Problems « Solutions in ORGANIC CHEMISTRY for JEE (Main and Advanced) 3e Surendra K. Mishra HOD (Organic Chemistry) Cofounder and Director Nucleus Education, KOTA al CENGAGEa CENGAGE . Problems & Solutions in Organie Chemistry ‘for JEE (Main and Advanced), 3 Surenda K. Mishra Printed in India {© 2020. 2016 Cengage Learning india Pt. Lid. eee [ALL RIGHTS RESERVED. No part ofthis work covered by the copyiight ray transite stored oF used inary form or by ary means grap, electvone ormash ae et but not limited to photocopying, recording, sanning, digitng taping, Webestiner ae retwort.or information storage and retrleal systems, without the prior water nen publisher. an a he [ia pertltniouseenisin OR encaproies sane sts online \wwew.cengage.com/peemissions Further permission questions can be emailed to [email protected] IN-13; 978-93-5350-4021 N10: 93:535-0402 3 ‘Cengage Learning India Pvt. Ltd. 7.303, 3rd Flooe DAY Complex, Pot 3 ‘Mayur Vihar Phase 1 elhi-t0091 ‘Cengage Learaingisa leading provider of customized learning solutions with office leeations arcu lobe, including Australia, Brazil, India, Mexico, Singapore, United Kingdom. and United States cate your local office at: worm cengage.com/global ‘Cengage Learning products. are represented in Canada by [Nelson Education, Utd For product information, visit www.eengage.eo.inPreface Wis a matter of great pleasure for me to Present this edition of Problems & Solutions in Organic Chemistry for JEE (Main and Advanced) before Joint Entrance Examination (JEE) aspirants. During teaching hours, I felt that the factsmay be made more and more cleat ts Students through problematic approach. Although an ocean of material inorganic chemistry is available: with students, the approach to design problems has been changed in recent years and if one tries in this ocean, it wil bea very dificult task to make ‘students more familiar with trends and tricks. to solve problems, The present Problem book has been presented as er the current scenario of stiff competition and is well equipped with the facts of subjece, Yet the winner is one who knows how to use these equipments with accuracy and efficiency. The book includes problems based on the latest pattern being followed by JE. ok have been divided into six sections, and the Problems in each section have i both the requirements ofan aspirant. e, knowledge of subject and practice |. Single Correct Answer Type 2. Multiple Correct Answers Type 3. Comprehension Type 4. Matching Column Type 5. Numerical Value Type ‘6. Archives (Previous Years! Questions) Surendra Kumar Mishra fiiAcknowledgments First ofall, [would like to-thank the Supreme power for giving me the patience and deter; abook for JEE aspirants. Next, | express my gratitude towards my father R.P. Mishra, mother Rani Mish wife Bhawna Mishra, sons Shubh Mishra and Shlok Mishra for their constant support and encouragemens Twould also like to acknowledge my colleagues Rohit Agrawal, Ashutosh Gautam, Vikash Kumar Shokle and Kapil Saxena Sir, Finally, I thank Cengage Learning India for providing me the opportunity and support in writing this book, The constant support and guidance provided by the staff at Cengage Learning has been immense and encouraging mination to write Surendra Kumar Mishra ivPreface 1. General Organic Chemistry (GOC) 2. Isomerism 3. Alkyl Halides, Alcohols and Ethers 4. Carbonyl Compounds 1 5. Carbonyl Compounds Il (Grignard Reagent and Name Reactions) 6. Hydrocarbons and their Derivatives 7. Carboxylic Acids, Amines and their Derivatives 8. Aromatic Compounds 9. Biomolecules, Practical Organic Chemistry (POC) and Polymers 10. TUPAC Nomenclature Contents1 General Organic Chemistry (GOC) JEE (Main) Exercises: Greece 1. Acompound with no tertiary hydrogen is (A) (CH,),CCH(CH,), (B) (CH,),CCH,CH, (© (CH)),CHCH,CH,CH, (D) ((CH,),CH),C 2. Which of the following is not a nucleophile? (A)H, (B)CH,OH (C)H,O (D)NH, 3. The shape of ethene is (A) planar (B) tetrahedral (C)linear (D)pyramidal 4. Which ofthe following compounds has highest boiling point? Ban muck (a) HC CH, (B) HY CH, (C)CHCH.CH,CH, (D) CH,CH,CH,OH 5. Acompound with highest dipole moment value is (A) CH,-F (B)CH-CL (C)CH,Br (D) CHI 6 CHL isatype of (A)secondary halide (B)vicinalhalide — (C)geminalhalide (Dy both (B) and (C) 7. The process of converting alkyl halides into alcohols is a/an (A) Addition reaction (B) Substitution reaction (C) Dehydrohalogenation reaction (D) Rearrangement reaction 8. Which among the following compound is hydrophilic?” (A) CH,-CH, (B) CH,-OH «C)CH-Cl (D)Allof these 3. Number of unshared lone pairs and shared lone pairs are respectively NH. NH wk >~* en ‘NH: NIL (A)2,4 (B) 3,3 (4,2 5110. i. 12, 13. 6. The correct -I effect order is (A) -F>-Cl>-Br>-1 (B) -F >-Cl > -CN > -NO, (C)-F > -NO, > -OH > -COOH (D)-CN > -F > -NO,> 1 The ratio of number of alcohol group in compounds: Glycerol, Ethylene glycol and Tertiary b Nutanol is respectively (Ay 1:23 (B)3:2:1 (C)2:3:1 (D) 3:12 ‘The numberof benzylic H and number of sp* carbon atoms are respectively in oe oo (A)5, 11 (B)6,9 (C)9,9 (D)9,11 The total number of unshared electron pair in following compound is OM) ‘NH, (A)3. (B)4 (c)2 (D)5 Fromamong the following, which compound yields the same carbocation on ionisation? — Br )- 7 ‘HX Br- Br Br @ ay ap avy (A) Land I (B) [and IT (C) Mand I (D)IV and II Which of the following pairis not resonating structure of mentioned compound? (A) swnne ] and CO (B) cor} and O OH © seene OA and af (D) Both (B) and (C) The maximum angle strainis seen in (D) Cyelohexane ee (A) Cyclopentane (B)Cyclobutane (C) Cyclopropane‘The correct stability order of following carbocations is 1H oy a wl (A IVs I5TI>1 (B)IV>II>I>N (C)1>IV>IM> (D)I>MI>IVoll ‘Which of the following compounds is not aromatic? wo Q S (A) (B) o © oh *§ : (D) Which of the following is not correct resonating structure ‘of p-nitroanisole? + 0 . Ra Ree bees Ph d (A) @) © (@) 9cn, gcu, gen, OCH, PK, value of ethane is (aya. (B)64 (C) 15.7 (D) 50 Which of the following is not a mera-directing group? (A)-SO,H (B)-COOH (C)-CF, (D) -NHCOCH, The solubility of the following alcohols in water decreases in the order: HT CH,CH,CH,CH,OH —CH,CH,OH CH,-CH-CH, o iy a (A)I>1> 11 (B) >> (C)U>1> ML (D) MI>l>1 Which of the following ions are aromatic? 5 @ of a Cl a O md, (A)I,ILand IV (B)1, Mand Iv (©) Land It (D) Mand Iv25. aT 29. s 31. ‘The most stable carbocatior 0. oO 0 4 a) ®) , of e 9 ©) c i @ b oO (AO (B)1 ©6 OH (oy isless acidic than (A) HO B) C (HCO, (D) cH, Which among the following compounds is the most acidic? (D)3 (A) HC=CH (B) Ph-OH (C)H,O (D) Ph-CH_OH The acidic strength order of alcohol is (A) I> 2?> 3° (B) 3? >2>1° (C)2°> 1 > 3° (D) 1° >3>2 The stability order of following alkenes is a = mM AQ a [~\ avy / \ (A) I>II>I>Iv (B)MI>I>I>IV (C)I>1>IM>1V (D) Il >I >1>IV The least stable carbocation is cH, cH, « ve ° te (A) CH,-CH, (B) CAEeHCH, (C) CH-CH,-CH, (D) CH,-CH-CH CH, ‘The bond length order in following compound is >w (A)x>y>z>w ()z>y>x>w (C)y>z>x5w (D)z>x7¥3h 33. 35. 37, ‘The correct order of bond length is BV ~ (Ax>y By=z yz (D)x>z Best nucleophilic site in semicarbazone (as shown below) is H,N-NH-C-NH, wi (yl om (D) Both Land It Which among the following intermediates. real? The compound which is not soluble in aq. NaOH is OH CH,-OH ONa “ (B)CH-CH,OH © ©) O CH, ‘The dominating factor for stability of -Butyl carbocation cH “His (A) Resonance effect of CH, (B) Inductive effect of CH, (C) Hyperconjugation of CH, (D)Electromeric effect of CH, Most favourable site for protonation in the following compound is nt ry [\_™ HN va H (AT (B) I (Cc) (DIV Which compound is the most appropriate for electrophilic attack? a (a) oO ®(O © 6al x 9, s 41. 42. 45. 47. 7 Urganic cnemisiry The most acidic hydrogen in the following compound is M1 “On 1 NH, (ul (DIV 1 (By The compound which has cross conjugation is Ww AZ BAAL OF YH ©) i “The compound having highest heat of combustion among the following is aed aky © AN ©) Av ‘The weakest electrophile is ° @) wae I (A) CHY cr (©) CH,-C-Cl Which among the following is a non-aromatic compound? (A) © (B) Cee «© O () oO The heat of hydrogenation per mole is highest for (AyPent-l-ene (B)Pent-2-ene ——(C) ental 3-diene (D) Penta-1.4-diene The compound which will give white precipitate with aq. AgNO, is, I (A) O- «>< © oO (Dy {)e Which compound on reaction with SbCl, can give an aromatic product? ci cl wo on-¥o GoD 0 ct ‘The intermediate having unpaired electrons is (A) CH,” (B) CH, (C) CH, (D) CH;49. Si. 52. 33. (oc) (47 General Organic Chemistry “The most stable radical is CH, (ACH, (B)CH,-CH? (C) CH,-CH,-CH; (D) CH, —C—CH, CH, ‘Which C-H bond can be most easily homolytically cleave? wt (B)2 3 (D4 ‘Which C-H bond has the highest bond energy? 4 u Hy | HC” H oo 2H H3 1 a (B)2 «3 (D4 ‘The bond with highest bond energy is . cron (A) C—C (B)C—H (c) C—O (D)O—-H ‘A compound in which eyanide group is notin resonances NC: CHO: CN N CN “ or ®) or © or © ‘The most acidic Hydrogen in following compound is i W-s es 1 1 (Ay T (B) I (Ctl (D)Can"tcompare ‘The most acidic hydrogen is 0, S. Cy a Ag Mun AT @B)0 (om M)IV55. 56. 57. 58. 59. 61. Resonance energy is defined as “esonating structure and resonance hybrid Which of the following cannot behave like both bronsted acid as well as bronsted base? (©) NH, ‘Which of the following compound is not quasi aromatic? (A) (B) (© X (D) Inthe given resonance hybrid, how many lone pairs are localised? & A)HO® (A) H,0 8) HO ()HS0; HH (A) 0 (B)4 (C3 ()5 Choose the correct option(s) about benzyne. (A) Represented as Oo (8) Aromatic in nature (C) Ithas one sp*-sp? weakest bond () Allof these ‘The compound conetly shown with direction of dipole moment is _S — a [=o 8) Cre © ee (D) Allof these — Which of the following is a spontaneous reaction? (A) Cra + AgNO, —> () wi )-Be Ae © a +AgNO,—> O 4 HANGS62. 65. 67. a General Organic Chemistry (GOC) ( 1.9 ‘Which of the following compound is aromatic? “ Co al oO oy oc) . The correct order of bond length is Or Or (A) S=y (B)x>y (C)x CICH,-COOH (B) PhCOOH > HCOOH (©) CH,COOH > PhCOOH (D) None of these The most stable carbon free radical is AW ANZ BAY © BY () Ahn The correct acidic strength orderis COOH COOH CH.-cooH «! > oH >| (B) CCl,-COOH > CBr,COoH COOH ‘COOH —-CH;-COOH : ns (©) HC= CH> CH,= CH, > CH,-CH, (D)Allofthese ‘The correct order of heat of combustion of the following compound is bb PX @ . a (ay (A) [> TI> IL (By > 1> 01 (QC) M>I>1 (D) >I >1 il Urea NH,-C-NH, is obtained during formation of ammonium cyanate by using KCNO and (NH,),S0; NH,CONH, —* NH,CNO Formation of urea suggests (A) Organic compound can never be synthesized in laboratory (B) Phenomenon of isomerism (C) Organic compound can be synthesized in laboratory (D) Both (B) and (C) ‘The true statement regarding glycerol is/are CH,OH ¢Hou é H,OH (B) Trihydric alcohol (C) ‘one 2alcohol (D)Allof these (A) two 1° alcoholeer General Organic Chemistry (G00) Gai 5. Comect statement fromthe followingis presentations shown arerclated as resonating struct 2 BO er intraconvertible and remains in equilibrium, (a) Bothre tures of each other ‘as shown below und are it o-9 (©) C—Obond seehincompainé_ =O JongertheirC—O bond engthin compound C~- {D) All statements in option (A), (B) and (C) are comrect (@) Resonating structures of acompo212) Orgamic Chemistry JEE (Advanced) Exercises ——k—<—————————————————SS—_, 3 ‘The compound containing lowest boiling point is (A) Phenol (B)Resorcinol (C) Catechol (D) Quinol If the transition state is product-like, then nature of reaction is (A) Exothermic (B)Neverpossible (C)Endothermic (D) None of these ‘Total number of structures in dihalogen derivative of propane is (A)3 (B)2 (4 (D)5 ‘The correct order of boiling point is CH,-OH CH,-OCH, ‘CH,-OCH, a OH-oH Ono amy ,-ocn, (A) >> 1 (B)1> I> I (Cj) > l1>1 (D) None of these ‘The correct order of boiling point is CH,OH CH,OCH, CH,OCH, CHoc Hy (1) CHOH a CHOH (ub GHOH av) CHocH, CH,OH CH,OH CH,OCH, CH,OcH, (A)I>0>1>IV — (B)I>1> HIV (C)U>IM>1>1V_ (D) Noneofthese Nitration of resorcinol and catechol maximum lowers their boiling point if nitration is carried out at posit respectively (A) 0-2, 0-2 (B)C2,03 (C)C-3, C-2 (D) C-4, C-3 Arrange the following in decreasing order of dipole moment: @ CH=CH, (I) CH,=0 (INCH,-CH-0 (IV) CH, -CH=CH-CH=0 (A) I> I> I> IV (B)IV>IM>H>1 (CUS II>IV>1 (D)IV>N>Ml>1 Total number of parallel P, orbitals in p-chloro-nitrobenzene is (A)6 (B)7 (Co (D)10 Arrange the following in decreasing order of boiling point: CH,C1,CH,Cl,, CHCL, CCI, (A) CH,Cl> CH,CI, > CHCI,> CCI, (B) CH,CI < CH,Cl,< CHCl, < CCl, (© CH,Cl,> CHC, > CHCl > CCl, (D) CHCI, > CH,C1,> CH,Cl> CCl, nw10. 4. a5: 16, General Organic LNenmion yy er Decreasing order of acidic strength order of following compound is Oo BD Co a ay (A) [> > TI "euhisiit (C)>1> Ul (D) I> MI>1 Arrange the following alkenes in decreasing order of their ionisation potential. HC. HES oth (CH, = CH, ACH,-CH=CH, AMD 5 oe CH OMe Noy, (AI>U>TI>IV— (B)IV> I> >I (C)IV>M>I>M (DIM >TV>I>T The compound with least pK, is (A) CHF, (B)CHCI, (C)CHBr, ()CHI, pK, of which compound is very close to pK, of Butanoic acid? 9 a 0 9 a cy AN ®) An © Wn oO” Yr a a a The highest rate of electrophilic aromatic substitution is observed in compound ‘NO, g NH-G-CH, Ks ° (A) (B) SO © oO Themostreactive compound towards electrophilic aromatic substitution is (A) Anisole (B) Toluene (C) Aniline (D)Phenoxide ion During hydrolysis of methyl chloride and acetyl chloride by aqueous NaOH interaction starts by overlapping between respectively (A)o filled) — 6 (vacant) and o (filled) ~* (vacant) (B) oe (vacant)— 6 (filled) and o (filled) ~7 (vacant) (©)o (filled) -o (vacant) and o (flled)—1 (vacant) (D) 0 (vacant) —o (fill 3ed) and o (filled) —7 (filled)1.14) Organic Chemistry ing i: ? Which of the following is not a resonance structure of the others’ oe | 17. (A) (BF NF Ne 9 oes ANC 18. Select the pair in which second acid is stronger than the first. (A) CC1,CO.H,CH,CO,H (B) CC1,CO,H, CF,CHOH (C) CH,FCO,H, CH,CICO.H (D) CHF, CHCI, 19. Theheatofhydrogenation of |-hexeneis12610mol, When a second double bond is introduced in |-hexene,te tt beat of hydrogenation of the resulting compound is found tobe 230 KI mot. The resulting compound ene (A) L.S-hexadiene (B) 1,4-hexadiene (C)1,3-hexadiene (D) 2,4-hexadiene 20. The compound which is mostacidic is COOH COOH COOK COOH ol (B) S © L of ‘COOH HOOC ‘COOH, 21. Which of the following orders is true regarding the acidic nature ‘of phenol? (A) phenol > o-cresol 0-cresol > o-nitrophenol (D) phenol < o-cresol > o-nitrophenol 22. If 1 mole Of H, is treated with 1 mole of the following compound, OS which double bond will be. hydrogenated? (Ae (B)b (a (D)d 23. ‘The number of p-molecular orbitals completely filled in the ground state of benzene is (A)3 (B)1 6 (D) None_— 1. “The enthalpy of tydrogenation for I-pentene is se-230 kifmol. Hence, estimate the resonance ( (a)+4eimol ‘Thecomectorderof acidity among the followin (@) Cyclohexane-1,3-d>b>e ‘The most basic group present inamoxyeillin is (AN General Organie:Chemistry (60°) Gas 126 u/mol. The enthalpy of nydrogenation for 13-pentadiene Iclocalization) energy of 1,3-pentadiene. (D)-22 KS/mol ‘The most basic nitrogenin given compound is (ay ‘What isthe product of the reaction shown below? (A) COM COM (B)+22Kmol—(C)-AKdmo zcompounds is (b)Cyelohexanone (d) Cyclohexane: carboxylic. acid (B)a>b>d>c (C)d>a>boe (D)ard>c>b ‘ H ae ‘ NS S. SOT RS He ‘ 3S. (Amoxycillin) . 7 ®)N os (b) OH ‘it @)2 ©3 (D)Can'tbe determined con on sos a CHOH vn CO.Na CONa 6) © ) OH a 1 CHOW ne Ton(LIB) Organic Chemistry 29, Arrange the following compounds in order of their decreasing acidic strength. (a) (b) te) (Aye>b>a (B)c>a>b (C)a>b>e (D)a>c>b 30. _Insirongly acidic solution, L-lysine is primarily adication as shown below. As the pH israised, which protonis lostto form the monocation? a con HN We 4 er @ CH,CH,CH,CH,NHy (ay )2 (©3 4 oO Me. coor 31. ne XS a! ‘What is the basic strength order of the marked. nitrogen in the above structure? (A)a>b>c (B)b>c>a (C)c>b>a (D)b>a>c 32. The following structures are resonance contributors for a ‘reactive intermediate formed during ozonolysis of alkenes. Energetically most favourable and the least favourable contributors are respectively. R of OR Oo oR peor - \ 7 cg a Se-Ge-As Sed x * 4 oO ay ay (yy (A) I andi (B)LandIV (C) and IV (D) Land Il 33. The order of acidic strength (K. ) for following compounds is i i i CH,-C-CH, CH,-C-CH,Br CH -C-CHBr, ao dD (qm) (A)I> I> (B) > MI >1 (C)M> >I (D) M>1>03 37. ) Gar General Organic Chemistry (GOCc; “The compound having all resonance, induetive and hyper-conjugation effect is Hh C=O (p)H,C=CH- CH=CH, i. ~ ‘Cc =CH, ~ © cor HCY, c-cH OB Yo ® jee HCO Which of the following resonating structure is most stable? A) B) © «Dy e ° ‘Arrange the following carbocations in the increasing order of their stability. co coo a ap (QI>T> (D) I> 1>1 «& (A)I> > Il (B) >>! Forthe following reactions enthalpy of reactions are shown: Bn —C ;AH =—keal/mole G89 ean, — (CC) atest ‘The correct relation between x, yand zis fA) y>c>x (B)x>2>y (r>x>y (Dyz>y>x Select the most appropriate pair of nitrogens that can be protonated. TNMs, 4 4H, Me. Me NQ \o) NB (A) Land2 (B) 1 and3 (©) land (D) 3and 4DIB) Organic Chemistry 39, 41. 42. 43. ‘The correct statement regarding the following compounds is cH, : | ee HOY Cy CH HCL cH, 1 ft i Iu 0 40 o 40 oO) ay (A) () can form a stronger hydrogen bond than (II) (B) UD) can forma stronger hydrogen bond than (1) (©) Both (1) and (ID) can form equally stronger hydrogen bond (D) Both compounds cannot form hydrogen bond because they are in open chain ‘The compound that does not liberate CO, on treatiment with aqueous ‘sodium bicarbonate solution is (A) Benzoic acid (B) Benzenesulphonic acid (OSalicylic acid (D) Carbolic acid (phenol) ‘The order of relative rates for marked H for base: catalysed deuteration of following ketones is Cl CH,-¢-cH, CH, -¢-cH-cH, cH -er ‘1 0 He 0 Hm O las (A)I> D> @)I>1> m1 (M>1>r @)M>1>0 Which of the following species can act as the strongest base? (A) °OH ®)°OR (© °0CH, ©) I>II>IV— B)IV>Ul>M>1 (C)lsIV>I>M ()IV>T>1> 1 Bond energy of keto form of phenol is~361 kcal /mole whereas total energy content of enol form is 379 keal/ ole. If enol form is more stable than keto by ~13 kcal/mole, then the resonance energy is (A)-18 ®)31 ©-13 )-5 ‘The correct order of basic strength of marked site is — st g J (AMT > I> I (By) >1> 11 (C)> I> (D) I> 1>T Which ylide is most stable? 2 § § oN6 (A) (I (B) OO ( (D)| ‘The compound with lowest pK, is (A)Ph-OH (B)CH,SOH = (C)HO (D) H,C-CH,-OH1.20) Organic Chemistry 54. 58. ‘The compound with highest resonance energy is C3} oA o> ‘The correct stability order of following carbocations is Oo (B)I< (I= Amongthe following, the srongsta oid is $8 2 Inwhichpaispcis-Lismorestblethan species? oO i i C wrt cu ; ud Soe 9 9 ° il I i C Cc. ®) uc~ “_— nc gH — =o (©) cn, -En-cn, - Wag 3 cu-cr, Bion, oe ‘Which compoundis paramagnetic in nature? —\o/H (A) (By o ©} I Su 2 [> Z (D) Cannot be predicted or “©61. 62. 63. “4, General Organic Chemistry (Goc) Cea The comet onter of stability forthe following compoun w | » [O) cy OD. (Ale I> (B)M> I>] (C)M>1>1 (D)I>Mf> If The comect order of acidic strength is ay 0 HC = H (A> > 1 (B)I>1>M (MM >I1>01 (D) I> M>1 The decreasing orderof Kis COOH GOOH cooH COOH ofl am) (al (Iv) (AVI>TeM>IV (B)IV>I>M>1 (I> IVs To mt ‘Arrange the following compounds in decreasing order oftheir acidic strength, (A)I>T1>0>1V (B)IM>I>I>IV (C)M>Ist>Iv re The compound with highest pK, is (A) Br,CCOOH (B)Br,CHCOOH (C) BrCH,COOH ~—_(D)CH_-COOH (D)I>M>1>1V Ca Which ofthe following reaction(s) will goin forward direction? OH Na wl ame, OY + CH\COOH (8) CH,-COOH S22 CH,COPNE + H,C0, H vou I's (© CH CNH, cy 6 Bit cP? o& +N Done Hy1.22) Organic Chemistry 65, 67. 69. ye c. H.N~ SNH, whichis known as Gu ne isa highly basic compound (super base) because (A) Formation of equivalent resonating structure of conjugate acid (B) -Leffect of -NH, groups (C) More electron density due to +R/+M of -NH, group (D) sp" hybridised nitrogen are more basic than sp* nitrogen The order of acidic strength (K,) for following compounds is > 9 cH, a) om) ow (CY oO (A Welll>l>1 (B)I>U>MI>1V (CM >1V>1>1 ()M> Ms 1Vs1 ‘The order of acidic strength (K.) for following o (A)I> > (B) M>1>1 (QU>1>m @)U>M>1 ‘The correct statement for given compoundis Oo Oro ay a (A) Tis more acidic because of planar conjugate ae which involve higher delocalisation, (B) Il is more acidic because of planar conjugate base which involve higher delocalisation. (C) Both Land Il are equally acidic (D) None of these The basic strength: der of following p compounds "OD OD aA @tbnm (B)I>MI>1 (C)MI>H>1 * (oytsiitom70. 11. 2. 7B. 74, GGenetal Organic Chemistry (GoC) Caza) ‘The compound with least pK, value is mt HW co) ®) © o) 9 O OH SH ‘What species would be dominantly present ifshown hydroxy acid is dissolved in water at pH =7? HO, 0 HK of HO. On" OO» *"O. ii 6 ‘The decreasing order of K, value is Ne se cn @ xc cx @ wy (Ui) xc oe i (A)I> > (B)I>m>0 (©u>i>m (Dy MI>1>01 The most basic site in neurotransmitter serotonin is eiceusm, no: ws o Ory ye (Al (0 om MV ‘Choose the correct option(s). NH, NH, NMe, NMe, 1 GY seems O) “6 tnontatson{OT cooH coou cu, Gu, © Oo is more acidie than @) is more stable oO),AD) Organic Chemistry 75. Among the following salts, which is ‘insoluble in water? a wy nuver COO Na | ( 0 (B) © © ©) | SON 30, orf 76. Thedominant species obtained when is dissolved in H,O at pH =2, PH =7 andat, pH =, ‘a sly respectively, is i ai coo 00" He Oo 2 9 9 oO I I ~oF -on ° » £07" LF nS K re ° My 9 -0 on -OH @) 0 0 HO Hoo on TT. Hooc- ace Bea) ° R % ‘The product obtained in above reaction is Nn00C. Nao, ONa on ‘A ‘ (A) mooc B) navoc- a x ow8. 81. General Organic Chemistry (G0C) 2B) 200€, Na00C, on ONa (C) nagoc- (D) maooc % 4 a ‘The basic strength order of following is NaOH Na NaHCO, NaNH, a qq Cy av) (A) I>IV> 11> 1 (B)I>MIsIV>H (C) Wsl>M> ()M>IV>l> I ‘The most acidic compound is CH, g CH CH, @ CH, CH, CH, (ay S07 @ c7 c © | i aE H Ht The order of decreasing half life of tetrahedral adduct is 8 8 $ 6 HC" hs uc] i HC” hse Ho ho a 1) a), am avy) (A)IU>MI>IV (C)I>M>IVetl (D) > M>IV>1 (D) CH, - CH, - OH Ifreaction-I favours product formation whereas reaction-I favours reactant formation: a t Reaction- ; CH,-C-OH +NH, = CH,-C-0 + NH, Reaction-II : CH,-CH,—-OH + CH,-NH, —CH,-cH,-8+cH,NH, then correct acidic strength order is o 8 (A) CH,COOH> CH,NH, > NH, > CH,-CH,-OH * ° (B) CH,COOH > CH,CH,OH > NH, > CH, NH, (©) NH, > CH,-NH, > CH,-COOH > CH,-CH,-OH (D) CH,-COOH > NH, >CH,-NH, > CH,-CH,-OH2B) Organic Chemistry 82. The orderof marked bond lengths is {Ay e>arb (Bya>b>c (Cjazcab (D)ceb>a ‘COOH | 83. Salicyclicacid imaqueous NaOH exist as COONa COOH COONa “a (B) (oL © (D) Impossible to predict H Na Na 84. Thecorrect order of basic strength in given compound is c NH, Ssxb a Hy (A)a>b>e (@B)b>arc ©b>era (D)a>c>b 85. The mostacidic compound is (A) HCOOH (8)Ph-COOH = (C)CH,-COOH~—(@D)CH,-CH,-OH 86. The stability order of isomer of butene is “N¢ = \_/ S\ a aay avy (A) I>IV>MM1>1 (B)IV>I>I>1 (C)l>Il>IV>1 (D)Ml>IV>1>1 NMe, 87. pK, of compound O would be lowest when —Me group is substituted at (A) Ortho (B) Mcia (C) Para (D)Both ortho 88. Thestrongest acidic site is cH iam (AY (By (Cy (D)IV91. 92. 93. 94. General Organic Chemistry (G0C) (27 ‘The compound of molecular formula C,H, N which is most basic in H,Ois (A) CH,- CH,-CH,-CH,—NH, (B) CH, - CH = CH- CH, - NH, ae «(C) CH, -CH,-C-NH-CH, (D) CH, - CH, - NH - CH, = CH, ‘The compound having aromatic conjugate base is A) > oc) OQ of) ‘Which of the following will highly inerease acidity of phenol? (A) Alkylation of phenol (B) Nitration of phenol (C) Chlorination of phenol (D)Acylation of phenol ‘The correct acidic strength orderis Pentane-2.4-dione Pentan-2-ol _1-Pentyne _1-Pentene a () call) (vy (A) H>I> I> IV (ByI>M>M>IV (Cj >I >1>1V (D) M>H>I>IV ‘The most acidic enol is OO 20 Whe weeewil be formed if one equivalent of HCl is added to HOCH,CH,NH,? 6-CH, - CH, - NH,JCr (B) Cl-CH,- CH, - NH, oY (D) HO-CH,-CH,~ NHC ‘The bond length order of C-Cl bond in following compoundsis oO ge ay" an Ww wast (B)IVeMI>H>1 (Ms M>IV>1 D)IV>I>I>112B) Organic Chemistry 96, 97. eee nis an isomer of following compounds is, ‘The most basic compound N= NH, wT HN NH CH, NH-NE, ‘NH-CH, ‘CH,-NH, NH CH, —=NH (©) H.N- CHE wo (D) HN: NH, NH-CH, ‘On dissolving in HO, which compoundis soluble? «eC ©O OD The a with lowest pK, value is w(O) OJ TO) © 2% &% The nucleophilicity order of alkoxide is . CH, SPR CH,-O" — CH,-CH,-0" cH os 3 2 air o cH—c-o a db «uly oH oy (A)IV >>> 1 (BYH>I>M>IV (C)I>H>MI>IV (Dy >HI>1V>1 1. Heat of combustion for the given compound is O00 ap au ayy (A) I> IV > 1 >I (BMsIVSI>1 (C)IV>H>{> ml (D)1> I> 1V>lGeneral Organic Chemistry (GOC) (4.29 {01, The most acidic compoundis: oH coon COOH cHon OH NO. « @ ©) (D) No. No, 102. Inascorbic acid, arrange the hydrogens in decreasing order of their acidic strength. oO) HO. . ‘0 (> Ht OH (ay (A)a>b>ec>d (B)d>c>a>b_ (Ce>d>a>b_ — (Dye >d>b>a 103. Which ion does not have pr-drrresonance? 0, S, 8 a, 3 wl » (B) Cel, (©) CH, PPh, ol. ye oO ‘0 104, The pairin which compound-I contains higher resonance energy than compound-Il is 08 Ce a ant CF SAKA (D) CH,-C CHC , OPP ORa SONa ® ® CH CHL 105. Ifcarbocation is less stable than carbocation |. then possible °G" is/are G (A)-CH, (B)-OH (€)-CN (D)-NH,TBO) Organic Chemistry 106. Compare the acidie strength of following compounds. _-COOC.H, Coch, _COOC Hy OS Soe, con, 1! Scocu, (A> Sm (B)M>m>1 (usioml (D)>m>1 107. The bond energy order of marked bonds in the given compound is, te He My TIO Hie (A)d>b>a>e>c (B)dd>a>e>c (D)d>b>asese 108. Which compound is neither aromatic nor anti-aromatic? (A) [ . of oC) oC) N n” Su nk ‘NH, 109. The best site for protonation is 0 ay (Ar (By (Om (D) Both I and IIT 110. ‘The compounds in which direction of dipole moment is from smaller ring to larger ring is 111. The reaction in which aromatic product is nat obtained is (A) Br __sgno, «B) & Pi Br © [> xn «D) OO sation,Id 5. 6. 17, General Organic Chemistry (G0C) (234 1. Arrange the following in decreasing order of heat of combustion: mo Oe am A, (AL > I> TLS 1V (BIN >M>1>s1V (C)IV>I>I>I (D)l>1V> MIM 3. Whichisa more stable base” e [og oF oe NO, a B) © ©) No, NO, Which ofthe following compounds) has odd number of resonating structure? (A)Phenol (B)B-napthot (©)Tropoliumion —_(D) Toluene Acompound of molecular formula (C,H,0,) is abenzene dicarboxylic acid which ean form anhydride on heating. ‘The correct statement regarding this compounds (A) Most acidic among all isomeric dicarboxylic acid (B) Less acidic than CH,COOH (C) Less acidic than PhCOOH (D) None of these ‘The given order is not acorrect for their: CH, =CH —CH = CH,> CH, =CH, (A)Heat of hydrogenation (B) Bond length of C=C bond (C)Heat of hydrogenation permoleof HH, —_(D) Heat ef combustion Arrange the following in decreasing order of stal Hype Mee Me Moxa Me 0 ay oO cult) (A)I> I> I (B) I> 1 >1 (C)M>1> 1 (D) I> 108. 119, 120. 121. 122. ge ey ‘Among the following, the correct statement(s) is/are (A) Displacement of sigma electrons in C-F bond in compound (Oo) and Os Issam, ener 8 ismore sable than cH, -cH,— Bin gas phase, cH, (C)In fluorobenzene, ring is electron deficient because ‘of (-R) or (-M) effect of fluorine 9 (D)Inphenyt tema) opayboth +R and-R effect is observed on phenyl rings, Among the following orders, conect order(s) of boiling point is/are (A) CH,CH,CH, < CH,OCH, < CH,CH.NH, < CH,CH,OH (B) CH, (CH,CHCH,CH, > CHsC-CH, I CH, oO) ‘Triene (P) which can be readily deprotonated twice with abase to givea stable dianion, Pmay be w€ Ty ®) OS © Gy ©) ‘The compound(s) in which C =C bond length is higher than bond length of ethene is cH. ) (B) CH, = CH- CH=CH, (D) CH, = CH- No, the correct order of resonance energy is/are oV7 > » > ° i) (C) CHy= CH- cH, Among the following orders,General Organic Chemistry (GOC) (4.33 123, Conjugated dienes which on protonation give carbocation having identical resonating structure is, HH, nO CH, HC. nH, © (D) cH, 124. Intermediates which are stablised by resonance is/are @ ‘Oo 1 z p 4A) (B) © (D) Oo 125, The correct order of activation energy of bond rotation energy barrier isvare Wt > Gs AE G LA 126. Which compound is not stable at room temperature?1.34) Organic Chemistry 127. 128. 129, 131. 132. strength ishare ‘The conmect onder of acid (A) Oxalic acid > Malonie ylic acid > Benzoie acid (D) Benzoic acid > Phthalic acid (B) Maleic acid > Fumaric acid dic strength is The convet onder ol (HOF HC= CH (B) HCOOH > Ph-COOH (C) Ph-OH < Ph-SH (D) HCN > H,0. The comrect onder of basic strength is/are ca Ga Sus nF (By P> 21 Br> cH, (©) CH,-O% CH,-CHL-O% CH, i O%X CH, i & (D) ¢\ < Cyr 'H, ‘Hy |. The correct order of heat of hydrogenation is/are (A) HC = CH > CH, =CH, (B) CH, ~ CH = CH, > CH, - CH = CH- CH. (©) CH,-CH=CH, A of J, 9 8 Lo Og R O c ©) ese > (D)CH,-C=C-CH LY y~ C=C-CH,> CH, -CH,-C=CH The correct order of resonance energy is/are ©) - OO) "LO OEDGeneral Organic Chemistry (OC) (41.35 133, Thecomecthasic strength onder isfare e, 8 oo e@ 6 8 yeu. s BS Br (NHS EIT (GH> BT (Dy OH > SH Ch 134, Thepairof compoundsin which compound-lis more stable than compound-Afis = QOL SO, SOLO. 8. CH,OH (pK, = 15.5) would never exist asa methoxide ion (CH, —O°) dominantly at pH (a2 (B)7 (c)10 (D1 136, The correct order of acidie strength isfare ‘OOH coon ot > Sw (B) CH,=CH, < HC=CH COOH = HOO coon COOK ofl > for (2) CHC, > CHF, ‘COOH HOOT 137. The correct statement regarding the given order is/are WS .O (A) Heatof combustion (B) Acidic strength a (C) Strain (D) Heat of combustion per CH, 138, The correct order of boiling pointivare (C) H,0 > CH,-CH, - OH (AANA? AA, ‘oll4.36) Organic Chemistry {gic thane 1? 139. In which pair, compound-1is more acidic than compound: (HO , R-C=CH (B) AN i OQ SH OH . of (oy (D) MeN, Me,NH EI ( : 140. The correct stability orderis/are H H, aH cH, CH, iG HAG hy iA) ee, > \ / ® > Loy HC Hy H.C CH, H, CH, 0 « or or oC T> 141, Whichion is/are aromatic? rr) a6) © © OH OH NO, ON’ Both compounds are arranged in order of their: (A) Acidic strength (B)Boilingpoint —_(C)Dipole moment (D) Solubility in HO 143. Which ofthe following options are correct? (A) para-chorophenol x nore acidic an para-uorophenol (B) Squaric acid dianion have identical resonating structures (C)AI1C-O bonds are identical in squaric acid dianion (D) All C-C bonds are identical in squaric acid dianion 144. ‘The compounds which have —COOH group is/are (A) Aspirin (B) Picricacid (C) Benzene sulphonic acid {D)Cinnamic acid145. 146. 147. 148. 149, General Organic Chemistry (GOC) (7 If Benzenoid resonating structures of Benzene, Napthalene, Anthracene and Phenanthracene are x, y,2and w, then correct relation is/are (Alxtysctin (B)xtzsy+w (Chrtwaytz (D) w= “OOH The acidic strength of is higher than benzoic acid if G is/are (A)-CH, {B)-NO, (C)-OH (D) -COOH ‘What are the stability orders of following reaction intermediates? 1H q il eu CH g cH oR fi HC~ i ges cr no “cw, ac beg | aay) o cH, ay an (AVII> I> 1V ®)I>M>0 (QI>IV> 01 (D)I>IV>0 ‘Among the following orders, the correct order of boiling pointis/are (A) CH.OH < C.H,OH < C,HOH le ®B) < N if 2 \ \ @ 0 d of J () (D) 5 > ce oO1.38) Organic Chemistry © compounds would not have aromatic character? 151. Which of the following heterocy' ne ai >, OWA wt as ih ® Le "ol ka LY 152. The correct statement (s) regarding given compounds is/are N N M Sy wlOL> w(OL> h i 4 H (A) Basic strength order is > 11> II (B) Acidic stength orderis I> Il > IIL (C) Compound-IH have all inductive, mesomeric and hyperconjugation effects, (D) All areheterocyctic compounds 153. Ambident nucleophileis/are ° ca) &v 8) So, (r-e @) So 154. The correct order of acidic strength is/are SO coon On o oO a OH OH @ on on On. NO, No, ge NO. ° ° me: ° Oo 0 No, No, No, (C) CH,-OH > H,0 > E\OH > CH,-CH,~CH,-OH > R-C=C-H > NH (D) HI > HBr> HCI > HF > H,O> NH, > CH F b> CH,General Organic Chemistry (G0C) 4.39 Gc Comprehension-1: (Q.155 to Q.157) Purine is aheteroeyelic compound with four nitogen atoms as shown below: ay Cy le Nv ic ; at 185. Thenumber of localised lone pairin purineis (A4 «B)3 (2 (D)1 136. Which nitrogen is most appropriate to be protonated? (A)I (®) 0 (© (D) MI 187. Which nitrogen is least appropriate to be protonated? (AI (8) om Div Comprehension-2: (Q.158 to Q.160) Few compounds are listed below : @ Carbolie acid ( Ascorbicacid (ii) Tartaric acid (iv) Pieric acid (w) Lactic acid (i) Malicacid (vil) Maloni¢acid (iil) Citric acid x) Barbituric acid (x) Aspirine (xi) Maleic acid (xil) Pyruvic acid sil) Succinic acid (xiv) Phthalic acid (xv) Cinnamicacid (xvi) Cynuricacid 158. The total number of compounds having absence of COOH group is (Ay4 (BS ©2 (D1 159. The total number of compounds which can show stereoisomerism is (a4 (B)3 (C)6 (D)1 160. The total number of compounds which are mono carboxylic acid is As (By3 (C2 (P)1 Comprehension-3: (Q.161 and Q.162) 0 on Aspirine oO isapainkiller medicine. . 0. i cH, oO 161. The functional group absent in Aspirine ivare (A) Ketone (B) Ester (C)Alcohel «D) EtherTAD) Organic Chemistry 162, Aspirineis pot solublein whe (A) Aqueous NaOH (B) Aqueous NaHCO, (C)H,O (D)Ether fi 167) Cc -ehension~ (Q.163 to Q. | es the following flow sheetto show the separationand recovery : ae water imei (Chlorobenzene, p-cresol, Benzoic: acid ff mixture Ether! sue ol Extract with dil. aq-HCl Lower HCI layer Upper ether layer salt da ag MO Extract with aq. NaOH (Tinether) Upper ether layer Lower NaOH layer Add aq. NaHSO, Mixture of two salts ‘Add dry ice (CO,), ether Lower ether layer ‘Salt Upper ether layer Lower ag. NaliCO, Q layer salt Jace ene il, HCI (ether) R 163. The compound ‘T" is ane rethylaniline (B) benzoic acid p-cresol ber 164, The compound Q' is _— ON Neat nine (B) benzoic acid D) 165, The compound*R’ is Disakinee ORNL detyalne (B) benzoic acid *) p-cresol ae (D) benzaldehyde (A)N, N-dimethylaniline (B)benzoicacid (C)p-cresol 167. The compound ‘P* is (Divenaaenye (A)N, N-dimethylaniline (B) chlorobenzene (C)p-cresol (D) benzaldehyde in almost quantitative yield of amixtur y Upper ether layer rGeneral Organi Chemistry (60C) (44a Comprehension-5: (Q.168 to Q.170) ‘Anorganic compound known as Retinal which absorbs light when we:see and convert visible light into nerve impulses. . SS (Resinal) 168, The number of double bonds in Retinal is (ays (B)6 (7 (D8 169. The most acidic His present at (ad (Bye (a (yb 170, The number of double bonds which can show. ‘geometrical isomerism are (aye (B)S Oo 7 Comprehension-6: (Q. 171 to Q.173) Resonance is a delocalisation of n-clectrons only. ts structures are hypothetical but hybrid is real. When we CH,OH NO, % No, m © ha 179. Choose the possible pair(s) of binary mixture which is appropriate forthe following scheme: 180. —Ag.NaOH _, | Salt of Binary mixture Binary Water Layer Mixture [Aa NHS, Compound | + Compound 2 (A) (Ryand(v) (B)(P)and(S) — (C)(Ry and (W) (D)(Qand (U) Choose the correct options(s): (A) Correct acidic strength order is: (U)>(W)>(T) >(S) (B) (S)has ‘5’ resonating structures (C) Correct acidic strength order is: (P)>(H,O)>(W)>(R) (D) Outof'8' only '2' are insoluble in aqueous NaOH Pe‘Taa) Organic Chemistry 181. Compound(s) correctly matched with effect of group is/are (B)(R)4R,-1 (D) (WW) => +R, @ U)s4R,-RA © =4R-1 Comprehension-10: (Q.182 to Q.184) In general organic chemistry, there are some permanant effect, which are inductive, resonance ang hyperconjugation. There are some temporary effect called electromeric and inductomeric effect. 182. Which ofthe following compound(s) has all three effects (Resonance, Inductive and Hyperconjugation) attached group to ring? HL COOH, CH, Oo WA) ee (B) © (D) CH, 183. Choose the correctly matched option(s): cH, OH (Group attached to benzene) (Effect of group) (1)-CH, P) +R/4M (2)-NO (Q-R/-M (3)-CH=NH ® 4 (4)-OH (8) 4H aa (A) I-ST (B)3-QR (C)2P.QR (D)4+-PR 184. Choose the correct option(s). (A) _ Inductive effectis partial shifting of o electrons (B) Fluorine has more (-1) effect than chlorine but less (4M) than chlorine (C) Both resonating and hyperconjugating structures are hypothetical (D) Resonance is distance dependent effect as inductive effectP General Organic Chemistry (GOC) Gas Comprehension-11: (Q.185 to Q.187) For the given mixture P,Q and R. [| sertager °) ies aR) Pal ed ee HHO, 7 QR) U___>| Ether Layer | 485. Second water layer contains QO OOH H NH, ONa @ 6 © © ©) 186. Choose the correct option(s): (A) Correct acidie strength is: (R)>HCOOH > (Q) @®)_Electrondensity in ring: (Q)>(Ry'> (Py (C) Number of resonating structure : (Q) = (P) > (Py' (D) If weuse aq. NaOH instead of aq. NaHCO, then ether layer will not contain (Q). Choose the incorrect options, (A) initial mixture of P, Qand R containing 1 mole of each is reacted with excess Nametal, then 2moleof H, gas.willevolve NH, (B) First HO layercontains © (C)_(P),(Q),(R) havecommon name aniline, benzoic acid and carbolie acid respectively (D) Correct basic strength: o-toluidine > (P)>(P)"(esc Match the columns: 188. Column-1 (Alkenes) (A) 3. 4edimethyl pent-l-ene 4B). 2.3timethy! pent-2-cne (C) S-methyt hept-2-ene —————SSSS ——SSS=SH*==S—_»yxy_ Colurnn-IT (Heat of combustion in kcal/mol) (P) 1160 (Q) 980 (Ry 920 (S) 875 ‘Column-II (Comparison) @®) xsy (Q) x>y ® x = ® f° “OO> TMB) Organic chemistry 193, Columns (Compounds) (A) CH-CH, CH 0 i ° ° ‘BIH c CH; --OCH,CH, Oo oO (©) CH.CH.O-G-CH, -¢-OCH.CH, o ° 1D) H.-F -CH, -C-CH, ° 0 184, Column (Campound) (A) Carboxylicacid (B) Picricacid (C) Squaric acid @) Salicylicacid 195. Column-I (Statements) (A) Aromatic compound (B) Heterocyclic compound (C) Only cyclic peripheral electrons (D) Unstable at room temperature Column-IE (PK, value) (Py 89 (Q 5 (R) 10.6 (S) 12.9 ‘Column-I (Statements) ®) Soluble in aqueous NaHCO, (Q) No COOH group is present () Soluble in aqueous NaOH (S) -OH group is present Column-I (Compound) © @{O) Gs [= tq ® (S) mr196, Column-1 (Compound / Intermediate) (A) CH.=C=CH-CH, © / 0 © OX o ALIN, 197. Column-[ (Compound) (A)HC=CH “On ~ou Ho oll on YH OM Suctuse3 organic Chemistry (G0C) G2 General Archives SSS ee method fornitrogen ‘compounds will be suitable for Kjeldah NH oY ‘The correct decreasing order for acid strength is: (A) NO,CH,COOH > NCCH,COOCH > FCH,COOH > CICH,COOH (B) FCH,COOH > NCCH,COOH > NO,CHCOOH > CICH,COOH «C) NO; oC ,COOH > FCH,COOH > CNCH < COOH > CICH; COOH (D) CNCH,COOH > 0,NCH,COOH > FCH. COOH > CICH,COOH Arrange the following amines in the decreasing order of basicity 990 [JEE Main (Jan)-2019] [JEE Main (Jan)-2019] H o @ aD (A> > (B) I> > 1 (Ql>m>0 (D) I> I> Which amongest the following is the strongest acid? (JEE Main (Jan)-2019] (A) CHI, (B)CHCI, (C) CHBr, (D)CH(CN), ‘The increasing basicity order ofthe following compoundsis: (JEE Main (Jan)-2019] CH,CH, (A)CH,CH.NH, (B) CH,CH,NH ory CH, c -N- One ho, (D) Ph-N-H (A) (D)<(C)<(B)< (A) (B)(A)<(B)<(D) <(C) (C)(A)<(B)<(C) CH, = CH, > CH,-C = CH (B) HC = CH> CH,- C= CH > CH, = CH, (C)CH.-C = CH > CH=CH, > HC= cH (D) CH,-C=CH>CH= CH> CH, =CH, Which ofthe following compounds isnot aromatic? ol wl oD of) N’ 8 SW Which compound(s) out of the following is/are not aromatic? [JER Main (Jan)-2018 ¥ Q @ © to) ww (A)(A) and (C) (B)(B), ne and (D) (C) (Cand D) (D)(B) ‘An organic compound is estimated through Dumus method and was found to evolve 6 moles of CO, ,4-moks H,Oand 1 mole of nitrogen gas, The formula ofthe compound is: (JEE Main Jan)200) (A CHN, (B)CH.N (CC, HN, (D) C,,H.N ‘The increasing order of the pK, of the following compound is: (JEE Main (April)-20! F s CHO. s » OAC . Aiko I | HoH A HGeneral Organic Chemistry (GOC) 155 » AAO "C10 = i i (A(D<@)< <2) (B)G)< (1) <(4)< (2) OM C,H,NH, > NH, (C) NH, > C,H,NH, > (C,H),NH (C) (C,H)NH > NH, > C,H,NH, (D) C,H.NH, > NH, > (C,H),NH Hinsberg's reagent is: (JE Main (April)-2019] (a) soci, (B) (COC), (OCH.COC] = (D)C,H,$0,Cl .Theinereasing order of nucleophilicity of the following nucleophilesis : (JEE Main (April)-2019] (a) CH, COY (0) HO (c) CH, SO? @) OH (A) (b) <(©)< @) <@) B) 0) <@<(@<@ (C) (a) <(@) <(c) (a) > (c) (B) (b) >(e)> (a) (C)(c) > (b) >a) (D) (e)>(a)>(b) ‘The increasing order of basicity for the following intermediates is (from weak to strong)[JEE Main (Jan)-2020) cm 8 mee HC=CH—CH, Ho=¢ Gh, én a (ii) Gi) oy) fi) (A) < fire Giv) p (filled) and o (filled) —+7* (empty) electron delocalisation {D)p (filled) — + (empty) and o (filled) > m (empty) electron delocalisation Find the total number of lone-pairs of electrons in melamine, (EE (Adv.) 2013] |. Hydrogen bonding plays. central role in the following phenomena: (JEE (Adv.) 2014] (A) Ice floats in water (B) Higher Lewis basicity of primary amines than tertiary amines in aqueous solutions (©) Formic acid is more acidic than acetic acid (D) Dimerisation of aceticacid inbenzene Findthe number of resonance structures for N. WEE (Adv.) 2015) OH Nor, Thecorectorder of acid strength ofthe following carboxylic acidsis [JEE (Ady) 2019] 0 ou=% a moon ‘OH iv p OH am Meo )-€ (V) ‘OH (A)I> sms Iv (B)1> I> i> 1v (C)>1>1V>m (D) I> > 1>1Vmos) “Urganic unemishy Answers 5.(B) 6. (C) 15. (D) 16. (©) 25.(C) 26. (C) 35.(D) 36. (©) 45.(B) 46. (C) 55,(D) 56. (A) 65. (A) 66. (C) 75.(C) 5B) 6.(B) 15.(D) 16. (A) 25.(C) 26. (A) 35.(C) 36. (A) 45.(B) 46. (D) 55. (A) 56. (A) 66, (A) 71.(B) 16.(C) 81.(D) 86, (A) 91.(B) 96.(C) 101.(C) 106. (D) 11.(A) 116.(C) 124. (A),(B),(C),(D) 126.(A),(B), (D) 131.(A),(B), (C),(D) 136.(A), (B), (C), (D) 141.(A),(B), (C), (D) 146.(A),(B), (C), (D) 151.(A),(B).(C) 157.(A) JEE (Main) Exercises Single Correct Answer Type 1.@) 2.(A) 30a) 4.(D) 1G) 120) 2B WO 2.0) 28) BO WO 31.(B) 32.(C) 3 CA) 34 0B) 41.(D) 42.(D) 43D) 44D) S1.(D) $2.(C) 53.(A) 54 0B) 61.(D) 62.(B) 63.(B)— 64 (BY 71.0) 72) 73D) 74.(D) JEE (Advanced) Exercises Single Correct Answer Type La 20 30 46) MCA) 12D) 1) 14 (CY 2. tA) 2D) 234A) 24D) 31) 3208) 33) 4 (A) 41D) 428) 43.(D) 44D) SL(C) 524A) 53,48) $4. (A) 61(C) 624A) 63. D) One or More Than One Correct Answer Type 4. (B),(D) 65. (A), (C) 69.(A) 70.(C) 74.(©).D) 75.(B) 79.8) 80.(B) #4.) 851A) 89.) 90.1C) 94, (D) 95.(A) 99.(C) 100.(C) 104.(D) 108.(C), 109.(B) 110.(A) 114.(A), (B), (C) 115.(A) 119.(A),(B),(C),(D)_ 120.¢A), (By 124. (B).(C) 125.(A),(B).(C) 129.(A),(B),(C).(D)_130.(4), (B),(C) 134.(A),(B)(C) AD) 135.(A),(B),(C),(D) 139.(A),(C) 140.(A),(B),(C).(D) 144.(A), (D) 148.(C),(D) 149.(A),(B),(C,(D)__ 150.6), (B),(C) 154, (A),(B),(C),(D) ‘Comprehension Type 155.(B) 156.(B) 160.(A) 161.(A),(C),(D) 162.(C) 7.(B) 17, (A) 27. (B) 37. (B) 47. (D) 57. (C) 67. (D) 7. (B) 17. (C) 27. (A) 37. (A) ‘47. (B) 57, (D) 67. (B) TRA) 71.00) 82.40) 87.(A) 92.(B) 97.48) 102.(C) 107.(A) m21C) 117.(D) 122.(A) 8.(B) 18.(D) 28.(A) 38.(A) 48,(D) 58.(D) 68.(D) 8.(D) 18.(D) 28.(D) 38.(B) 48.(A) 58.(B) 127.(A), (B). (©) 132. (A), (B), (C), (D) 137.8.) 142. (A), (B), (C), (D) 147.(B),(€),(D) 182. (A),(B), (C),(D) 158.(B) 163. (A) 9(C) 19. (B) 29.(A) 39. (A) 49.(B) 59.(D) 69.(D) 9.(B) 19.(C) 29.(B) 39.(A) 49. (D) 59.(A) 68.(A) 73.(C) 78.(D) 83.(C) 88. (A) 93.(C) 98. (D) 103.(A) 10.¢a) 20.(D) 30.(B) 40.(D) 50.(D) 60.(D) 70.(D) 10.4) 20.(a) 30.(B) 40.(D) 50.(D) 60.(C) 108. (A), (B). (D) 113.(D) 118, (B).(D) 123.(A), (D) 128. (A). (BAC(D) 133. (A), (BAC). 138. (B).(C.1D) 143. (A). (BLKOD) 148, (AD, (BL AC)(D) 153. (A), (B.C) 159.(C) 164.(C) J165.18) 166.10) 167.() 70.8 Imac) TRGALICD TreaR)ADY 176.18).(B) TIA. (BY.AC).CD) 180.8) ABLAALC) TRAC) 1D 186.1B.(C.D) 187.04, (BAC).CD) Matrix Match Type 188 ADB), (CPD RY 19,AP.Q)BQR).(C3.Q). (DROS) IRIA-RS)(BAPRS)(CPOR), DPQR) 194.,APR}. (BSP.Q.RS).(CP.OR. 5S). (D9PR,S) 1% (A+9).(B4P).(C-3Q),(0-9R) General Organic Chemistry (GOC) 1.59 168. (8) 149.18) 173. (AAD) 174.44), (81. (C).4D) 178, (A), (1) (C 179.18). (D9 183.(A).(B).(C). (0D) 184.04).(C) 189.(A-9R.T}(B-4PT), (C4Q.T), (DRS. 191. (A9Q.$}.(B8.T).(C9PR}.(D-90.5) 193, (A+), (BR). (C18). (DP) 195, (A-4P.QRS), (BPR), (CIP.QRT).DT 197, (AP), (BPR.T) (C>PQRS.T)DPT) Numerical Value Type 185 199.7 200. 5 201.7 202.6 203, 5 204. 7 205.7 6. 6 207. 8 208.5 Archives JEE (Main) Questions LA) 2A) 3.(D) 4.(D) $.(D) &(C) 1) 8. (D) 9A) 10(B) ALMA) ARC) ARCA) 14D) SD) 1K CYC). YB) JEE Advanced Questions Ltt 211c) 3.6) 4. (B)(C) (Dp 6. (B),(D) 7, (D) (Ay 940 1A), (B). (Dy 11.9) TRAA)1.60) Organic Chemistry Hints and Solutions JEE (Advanced) Exercises comparable then type oj Hydrogen Bonding is leciding factor. Intermolecular Hydrogen Bonding increases boiling point more tay intramolecular Hydrogen Bonding, S. — Referquestion number 1. 6 Referquestion number 1. UL. Higherthe electron density in alkene, higher will be the ionisation potential. 14. Higher the electron density in benzene nucleus. higher will he the rate of electrophilic aromatic substitution WANNA + y—$—> ALA 126 ki/mole) LNANF + H;—$<—> “NY __230 ki/mole) (GH) should be 252 ki/mol but it is 230 Id Jmol. So itindicates that (~22 kJ/mol) is resonance energy, Aas bonding Molecular =. orbit Es Wd Neda wnt TE (Band UD) both have 4’ (out of 7) resonating structures which contains benzene but (IID have only *2" (outet 6). 39. Hydrogen of enol (1) isrelatively more acidic than alcohol @. 46. Conjugate base of (IV) is aromatic 52. Duetoresonance ylide (I) is most stable. Ylide is spe ciesin which carbon contains negative charge and direth attached heteroatom contains pos charge. sp — AS 58. Antlaromatic compounds are unstable at room temperature, ‘They are paramagnetic in nature COE} une LT Sas} Poor solvation of conjugate ucid of ie. 78. An electropositive metal is Strongest base because it will loose electron readily. 108. Carbocation is destablised by electron withdrawing group by resonance like -CN.General Organic Chemistry (60c) (4.64 106. Estershows less stat 107. Bond bond. 108. Compound in option (A) is non ion than ketone because in ester resonance is already present, ney is indivectly proportional to stability of frve radical obtained byhomolyticcleavage of marked C-H romatic duc to sp nitroge om whereas compound in (B) is non-planar beca © of repulsion between two rrans-Heatom, Ss eH i. Ors ‘ankiaromatic, hence no reaction takes place and no aromatic product is obtained. 112, Heat of combustionis directly proportional to number of carbon atom, 113. Higher the extent of resonance, weaker the strength of base, Hence most stable. 117. Carbocation (IL) is less stable because of absence of resonance (steric inhibitation of resonance), U8. (B) Higher dispersion of negative charge in higher number of C-C bonds, hence more stable. (C) -Idominates over +R effect ofhalogens. (D)_ Twobenzene rings one has +R direcily connected withO andother has -Reffect, 119, Refer question number 1. = ).0..O"D 121. Resonance increases bond length of C=C. 122. Resonance energy is directly proportional toextent of resonance. 123. Inoption A and D protonation provides same carbocation. lowe 124, ‘Bridge head center never hold planarity in smaller ring (Bred’sule). 125. Higher the bond order, higher would be activation of energy barrier. 126, (B) is anti-aromatic, hence not stable at room temperature. (A}Cyclopenta-1,3-diene at room temperature is easily dimerised by Diels~Alderreaction. Ow=-OO\ Tez) organic Chemistry first compound whereay,| sterference of electronic wavefront takes place in 134, Inoption ‘A’ and “B* constructive i ference takes place. second compound destructive inte cH, H Se, HoN ll =CH =C Hey se cH, 146. Due to ortho effect (non-planarity of COOH) ortho substituted acid is more acidic. N Ni = (Ol)-CD > OY - OG a i Box indicates acidic sites and circle indicates basic sites in above compounds.) Ged General Organic Chemistry (G00) ay, ihe soi of Me ‘Exc with oq HCI © ESS Lowe tte Ups cpr CH ~ ot Farah ag. NO Oo Sabo (Vinether) 6 6 6 perce eet au Aad Nab tomer 20H ie Nana cferotos pasayiee(COneier Lent ine Sipe eine " i) >—— {pace ete A owas aco, = > au neta 4 ¥ rere S C5080 -ob-o-had at 171-173, 8.TED organiechemistry 174-Q. 176. we ao ng we ay cl Sa wey 0H H CH; cy CH, Ss (OV ED oa, 182 184. OH +Ra CH; -H41 CEL 189. Compound having exactly same resonating structures contains same bond length, are responsible for aromaticity, hence eee Tr 198.6) ,(ilip fi) (vii) (xy 200.41) Gi) ,Giiiy, ivy (vy 202.11) (ii) ivy ti), Oxy Ci) 2OS.Ci) (ii) Av) (vii ,Avitip, (ix Oxy — 1 ~ a HACC By gs ine 0 (D) CH,-CH-CH, 0 ince peripheral p-electons Br, Mi a 199.41), HD) OD evi, GND 48) 201-1. AIV9.09, (VD) Qi), dvttad ex) 203. GD AI) 009, (Wi), (vind) 206.440) G10 40), (9) vir, (vtiiyGeneral Organic Chemistry (G0c) (65 Archives ‘JEE (Main) Questions: 12. Basicity: +R/+H/H 1 “CRI-HI=1 13. Basicity of amine 2°> 1°>3°NH, 9 14. Hinsberg Reagent OH -a o [Benzene Sulphony! chloride] oO 15. “OH cuto > HO I 0 ‘Charged ion Ton pair donating ability decreases ‘eat system Ton pair tabiiy increases Nocleophiisny Soc 16. aya” . a aad NO; NO; fod Asthe delocalisation of charge increases, stability ncreases. 1 17. Basicity order Scabiity of anion CN «CH= C + Sc, <> He ope +SbCl, tf “~~ oi SbCl, <— (A)>1 @)) Organic Chemistry 23. MW. 22. 29. Most stable conformation of ‘eyclohexat (A) Chair (B) Boat (C) Twistboat (D) Halfchair The compound AN / isan isomerof wll | ®) A o De @) A Trans-but-2-ene on anti- addition of Br, gives (A) Enantiomer (B) Meso compound (C) Diastereomers (D) Compound which cannever show stereoisomerism Cis-but-2-ene on anti-addition of Br, gives (A)Enantiomer (B) Meso compound (C)Diastereomers. (D) Compound which can never show stereoisomerism ‘The compound which cannot show geometrical isomerism is oC) oe 1¢ oC nN | H ‘The following compounds are related as cH, cH, u——On HO—-—t H—}—OH OH HO—}—H on cH, cu, (A) Diastereomers (B)Enantiomer —_(C) Identical (D)Epimer ‘Meso compound is, war wAA oAy oA32. tr Isomerism Arrange the following in decreasing order of % enol content. p Po ® ct a) me ay oN (A) > I> TT (B)I>1>10 (C)MI>1>1 (D) Il >1> Ih ‘The sex pheromones of the cigarette beetle “Lasioderma serricome” is given below: AWK How many chiral centres are present in serricome? (Ay @)3 4 (D5 ‘The most stable conformation of trans-1,3-dimethyl cyclohexane is CH, H, cH, (a) ®) mer (CH, wT OH an Which is anexample of structural (constitutional) isomer? HC Hy HC H wy cach Ne=cQ @H OH HO H H 0TH H CH, ce CH én, dn, CH, be Which compoundcan show otto isomerism? (C) Propene {(D) Lsobutene (A) Butene (B)AlleneBEY organic chemistry 35. 37. 38. 39. 41. A.compound of molecular formula C,H,,0, may have (A) Ketone and Ester both (B) Acid anhydride only (©) Etherand Ester both (D) Alcohol, aldehyde and ketone al ‘The total number of benzenoid isomer of molecular formula C,H,Cl, possible is 1 (B)2 «3 (D4 ‘The compound represented in ts most stable conformation is 4 Ma WH H e J H a He oan ) 4 Sec \ B) eo, Hf yo Sa if A, i HH a H Or H ©) ET, 1 A chiral compound must have (A) Chiral centre (B) Super-imposable onits mirror image (C) A diastereoisomer (D) A minror image isomer with opposite optical rotation A.compound contains total of three optical isomers. The correct statement for these optical isomersis (A) Allare active (B) One isomer active and two isomers inactive (C) Two isomers active and one isomerinaetive (D) Allof the above Conformation obtained on 60° clockwise rotation of C, and then 180° anticlockwise 2" of Cis qa u cl H u H (A) Belipsed (ByGauche (C) Partially vclipsed (D) Staggered Enantiomers musthave (A) Chiral centre (B) Same rate of reaction with chiral reagent (C) Samedirection of angle of rotation with PPL. (D) Same boiling pointa2 Isomerism Or ‘The incorrect statement for meso isomer is (A) Optical isomer (B) Intemal compensation of angle of rotation (C) Resolvable compound (D) Kdentical with own mirror image ‘The most stable conformation of ethyl alcohol is cH, H H cH, i, OH (a) west ®) TE, © nee @) a H HC H H H iy H H H H CH, Asymmetric compound is 6 COOH ae HAC er00H Hi OH e pry, H on cH, m CooH @) @ ic7 TH ® (s) (PRQRS (B)PR.QS OPQR D)QSR Incorrect statement for compound "X' is coon H oH H ‘oH COOH oe (B) Achiral compound (A) Meso tartaric acid (C) (2R, SRY The compound having absence of axis of symmetry is HC a) —- Bee (crcl, (D)2,3-dihydroxy butane divie acid ath2B) organic Chemistry 47. 49, 50. 8 52. Conformation of cyclohexane contains centre of symmetry is (A) Chair (B) Boat (C) Halfchair (D) Twist boat If cis isomers of a compound can exist as an enantiomeric pair, then compound must be HAC cn. r An, wy praca ch 6) an © ween, (wy HC CH, I, 3 Compound(s) having more than one stable conformation is (A) Propane (B) Isobutane (C) Butane (D) Neopemtane (+)-2-bromobutane indicates (A) Meso compound (B) 80% (+)-2-bromobutane and 20% (~)-2-bromobutane (C) 75% (+)-2-bromobutane and 25% (—)-2-bromobutane (D) Equal amount of (+)-2-bromobutane and (--)-2-bromobutane ‘The compound which is enantiomeric with compound OOH H CH, OH 00H COOH ak (a) seh (B) won Ole ~on (py a scons a CH, CH,OH HC ‘The total number of chiral centre in compounds are respectively Lo at fen f CH, CH, CH, i fu Ras, Br cl (A) 2,11 (B)2, 1.0 (C)2, 3,3 (D) 23,053. 55. 7, The compound having two fold axis of symmetry (C,) is (A) CHC (B)CF,CIBr ‘The compound which is not chiralig “ “S (C)CFCIBM (D)Cccl, oH One Cl CH, © cI © we, CH, ‘The compound which does not have exactly 4 optical isomersis (A) 1,2,3+trichloropentane (B)2.3.4-trichloropentane (©) 1,2,4-trichloropentane (D) 1,2.5-trichloropentane Which among the following is not correctly matched ? (a) Ay and AM. Position isomers 1 9° ®) and mw, Funetional isomers 1H (c) bj and 6 ‘Tautomers (Dy AN and AK Position isomers | most stable conformation of following compound, position of both -OH and —Fis respectively HH ar asc (B)Equatorial-Axial (C) Axial-Equatorial @)Anial-Axial Isomerism (2.9.210) Organic Chemistry 58, Enol formof compound *X’ on prolong treatment with D°/D,Ois (x) eo D D 1D Db @ QO @) r¢ © aon © 5 D 59, Therelation between following compounds is cH, cl H.C. Hoa ASO H cl Bch, cl cl (A) Enantiomer (B) Identical (C)Diastereomer —_ (D) Conformational isomer 60. The correct stability order for conformation of ethylene glycol is (A) Anti> Gauche > Partially Eclipsed > Eclipsed (B) Gauche > Anti > Partially Eclipsed > Eclipsed (© Eclipsed > Partially Eclipsed > Gauche > Felipsed (D) Partially Eclipsed > Eclipsed > Gauche > Anti 61. Composition of mixture at which observed rotation of mixtures maximum is (A) 100% racemisation (B) 20% racemisation + 80% retention (C) 50% retention + 50 % inversion (D) 20% retention + 80% racemisation 62. Esterification takes place when (~)-lactic acid is treated with methanol. (+) methyl! lactate is obtain! product. CH,-CH-COOH + HO-CH N+ Ci,.cH-coocH, +H,O OH OH (-)-Laetic acid (+)-Methyl lactate ‘The correct statement regarding reaction is (A) Sign of rotation toward PPL changes (B) Configuration of chiral centre is not changed (C) Configuration of chiral centre is changed (D) Both (A) and (B)65. 67. Isomerism Acompound with molecular formula: C3H,CL, where x+y =6. The correct set of values of x so that the compound may exist in optically active formis (A) 01,2 (B)1,3,4 )3.5.6 (2, 3,4 Optically active *P’ has the molecular formula C,H, ,and catalytic hydrogenation converts into achiral C,H, ,. ‘The structure of ‘P’ is wos BWW ONS OFY™ ‘The compound which are chiral but having absence of chiral centre is “ “> on B SOX" 1 “CHCH, Ba a acl, "Se" © Swe ' "cl ‘The most stable conformation of compound is AX wx of=2r Oud oor, The correct potential energy diagram for conformation of cyclohexane is r + (A) PE (B) PE’ or /\r om ‘Thecompound which mainly existin its enol form is @) cHy- - By wee -CH © green (©) GH-CH-C-CH, oO 82.12) Organic Chemistry 69. 70. 71. 72. 73. 74. ‘Which compound is non-superimposable mirrorimage ofthe following compound? Br e Cl al var Br, a a) oh © ©) ‘ Br Cl cr Cl The compound shown below is known to lower serum cholestral levels. How-many chiral centreg are re) inthis compound called as "Mevacor"? ¢ Ad, A) 6 (B)7 ©3 (D9 am ‘he following in decreasing order of priority according to Cahn-Ingold Prelog (CIP) system. @- (1) -CHF (U)-CH,CH,CL (IV) -CH,CH,CH,Br Sistem @®)IV>M>>1 ()M>M>IV>1 ()IVS> M1 How many chiral centers are present ina fungicide propiconazole given below? a Con yl ®)2 (23 D4 Which of the following isnot aconformation of cyclohexane? oF o> ob © LQ Total number of ‘D* atoms presentin fina pro ofthe following reaction aftera prolong teatmett® (Ay2 (B)3 (Os (D)71% 16. 1. Isomerism (2.13 Which of the following is arigid conformation? wc oY ow ow AY If population of anti-conformation of isopropanol is 24%, then population of following conformation is H H CH, CH, (A) 24% (B) 38% (C) 62% (D) 76% Which of the following is not achiral compound? ca ch x E F a " F a Ma «| ® It © IT ©) IT tT */ a Br Br i Br f “Absence of which of the following symmetry is a must condition for chiral compound? (A)C, (n-fold axis of Symmetry) (B)C, (Centre of Inversion) (C)S, (n-fold altemating axisof Symmetry) _(D) 6 (Plane of Symmetry) Correct statement regarding following reaction scheme is cooH COOH COOH 1 = | ss 1 ‘CHC! <— cCHOH —— CHa | 1 t CH,COOH CH,COOH CH,COOH (+ (+) oO es | Reaction-I Reaction-II (A)Reaction-I shows retention of configuration. (B)Reaction-II shows inversion of configuration. (C) Both reactions together shows that anyone isretention and anothe nof configuration, (D) Sign of rotation is related to configuration. Coorect CIP order for following groupsis (A) —C = CH > —C(CH,), > —C(CH), —CHICH ), (B) —C(CH,),—CH(CH,), > —C = CH > > —C{CH), (©)—C= CH> XO) > —C(CH,), —CHICH)), > —C(CH)), =CH>—C(CH), (D) —C(CH,),—CH(CH,), > 229) organic chemistry JEE (Advanced) Exercises EIOnLunn Maximum number of ing 7 carbon atoms) in the folgy, reaction on prolong treatments, (ys (B4 7 (D)8 ‘The compounds which slowly racemises on addition of SbCI, is 1 1 al cl ‘The decreasing order of enol content of following 1 ,3-dicarbonyl compound is oO oO oO 9 oO oO Oo AAA ap AN ap AN (A)I> 0501 (B) I>1> Tr (C)MI>0>1 (D) >IT >1 ‘The compound which predominantly exists in its enol form is Q 9 o © (A) ) ( (B) AK «) oo DN, ok Oo ‘The product obtained in reaction is ° +4D,0 —S25 bop bop R RD D ~ Dy (A) (B) a (C) ‘9 (D) ‘0 D a ' D wp SpIsomerism (245 ‘The deereasing order of enol content of following 1,3-dicarbonyl compoundis 0 Oo oO oO o 0 BAA ay yy ‘ip ye K (A) I> > (B)I>1>1m (C)Ill> IST (D) >t >t ‘The number of deuterium atom in enol form of But-2-enal on prolong treatment with OD/D Cis (aya B)3 4 (D)5 ‘ Select the correct statement: (A) Number of stable conformation of -butane is 3, (B) Anti-conformation is always more stable than Gauche conformation, (C) Torsional strain in Gauche conformation is more than torsional strain of anti-conformation of 1,2-dichloroethane. (D) Ethanamide can’t show tautomerism. ‘The most stable conformation of Butane is ¥, H, CH, H 4H HO Ha CH; (B) H Hs CH, H, H HH Ms [ CH. Hin, Hon. b © or a cH, | cH, The following pair is related as cH, cH, H cl 4. C1 " cl WW Mm cH, cuel (C)Enantiomers «D) Structural isomers (A) Samecompound _ (B) Diastereomers The most stable conformation of propane is (B) W it H ut H Wt u i H () way Wo HZAG) organic Chemistry R. 13. 14. 15. Select the correct options. Use (T) for True and (F) for False statement. H | @ L~~fy ~y 8 mostsable conformation of methyl cyclohexane H i) is most stable conformation of cis-cyclohexan-I,3-diol OH OH ‘Bt iii) L~7, is most stable conformation of cis- l-ethyl-2-methyl cyclohexane. Me (ATIT (B) FTF (C) FEF ()TIF Cis-lactide is shown below, it can have eg o. Me H | (A)Plane of symmetry (B) Centre of symmetry (C) Axis of symmetry (D) Three chiral centre In which compound each Axial-Equatorial bond interconversion takes place during ring flipping? wl ®) © grgad oL The symmetry in following compound is CH, Ht H areal CH, (A) Plane of symmetry (B) Centre ofsymmeiry (C)Axisofsymmetry — (D) None16. 17. 19. Isomerism (2.17 Following compound ‘X" contains (9) (A)2 chiral centre and 2 optical isomer (B)4 chiral centre and 3 optical isomer (C)4 chiral centre and 2 optical isomer (D)2 chiral centre and 3 optical isomer ‘The compound with observed angle of rotation (¢.,,) not equal to zero is, cH, cH, HH ch H (a) ae ®) +; cl cH, oe HC H WON H—}—cl es © D) c=, Hcl O77 cn, cH, How many stereoisomers of ‘X’ can have centre of symmetry? H o cl c 1 a oo (A)3 (B)O (4 (D)2 Compound R-2-chloro-3-methyl butane is CH, CH,-CH,-CH, 2 oct H (A) cr H (B) cl cH, ©) cH, CH,-CH,-CH, 4 cH, Select the correct statement: (A) 23.4-tr-chloropentane has two assymetric centre (B) D-configuration of acompound always rotate plane ; {C) Alloptical isomers of a compound always route plane polarised light (D) 1-chloro-I-phenyl ethene is dissymetric compound polarised light towards clockwise directionFAs) organic Chemistry 21. I-r=Total numberof plane of symmetry in eclipsed conformation of ethane and = Total number of two fold axis of symmetry (C,)in methane, Then value of (x+y) is: (Ay4 (B)7 (C)6 (D)5 ive of 3-methyl pentane on reaction with Cl/hv is The total number of possible monochloro der (Ad (B)6 (7 (Dy8 The total cyclic isomer of compound C,H, is: (a3 (B)5S (C)6 (D)7 The total number of cyclicisomer of molecular formula C,H,Cl, having centre of symmetry is (A)3 5 (C)6 (Ds ‘The correct statement regarding following compound is cl H (A) Iecontains plane of symmetry (B) Itcontains centre of symmetry and alternating axis of symmetry (C)Itcannot show geometrical isomerism (D) Itean have axis of symmetry If. x= Total number of chiral stereoisomer of 1, 2.3, 4, 5, 6 hexachloro cyclohexane ‘y= Total number of achiral stereoisomer of 1, 2, 3,4, 5, 6hexachloro cyclohexane ‘Then correct relation among x and yis fare (Ayx-y=0 (B)y+x=8 (ety (Dy Incorrect statement regarding following compound *X’ is Fr Br cl ) (A)Double bond equivalent forX isthree __(B) Only two optical isomer possible (C) Xcontains three chiral centre (D) X contains fourchiral centreDB. 3. 32, _ Isomerism (2.19 Select the incorrect statement, (A) Meso tartaric 'S more stable than optically active tartaric acid (B)Meso-butane-2,3-diolis more stable than optically active butane-2,3-diol (C)Mes0-2,3-dideuterio butane is more stable than optically active 2,3-dideulerio butane (D)Meso-1,3-dichloro eyclo hexane is more stable then opt Meso compound containing no plane of symmety is 9, oO cy) en< > ni / . ©) ~ O, Which mixture of following compounds cannot be separated by fractional crystallisation? lly active 1,3-dichloro cyclohexane 0. 4 Me Me @ 4 a eg t—feon tion A) aha (A) a cue” i Nec” (Bu OH HO. H Hu” NH HH” NH on Eo ae Me le Me Me i cl Br. H © (D) Br Het H ie Me ‘The possible number of monochloro products in given reaction is Ce (Ay10 yu (12 (D)8 ‘The number of possible optically active products obtained on monochlorination of following compoundis cH, H cl CH-CH, (A)2 ®)3 «4 (D)5 ‘The total number of possible stereoisomers of given compound is cr ch cl cl (ay? (B)4 oe v7