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    HALOALKANES AND HALOARENES BASIC CONCEPTS 1, Haloatisanes or alkyl halides are the compounds which have the general formula RX, where R isan alkyl ‘or substituted alkyl group and X is a halogen (F, Cl, Br. 1) Likewise, haloarenes or aryl halides are the ‘compounds containing halogens attached directly to an aromatic ring, They have the general fornmula ArX (where Ar is phonyl, of substirated pheny!) REX Ar—x An alkyl hal Anat! halide (Haloalkane) (Haloarene) R= Alkyl or substituted alkyl henyl or substituted phenyl X=F,CLBrI P.CIBret Classification: (@) Classification based on the number of halogen atoms: These may be classified as mono, di, ot polyhalogen compounds depending on whether they contain one, to or more halogen atoms in their structures. For example, CH)X Wu a CoHsX | CHX ie |] Gece Co om dc : Fale eee Dihalogen compounds may be further classified as discussed below: © Gem-dihalides: ‘The two halogen atoms ate attached ro the same earbon atom in gem-dihalides, — on uy ee ae © Vic-dihalides: In these compounds, the two halogen atoms are attached to adjacent carbon atoms. For example, i. c-cH,—c,—c1 cH —CH—cH,—ct Biya alete Tomine ie 12" Debiometme) (2 Deaememy) 74 | Chemistry-Xll: Term-1 (6) Classification based on hybridisation of carbon atom: (@ Halogen compounds in which halogen is bondled to sp" hybridised earbon, This class includes: (u) Haloalkanes or alkyl halides: They are the halogen compouncls of saturated hydrocarbon, Their general formula is C,H, ..X. They are further classified as primary haloalkane. secondary haloalkane or tertiary haloalkane according to whether the halogen atom is bonded to primary, secondary or tertiary carbon atom, i i t amas Rik no H H R Prima aaa Sony natane Teniy thane If in R—X, R is an alieyelic, ie, eyelic aliphatic hydrocarbons such as cyclopropane, cyclobutane, eyclopentane, ete, they are known as halocyeloalkane or eyeloalkythalide. For example, x 1 oa Hy He cH_X nC hh cx ini Tea HC CH; HC — CH, steyelpopane Heyeabwane “Hosoi (B) Allylic halides: In these compourds, halogen is bonded to allylic carbon, ‘e., to the sp* hybridised carbon aiom nex! to a carbon-carbon double bond. Examples are: CH.-CH- CH, x lly lide (G-ttlo--propene) SHalosyelobes: (©) Benzylic halides: In these halides, the halogen atom is bonded to an sp" hybridised carbon ‘alom next to an aromaliv ring, £e., to a benzylic carbon, For example, a ool Bent Diatkybenzyliaide Benzylic halides may be primary, secondary or tertiary. ii) Halogen compounds in which halogen is bonded to sp* or sp hybridised carbon. (a) Vinylic halides: In these halides, halogen is bonded to one of the carbon atoms of a vinylic carbon, j¢., carbon-carbon double bond which is sp" hybridised. The examples are x cnscn—x r Vinyl halide 1-Haloeyelobex-1-ene (©) Aryl halidey: In these halides, the halogen atom is directly bonded to carbon atom of aromatic ring. These are called haloarene or aryl halides, ey. halobenzene. Co Halobenzene Haloalkanes and Haloarenes | 75 2. Chemical Properties of Haloalkanes ‘The chemical reactions of haloalkanes can be divided into following types: (a) Nucleophilie substitution reactions (0) Dehydrohalogenation or B-elimination reactions (©) Reaetion with metals (a) Nucleophilic substitution reactions: When an atom or group of aioms is replaced by a nucleophile, the reaction is called nucleophilic substitution reaction, In haloalkanes, the halogen atom is attached to the carbon atom. As the halogen atom is more electronegative than carbon, the bond between carbon and halogen is polar in character a >c—x Duicto the presence of patil positive charge on the carbon stom, the nucleophiles ean attack on electron dtcien carbon thereby resulting in the displacement of weaker nucleophile, the halide fon, eB ° 8 SCX + 7% — dpor+ x ‘ubsuate ——_Nucleophile Product Leaving up Nucleophilic Substitution of Alkyl halides (RX) —Kolted) ROH + KX Aleohol shor ROR! + MAK Ether Ke) RON + KX ‘Al cyanide [+ACN RNC + Agx “iy neice RX tO: RO NO + KX Ahi Alkyl mtte | +N. R NO, + ABX 9 | won, R-C_o-® + Aax Ester Liat pM RONH; + HX et ROSH + NaX Thicalcobl LERCH. RCHCH + NaX Higher alkyne (0) Elimination reaetions: When halvalkane with PHhydrogen atom is heated with ethanolie potassium hydroxide, thore is elimination of hydrogen atom from B-carbon atom andl halogen atom from a-carbon, atom. As a result, an alkene is formed, Since fi-hydrogen atom is involved in elimination, it is often called -climination reaction, CHy—CH)—CI + KOH(wle) —4~ CH, = CH; + KCL + 1,0 76 | Chemistry-XIl: Term-1 i H s Serre tS ee, + HOF cr jp SERCH Clly—CHCH—Clly + Cll —CH—CH= CH, toe hte aia conan (c) Reaction with metals (9 Reaction with magne see a "tide CH,—CH.—Br + Me 2°". CH, —CH,—MgBr ‘Ag mast oe (Gi Reaction with sodiuun (Wurts reaction) R tana xpeR PR RoR 1 ONGX CH;—CH.—[cl + 2Na_+ Cl|—cH,—cH,; 2" CH,—CH,—CH,—CH, + 2NaC1 yale wine 3. Preparation of Haloarenes (a) By direct halogenation of benzene O°» 2+ Or+» ee Oo + —m o + HL a aro oddone (X-CLBn (0) From diazonium salts =NcT NaNOs + HCL “Hak Bexzone azo clei NHy coc Custer ae ich ol eee ae #4 1+ KCI +N, Geant lie xan Sandmeyer’s reactions 4. Physical Properties of Haloarenes (a) Melting and boiling points: Boiling point of isomeric dihalobenzenes are very nearly same. However p-somer have higher melting point as compared (o their ortho and meta-isomers. [ts due to symmetry of pars-isomers that fits in crystal lattice better as compared to ortho and meta isomers. Haloalkanes and Haloarenes | 77 (6) Nature of CX bond: The C—X bond is polar as *X’ is more electronegative than carbon, The carbon haas partial positive charge whereas halogen has slight negative charge because shared pait of electrons. are more towards halogen atoms. ee cx Dipole moment of CH,Cl is higher than CH,F du to greater bond length in CL bond. 5. Chemical Properties of Haloarenes: (a) Nucleophilic substitution reactions of haloarenes Aryl halides are extremely less reactive towards nucleophilic substitution reactions due to the following, reasons: @ Resomance effect: In arylhalides CX bond acquires « partial double bond charweter due «0 resonanee, Asa resuli CX bond eleavage in aryl hahides i difficult than alky! halides and therelore they are less reactive towards nucleophilic substitution reaction. $—3—)-4_3 Canons Resonance hyd structure Difference in hybridisation: X-men Hh Sop tit onton i (iii) Instability of phenyl cation: In ease of haloarenes, the phenyl cation Formed as a result of self ionisation will not be stabilised by resonance and therefore Sy1 mechanism is ruled out (iy Because of the possible repulsion, it is less likely for the electron-rich nucleophile to approach cleetvon-rich areas. ‘However, at high temperature and pressure several nucleophilic suibstision reactions are carried out ‘© Substitution by —OlI group (Dow's process) oO ys 68, Oo om © Substitution by —CN group, cL uc. DME — aa Bena © Substitution by NH, group 1 I, nih, OTK ae Aniline 78 | Chemistry-XIl: Term-1 (b) Reactions with metals a CChlrabenzene Chevabenzene © 200 “TU esc Tinton Diptem? 2 NacHy cL git (O)—cris Toten =n , Fiber MgCl ‘Phy magnesium cherie (c) Electrophilic substitution reactions of haloarenes =i 65 Due to resonance, the electron density inereases more at ortho and para positions than at meta positions, ‘Therefore, electrophilic Chovabenzene substitution reactions take place at ortho and para positions. Chany ech << ed pPiitecenene eee [_mvoxfom< t,S0ucone) - oe a -Chlronitobevene (Oiejr poset) —ae— 6. d~ _>-Chiorsbenzenetlponi aid (Bajo poder) apes (Alkyl H; ut pee pChloroaeetopenone (Majer pret) Haloalkanes and Haloarenes | 79 6. Mechanism of Nucleophilic Substitution in Alkyl Halides ‘The nucleophilic substitution reactions in alkyl halides can take place by either of two mechanisms: Syl and Sy2 Substitution nucleophilic unimolecular (Sy1) It takes place in two steps and the reaction is of first order, In the first step, alky! halide undergoes slow heterolysis to produce carbonium ion (an intermediate) and a halide ion, In the second step, nucleophile rapidly combines with the carbonium ion to complete the Substitution resetion, Step 1: 1x Caoninn ion ‘caer R Re RS , Se Step 2: —- Ee Syl reactions of optically active hulides are accompanied by racemisalion, This is because the carbonium formed in the slow step being sp* hybridised is planar (achiral) therefore, the attack of nucleophile on it ean ‘occur from both the faces with equal ease giving a mixture containing two enantiomers in equal amounts, ‘This may be illusirated by hydrolysis of optically active 2-bromobutane, which gives (+) butan-2-ol. He 0 Hu oi on EE | fe Foi C een Geeta) us HCH, Nici, “cuch, CH Substitution nucleophilic bimolecular (Sy2) It takes place in one step and the reaction is of second order. In this process the nucleophile attacks the ‘pattally positive carbon of the CX bond of the substrate, alky! halide, from the back side of the C—X bond and the leaving group, X-, departs simultaneously, A a i He HL i “Transition state. H ‘S\2 reactions of optically active halides are accompanied by inversion of configuration. This is because the attack of nucleophile occurs trom a direction opposite to the one trom where the halogen atom leaves. ‘The order of reactivity of alkyl halides towards Sy1 and Sy2 reactions is as follows $y sactivity increases i ciiye ROK RK RO k © 2 reactivity increases 80 | Chemistry-XIl: Term-1 ‘An alkyl group at the a-carbon, being bigger in size than H atom, tends to block the approach of the ‘nucleophile to carbon due to steric hindrance in x2 mechanism and makes the reaction difficult to oceur. In the Syl mechanism, a carbocation is formed in the first, slow step. The more stable the carbocation, ‘more easily is the product formed, Tertiary alkyl halides undergo Sw reaction very fast beeause of the high, stability of tertiary carbocation, Pi Fei REM SOR R Primaay allylic and benzylic halides show higher reactivity in $1 reactions than other primary halides. This is due fo stabilisation of allylic and benzylic cazbocation intermediates by resonance. 3 8 cufon én, «+> Gn, cucu, Reseamee in ally cubocaian bef 8-3 Resonance sailstion inher carbocation ‘Thus, primary alkyl halides almost always react predominantly by S,2 mechanism. ‘Tertiary alkyl halides react predominantly by Syl mechanism, Secondary alkyl halides may react by both the mechanisms without such preference. Polar solvents favour Sq1 and non-polar solvents favour S42 reactions, 7. Important Name Reactions (a) Sandmeyer’s Reaction: Benzene diazonium chloride is converted to chlorobenzen with CuCVHCI, CuBr/HBr and CuCN/KCN, respectively. Neer 1 oO ene +N; Benzene horsbeazene gona clogs Sere bromobenzene, eyanobenzene on treatment Br ©o +N: Browobeazeve Cymotenrene (6) Finkelstein Reaction: Chloroalkanes or bromoalkanes are converted into corresponding iodoalkanes by creating with sodium iodide dissolved in acetone CHCH,CI + Nal 2". CH SCH I + NaCl Tl le win ake CHCH,Br + Nal 2". CH,CHaI + NaBr (c) Wurtz Reaction: Alkyl halides react with metallic sodium inthe presence of dry ether to form alkanes. ‘This reaction is used for the preparation of higher alkanes. For example, CH;Br + 2Na + Br—CH; —\~ CH,CH; + 2NaBr Maloalkanes and Haloarenes | 81 cH or CH CH, (CH)—CH—Br + 2Na + Br—CH—CH, "CH, —CH—CH—CH, + 2NaBr ‘Wurtz reaction is only useful for the preparation of alkanes containing even number of carbon atoms and. not for the alkanes containing odd mumber of earbon atoms. (@) Wurtz-Fittig Reaction: Aryl halides when treated with alkyl halide and sodium in dry ether give alkylbenzenes. Oper mes cen, BH Gory + 204 (0) Fittig’s Reaction: In this reaction two molecules of haloarene combine with metallic sodium in the presence of dry ether to give diphenyl or biphenyl. Opa +m +0-@) =~ OHO) +0 (P) Friedel-Crafts Alkylation: Benzene and other aromatic compounds react with silky] halides in the presence of anhydrous AICI; to fori alkyl benzene. “iy © + ane + uel enzene Tobe Hy Hs He emer ei CUy Sara Tolvene eae 7 pXplene (g) Dow’s Process: When chlorobenzene is treated with an aqueous solution of NaOH at 623 K, 300 atm pressure sodium phenoxide is formed which on acidification gives phenol : —e G snow 39 G a G (H) Hunsdiecker’s Reaction: Bromoalkanes are obtained by this method by refluxing silver sats of fatty acids with Br, in CCL, R—COOAg + By ct + + 8. Rr + AgBr + C0, CHCH,COOAg + Br; SE CH,CHBr + AgBr + CO, “iets emlayad mens ontareton me (0 Gattermaws Reaction: The teaction of diazonium sats ih “Cu? powder in the presence of corresponding halogen acids is known as Gatterman’s reaction, Onc. Ht Oa sw Orv — 20m Goer 1 a 82 | Chemistry-XIl: Term-1 8. Distinctions between Pairs of Organic Compounds Containing Halogen Silver nitrate test: In this test, the halide is warmed with aqueous or alcoholic KOH. The solution is then acidified with dil, HNO, followed by addition of AgNOs solution, Alkyl, benzyl and ally! hatides give precipitate. Aryl and vinyl halides do not give precipitate, ‘It may be noted that the precipitate formed should be insokable in TINO. MULTIPLE CHOICE QUESTIONS Choose and write the correct option in the following questions. 1. Which of the following is vim Br 1) } © xr @ ues (@) CHyCH=CHCI 2. The position of Br in the compound in CH,CH=CHC(Br)(CH,), can be classified as INCERT Exemplar (@) Ally () Ary (© Vinyl (d) Secondary 3. Which of the following is an example of vie-dihalide? [NCERT Exemplar (@) Dichloromethane —() 1,2-dichloroethane (©) Ethylidene chloride(d) Allyl chloride 4, Ethylidene chloride is a/an, 4 [NCERT Exemplar] (0) viewdihalide (0) gem-dihai (© allylic halide (2) vinylic halide 5. Which is the correct IUPAG name for er alae ? INCERT Exemplar] GH (0) 1-Bromo-2-cthylpropane (6) 1-Bromo-2-ethyl2-methylethane (©) 1-Bromo-2-methylbutane (@) 2Methyl-1-bromobutane 6. ‘The IUPAC name of the compound ist cH, (@) 4-Auore-I-methyl-3-nitrobenzene © 1-fluoro-t-methyl-2-nitrobenzene (©) 2huore-5-methyl-L-nitrobenzene (@) 4-methyl-L-Alyoro-2-nitrobenzene 2 de from aleohol? (a) Pel, 8, Arrange the following compounds in the increasing order of their densities. [NCERT Exemplar O 9B HO, OL O ch ‘cL (@) @ < (i) < (i) < @) () @ < Wii) < (iv) < Gi) ©) @)< @)<@<@ (d) @@) < @) < @) <@O Haloalkanes and Haloarenes | 83 9. Arrange the following compounds in increasing order of their boiling points. INCERT Exemplar] cH, cn, | 0 cng CRE GREER [ay RiG cr Br @ @B>OQ HO C>B>A OB >A>O Wid>C)>(B) ying molecules carbon atom marked with asterisk (*) is asymmetric? " p i i INCERT Exemplar} Ata a Son San ‘ 2G. Se Ga o co) ii (i) (0) Gi, Gi, ») Wat. Git) © Gi. i, o) (A) De td, Go) 15. Which of the following structures is enantiomeric with the molecule (A) given below: INGERT Exemplar] fa) r (dy tr Cols oH we ne HsGy i Nap Wen, 16. Iwo possible stereorstructure of Clly—CI(OH)COOL which are optically active are called @) mesomers (® enantiomers (©) diastereomers _(d) atropisomers 84 | Chemistry—Xll: Term-1 17. 18, 19. 20. a1. 22. 23. 24. 25. 26. a 29. 30, 31. 32, 38. 34, 35. Alkyl! halides undergoing nucleophilic bimolecular substitution involve {@) retention of configuea (&) racemic mixture (©) inversion of configuration (@ formation of carbocation Which of the following alkyl halides will undergo Sy1 reaction most readily? [VCERT Exemplar] (@) (CHy)C—F © (CHy),c—CL (© (CH)sC—Br (a) (CH yy For the following (i) 1°, (i?) CI°, (ii) Br®, the increasing order of nucleophilicity would be: (@) ‘Toluene reacts a halogen in the presence of iron (III) chloride giving ortho and para halo compounds. The reaction is Z INCERY Exemplar] (a) Electrophitic elimination reaction (b) Electrophilic substitution reaction (6) Free radical addition reaction (@ Nucleophilic substitution reaction Among the following compounds, which one will have a zero dipole moment? @) 1, L-Dichloro ethylene (6) cis, 2-Dichloroethylene (© trans-1, 2-dichloroethylene (@) None of these compounds Which of the following will have least hindered rotation about carbon-carbon bond? (@) ethane (@ ethylene (© acetylene (d) hexachloroethane “The number of structural and configurational isomers ofa bromo compound C,HyBe formed by the addition of HBr to pent-2-yne respectively are @) Land 2 () Qand 4 (©) dand 2 (4) 2and 1 ‘The Cl—C—GI angle in I, I, 2, 2-tetrachloroethene and tetrachloromethane will be about (a) 120° and 109:5° (6) 90° and 109:5° (©) 109-5° and 90° (d) 109-5° and 120° ‘The C—HI bond distance is Longest in (a) Colle (b) Coll, © Cs (2) CoHBr, Chlorination of toluene in presence of sunlight and h Naot and followed by treatment with aqu (@) o-cresol (©) pcresol (©) 2, 4-dihydroxytoluene (@ benaoie acid 1-chlorobutane on reaction with alcoholic potash gives @) but-l-ene (6) butan-L-ol (© bur2-ene (@) butan-2-o1 In the addition of HBr to propenc in the absence of peroxides, the first step involves the addition of @u ©) Br ir @) Br ‘When HCI gas is treated with propene in presence of benzoyl peroxide, it gives (@) 2chloropropane (6) allyl chloride (©) no reaction (d) n-propyl chloride Geometrical isomerism is shown by @) CH, =C(Brl — ) CH,CH = C Brit (© (CH,), C = C (Br) @) CHJCH = CCl, Toluene reacts with chlorine in presence of sunlight to give (@) benzylehloride —(b) benzoyl chloride (¢) p-chlorotelu ‘The compound which reacts with HBr obeying Markownikov's rule is © (d) o-chlorotoluene (@) CH, = C1 (©) frans-but--ene (a) (CH), © = CHy Silver benzoate reacts with bromine to give (@) CoH () GoH;COOBr (©) m-Br-CgHyCOOAg (7) CoH5Be ‘The reaction involved in the formation of fluoromethane from methyl bromide in presence of silver Muoride is called (@) Swarts reaction _(b) Finkelstein reaction (c) Sandmeyer reaction(d) Wurtz reaction ‘The intermediate during the addition of HGI (© propene in presence of peroxide is (@) CHJCHCH,Cl — (b) CH,CHCH, (© CHjCH,CH, — (d) CH,CH,CH, Aaloalkanes and Haloarenes | 85 36. 37. 38. 39, 40. a. 42, 43. 44. 45. 41. 48, 49. 86 ‘The number of possible enantiomeric pairs that can be produced during monochlorination of 2-methylbutane is @?2 Oy 4 at During debromination of meso-dibromobutane, the major compound formed is (@) n-butane () but-l-ene © csbur2ene (a) frans-but-2-ene (CH,),CMgBr on reaction with D,O produces (@) (CHy)yCD () (CHy)sCOD (© (€Ds,CD (@) (€D,CoD The re CHYCH), - _ACH,)CHy Hr HO cH cH, is described as (a) S,2 reaction ——_() Syl reaction (©) Sy2reaction —_(@) $x reaction ‘The alkyl halide is converted into alcohol by (@) addition © substivution ©) dehydvohalogenation (@ elimination “The replacement of chlorine af chlorahenzene to give phenol requires drastic conditions but chlorine of 2, 4-dinitrochlorobenzene is rea (a) NOs makes the ring electron rich at o-and p. (6) NOg withelraws electrons from the m-position. (6) NOg donates electrons at n-position, (@) NO, withdraws electrons from o-and p-positions, replaced since Aromatic hydrocarbons show mostly (a) electrophilic addition (&) nucleophilic addition (6) electrophilic substitution (@) nucleophilic substitution C,H, + Cl, C,H, Cl+ HCL isan example of (@) substitution (6) elimination (©) addition (@ rearrangement reaction A solution of (+)-2-chloro-2-phenylethane in toluene racemises slowly in the presence of small amount of SbCl, due to the formation of @) carbanion () carbene (6) fee radical (@) carbocation ‘Which of the following is a best example of Sy2 reaction? @) CHybr + OH —+ CH,OH + Br (@) (CH)_yCHBr + OLE —+ (CHy)yCHOU + Br” (© CH,CH,OH "2 C1 (@) (CH)sC—Br + OH” — (CHy),C—O + Be Which of the following possesses highest melting point? Hy (@) chlorobenzene —_(b) o-Dichlorobenzene _(c) m-Dichlorobenzene (@) p-Dichlorabenzene Which of the following will not give iodoform test? (@) ethanol () ethanal (© isopropyl alcohol (a) benzyl alcohol In Friedel-Crafi alkylation besides AICI, other reactants are (a) CoHy + NH, () CoH, + CH (©) GoHy + CHjCl (a) CoH, + CH,COCI ‘The addition of HBr is easiest with (@) CH, = CHCl () CICH = CHCl (©) CHJCH = CH, (a) (CH)gC = CH, Chemistry—XIl: Term-1 53. 55. 37. 58. 59. 61. 62. Which among MeX, RCH,X, R,CHX, R,CX is most reactive towards Sy reaction? (@) MeX (@) RCH.X (©) R,GHX (a) RJCX Which of the following has highest nucleop! @r @) OF (@) NIL ‘The order of reactivity of the following alkyl halides for Sy2 reaction is (a) RF > RCL> RBr > RI (® RE > RBr > RCL> RI (©) RCL> RBr > RF > RL (@) RL > RBr > RCL> RF ‘The decreasing order of reactivity of the following compound towards electrophilic substitution is 9 cH, och CRs 1 1 m Vv @ML>1>U>1V ®IV>1>U>I @1>U>U1>1V @>1>U1>1V 1, 2-Dibromopropane on treatment with 2x moles of NaNHy followed by treatment with ethyl bromide gives a pent-2-yne, The value of x @ one &) wo © thee (a) four set, Fe |g _ zane GH, a ‘The compound Gis (@) ebromoroluene (© m-bromotoluene (© pdromotoluene @ S-bromo-2, 4, 6trichlorotoluene ‘Two isomeric alkenes A and B having molecular formula CsH,Cl on adding hydrogen, A gives optically inactive compound while B gives a chiral compound. The two isomers are (@) Ais 3-chloro-pent-L-ene and B is (6) Ais 4-chloro-pent (© Ais S-chlore-pent (@) Ais L-chloro-pent- When chlorine is passed through propane in presence of sunlight which of the following products is/are formed? (a) PVE (6) 2chloropropane _(c) I-chloropropane (4) Both (6) and (c) ‘The number of stereoisomers of the compound 2-chloro-4-methylhex-2-ene ivare @t we o4 (@ 16 Which of the following is an example arylalkyl halide? (@) Benzyl chloride () Allyl ctiloride (© Chiorobenzene —_(@) p-chlorotoluene ‘The product (A) formed in the given reaction is, as Neat Of +r (@) Diphenyl () Benzene (© Todobenzene ——_(d) Toluene Jodoform on heating with KOI gives (@) CHYCHO (6) CHjCOOK (© HCOOK (@ CHO Hydrolysis of 1,1-dichloroethane gives (@) CH,CH,OHL () CHCl, (© CH,CooH (@) CH.CHO Chloroform on reaction with zine and HCI gives (o) formic acid (6) chloropicrin (© methylene chloride (@) phosgene Heloalkanes and Haloarenes | 87 64. CH,CH,CIICICH, obtained by chlorination of n-butane will be (a) meso form (b) racemic form © @form (@) Lform 65. An organic compound on treatment with Br, in CCI, gives bromoderivative of an alkene, The compound will be (@) CH,CH =CH, (6) CH,CH = CHCH, (©) HC=CH (@) CH, = CH, 66. ‘The reaction of alkyl halide with RCOOAg produces (a) esters (0) ethers (© aldehydes (d) ketones. 67. ‘The addition of propene with HOCI proceeds via the addition of (a) 11 in the first step (©) Ql’ in the first step (©) OH in the first step (@ Cl and OH ina single step 68, An Sy2 reaction at an asymmetric carbon of a compound always gives (@) anenantiomer of the substrate (6) a product with same optical rotation (©) a mixture of diastereomers (a single stereoisomer 69, The number of isomers for the compound with molecular formula C,BrCIFT is, @s oa wos @s6 70. In the presence of peroxide, hydrogen chloride and hydrogen iodide do not give anti- Markownikov's addition to alkenes because (a) both are highly ionic. (6) one is oxidising and the other is reducing. (6) one of the step is endothermic in both the cases. (d) all the steps are exothermic in both the reactions, 71. Identify the set of reagent/reaction conditions *X" and *Y* in the following set of transformations: CH, CH, CH, *— Product A. PRR, Br (a) X= dil. ag, NAOH, 20°C: ¥ = HBriacetic acid, 20°C (6) X = cone. ale. NaOH, 80°C; ¥ = HBr/acctic acid, 20°C dil. aq. NAOH, 20°C; Y = Bra!CHCh, °C lc. NOH, 80°C: Y = BrylCHCl, 0°C 2 ides for dehydrohalogenation is (@) RF > RCI> RBr> RI ( RI> RBr > RCL > RF (o RI> RCL > RBr > RI (@) RF > RI> RBr > RCL 73. Which of the following is known as Sandmeyer Reaction? (@) CoHg + CHCl “=~ ©, Hy CHy () GyHyOH 2 CyH;(OH)COOH (© CoHsNFCr SEE. CHC + Net (@) ZHCHO —+ CHJOH + HCOONa 74. mpropyl chloride on reaction with aqueous KOH gives @) propanol (@) propanal (©) propane (@) propene 73. Which of the following is « free radical substivution rea te. =, a Anhydrous ‘CH © O+ ara 0 OO + as, — GF @ CH,CHO + HCN — CH,CH(OH)CN 88 | Chemistry-XIl: Term-1 jont 76. Which of the following are arranged in the decreasing order of dipole moment? (@) CHC, CHsBr, CHF © CH,CL, CHF, CH,Br (©) CHBs, CHL CHF (@) CHBr, CHF, CHCl 77. Which of the following reaction involves both aryl and alkyl halide? (o) Wurtz reaction (© Wurtz ftig reaction (©) Sandmeyer reaction (@ Friedal-Crafis reaction 78. Which of the following compounds is not formed when a mixture of methyl bromide and ethyl bromide is treated with sodium metal in the presence of dry ether? @) butane (0) ethane (© propane (@) methane 79. C-Cl bond of chlorobenzene in comparison to C-Cl bond in methyl chloride is (@) Longer and weaker (&) Shorter and weaker (© Shorter and stronger (@) Longer and stronger 80. Which of the following undergoes nucleophilic substitution exclusively by Sy1 mechanism? (a) Benzyl Chloride (6) Ethylchlotide (@) Chlorobenzene _(d) Isopropyl chloride 81. A Grignard reagent may be made by reacting magnesium with (@) Methylamine (2) Diethyl ether (©) Ethyl iodide (@) Ethyl alcohol 82, The conversion of an alkyl halide into an alcohol by aqueous NaOH is classified as IGBSE 2020 (56/3/1)| (a) A dehydrohalogenation reaction (®) A substitution reaction (©) An addition reaction (d) A dehydration reaction 83. Fitting reaction can be used to prepare (a) Toluene (b) Acetophenone (c) Diphenyl (a) Chlorobenzene 84, Identify the end product (c) is the following sequenc GH; OH 2S a) KES (Hy 208 (ey (@) GJHjCHyNHy (6) CgHyCONHy (d) CyHyNHy + HCOOH, 85. CHACH,CH,CL 4, gp HPL, ¢ eee, In the above reaction, the product D is (@) Propane (©) 2,3-Dimethylbutane(c) Hexane (@ Allyl bromide & CH—CHy + HBr > A; "A is (@) CHy—C—CH,—CH, @) CH,—CH—CH—cH, Hy eH (©) CH.—GH—CHe—CHSBr (@) BrCHt—GH—CHy—CH, CHy cH; 87. Which of the following alcohols will yield the correspon: concentrated HCl at room temperature? (@) CH,CH,—CH,—OH © CHCH—HOOH ny gh © CHCH—EH—CHLOH @ cucn.——on CHs Hy Haloalkanes and Haloarenes | 89 88. Identify the compound Y in the following reaction. NH: Aci NaNO, + HC Cayce aa Ont + Naf 1 @) oo oO © o @ G a 1 89. Which of the following is halogen exchange reaction? (o) RX + Nal —> RE + NaX ©) Soacl + HX—> Dee x © R-OH + HX 2, Cg COO 90. Which reagent will you use for the following reaction? RUX + H,O CH,CH,CH,CH, —- CH,CH,CH,CH, Cl + CH,CH,CHCICH, (@) ClyUV light () NaGl + HyS0, (6) Gly gas in dark, (@ Gly gas in the presence of ino 91. The position of -Brin the compound GH,GH = CHG (Br)(CHy)y.can be classified as, ; @) Ally () Aryl (© Vinyl (@) Secondary 92. A primary alkyl halide would prefer to undergo a (d) Racemtisation (a) Sxl reaction (b) Sx2 reaction (© eB 93, ‘The correct IUPAC name for diethyl bromomethane is (@) 1-Bromo-1,1-diethoxyethrane ( 3-Bromopentane (¢) 1-Bromo-I-ethylpropane (@ 1-Bromopentane Wi, Rizwan cRNA ni We aqua ode layelvciats Wallace, : @syleutanks (@) Sy2 mechanism (©) Any of the above two depending upon the emperature of reaction (d) Saytecf¥ rule 85. Which of the carbon atoms present inthe molecule given below are asymmetric? HO, Pie az ok, fbn @abed ®be ad Wade of the following compounds will give racemic mixture on nucleophil substitution by a (@ CH.—CH—Br Gi) CH, —C—CIy ii) CHC Br CoHy Hy Coy @@ (8), Gi, Giiy ©) Gi, tii) @) ©, Gi) 90 | Chemistry-Xll: Term-1 97. 98, 100. 101. 102, 103, 104, 105. Arrange the following in increasing order of rate of reaction towards nucleophilic substitution reaction. as a a so, OC wr OL 0, HO > Br” > Cl- > F>. Therefore, in four halides with the same alkyl and clifferent halogens, the order of substitution veaction rate is RE'> RBr > RCL> RF. In the leaving group is very easy to leave, many carbocation intermediates are gencrated in the reaction and the reaction hasecl on Sy1 mechanism. If the leaving group is not easy to leave, the reaction is based om Sy2 ‘mechanism. Influences of solvent polarity: In Syl reaction, the polarity of the system increases from the reactant to the transition state, because polar solvent has a greater stabilizing effect on the cransition state dian the reactant, thereby reduce activation energy and accelerate the rea In Sx2 reaction, the polarity of the system generally does not change from the reactant to the Dieloalkanes and Haloarenes | 93 transition state and only charge dispersion occurs. At this time, polar solvent has a great stabilizing effect on Nu than the transition state, thereby increasing activation energy and slow down the reaction rate. For example, the decomposition rate (S,1) of tertiay ehlorobutane in 25°C water (dielectric constant 79) is 300000 times faster than in ethanol (dielectric constant 24). The reaction rate (8,2) of 2-bromopropane and NaOH in ethanol containing 40% water is twice slower than in absolute ethanol. Ia a word, the level of solvent polarity has influence ou both Sy1 and Sy? reactions, but with different results. ‘enerally speaking, weak polar solvent is favourable for Sy2 reaction, while strong polar solvent is favourable for Sy1 reaction, bee of polar solvent can halogenated hydrocarbon dissociate into carbocation andl halogen ion and solvents with a strong polarity is favourable for solvation of carbocation, increasing its stability Generally speaking, the substitution reaction of tertiary haloalkane is based on Syl mechanism in solvents with a strong polarity (for example, ethanol containing water) (Ding, ¥. (2013). A Brief Discussion on Nucleophitic Substitution Reaction on Saturated Carbon Atom. In Applied Mechanics and Materials (Vol. 312, pp. 433-437). Trans Tech Publications Ltd.) wse only under the action The following questions are multiple choice questions. Choose the most appropriate answer: (@) Sy1 mechanism is favoured in which of the following solvents: G@) benzene (6) carbon tetrachloride (©) aceticacid (a) carbon disulphide (i) Nucleophilie substitution will be fastest in ease oft (@) 1-Chloro-2,2-dimethylpropane (6) elodo-2,2-dimethylpropane (© L-Bromo-2,2-dimethylpropane @ 1-Fluoro-2,2-dimethylpropane (ii) Syl reaction will be fastest in which of the following solvents? (@) Acetone (dielectric constant 21) (b) Ethanol (dielectric constant 24) (©) Methanol (dielectric constant 92) (@ Chloroform (dielectric constant 3) (iv) Polar solvents make the reaction faster as they: (a) destabilize transition state and decrease the activation energy () destabilize transition state and increase the a tion energy (©) stabilize transition state and increase the activation energy () stabilize transition state and decrease the activation energy (©) Sx1 reaction will be fastest in ease oft (@) L-Chioro-2-methytpropane (© I-Chlorobutane (@ Modobutane 94 oo wo Giy(e) ora) wo 2. Read the passage given below and answer the following questions: “The polarity of C—X bond is responsible for the nucleophilic substitution reactions of alkyl halides which mostly occur by Sy1 and Sx2 mechanisms. The rates of Sy! reaction are governed by the y of intermediate carbocations while that of Sy2 reactions are governed by steric factors. Chirality has a great role in understanding the mechanism of Sy1 and Sx2 reactions. Sy1 reactions ‘of chiral alkyl halides are accompanied by racemisation, Whereas Sy2 reactions are characterised by inversion of configuration. meltcer: WW, & Young, DJ. (1973. Oxidation properties of transition metals. Progress in Solid State Chemistry, 10, 17-54.) (Source: Chemistry—XIl: Term-1 The following questions are multiple choice questions. Choose the most appropriate answer: (@) Ally! halides undergoing nucleophilic bimolecular substitution involve (a) retenti © (id) In the following r n of con ) racemic mixture wersion of configuration (@ formation of carbocation (ii) Which of the following alkyl halides will undergo Sy1 reaction most readily? (@) (CHF) (CH CCL) (CH CBr (a) (CH) tion, ‘A is CH, CH, cl =. +4’ (b) CHsCHyN¢ {e) CHsCH,OH (d) CHyCH,KO give a racen Feit accreted crac cc iba AT ixture of products. The compound is 1) yy TG.) FLY AELY f g gy Br CH cs I (¢) CHy—CHy—CH—C GH CH, (qd) CHyCH, CI # —CH, Br I Br CHs Answers ao wd, Gi) HO ASSERTION-REASON QUESTIONS In the following questions, a statement of assertion followed by a statement of reason is given. Choose the correct answer out of the following choices. Assertion and reason bath are correct statements and reason is correct explanation for assertion. Assertion and reason both are correct statements but reason is not correct explanation for assertion. Assertion is correct statement but reason is wrong statement. Assertion is wrong statement but reason is correct statement. @ oy © (a ie Reason (R) ¢ “Assertion (A) Reason (R) “Assertion (A) Reason (R) + lert-Butyl bromide undergoes Wurtz reaction to give Phosphorus chlorides (tvi and penta) are preferred over thionyl chlovide for the preparation of alkyl chlorides from alcohols. Phosphorus chlorides give pure alkyl halides. Boiling points of alkyl halides decrease in the order ROT > RBr > R-Cl> RF [GRSE 2020 (56/2/1)] Van der Waals forces decrease with increase in the size of halogen atom. KCN CNT is an ambident nucleophile reacts with methyl chloride te give methyl isocyanide -tetramethylbutane. + In Wurtz reaction, alky] halides react with sodium in cry ether to give hydrocarbon Assertion(A) + Reason (R) + the halide, Hydrolysis of ()-2-bromooctane proceeds with inversion of configuration, containing double the number of carbon atoms present This reaction proceeds through the formation of a carbocation. Heloalkanes and Haloarenes | 95 6. Assertion (A) Reason (R) t 3° alkyl halides are most reactive towards Sy! reaction. In Syl reaction, the rate of the reaction depends only on the concentration of alkyl halide. + Presence of a nitro group at ortho or para position increases the reactivity of haloarenes towards nucleophilic substitution. Reason (R) + Nitro group, being an electron withdrawing group decreases the electron density over the benzene ring Nitration of chlorobenzene leads to the formation of m-nitrochlorobenzene, Assertion (A) Reason (R) + —NO» group is a m-directing group. 9. Assertion(A) + It is difficult to replace chlorine by -OH in chlorobenzene in comparison to that in chloroethane, Reason (R) + Chlorine-carbon (G—Cl} bond in chlorobenzene has a partial double bond character due to resonance. 10. Assertion(A) + In monohaloarenes, further electrophilic substitution occurs at ortho and para positions Reason (R) + Halogen atom is a ring deactivator IL, Assertion (A) + Aryl iodides can be prepared by reaction of arenes with iodine in the presence of a oxidising agent Reason (R) + Oxidising agent oxidises Ip into HI. ‘Answers L® 20 3@ 4) B®) 6) Tea) 8.(d) %@ 100) ILO HINTS/SOLUTIONS OF SELECTED MCQS 9. 4. 18. Bm 23. 24. 96 (c) With increase in surface area boiling point increases. () The carbon atom having four different group is called asymmetric carbon atom, (@) The reactivity of the halides are RAI> R-Br>R-Cl>>R-F. Hence, (CHy)sC—I will undergo the reaction most readily. (@) Free rotation around carbon-carbon bond takes place easily in alkanes. Now ethane and hexachlorocthane both are alkanes, but in hexachloroethane bulky chlorine atom is present due to which rotation of C—C hindered, HyC—H,C— 0) CCH, + HBr — H,C—H,C Ho Br « Both (A) and (B) exists as a pair of geometrical isomers. Therefore, there are 2 structural and. 4 configurational isomers. (@) The Cl—C—Cl angle in 1, 1, 2, 2tetrachloroethene (carbon is sp? hybridised) and tetrachloromethane (carbon is sp" hybridised) will be about 120° and 109.5° respectively. Chemistry—XIl: Term-1 26. 27. 29. 30. 32. 33. 35. 36. 37. 7 CHy cc HO—G—OH OOH fF Benasie acl Ak KOM @) H,C—CH,—CH,—cH,—cl 482! H = CH, 1eerbe (@) CHCH=CH,+ HEI CHsGHCHs Propene [re Peroxide effect is not observed with HE, HCland HT] HC. Br @) Only Ye eee will show geometrical isomerism because of presence of two different ‘groups on the same carbon atom, CH, CHy I | @) CHy— CH=CH, + HBr + HyC—HC—CH,Br 2-matintpropene CHy, rum? 1-2-methslpropane (ation | ‘hin All others are symmetrical alkenes. COOnAg* Br Bromobenzene (6) The intermediate formed during the addition of HCI to propene in the presence of peroxicle is CH, CH CH. In case of HCI, peroxide has no effect. Secondary carbocation is formed as it is more stable than primary carbocation, (a) Two enantiomeric pairs can be produced, ie., 1-chloro-2-methylbutane and 2-chloro-S. methylbutane, ‘The given reaction is undergoing substitution 100% inverse of configuration and is a one step reaction. Therefore, it follows $x2 mechanism (substitution nucleophilic bimolecula), ® cH, cB n cls n Nee eae a oo Hoe ma Sh ae | a cmmran CHs (Minor) (Major) Meso-dibromobutane (@) When (CH,),CMgBr reacts with D,O the C—Mg bond donates its electron pair to a deuterism ‘atom, forming (CH), C—D and Mg(OH)Br. This occurs becanse the C that is bonded to Mg is strongly nucleophilic and can attack a 11 of positive charge density such as the deuterium atom in a water molecule. Heloalkanes and Haloarenes | 97 41. 41. 48. 49. 51. 54, 5B. 98 (@) NO, group shows —M effect due to which electrons are withdrawn from ortho and para n reaction and position which makes the berrzene ring more prone to nucleophilic substitu hence replacement of Cl ean be done easily 's. Hence, the charact The more loosely held electrons are open to attack by electrop! 1 of benzene is electrophilic substitution reaction. te (@) Formation of carbocation occurs: + SbCl, — Gath —eH + SbCl; CHy ve easbotsion The order of reactivity of alkyl halide towards Sy2 mechanism follows the order: CH,Br > (CH, CHBr > (CH,)C—Br Thus, reaction (a) isa best example of Sx2 reaction. @p re, $0 it fits closely it has highest melting pois Benzyl alcohol does not have CH;CO” group or CHsCHsO~ group s0 it will not give positive iodoform test o Hs QO ron enc: Benrene Toluene @ chlorobenzene has symmetsical stru the crystal lattice. Therefore, @ @ More the number of alkyl groups, more will be the stability of carbocation and easier will be the reaction, Annueleophile is a chemical species that donates an electron pair to an clectrophile to form a ity more the nucleophilicity © chemical bond in relation to a reaction. So, less the electronegs of ion. Thus, CH; has the highest nucleophilicity NaNH, HL CHy—c oNaNH, (6) HGCA CH Br Br GIBBS CH. 6 = CCHY Chemistry—XIl: Term-1 58. 59. 61. 62. 65. 67. ) HsC—CH.—9=cHl—cH, HsC—CH.—ChCH.CHs a a Sechlovo-pen2-ene Sectdotopentane 5 ‘Opuealy inactive CH, —CH,—Cl=¢—CH, —+ CHsCH,CHsCHCH, a ol 2ehlropent2-ene 2elorapentane B Opts active © cay ol J one chi Here, the molecule has one double bond, so there is one geometrical centre 2 and numb Therefore, number of stereocentres(n) of stereoisomers CHCl @ is an example of arylalkyl halide as halogen atom is attached to the side chain Bena horde of the carbon atom of benzene ting. (6) CHL, BL [cHOHy) pyr HCOOH 2 HCOOK @) cL OH 2b sxoria ic cron) 0H ec “a on A-dichloroethane I no crcHo tinal fe) a noc-a+Ha H (Mexiglene lore) © Wo=CH + Br, CH Taiyo i Br Br 1-dibomoetone (a) RX + RCODAg —~RCOOR’ + Asx ah de se @) HOC. + HOC! — H,0 + ocr +cl" cn-ciimen, +1 cngncn.el lou exienicnscs i OH Maloalkanes and Haloarenes | 99 69, 70. a. 73. 74. 75. 76. 77. 78. 100) (@) The number of possible isomers is 6: Fe Br GN Br i : c= aw ro F ca Br a Neer Neer poe, Les BeBe Fd c=: : c=€ 1 17 Br (¢) In case of HI, HF ane HCI, one of the step is endothermic while in case of HBr, hoth the steps are exothermic and therefore HI, HF and HCI docs not undergo tnti Markoynikov's addition in presence of peroxide. @) CHYCH CH Br SSE CH) CH=CH Sarge CNC CHy Br (c) The reaction in which chloroarenes can be prepared by treating benzene diazonium chloride «with cuprous chloriele is known as Sandmeyer’s reaction. Or aa. Os Chlorsbenvene @ CHyCHsCHyCl + aq. KOH —~ CHsCH,CH,0H + KCL se prpyl chloride Propel ct cinct This can be explained as _ Step I: Cl, "aC Step Tt CH, cH, = r +h oma & ‘The other given reactions involves the formation of ions, @ Step III: (©) The dipole moment decreases on decreasing the electronegativity of the halogen from Cl to 1, Moreover, the CHF has lower dipole moment than GHgCl because of very small size of F which outweighs the effect of greater electronega 0) In Wntz-Fintig reaction, aryl halide is heated with alkyl halide in the presence of sodium in dry ether: Here, halogen atom is replaced by alkyl group and alkylarene is formed Dry ether (@) CHyBr + C)HyBr + 2 (CHjCH,CH, + 2NaBr CHsBr + CHyBr + 2Na —“*"". CHy—CH, + 2NaBr tans GoHsBr + CgHyBr + 2Na P28. CH, CHsCH2CH; + 2NaBr Chemistry—XIl: Term-1 79. 81. 88. 93. (6) In chlorobenzene, chlorine group is attached to sp? hybridised carbon and in methyl chloricle it is attached to sp* hybridised carbon so the C—CI bond is shorter and stronger in chlorobenzene. CH, CHyI + Mg ““*~ CH, CH» Mg ingest ce ipheast = Cl. Be te (©) G:Hs01 SEE Calls SSL. GytgeN oo) CHCHCH CE BO Cr, —cHacH, I-elroprepane cry—cn—cn, cH, Br 5 CMs, : ite @ CHy—cHscH— cH, cH CHCHCH, nt cHsc—eHscH, CHs CHs CHy Br Be I S cuyc—cn,cn, CH, 2-brome-2methsibatane NE axon + Nici oye cl oC Ss OF ats 0% (@) The halogens X and I are exchanging their position in this reaction: RX + Nal — RI + NaX cH, products via free radical (@) CH,CH,CH,CH, —~ CH,CH,CH, CH, Cl + CH,CH,CHC jp in presence of UV light gives monochlorinated isome mechanism. o fat Hb pr cue SHs aroma @ cHsBe CH CH.OH sep Ss ee oot Ber Benas bron (Susbe carbocation) Dens aesol Heloalkanes and Haloarenes 1101 95. 97. 98. 101. 105. 107. 108, 109. 110. 113. 14, 1s. itis 102) () They are sp° hybridised carbon and attached to different substituents. Assymetric carbon atom is the chiral carbon which is sp" hybridised and attached to different substituents, Here, carbon atom (b) and (c) are assymetric. (@) Forracemic mixture, thecompound should contain at least one chiral carbon in the compound. As (a) contains chiral carbon so it forms racemic mixture. (6) Electron withdrawing gro te of reaction towards mucleophi reaction, Its effect is more at ortho than meta position Boiling point of chlorides, bromides and iodides are higher than those of parent hydrocarbon ‘due to greater polarity and higher molecular mass. Thus, the correct increasing order is Butane < 1-Chlorobutane < 1-Bromobutane < 1-fodobutane » increases the c substitution @ @ os Anky Aly —CHs + (CHy)CHCH@Cl ——> i CHs {uty benzene (@) Suonger the attacking nucleophile, highey is the reactivity. The order of nucleophilic suengul, follows the order CN-> OH” > F-> NO} . Thus, CN" favours $2 mechanism. sya Dycber OD + Mg RMX. (vigor Reagent CHyCH2OH + SOC, BMY CHyCHyCl + SO. 1 + HCI Ei “ions chloride Chiorocthane @ (a) Since alkane formed is propane, therefore the alkyl halide may be isopropyl chloride ae : =MOH FG _¢4 HyC—GHACH, + Mg — NyC—e1Ie1ty SSG HOCH CIy 1 MgCl isopropyl chloride i @ Gna 22. GH,—ON=0 + KEL Chiron iyi I Hg + Cl ie H5Cl + HCL ores In this reaction, if we use Cl, in excess, then mono, di, tri and tetva chloroalkanes are formed as product and if ethane is used in excess, then ethyl chloride forms as major product. @ ent cr or, onto, te Hal +c, ton, 1 A 1 () Elmioaton reacon acts : tetanic KOHL CHAE ie CH ‘prop bromide Trepene The correct IUPAG name of the 1 CH, @) -n compound is, HyC—CH—CH, I CHaCHs eho -methlpentane a Chemistry—XIl: Term-1 cl cl “8 6 ws se o-dichlorobenzene ol Toluene medichloroben Clgis less = 120° 0= 60° = 180° electronegative Maximum —_ pedtichlorozene than Cl lipole moment It has zero dipole moment so has less dipole moment So, the order is IV <1< 1

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