Which of the following alkyl halides will you expect to give the highest yield of substitution products under conditions favourable to a bimolecular reaction? (A) CH,CH,CH,CH,CH,Br ®) CH.CH.CHGH—cH, Br jr (©) CH,CH,—CH—CH,Br (©) CH,CH,—C—CH, oe, Hy In the 8,2 reaction of cis-3-methylcyclopentyl bromide with alkali, the product formed is (A) a cis alcohol (8) atrans alcohol (©) an equimolecular mixture of cis and trans alcohols, (©) there is no reaction Which of the following alkyl halides is unreactive in an Sy2 reaction? (A) Primary (B) Secondary (©) Tertiary (0) Methy| chloride In $2 reactions, the order of reactivity of the halides CH.X, CjH;X, n-CzH,X, n-C,HeX is (A) CH.X>C,H.X> n-CH,X> n-C,H,X (8) C,H.X>n-C,H,X > n-C,H,X> CH.X (C) C.H.X> n-C,H,X> n-C,H,.X>CHX (O) 1-C,H,X > n-C,H,X> C,H.X>CHX Correct statement regarding SN, is (A) If cone. of Nu® and substrate will be respectively doubled and tripled then Rate of reaction of SN, remains same (B) Rate of SN, increases if number of branches increases in isomeric bromobutane (C) Approach of Nu® takes place from frontside as well as from backside in SN, mechanism (0) Approach of Nu® always takes place from backside in SN, mechanism H F DOS + Nal (one mole) ses Product will be I F Wy MH H H © Bx © 5, Hydrolysis of methyl bromide takes place much faster in the presence of (A) KF (B)KT (C) KBr (0)KcI10. 1. 12. 13. Treatment of (S)-2-bromobutane with sodium hydroxide results in the production of a compound with an (R) configuration. The reaction has most likely taken place through : (A) an Sy1 mechanism (8) an S,2mechanism (C) both 8,1 and SN2 reaction (0) cannot be determined ‘Which of the reactions shown below will be faster ?, Br OH Br OH Reaction 1: KOH, Reaction 2: KOH, #0 Crown ether \ (A) Reaction 1 (B) Reaction 2 (C) Both have equal rates of reaction (0) Cannot be predicted 1 oH xsi H SH H H SH Me—|—H Me: HW HS—1—Me Ht Me (a) Et D (8) Ft D (©) Ev D (0) Et D H I H n cl AN nas OH °O cl MAA, OAN () AA ~OH OH OANA, Give the structure of the reactant that could be used to convert iodoethane into given compounds ? [ >= —CH,-CH, OH on [esi [=e Transition state of given SN, is CH, Br CH,-O-R Ro? Nz reaction @ on ©) cut”sca: CHCl og O PhSPNe®, major product RY SPh 1 Ph SPh alo a) (©) SPh_@) ‘SPh Br CHCl O KOSH? major product SH SH SH Br UA Us a[O ®) HG) cl wD) 4 Most reactive towards SN2 reaction is T T Br Br ZA a) ®) (c) ©) Most reactive towards SN1 reaction is (A) > (8) (0) H,C =CH-I Under the following conditions, cH, H, CH, H cH cH Fs ho bX SH > a No Non on, no ou Nu +Br CH, CH, ‘1-bromo-4-methylpentane will most probably react via (a)SN1 (8) SN2 (C) Both SN1 and SN2 (D) Neither SN1 nor SN2SN1 reactions show first order kinetics because: (A) the rate-limiting stop is the first step to occur in the reaction (B) the rate-imiting step involves only one molecule (C) there is only one rate limiting step (D) the reaction involves only one molecule Which of the following would be the best solvent for an SN2 reaction ? (A)H,0 (8) CH,CH,OH (C)CH,SOCH, (D)CH,CH,CH,CH,CH,CH, Which of the following would be the least reactive in an S,2 reaction ? (A) bromocyclohexane (8) t-bromo-2-ethylhexane (C)3-bromoheptane (0) 1-bromo-3-ethyipentane —_(E) 1-bromo-4-methylhexane Compare rate of SN, 0 ay (uy (Ay til> 1 (B) > 1> Ul (C)t> tll (D) >> 1 CH. HBr NaN, H,C——H DMSO, 26°C’ CH,CH, What is the major product of the reaction shawn ? CH, CH, CH, H CN NC: H 4 CN (A) H.C. H (8) H.C: H (C)H CH, CH,CH, CH,CH, CH,CH, What are reactant X and product Y in the following sequence of reactions? NaN, ReactantX ————_—°_> ,," i ————> Product pyridine Ethanol-water Reactant X12. 13. 14. Trimethyfoxonium tetrafluoroborate reacts with methanol (CH,OH) to give dimethyl ether (CH,OCH,). Which equation, including the curved arrows, best represents the rate-determining step in the mechanism? CH, Hc, BFE cH, “Trimeth foxonium tetfuoroborate cH, He. Lot ws Lc-0 > HC" ‘CH, c () HC- H.C 0, co! + :0: “ \ OK woe \ H cH, CH, Which of the following conditions are best for an S,,1 reaction and not an $2? (A) strong nucleophile, high solvent polarity. (8) weak nucleophile, high solvent polarity, (C) strong nucleophile, low solvent polarity (0) weak nucleophile, low solvent polarity Match the column : Golumn-| Column4i wo ol \ reaction cardinate SS 2c5 eh ole 6 wl JM, Teacton oarcinale ksH © CH, } I 10H i (©) Pr-c—GH- cH, EA (A) major (SE CH, Br L____, mH FY [| __“\Q. Type of mechanism & more reactive reactant is (1) ANNs, of Ag atte acetone Gis (2) CH.-CH,-CH-GH, er CH, ~CH,~CH,~ CH, ~ CH, ~ Cl cl al ‘ NaN 3) b ® oF CH, ~CH,~ CH, ~ CH, ~ CH, ~ CH, ~ cl AaNa gr gr @ — CH,-G-CH,-Br or CH, -G—Br EtOH , CH, CH, 5 H,O (8) Iso-butyl bromide or sec-butyl bromide 22 , ee CH,-Cl g (7) CH,-T or CH,-Br —22KOH, EtOH or 10H , ®) On. On Ny OS, HSH Oy acetone Br Ph CHy (1) Ph-G@—Br or CH,-C-Br _EIOH Ph CH, NaN DMSOMajor product of the reaction is CH. et Et ) 0 @) © HWILLIAMSON ETHER, SYNTHESIS Passage : (1 to 11) ‘An important route to synthesize unsymmetrical ether is willlamson ether synthesis. This reaction is an example of Nucleophilic substitution reaction. (SN, Reaction) Itinvolves the reaction generally between alkyl halide and alkoxide ion. 1° Alkyl halide and 1° Alkoxide ion gives best yield of ether during this reaction. 1. Best method to prepare pre-e, is the combination of won KOH, __CHst on No, CH, (C)MeOH _Na_, 2a, (D) (A) & (B) both 2. won NaH, (x) Met, (y) Identity (Y) ay TOME) Me H (cy #7 OMe (D) None of these 3. Identify product Et0° + Ph — CH, - Cl—> A) pie No) pie Ng (0) 0H, = CH, ©) pyp-ON 4 Which of the following is an appropriate sets of reactant for the preparation of 1-methoxy-4-Nitrobenzene : Na (A) +CH,ONa (8) +(CH,Br NO, ONa ONa () +CH,Br (0) + EtONa Noy Noy10. 11 12. Suitable combination of reactant to prepare aa . ONa Na + By pro @ A ra K Prr (©) pyr KOE) py Ne NOE CH, HTT OK ee product H——ChH, et Correct stereochemical relationship between reactant and product will be (A) Enantiomer (B) Diastereomer (C) Structural isomer (D) None of these Which of the following can't be prepared by willamson ether synthesis AAALN 8) No Incorrect statement regarding williamson ether synthesis is (A) Less hindered halide is used in this reaction (B) Less hindered alkoxide ion is used in this reaction (C) Mechanism of reaction will be SN, (D) More hindered halide is used in this reation Which of the following ether is not synthesied by willamson ether synthesis (A) (oom (e) (ox ork (2) (Opt ROPNa®+R'-L} —* ROR’ + NAP Rate of reaction wil maximum when L is. (A) CF,SO,> (TRIFLATE ION) (B) oar{O rset (p-Tolvene sulphonate) (Br (o)r Identify the products aektL Wg, Boke Ik B The best combination for the preparation of ether by Williamson's synthesis are (A) (CH,), Brand CHO Na (B) (CH,),C Brand CH,OH (C) CH, Brand (CH,), CONa (D) CH, Brand (CH,),C OHWrite the product of the given reactions ? R-oH Poh, cH,-0-cH, Poh Oo OCH, ggg “O! 1H Pent-t-yn-3-ol _ PBI, Product 'P’ is (A)Inverted Product (B) Racemic (C) Retention Product (D) Meso cH, CH, ~ CH = CH, —* CH, - CH-CH, CH, -CH-CH, (CH, —-CH= CH—CH, » CH, -CHO How do you account for the formation of ethane during chlorination of methane? Why is Wurtz reaction not preferred for the preparation of alkanes containing odd number of carbon atoms? Illustrate your answer by taking one example.Analkene ‘A on ozonolysis gives a mixture of ethanal and pentan-3-one. Write the structure and IUPAC name of ‘A An alkene ‘A contains three C—C, eight C—H c bond and one C—C a-bond, ‘A’ on ozonolysis gives two moles of an aldehyde of molar mass 44 a.m.u. Write the IUPAC name of ‘A. Find the value of (X+¥) ? (including stereo) Y= Number of isomer separated by fractional distillation How many of the following ozonolysis reactions would give the product(s) drawn ? 9 (0, H (2)Zn,AcOH ° Oo (1) 0, an (2) Zn,AcOH (1) 0, Hy pe (zn AcOH Ht H H ° @ H Cr er Oo (yo, (2)zn,AcOH” ey (10, °. > (2)2nAc0H Avyk (1) 0, (2) Zn,AcOH Reg 1.0, Soe 2. ZniHOAG $eIdentify the missing structure in each reaction ? e e HO", (ay HES mosorheimor complexKNH, liq.NH (8) (major) Energy profile diagram of given reaction is Most reactive towards SN-Ar Br jr NO, (A) (8) (c) NO, NO, Steps involve in given reaction FE H ° O . No, No, (A)Addition-substitution (B)Addition-Elimination (C)Elimination-Adaition (0) Substitution-elimination Most reactive towards SN-Ar is No, No,(A) SN, (Substitution nucleophilic unimolecular) TOTAL PRODUCTS | Compound me Excluding Stereo isomer Tneluding Stereo TsomerCompound Structure of Product (After reaction with dilute H,0*)SNo.| Compound Structure of Product Structure of Product (When react with cone. HI) (When react with conc. HT excess) 1. ot 2 |—o— 0. 3. | ph cn, an ai 0. 5. | pn pn 6. | PhoH on — 8. | CH,—CH,—OH 9. ° oY 10. rh : 0 fae Ph 12, | py So Co iii 15. 0.Which of the following ether can not react with Hi? ©. °. o 7 (a) Ph-OCH, (8) py Opy7-r0 0) OH McQ 2. Identify the compoundis consume even no. of moles of Hl a oxor.cx,oo4<_) (8) QO 0 (C. (D) () OO oXScr, Match the Column OCH, 3 A) (CL (P) 2moles of HI consumed ‘OCH, 0. 2) (CL ) (Q) 3moles of HI consumed ‘0’ Et-O-Et (R) Odd no. of moles of HI consumed (Cc) (0) €S-cro_ {S) Even no. of moles of HI consumedQuestion numbers 4 to 7 are short answer questions and carry 2 marks each. 4. (i) ti) (iy Howare the following conversions carried out e-o™ CH, -Cl—> Br I H.C = CH, —* FH= CH, Br Write IUPAC names of the products obtained by the ozonolysis of the following compounds. () Pent-2-ene (i) 3,4-Dimethyihept-3-ene (ii) 2-Ethylbut-1-ene (¥) 1-Phenylbut-1-ene. Arrange the following set of compounds in order of their decreasing relative reactivity with an electrophile, E* ( Chlorobenzene, 2, 4-dinitrochlorobenzene, p-nitrochlorobenzene (i) Toluene, p-H,C—C,H,—NO,, p-O,N—C,H,—NO,, Draw the cis and trans structures of hex-2-ene, Which isomer will have higher b.p. and why?10. 11. 12. 13. Identify the product(s) of the given reactions. CH,CH,CH,OH + Hl —S+ OH CH,CH,CH,CH,OH + PBr, a> Prine GH,PHCH.CH,OH See CH, CHACHCH,CH,OH —1:2#2tsnesuifony! chide 2 € po CH, CH, CH.CH,POH + Hcl —+ CH, 2enetyt2-buanet CH, CH,CCH,CH, + HBr ——> OH CHyGHCH.CH, + HBr A> OH OH si OH ay () ROH + HBr —*-> (i) ROH + HI Ay (iv) ROH + PBr, saan (¥) ROH + PCI, sans Sow, _ 1302, we He, Sn, 0! > (ii) ROH + HCI (vi) ROH + SOC, a Prisfbenz0-1,4-dioxane (dioxin) CH,CH, —O — CH, -excessHI, a 4g choc, cH,ch, HH, a+ HA, ¢ ChyeHeH,OCH, +H 4s a+p HlA,o CH, €Y—croct.crcn, Hh arate Ph—OH +Et—Br 04 (aq) —22et_B)+(C) [—O-CH, '—o-CH, on —CH,— CH, + His —> CH, CHFOCH.CH, +HBr cH, Give the major products that would be obtained from heating each of the following ethers with concentrated HI CH, (a) CH,CH = CHOCH,CH, (b) O10 CY (c) cneHLcHooH,Ch, cH, OCH, “oo oles ‘O" CH,