three chlorides in decreasing order towards S ., reactivity. ac @ ar @ oY (a) 1>2>3 (b) 2>3>1 (© 2>1>3 @3>2>1 Which compound undergoes nucleophilic substitution with NaCN at the fastest rate ? Om AX © BAA Omer © oa Rank the following in order of decreasing rate of solvolysis with aqueous ethanol (fastest > slowest) BOS at H,C =C—Br ‘Br CH, ~CHCH,CH(CH3)2 a @ @ (2) 2>1>3 (b) 1>2>3 © 2>3>1 @1>3>2 The reaction of 4-bromobenzyl chloride with sodium cyanide in ethanol leads to the formation of : (a) 4-bromobenzyl cyanide () 4-cyanobenzyl chloride (©) 4-cyanobenzyl cyanide (@) 4-bromo-2-cyanobenzy! chloride Which of the following reactant will not favour nucleophilic substitution reaction ? @ (b) Ph-Br Br CH; © CH, < CH, ~ Br (d) All the aboveConversion of I to II: (a) takes piace by $1 (b) takes place by $2 (©) takes place both byS,, and $2 (@) does not take place 15. Which is the correct reaction coordinate diagram for the following solvolysis reaction ? CH Hy OH tn, #0 t, /, "3 ——> MOH + "Hg AG 4G (a) (b) Reaction Coordinate “Reaction Coordinate AG AG o @ Reaction Coordinate arg Comte 14¢ labelled y OTs 16. Oo —AO228_, product; Product of this reaction is : ‘no label 4 -OCOR OCOR (© both (a) and (b) (@) None of these 1 CH, 17. ES, (4) SB, (B), Product (B) is@ ) $-CHy CHy-Br © (4) None of these 418. Which of the following represents the correct graph for $2 reaction ? log (rate) (a) (Cis ~Br Clig~CHy- Br CH —CH- Br CH CH; CHy-C-Br Hg, log( rate) | @) CHy-Br -Et-Br i-Pr-Br ¢—Bu-Br log (rate) © CH,-Br —-Et~Br i-Pr-Br ¢-Bu-Br Gsopropyi)a log (rate) @ 4S (CHg - Br Et-Br i-Pr-Br t-Bu-Br 19. Which of the following graph represents correct graph for S,1 reaction : Jog (rate) (a) (His ~ Br City ~ CHs- Br CH - CH- Br ee BF CH, Hy Br 5 log (rate) > [) CHy-Br Et-Br i-Pr-Br ¢—-Bu-Br log (rate) © CHj-Br Et-Br -Pr-Br ¢-Bu-BrALKYL HALIDES (SUBSTITUTION) 21, 22. log (rate) @ NY CHg-Br 9 Et-Br i-Pr-Br t-Bu-Br Which of the following is most reactive toward $ .2 reaction ? cl cl cl cl Hg cl NO, Among the given pairs, in which pair first compound reacts faster than second compound in Syq reaction ? (a) CH, —CH, -CH, -CH, ~ Br orCH, ~CH2 -GI-CHs Br ft e (©) Hig -C-CiI, ~CH, or Gifs ~CHI~ CH ~cHts Br Br Br Br CH, CH, I I (@) CHy -C-CHy or CH -C-CHy I 1 Br I ‘What is the major product of the following reaction ? HC =CH -CH, -OH #5" Product Br 1 (a) CH -CH-CH, -Br (b) H.C =CH -CH, ~Br Br OH 1 t (©) CH, -CH-CH, -OH (d) CH -CH-CH, -OH23. 24, Sq andS,,2 products are same with (excluding stereoisomer) : “CX ‘cl © a cl ) en (@ Ph- CH -CH-CH CHs Consider the nucleophilic attacks given below. Select in each pair that shows the greater $2 reaction rate. per tN oO kee “CN or an (B) gC -Br + "SH or HgC —Br +CHSH ay oO Cs +c or C-™ +1 inDMSO. o wo © Cys +c or ()- +1 in methanol wun A B C D (@ @; Gv); WD; Wud © @; a;M™); cmp A B Cc oD (b) ID ; CID ; CV) ; (VID @ @ ; amp; ; wip Which of the two stereoisomers of Ae butyleyloheny! io iodide (?71-) will undergo $ substitution with }8I- faster, and why ? yi27 pdite pegh (a) A will react faster vecse it is the more stable of the two isomers (b) A will react faster because it will yield a more stable product, and the transition state for oth reactions is of the same energy (©) Awill react faster because the approach of !?81- can depart unhindered. (@) B will react faster because it is less stable than A, and the transition state for both reactions is of the same energy26. 27. (Z}2-Butene reacts with Br2/Hz0. The resulting bromohydrin when treated with methoxide in methanol undergoes an intramolecular Sa reaction. Taking into consideration the stereochemical consequences of the reaction mechanism dnvolved, choose the final product(s) of these transformations. Q 2 @ # of et (DCNet... (* es Hye - ae ‘CH (@) @ only ok ©) Mony Ty (©) (I) only © - ‘te dd) Equal ai amounts s of (1) and i 1D ay Rank the following specié¢ fh dbs 5 deceasi nucleophilic i ihe Polar Brade solvent (most - least mueldophilic)"S ne ‘sn ° se hante Sir mcd @ Mideiazllnianlt Vat te cues in Ob CH,CH;CHjO-™ tau Ale Cie Hiciis oid, foro Kons Mt a cael tes tae Ob G) HO HS ui “2 9 y(O(E) Oar © Jui (a) 3>1>2 3r(b).2 23a) (©) 1 w3->,2) (d) 12, >c1 >¢3* sat erica? PrOMUCE NMe Jb) Identify products of the given reactions : . OTs ok , neactign’t “Ba AD Bijdo,a ts} vi) Sa, eit a Product’? (cH) ‘ SOR Lier C , @ coe gs 9 sgim.e OD © NMe,‘* NMe, . 3 WON Hay snois ta) OS As -2KOY Pp cy ‘nana é NMeg fac 'ros neurnind’s as a NM@2 gaiwolict to dan SE st CHE ran : OQ. fea Product is o anys both the “EY t NMe, we . . sf , @ at single rout obi Jed i-hoth the reactibhs oy one oe) mort ops ne wt +) Ne.| i 38. In the given pairs of alkyl-halide, in which pair the first compound is moré Feactive than second compound toward Sya reaction? °°" (ROTO py QM (@ (CH3),CHBr or CH,"-CH, ~CH, ~Br (b) CHy -CH3*=CH 2 Bri lor ICHy'~CH3+ CH; = Id01g yniwollot af) to rlaidW (©, Ph—Br_ of *CH, “CH, ~CH, ~Br 29. (4) CH) =Cl+CH30” —9 Et4 fom) eto” OMY HD HO ov ORR OR eg ar in DM! H Hera Bt-Br,PPhgNt5 E+ Bonga ‘et Hien ire H (5) Y ng par of retions in which’ Bai'thé tSdond action is more reactive than 40. F-Among the foll first ins inS,, reaction ? “wo a W)>. an, @yMesccl+ + HO 3 MesCOH ¢y — (or) we EE Me,CBr + HzO idscon acidity tMe3CC CH: OH $ MesC = OCHS? (61) MesC=Cl'+H,0! 5d biuow tofW 2 ° (ouiqos pun Isausir= uM) § enoizeot 2 x55 seul (A) ato 59 RF St CHa eee Bla ames SH ae) commni (8) (©) MegcCl+ H,0 —> (or) MesCCl+ H,0 og ey (a) ca) a sib (@) Allof hese °, — sasten09 (0) zsessmoni (a) fot eV we CLEC OP rare ab aoa a 41. Whichis a'erie ‘statement concer n state oF anc giireaction ?idW BE (a) Closely reseinbles a carbocation intermediate 92. (b):The electrophiléis responsible'for the reaction saction 3” S#O~ HO = HD (6) (©) Lower is energy than the starting materials *o=oM ©) (@) Involves both the cleophile and electophile “Fear 3 42. Inickedsing the Concentration of a hiicieophile it'd typical $¢y' reaction by a factor of 10 Will cause the réaction rate to : SQ@ANe) (a) HOM + lonsud-Fonoldo- XE (a) increase by a factor of 10 (b) increase by a factor of 10? (© decrease by a factos of 10 H @ feitain about tie same) Pubord 48x, Déereasing the concentration of an elGtitéphilé i 2 Fypical s 8 Faction by a factor of 3 will © cause the reaction ratio | AG)! { t @) @ () (@) increase by a factor of 3 » ® bed, by a factor of 3? (©) decrease by @ factor of 3 (@) remain about the same 1