1. What are hal alkanes? ‘Ans: Halogen derivatives of alkan« oa Mathylchhase) (dichloro methane) (Trichloromethane) 2. Write the general formula of monohaloalkanes. Ans: CoH where X =F, Cl, Bror I. 3. What are haloarenes? _ " : ‘Ans: Aromatic hydrocarbons in which halogen atom is directly attached to the benzene rin Examples: ‘i Br a 05 HC : Chlorobenzene p-bromotoluene 6.1 Classification i! 4, Give the classification of haloalkanes and haloarenes on the basis of number of bi Ans: Depending on the number of he sad} a aber of halogen atoms in their structure, haloalkanes and h @ Monohalgen compounds: They contain on} ‘ ‘ ° ly one halogen atom in their structure. Examples; C)H;—Br , ” C,H, -c1 te i. Ethyl bromide ie z (bromocthane) Chlorobezene : i Dinalogen compounds: They contai in two halogen com pounds in th Examples; _ CH, -CHBr, Br eir structure. Ealedinebromide CL es are called haloalkanes. (12-dibromoethane) es » Tribro: Son the basis 10 Which halo, 5. How do you classify mono haloco Ans: On the basis of sp? hybridisca ae » into three types. @_- Alkyl halides BEN is attach A Allylic halides od ncaaBenzylic halides Alkyl halides: In this type of compounds, the halogen atom is attached to alkyl group or Monohalogen derivatives of alkanes are called alkyl halides, igeneral formula alkyl halides is C,H,,., —X where X=F, Cl, Br, L mle: CH.~Br , . CH,-cL Ethyl bromide (bromoethane) Methyl chloride halides In ally lids, the halogen atom is bonded tsp hybridise carbon atom next othe carbon double bond. General formula." Examples: Br Zw Ln r Allyl chloride 3-bromo cyclohexene (IUPAC 3-chioro propene) : enzylic halides; In benzylic halides, the halogen atom is bonded to sp? hybridised carbon atom ‘(adjacent) fo the benzene ring, % General formula ‘Brample: cy x co coe Reet ‘Name the types of alkyl halides? There are three types of alkyl halides: alkyl halides or 1° alkyl halides alkyl Kalides or 2° alkyl halides ay alkyl halides or 3° alkyl halides are primary alkyl halides? Give an example. ‘compounds, the halogen atom is attached to the primary carbon atom. formula of primary alkyl halides is Examples: (i) Cy “CH —Cl., Gi) CH, ~CH, ~Br A chlor loride Ethy fl le (Chto tans) Eales ‘secondary alkyl halides? Give an example, compounds, the halogen atom is attached to the secondary carbon atom, The A halides is ee Nox general formula of @ cH, aoe i): : 198 halides? Give an exam iN jLhalides? Give aa to the terti ary carbon atom. The ge the halogen atom is attac! " 9. What are tertiary al ‘Ans: In these compounds, aliky] halides is ~ Examples R 1 H, a ca Rot A ee : 2 -promo-2-methyl propane <. ba on the basis of sp” C-X bond? 10, How do you classify the halogen compound: ‘On the basis of sp” C-X bond in halogen compounds, (@_ Vinylic halides (i) Aryl halides (@ Vinylic halides: In vinylic halides, the halogen atom is bonded to sp? yb carbon double bond. General formula they can be classified into two types: + sp hybridised carbon atom sp hyo Xx x haloethene halocyclohexene Examples: é ‘Br oe CH, =CH, Cl or = 7 Ties. ‘inyl chloride : ‘Vinyl chloride ‘Bromocyclohexene - (ii) Aryl halides: In atyl halides, the halogen atom is bonded to an sp? hybridised car General f i = formula: : Examples i ee Cr ¥ eee ion ree manne aon nthe oliowing? ~ (iii) Vinylie halides (iy) Allylic halides Ans: ()- Allythaldessp' Gi). Anyitatigg 2? Benzylic halid (iii) Vinylic halides sp? (iy) Ale ie ; 12. What are alkylidenes or alkylene dihalides? Ghen les Ans: The dihaloalkanes having the same pe of halons; nn ey Tassification with exar en ‘They are classified into two types: 6 om are called alkylidenes of alk ©) Geminal hatides (Gem = same), : ae : (ii) Viei a % © Geminat hatia ‘ “nal halides (Vj : les: If two hal (Wie = adjacen =. Example: Togen atoms are bonded tothe sclecent) Stisent’sinuminator ® carbon atom, thewi Publications H H H =a | } hy c—8 Hoax [Boer ‘geminal halide E 11-Dibromo et : Gy Vieinal halides: If two halogen atoms ibromo ethane (Ethylidine bromide) are bonded to the adjacent carbon atoms, they ae called vicinal halides. HOW é ll H 10a 1) H—c—c— Br XH vicinal halide 2 Nomenclature Br H 1.2-dibromo ethane J For dihalogen arenes, the prefixes o-, p-, or m- are used in common names and 1,2, 1, 3, 1, 4 are used in TUPAC system. , [uly 2016] ‘Common name "TUPAC name see — Butyl chloride 2—Chlorobutane I(CH,),CCH,CI neo — pentyl chloride + ‘| 1-Chloro-2,2-dimethyl propane (CH,),CCI ter— Buty! chloride 2-Chloro-2-methyl propane ICH, = CHC! + Vinyl chloride -Chloroethene Allyl bromide _ | 3-Bromo propene or CH= cH ee [3-Bromo-prop-1-ene] ‘—Chioro toluene 1-Chloro-2-methylbenzene or 2-cholorotoluene Benzyl chloride ') Chlorophenylmethane Dichlogomethane | Methylene chloride 1NPU Chemistryee prmemesmsmis S (ix) | CHC! Chloroform (o | CHB, Bromoform ® ide 0 | Cl Carbon tetrachlori eS alk ide ‘xiiy| CH,CHCHF ‘n— propyl! flour : Br (Gail OG ‘o- dibromoberizene Ethyledine chloride (xiv) CH,— CHCl, Br ‘sym Tribomobenzene () S Br ow] 6.3 Nature of C - X Bond = 14, The C — X bond in alkyl halides is polar in nature OR Explain. Expl halogenated compounds. 4 ‘Ans: Since halogen atoms are more electronegative than carbon, the carbon-halogen bond caries a partial negative charge. Hence C - X- bond is polar The strength of C— X bonds in alkyl halide follows the order: -F>C-Cl>C-Br >C-1, The reactivity of alkyl halides follows the order: R-I>R-Br>R-Cl>R—F, where R is any alkyl group, a 15. Carbon —halogen bond length increases from C - F to. CI. Give reason, ‘Ans: Because size of halogen atom increases from F to 1. 6.4 Methods of Preparation of Haloalkanes 16. How do you prepare alkyl halides from alcohols? Ans: a (From alcohol using cone. HCl and Anhydrous * 2 yd “001 heating alcohols with anhydrous ZnCl, and Sean oa me proces): Ay h R-OH+ uaa Za OH +HCIA Ch, RG 50, = aleohol Alkyl halide ‘Students illuminatorpn pubicalions a alcohol (Ethanol) From alcohols using thionyl chloriae : i alkyl chlorides are produced, Oatzen's process: When alcohols ire tested wih thionyl éhloride, Re OH +Soci, R=Cl+so, +Hc1 Example: C,H, -OH +SOCI, —Eyidine cu. eo en Ethyl alcohol, me gia 2 +HCI(g) ot crs, ote: Thionyl chloride is preferred for the preparation of, cescapable gases. fi) From alcohols using PX; : Alkyl halides are formed when alcohols are treated 3R-OH+PX,—> 3R-X + " HP0, Alcohol Ally balide Phosphorus acid alkyl chlorides because the other two products are with phosphorous trihalides. f) Alkyl chlorides are prepared by treating alcohols with PCI. 3R-OH+PCl—> 3R-Cl +) HPO, Alcohol Alkyl chloride phosphorus acid _ Example: 3C,H, ~OH+PCl,~—> 3C,H, -Cl +H,PO, Ethyl alcohol _ Ethyl chloride (ethanol) (Chloroethane) b) Alkyl bromides or alkyl iodides are obtained by the reaction of red phosphorous with bromine or iodine respectively. RedP R-OH———— > R-X Xjeby chef ‘amples CH, -OH Ss CH, -Br cH, OH #25 CH, =I i 2 : z , by the reaction of red phosphorous with bromine or iodine Wt: PBr, and PI, (unstable compounds) are repared by the cg "spectively, ; . Fis From alcohols using NaBr and H;S0.¢ Alkyl bromides ean Sodium bromide and cone. sulphuric acid. R-OH +NaBr+H,SO,—? ® 4 E + mle GH, OH + NABE+H,SO, —* 20! D aH, oa Tom alcotiols using PXs or PCI: Be POX R-OH+PX,——> R-X * alcohol Allyl halide : 4 prepared by treating alcohols with — Br + NaHS, +H,0 NaHSO, +H,0 PU Chemistry. ny iluminator=) +HEl+POC!, Example: C,H,-OH+PCl,—+> CoHs | chloride Re ‘ot eae radical halogenation of alkanes, 17. Give the preparation of isomeric haloalkanes DY free "OV light (or heat), a complex mi ace of ‘Ans: When altanes ae treated with Cl of Bra i SERS Tt chlorine hep ‘ ample, - mono = and poly haloalkanes aré formed. For exar i | gives I-chlorobutane and 2-chlorobutane. a I g CH,CH,-Cl + CH,CH, CHCH, |= ” cu,cu,cH,cH, + cl, 2a cH CH Coe 3 x 1-chlorobutane . ee ing @ n halides 18, How do you prepare’alkyl halides from alkenes by adding @) Hydroge by examples, ‘Addition of HCl, HBr or HI to alkene gives corres | Ans: (i) Addition of halogen halides: ea higher alkenes addition of hydrogen halide takes eae part of hydrogen halide (H*X-) is added to double bonded carbon of alkene i hydrogen atoms. Examples CH, =CH, +HX —> CH, -CH, -X __—_—> CH, CH,CH,—I oe 1-iodo propane (minor, 19%) ound —CH, T 2-iodopropane (major, 81%) Note: In the presence of peroxide catalyst, addition of HBr takes place against to the Mar called Anti-Morkovnikov's addition, (ii) Addition of halogens: Alkenes react with halogens in carbon tetrachloride to form vieinal Halide Example: CH, =CH, + Br, “yr cH, cH, Br Ethene (ates i 19. What are X and Y? : ia ; + HBr Oo .CH,— CH=CH; + HBr my Ans: o~ Ee cra 20. Name the halogen exchange methods Ans: (i) Finkelstein’s reaction (ii) Swart’ op | be for the preparati 2 3 Sreactign PON Of haloalcanes,143 What is Finkelstein’s reaction? F; tlosalEine 6 Bassa pe In with an example,[July 2014, March 2015, July 2015, July 2018) ating with sodi ti I roasts 'ng with Sodium iodide in dry acetone gives alkyl iodide. This reaction # acetone R-X+ Nal —tevseetone sy 1, ax where (X = Cl, Br) C,H, -Cl +Nal. CH, -1+Nacl Ethyl chloride Ethyl iodide GH, ~ Br +Na1—Svacetone | Gy 1 Nap Ethyl bromide » = | Bthyl iodide 22, What is Swart’s reaction? Explain with an example, [March 2014, July 2016, March 2018, April 2022] iAns: Ally! chloride or alkyl bromide on heating with metallic fluoride like Ag, CoF, ete gives alkyl fluoride. This friction is called Swart’s reaction. : R-X+AgF—4 RF +Aox where (X= Cl, Br) Allyl fluoride Bsample. CH,-Br+AgF—> C.H,—F +AgBr Ethyl bomide Ethyl fluoride Ans: Swart’s reaction. 6.5 Preparation of Haloarenes " 24, Give the preparation of o —and p- chlorotoluene and o— and p~ bromo toluene by electrophilic substitution reaction. ‘0-Chlorotoluene a p-Chlorotoluene CH, 2 CH, o-bromotoluene Br p-bromotoluene 13) &S: Give the preparation of aryl halides by Sandmeyer’s reaction. (Discussed in U Bsa Be ‘amines react with nitrous acid (prepared in situ from NaNO, and a mineral acid such as — 278 K) to form diazonium salt. This reaction is called diazotisation. Freshly ) at low temperatures (273 i It cocina sana ee with caprous chloride or cuprous bromide to give aryl chloride or aryl bromide MPU Chemistrya : sk + NC + NaNO, + 2HX Reconium halide Benzene diazonium Aniline cl see oe i Nxt Chlorobenzene sui Beas Benzene CuBr /HBr uN diazonium salt, Bromobenzene ; jum salt-with potassium Note: Jodobenzene can be prepared by simply by shaking the diazonium salt with po Nx 1 ag O + KI —> oO +N, + KX : 6.6 Physical Properties 4 26. Haloalkanes are slightly soluble in water. Why? Ans: Because haloalkanes have sufficient polar nature to break the existing H-bonding in 27. The melting and boiling points of haloalkanes and haloarenes are higher than pal Why? a ; - ‘Ans: Due to greater polarity and higher molecular masses of organic halides compared to GOme the intermolecular forces (dipole-dipole interactions and van der Waal's forces) are stronger Therefore, boiling and melting points of alkyl / aryl halides are higher than the corresponding ps 28, Write the decreasing order of boiling points among different alkyl halides having s ‘reason. ‘i Ans: Decreasing order of boiling points in alkyl halides having same alkyl group: R=I>R= This is because with increase in size and mass of halogen atom, the Magnitude of van der Wa Note: The boiling points of isomeric haloalkanes decrease with increase in branching. ~ 29. Among isobutyl bromide and ter-butyl bromide, whieh hag higher boi uae Ans: Iso:butyl bromide has higher boiling point than ter-butyl vacua Thi eal as boilig point decreases. “30. Arrange each set of compounds in the order of increas 3 © bromomethane, Bromoform, Chloromethane Dibromony meee al 2 ethane (i) 1- chloropropane, Isopropyl chloride, 1. Chlorobutane. Ans: () Chloromethane < Bromomethane <'Dj : increase in molecular mass. (ii) 1sopropyl chloride <1- Chlorop boiling point, : lbromomethane ‘S Bromoform. mopane < 1- Chlorobutane. Since isopropyl chlorideth Publications oarenés, para- isomers have hi Fy? e ss have higher melting point as compared to their ortho- and me isomers. Y A ¢Itis due to symmetry of para : [uly 201 Pee decay oft eMart aics boner as compared to ortho and nid doer. How does density of halogens changes with inerac, gs: Density increases. ein number of | Among n-propyl iodide and n-propyl bromide, ns: n- propyl iodide. 85, Haloalkanes areless soluble in water. Give reason, ¢ Because they do not have sufficient polar nature to b Haloalkanes are soluble organic solvent, Why? which has higher density? reak the existing hydrogen bonding in water. is: This is because the attractive forces between haloalkane molecules and organi¢ solvent molecules are almost Bramples:’ OH, CN” ete Hydroxylion Cyanide ion R-X +KOH (aq) > R-OH + KX R-X +NaOH (ag) “> R—OH + NaX 2R-X +Ag,0 42 92R -OH+2A8X (Ag,0+H,0 —>2Ag0H) m Moist. Emples: CH,~Cl + NaOH'(aq) —*> CH;-O) H+ NaCl Methyl alcohol -OH + KBr Methyl chloride a GHs-Br + KOH (aq) > Gls Bromoe ae ve moethane ae : PU Chemistry146 #0. 9 2C,Hs=Br' + | Ag,O —5 20) Bromoethane 40. Name the reagent used to ‘Ans: Aqueous NaOH or KOH. z with alcoholic KC! 41. How do alkyl halides react ‘Ans: Alkyl halide on heating with alcoholic potassium ¢ + KX H,-oH + 2A88r ethanol R- OH from alkyl halides. get substitution product ssium cyanide]? Give equation, IN [Pota: ide gives alkane nitrile (cyanoalkane), vyani R-X + KCN(ale) —2> R-CN Examples, CH,I +KCN (alc) —4, cH,-CN+KI . a Todomethane Ethanenitrle G)H,Br + KCN (alc) > CHj-CH,-CN + KBr Bromoethane Propanenitrile é 42. How does alkyl halides react with alcoholic AgCN? Give equat [July 20 ‘Ans: Alkyl halide on heating with alcoholic AgCN gives alkyl isocyanide (carbylamine). R-X +AgCN(a@lc) 49> R-NC + AgX Alkyl isocyanide Examples CH;Br + AgCN(alc) 49> © CH,-NC + — AgBr Bornomethane Methyl isocyanide HBr + AgCN (alc) —4> CH,-CH,-NC + AgBr Bromoethane Ethyl isocyanide 43, How does alkyl halides reacts with silver sal f les reac Iver salts of carboxylic acids? Gi ie ‘Ans: Alky| halide on heating with silver silt of carboxylic i asee oe RCOO-[Ag+X] -R —>R-COO-R +Ag-x ae Ester i CH,coo Silver acetate ane CH, ~COO-CH, + Ag-1 i). cHCoo Methyl acetate SCH Silver ethanoate yoni eo eae 5 Ethyl ethanoate 44. How does alkyl halides react with alcoholic ammo ‘Aus: When an alkyl halide is heated with aleotoli ann tertiary amine and finally quatemary ae ammonia in RNH, 22 RN RX, Re ae Bea RN RX, amine "amine Fran AN'X- re Semine Guana 4 ‘ammonium salt ‘Student's illuminator § 4 sealed tube, primary amia) With potassium nitrite [KNO,] halide on heating with potassium nitite gives alkyl nitrite is formed, RX+KNO; Mt RE ONO Hx alkyl nitrite C,H,Br © + KNO, Bromoethane ‘With silver nitrite [AgNO,}- analy! halide is heated with silver nitrite nitroalkane is formed. R-X+AgNO, > RNO, +Agx s at C,H,ONO + KBr Ethyl nitrite nitroalkane met: CH,CH,Br+ AgNO, RNO, + Agpr ‘ 7 Bromoethane nitroethane Reaction with lithium aluminium hydride n an alkyl halide is heated with LiAIH,, alkane is formed. RX+H EAM RH x 4C,H,Br + LiAIH, —>4C,H, + AIBr, +LiBr Bromoethane ¥ Ethane What are ambidentate nucleophiles? Give an example, > bs: Groups likes cyanides and nitrites possess two nucleophilic centres which are called ambidentate ophiles. Cyanide group is a resonance hybrid of two contributing structures —cEN ——=6 * The nucleophile OH from aqueous NaOH attacks pl Sorirh tertiary butyl alcohol. Oe a | OH no a cae ‘ 7 CHy 2s, 3 Tertiary butyl aleobol ‘The product tertiary butyl alcohol obtained i ; Ee 53, In case of alkyl halides, 3° allyl halides undress nian = Ans: De tthe higher stability 03° arocaons, ns nt YOY ast GW reasO8 = ae 54, What is the type of hybridization of carbon . ome ‘arbon atom involved in Sy mechanism? _ 58. Which mechanism gives racémic mi i , SMe ‘mixture as the product? 56. What is the order of reactivity amon; ae = ° 1g 1°, 2°, and 3° ‘Ans: The decreasing order of reactivity of haloalkones Pe es in Sy1 reactio °> CH= Xie eis Studont® ituminatorpublications. rds Syl reaction? wl reaction, Bécause formed carbocation is stabilized by the Sy2 reaction? — f Sy2 stands for bimolecular nucleophilic substitution reaction, Explain Sx2 mechanism or explain the mechanism involved in the conversion of chloromethane (methyl chloride) into methanol (methyl alcohol). July 2015, July 2016, March 2017] E rimany alkyl halides undergo Sy2 reaction. S\2 mechanism follows 2™ drder kinetics. Example: Methyl ide reacts with aqueous NaOH to give methyl alcohol. ‘ 2 CH,-Cl_+NaOH,., —>CH, -OH+Necl Methyl Methyl alcohol Chloride Methanol (chloromethane) : thanism: Sy2 mechanism involves only one step. It follows 2™ order kinetics. tucleophile OH” attacks electron deficient carbon atom from the rear side (back side) of the carbon atom to a tansition state. Itis unstable. In the transition state a partial (HO ~ C) bond is formed and partial C-Cl bond ken. The product methyl alcohol obtained has inversion configuration, I OHT fot eee HH Methyl alcohol Methyl chloride Transition state Mi What is the order of reactivity among 1°, 2°, and 3° alkyl halides in Sy2 mechanism? The increasing order of reactivity of baloalkanes is 32 <2° <1° < CH, ~X. ive any two differences between Sy1 and Sx2 reactions. . ‘Sy2 Reaction Syl Reaction ceo | It is bimolecular reaction. imolecular reaction: ul =i It follows 2" order kinetics. follows 1* order Kinetics. ; — sing of activity of halk canes Thea sof eotvly of hao alkanes is] The deseating order of ectvity oF halo alkanes i 3° decreasing order of reactivity CH, -X>1°>2°> >> Ca nator eea 7 = = ay ut | Veet e a e rE 71. What is chirality? What i Tactic acid : 2 the condit - Ans: The objects which Crap aot chiralty? u resulting propery is called canny ePeTItPOSable on me r S. aee 7. Giverny Balled chirality. The chirat no IMAGES are said to be’ chiral ive examples for chiral molecules seule should contain as Rate depends on the concentg and nucleophile. nly on the concen : oe The product obtained has i = mic mixture. 7 | The product obtained is a race a 3 aca Aspects of Nucleophilic Sul hn fereoc! 63. What is optical isomerism? formula but von the eame molecular formula and same structural z pte Paieeraas jomien led optical isomers and the phenomenon ti rotation of plane polarized light are cal ee 64. Name the instrument used to measure optical isom i device used t “ polarised light. 2 : a ‘Ans: Polarimeter. ; 5. What are dextrorotatory substances? e ae eae olution ofthe substance which rotates the direction of plane polarized light to the 1 rotatory substance. Itis denoted by (+) sign or ‘d’. Example: (+) lactic acid or ‘d’ 66. What is laevorotatory substance? “- ~ Ans: The solution ofthe substance which rotates the direction of plane polarized light t9 Taevorotatory substance. Itis denoted by (-) sign or ‘”. Example: (~) ~ lactic acid or !— lactic acid 67. What is a racemic mixture? [March 2019, July Ans: Equimolar mixture of dextrorotatory and leavorotatory isomers is called racernie mitre Itis denoted by (+) sign or dl Example: (4) ~ Lactie acid or dl — lactic acid, 68. Give reason: Racemic mixture is optically inactive. Ans: Because the optical activity of d- isomer gets cancelled by that off isomer, lactic acid. 2-bromobutane ‘ymmetric carbonPropan-2-ols achiral molecule and optically inactive. Explain, ; In propan-2-ol, all the four groups attached to the tetrahedral carbon atom are not different and hence the dral carbon is not asymmetric and some of its mirror images are superimposable. Therefore propan-2-ol is irl molecule. Due to the absence of chiral carbon in its molecule, propan-2-ol is optically inactive. 3. H A Cis obtained by rotating B by 180° Cis superimposable on its mirror image A What is the condition for optical isomerism? : Compound should contain chiral carbon atom. : vas i [uly 2015] L What are enantiomers? : Besa : Optically active isomers which are non-super impossible on their mirror images are called enantiomers. ple: 2- Bromobutane HC CH, ie f | & —Br — Be —OH HO: H CHT ‘a aed. \ nee ie H COOH COOH ae : * ()-Lacticacid ; — (-)-Lactic acid CH; What is the ait o serty among enantiomers? as, pace . Ss ance nore are ottion of plane polaizd ight If on ofthe enantiomer is tr 1s differ ere : : “sory the other will be laevo rotatory. : i PU Chemistry182 end H 7p deny eiat and A ned ‘oH oe o on cH, Br ‘ i @ cH, a cH cH, CCH CH,CH,Br 1 oo @ ‘ans: Chiral molecoles oe i X~ @ @ wong, Hy cH, BY OH ‘chiral molecules z ff i @ weg, @ 4X oH, - ii) ‘ Br 3 Br’ @) 80, What is racemisation? ‘81. What is retention? Give a general illustration. ‘Ans: The retention of configuration is the preservation of integrity of the spatial arrang asymmetric centre during a chemical reaction or transformation. During retention, no bond broken 3 a ee x WN 82. Give a chemical reaction that proceeds with retention of the configuration, - ‘Ans: When (—) -2-methylbutan-1-ol is heated with fe ic aci aes Mit) 2 concentrated hydrochloric acid, reac (-2-methylbutan-1-o1 83. What is inversion? £ : ()-1-chloro-2-methyl butane ‘Ans: The inversion, + Product ob tained has the configuration opposite to that of the reactantnea utration to sow inversion etention an : There are three outcomes for a react and rasimisation. fy ‘y’ inthe following reaction, ©" ®t 8M asymmetric carbon atom. Consider the replacement of a group ra aa iS a CH, ‘CH, B (Inversion) | : y Hy 2 pa ‘cH, Zz A (Retention) Recemisation sA’ is the only compound obtained, the process is called retention of configuration. iB’ is the only compound formed, the process is called inversion of configuration. ual amounts of both A and B are formed, the process is called racemization and the resulting product is cally inactive. 3 Boos ‘Sx2 reactions of optically active halides are accompanied by inversion of configuration. Explain with an cn atom. Hence inversion of configuration takes place. ple: =e e i (C) -2-bromooctane is heated with aqueous sodium hydroxide, (+) octan-2-ol is formed: Here the — OH group es the position opposite to that of bromine. Hence inversion of configuration takes place. + BE CH; (.2-Bromooetane (4) Octan-2-01 - reactions of optically active alkyl halides are accompanied by racemisation Explain with an 1 seatiog of optically : Eee r step involves the formation of carbocation. Here the carbon atom .ce carbocation has planar structure. Therefore, the at it i i ide gives a: racemic mixture 2 2 heating with aqueous solution of sodium: hydroxide gi pl: 2-romebts on Wty pana Hence xt scaled) na Br ee Agee © 5: “ NPU Chemistry Oei —oH a (disomer) HO- AN (Slightly larger yield) re ‘GH, Elimination Reactions : : £87. Explain dehydrohalogenation reaction or P-elimination reaction with an example. * ri 94. Explain ' 5 X= Leaving group < Ans: Alkyl b reaction, (aleobaticy 88. Explain Zaitsev rule with an example. Examples: Ans: Zaitsev rule states that [Cth CH,— CH= CH—cH + kB + Note: Ifa mi Pent2-ene (81%) (Major product) Example Cop Ce ch Ci HH, + KOH—-| _ a 8. Aryth 2-Brome-pemtane "7 CHy~CH,— CH CH=CH, + KBr Aas: Less Pent--ene (19%) © Reson “(Minor produc) Stronger. + entify Q (major. Product): . alc, KOH ——-Qn punlice —— ie LC Ja ao r actions with Metals at are OTEANOMtalle Compoung. > 0. ganic chlorides, bromid re a os called organometallic epen gOS react wag ee sre ANNE Compounds," With certain metal al Ethyl magnesium bromide. 10 give compounds containing carbon-metal 4, what are Grignard reagent? Give c an examp organomagnesium halides are catleg ge ys OF led Grr [Jul i oe Ethyl magnesium bromide (CoHintes, » és Feagent, Pr [uly 2020, Aprit 2022] ‘g, Write the general formula of Grignarg re ylmagnesium chloride(C,HMgct). n nt, ys: R-Mg-X w do you prepare Grignard 43, How do 9 Teagent from alkyl «Grignard reagents are halides? ( aus: Grignard regen are prepared By the action of magnesign on [uly 2014, March 2016] RX +Mg—Svetter RNa organic halides in dry ether. Grignard reagent “HC ai CH,CH,Br +Mg—S5vether CH,CH,MgBr Ethyl bromide Ethyl magnesium bromide 44, Explain Wurtz reaction with an example, tu: Aly! halide on heating with metallic sodium in dry ether gives higher alkane rection. [March 2019} This reaction is called Wurtz 2RX +2Na—HWether 5 es oNax 2CH,Cl_ +2Na—>CH,-CH,+2NaCl Methyl chloride Ethane 2C,H,Br +2Na—S2ethet, CH, CH, -CH, -CH,+2NaBr Ethyl bromide n-Butane Note: Ifa mixture of two. alkyl halides is subjected for Wurtz reaction, three alkanes are formed. CH,Cl+C,H.Cl—gy ater? CH, CH, + CH, ~CH, ~CH, ~CH,+CH, CH, -CH, Ethane butane Propane i Hi jlic substitution reactions. Give reasons. : ‘oad are ee 2014, ‘March 2015, March 2017, July 2017, July 2020] ‘ws: Less reactivity of aryl halides is due to: 1) Resonance effeet: C-X bond acquires double bond character Stronger, fue to resonance and hence C-X bond becomes MPU Chemistry.\d: In haloarene, the fom in C-X bon ne ees ‘with respect to halogen atom te 8 aie an Ca ld hy Jloalkane with Tess s-character, .nes. Hence, haloarenes are less reactive ii) Due to difference in hybri o marae is sp? hybridised where as "Tt ‘The sp” hybridised carbon wih eae + ‘EEX bond more tightly than sp" hybrid Tength becomes shorter and stronger substitution reactions. 96. Sxl mechanism is ruled out (m Ans: In haloarenes, the Pe a Therefore Sy1 mechanism is ruled out . i to phenol by Dow’s process! 497. How do you convert chlorobente hydroxide at 623K under 300 atmosphere ous [ + 2NaBr * Bromomethane Bromobenzene i Toluene .. Explain Fittig reaction with an example. [March 2014, March 2015, March 2017, March 2018] : Two molecules of aryl halides reacts with sodium metal in dry ether to give biphenyl. This reaction is called ig reaction. : i i Haloarene “Hialoarene Diphenyl example, biphenyl can be prepared by Fittig method as follows: es ether pnt) 2 OO) + nam Bromobenzene Bromobenzene Dipheny! 0.8 Polyhalogen Compounds Hl. What are polyhalogen compounds? 2 : The compounds with two or more halogen atoms are called polyhalogen compounds. Give the uses and environmental effects of Dichloromethane (CH,Cl,)? * Environmental effects ‘ Methylene chloride harms the human: central nervous system. s ae i Exposure to Jower levels of methylene chloride in air causes slightly impaired hearing and vision, WPU Chemistry2 ‘and numb 2 (ieee? Gi Higher levels of methyzene chord (eee toes. y | dges: Dichtoromethane is used ()_ Inpaint strippers and paint removers. (jiy Asa solvent in the manufacture of drugs. (ii) In metal cleaning and finishing ee jv). As an aerosol spray propellant for Pain : : ta What are the uses and environmental effects of weal netiene (Cae ‘pat: Breathing about 900 parts of chloroform PP million parts 00 as ea cause dizziness, fatigue, and headache, Chronic chloroform exposure may emus damageitd 2COCL, + 2HCI | Phosgene 114, Give uses of iodoform (Triodomethane). Ans: (i) It is used as an ingredient in many ear powders for dogs and cats, to prevent infectic and propanoie acid. : : | (ii) Earlier, it was used as an antiseptic. (The antiseptic properties aré due to the liberation of free iodine and not dist ied 115. Give uses of tetrachloromethane (carbon tetrachloride). 4 ‘Ans: ())‘Ttis used to make refrigerants and propellants for aerosol cans. (il) It is used as a dry cleaning agent ‘ ii) Used as degreasing agent (iv) Itis used in fire extinguisher (¥) _Ttis used as pesticide and general solvent, = wi) It : 's used as feedstock in the synthesis of chlorofluorocarbons (CFCS). ‘What is the effect of carbon tetrachloride on human health and environment? rachl a 1 : Excessive exposure to te : trachloromethane ma 'y cause health effects on thepublications 161 | Whiat is the effect of D 5 DDT is vontiade ead “dichlorodiphenyltrichloroethane) in the environment? DT raids vena a at because ithas ow water salty and ih sly i issues because of ts non Write the structure of DDT. rare geeeboen in inne ses, ‘The homologous series of alkyl halides are represented by general formula (2) C,HaaX (b) CyHsaXo (© CHa Xs @ CHa If halogen atom is attached carbon atom containing two alkyl groups, then itis called (2) primary alkyl halide (b) secondary alkyl halide (©) tertiary alkyl halide (@ none of these The compounds in which the halogen atom is bonded to an sp’ hybridised carbon atom adjacent-to carbon-carbon double bond are ‘(Allylic halides (b)Benzylic halides (c) Vinylichalides (4) Aryl halides : Vinylic halides in which the halogen atom is bonded to (2) sp? hybridised carbon atom of carbon-carbon. double bond (b) sp’ hybridised carbon atom of carbon-carbon single bond (©) sp hybridized carbon atom of carbon-carbon triple bond (@) all of these alkyl halide is polarized to more electronegative than carbon electronegative than carbon than carbon (@) Halogen atoms are (b) Halogen atoms are les: y (c) Halogen atoms are more electropositive preparation of alkyl halides from alcohols is thionyt chloride. This is .0,and HCI) and escapable MPU Chemistry laminatortoxic 162 (@ Thieny! chloride is easily available ‘and now: (all of these % -qhe name of the reaction Roxen SRE is : 3 (a) Wurtz reaction (Fits reaction (©) Swartz reaction (@ Fin it ction * & ‘Which of the following is Swarts reac i @ CH, —Br+AgF > CH, -F + AsBr (b) 2CH,Cl+Ne—2> CH, a © aan —Cl+ NaS Ar Art 2NACl (@ None of these i jth increase in branching |The boiling points of isomeric haloalkanes witt : oe (b) decrease (© remains same , _(d) none of t 10. Metting points of p-dihalobenzenes are high compared to their ortho and meta is (@) symmetry of pisomers that fits in crystal lattice better compare to their o- and m- is ce better to ortho and meta isomers {bynon symmetry of p-isomers that fis in crystal lati (©) symmetries are same in all types of isomers. (@ none of these 11 Sx2 reaction follows Eas (b) second order Kinetics (© zero order kinetics (@ fractional order kineties 12, In $2 reaction : é ‘ (@) the rate depends upon the concentration of both the reactants (©) no intermediate is formed (© inversion of configuration takes place (Wall of these 13, The reactivity of alkyl halides towards Sy? reaction (@) primary halide (1°)> secondary halide (2")> tertiary halide (3°) (b) secondary halide (2°) > tertiary halide (3°)> primary halide (I) (©) tertiary halide (3°)> secondary halide (2°) > primary halide (1°) Ee: (@ secondary halide (2°) > primary halide (1°)> terry halide (3°) 14, Sy1 reactions are generally carried out in (@) polar solvents (b) nonpolar solvents it po ; solvents (e) CH,CH,CHCH, + CH,CH,CH,CH, — Cl ‘ards Sy2 reaction because of (©)Resonance effect (A) Electromeric effect (@ Isopropyl chloride (0) ChiFe (b) Cl, /UV light (0) Cl, /H,0 (@ Cl, /Dark al dihalide is (@) Dichloromethane (@) 1, 2-Dichloroethane (c) Vinyl chloride. (4) Allyl chloride The reaction of alkyl chlorides with alcoholic KOH is an example of . (2) Substitution reaction _(b) Elimination reaction (c) Addition reaction * (4) Condensation reaction Aryl halide acquires C-Cl double bond character is due to__ {@) Inductive effect (b) Resonance effect » (¢) Hlectromeric effect (4) Hyperconjugation effect Syl reaction of optically active alkyl halide leads to z (@) Retention of configuration (b) Racemisation (©) lnversion of configuration (@) None of these The optical inactivity of racemic mixture is because of_______ (@) Molecular dissymmetry (b) Internal compensation (0) Presence of chirality (d) External compensation Which of the following has highest boiling point? Bo Penty cies (oy seepeni chloride (c) Isopentyl chloride (4) Neo-pentyl chloride The most reactive compound towards nucleophilic substitution in the seine ss canBr (b) CoHGCI (© CoH a . FER PU Chemistry aSet-1 * | chioro-2, 2-dimethyl propane, pep of chlorobenzene and (Thiony! chloride, inc ‘The compound which is en : sodinm metal in dry ther ered for the preparation of alkyl chlorides fi ‘2. The reagent 5 i oa eee 3. The IUPAC name of meen Alrite pase FE 4. Major organic compound ol inb ea &. “The boiling point of isomeric haloalkenes decrease with _in Dranching ; Set—2 a (DDT, Increases, Carbonyl chloride, Geminal dihalides, 2-methyl L poisonous gas is obtained by slow oxidation of chloroform in the p 2. Density for haloalkanes with increase in number of carbon atoms. 3. is an non biodegradable compound. i 4. Organic compound formed when 2-bromo-2-methyl propane is treated with 5. When two halogen atoms are bonded to the same carbon atom, they are called 7 Set -—3 ae (Elimination, Branching, CCLF,, Chlorofluoro, Sx2) 1. The boiling point of isomeric haloalkanes decreases with increase in" ___ 2 ______. ___ derivatives of methane and ethane are called Freons. 3. ______ mechanism have inverted configuration 4, 5. |. Freon-12 . _Dehydrohalogenation of ethyl chloride is an example of Set—4 (Hydrocarbon, 2-Chloro-2-methyl propane, Chiral, Gri , Grignard 1. IUPAC name of tertiary butyl chloride is enard resgent Tu 2. Alkyl halides are formed when —and alcohols : i 3 3, The common name of alkyl magnesium halides lS #*€ Fefluxed in the 4. Grignard reagent react with any source of pro ; 5, The objects which are non-superimposable on ae ton to give : their mirror images are Set—5 (Halothane, Methyl 1. Ethane nitrile can be preparea norte PHOSEene, Plane of symmetry, Enantio pared by heati 2 in is used as an anaesthetic a With alcoholic KCN. ‘sion of ry.publications Answer keys (Mca’s) ul rT b b 2 26 € b Answer keys (Fill in The Blanks) Set 1 : 3.2,2-dimethyl prppane 5. increase . Set 2 | carbonyl chloride 2. increases 3.DDT 2-methyl propan-2-o1 5. Geminal dihalides Set 3 Branching 2. Chlorofluoro 3.92 CCF: 5. Elimination Set 4 2-chloro-2-methyl propane 2. Thionyl chloride 3. Grignard reagent Hydrocarbon 5. Chiral 7 Set 5 Methyl chloride 2, Halothane 3. Enantiomers 5. Plane of symmetry Toluene 2. Thionyl chloride f 2-bromopropane Phosgene