x x Q.3. Outof O and (eg , which is an example of allylic halide? nowy Q.4. Which of the following two reactions is Sy2 and why? GH Q.5. Wurtz reaction fails in case of fert-alkyl halides. Why? Ans. This is because fert-alkyl halides prefer to undergo dehy instead of undergoing Wurtz reaction. (CHy);C—Br + 2Na —ag—> (CH3);CNa tert Buty bromide tertButyl sodium anol a (CH; eee i) (CH,);CNa + HCH, “CH, ———+ (CH9)x 5 Br sgphaangal Q.6. Identify the chiral molecule in the following pair: Ai eae a et Ans. a Out of chlorobenzene and cyclohexyl chloride, substitution reaction and why? Ans. Cyclohexyl chloride is more reactive than to resonance the CCl bond in chlorol ac substitution of chlorine more difficult in chloro has pure single bond character, Q7. 272 Xam idea Chemistry-Xlleactive towards Sw1 reaction as compared to n-butyl bromide? ICBSE 2019 (56/4/1)) jde more ‘yl promide put) of tertiary carbocation than primary carbocation, lit a stability o distinguish between C,HBr and C,H,Br. em oe HBT with aqueous KOH followed by acidification with dil, HNO, and subsequent a a eth. ot aust Of ENG, gives light yellow ppt of AgBr whereas CgH,Br does not give tis test c me a with Agi and benzyl chloride, which one gets easily hydrolysed by aqueous NaOH and penzene (CBSE 2018} ight! oie cial test te sie Gi oral tl ut (opper’s Answer 2018] Short Answer Questions-I sie folowing questions are of 2 marks. M Daw the structure of major monohalo 9 Chon —socn : ()-c#,cacn, + HB Peosse, ® OF i ‘i Opa ; H, E eee hy, Ns i Product in each of the following reactions: {CBSE Dethi 2014] "hone op : the for lowi Ky, CH ‘ng compounds i . oe ttc er Pounds is more easily hydrolysed by KOH and why? t Tats alkyl fe : re SOHCHCL + eee iar Mesa Sab then the 2° carbonium ion CH;—CH-—CH, cH, derived from sec. butyl "0 chocide pete he gettbonium ion CH;—CH,—CH, derived from n-propyl chloride 'ydrolysed more easily than n-propyl chloride under Sy1 conditions.Q.3. Am alkyl halide (A) of molecular formula C,H,;Cl on trea isomeric alkenes (B) and (C) of molecular formula C,H, 2, 3-dimethylbutane. Write the structures of (A), (B)and (G), Ans. Alkyl halide reacts with alcoholic KOH to give B-elimination reaction, Sines the compound (A) should have two types of -carbon from which CH; CH; Pydope HyC—¢—C—CHy cl Elimination: CH; CHy HyC—¢ —C—CHs Cl, Ha Q.4. Give reasons for the following: (@ Chloroethane is insoluble in water. (i Thionyl chloride method is preferred for preparing alkyl chlo Q.5. Differentiate between retention and inversion. Ans. Iftherelative configuration of the atoms/groups aroundachiralcentrei On the other hand, if the relative configuration of the atoms/groups is opposite to that in the reactant, the reaction is said to proceed example, é OH. H. He aw co 1S aes CH, 5 Invetion Reactant Q.6. Give reasons: @ C—C1 bond length in chlorobenzene is shorter than Ans.ali he follows iky! halide from win Batiste Chir > i undergoes faster Sy’ 2 reaction? @) ’ 2, which reaction occurs with guration (@®) Racemisation ICBSE Dethi 2014) snobutane is a chiral molecule. ia) 1 Co, 2bro! ot mary halides undergo faster Sy2 reactions than (i Sw secondary halides due to less steric “~~ Br pinderance- y sy2 reaction OCeUFS with inversion of configuration. vom cours with racemisation. 5) predict the order ir reactivity of the following compounds ie ‘Sel and Sy SC A,CHBE Col (C,H) Br, CoHsCH(CHS Bre CgH.C(CH)XCHBE Bees m *C(CHa)( CoH BE > CgHjCH(CeH9)Br > CoH CH(CHs)Br > CoFlsCtaBr yD. GAAC(CHS) iS eae CaHGCHCH,)Be< CLCHLBs (552), i ¢ carbocation intermediate obtained dary ied from C¢Fl;CH(CHa) st ieassamaats stabil ey, eee ee the former bromide i: is i @ (b) Sxl reac’ jence, t is more reactive (CoH sCH(CeHs)Br {bulkier than a methyl BrOUP- ‘Thus, reactions. Cire reasons for the followins ¥ hlorobenzene undergoes nucleophilic substitution faster than chlorobenzene. Explain ving the resonating structures as well.) A PAS! ela: . . oform is obtained by reaction of acetone with hypoiodite ion but not iodide ion. carbanion intermediate is roc! ts () Inp-nitrochlorobenzene & below. Sa clon ZY Slow Os scent i Os ) Canes oe Se Fis 4 ‘i tabili The -I effect of nitro group further taP4 ae ae ter than chlorobenzene. m1 x Soi fon can act as an OnINP agent while jodi ae ou distingiaay between the following P q ty gieroferm and carbon tetrachloride. Oo hloride and chlorobenzené sentcating chloroform and arb - ‘arately chloro! oped form forms pung CoH. ‘oHsNI : S 'H, + CHCl, +3KOH (eth On ad lin; S a Prec; Se intermediate. ——— 'g Sodium hydroxi init dro end but chlorobenzene 'SCHACl + NaOH acl 4 AgNo, ——=7 i,” Q. 11. Give the structural formula and IUPAC name of the following compounds: - (@ BAC (i) DDT mde: Ans. (i) BHC (i) DDT r a9 a 1 cXO) tg ct 1 ¢ t © 1aaseaetiow 4 142.22.tichloroethane--4y ‘bis(4-chlorobenzneey Q.12. Write equations for the following: fe (@ Oxidation of chloroform by air and light BSE 2M, (i Reaction of chlorobenzene with CH,CVanhyd. AICI, Ans. (i) 2CHCI, +0, —H#+ 2cOCI, + 2HCI ec ma cl ca a w O ome, om i aS cians Peseta oa an Poe coe re Short Answer Questions-il Each of the following questions are of 3 marks. Q.1. Draw the structures of ‘the major monohalo Product for each of the following reactions: - flex 0 lero Bra, heat (i) e—< + ? a @ yaa + HBr —__, » ou ~ Sy tears. HO—CH, ‘CH.—CH, ro 9 eae hee GH—CH, ‘ eat (ii) +H-Br ——_. OU, Ir cH, a Onna OH Co) J Hee or / HO—CHs clL-cH; ng sit is si [CBSE Marking: 276 Xam idea Chemistry-Xl!cane fllowtng? [cBSE 2023 (s6r2/1)) 3 oer of Cafu gives a single monochloro compound C3H,Ctin bright sunlight? som following compounds in increasing order of reactivity towards $42 reaction : inane, EBromopentane 2-Bromo-2-methylbutane Bro worobenzene has higher melting potnt than those of ortho- eng B in the following : yA : an arrange (com oPe! ‘and meta-isomers? Mg A — +B Br _ ie . Ke = gt ak mage ogame openane reasons the order of reactivity in Sy2 reactions follows the order 3° <2° steric reas CH;—CH,. Br Mechanism: H,CH,C. igre Ca tc anes Bu call CH,CH, “on ol (b) Hi Kas N. ‘CH,CH,CH, HC H,CH,CH,, (4) 3-Methylhexan-3-ol + 108 Q.6. Compound ‘A’ with molecular formula C,H,Br is treated with aq. Kt Teaction depends upon the concentration of the compound “A? only. isomer ‘B’ of this compound was treated with aq. KOH solution, the r dependent on concentration of compound and KOH both. J (® Write down the structural formula of both compounds ‘A’ and *B’ (@ Out of these two compounds, which one will be converted to configuration? CHs oe | : Ans. (i) Compound A: Chace Br Compound B: CH, —Cih— GH cH, (i) Compound ‘B”q 0 i n CH _—C—CH3 ety steP | ; . CHy > ‘ f replac ___ ne three types of replacement of ; ae Hs mroup X by group ¥ as ; CH; ig ae H ¥ Gls _ x ot 3 ° cu, Y (B) ali [ esult in giving compound (A) or (B) or «. is hi i, the only compound obtained? ote i 1 (isthe only compound obtained? roe @ Wh: 4p cand @) are formed in equal proportions? (@ Retention — oa (i) Racemisation 4g, Following compounds are given to you: 0 | promopentane, 2-Bromo-2-methylbutane, 1-Bromopentane gf, (9 Write the compound which is most renctive toviards 5.2 ’ ix? reaction. a " (i) Write the compound which fs optically active. {i Write the compound which is most reactive fowards f-climinato —$—$——— scail mn reaction, a Given eovoponads oxe— = (CBSE Dethi 2017) a “i _ CBSE. ciQ.10. Give reasons for the following: (@ Benzyl chloride is highly reactive towards the Sy1 reaction, (ii) 2-bromobutane is optically active but 1-bromobutane is optically ing (ii) Electrophilic reactions in haloarenes occur slowly. [CBSE Bh Ans. () Benzyl chloride is highly reactive towards the Sy1 reaction becau carbocation formed in slowest step is stabilized through resonance, Ch, CH, 5 §< fae ‘Benzyl cation stabilised by resonance (i) 2-bromobutane is a chiral molecule as it contains an asymmetric atom therefore, itis optically active whereas 1-bromobutane is an molecule as it does not contain asymmetric carbon atom therefore optically inactive. (ii) Halogen in haloarenes withdraws electrons through ~/ effect and re The inductive effect is stronger than resonance effect and causes net el the electrophilic substitution reactions in haloarenes occur slowly. Q.11. Give reasons for the following observations: @ p-dichlorobenzene has higher melting point than those of o; (i Haloarenes are less reactive than haloalkanes towards nucle (i) The treatment of alkyl chloride with aqueous KOH leads to the: Presence of alcoholic KOH, alkene is the major product. Ans, () Itis due to the greater symmetry of para-isomer that fits in the ory meta-isomers. (i As C-X bond in aryl halide acquires a partial double bond bond in alkyl halide is a pure single bond. (Gi Alkonide ion present in alcoholic KOH, is not only a strong, Preferentially eliminate a molecule of HCl from alkyl 12. (@ Why are alkyl halides insoluble in water? @ Why is butan-1-ol optically inactive but butan-2-ol is op (@ Although chlorine is an electron withdrawing group, yeti aromatic substitution reactions. Why? aw Ans. () Thisis due othe inability of alky1 halide molecule to form i molecules, OH BI oe ( CCC pect chin 280 Xam idea Chemistry-Xilhas higher boiling point than butyl bromide, A gxic mixture 1S optically inactive. aR vesence of nitro group (NOs) at o/p positions increases the reactivity of haloa re nucleophilic substitution reactions. ERE oe 1 promide being a straight chain alky] halide has larger surface area than cert butyl bromide. .e surface area, larger the magnitude of the van der Waal’s forces and hence higher is the (a ee ive FT atyl bromide Ie ii) TH o towar" n-Buty! ws w arger poiling point: ») Aracemic mee (0 one enantiomer * ejcally inactive. ¢ of NO} group at o/p position in haloarenes helps in the stabilisation of resulting ~_p and -Teffects and hence increases the reactivity of haloarenes towards nucleophilic ture contains the two enantiomers d and J in equal proportions. As the rotation due is cancelled by equal and opposite rotation of another enantiomer, therefore, it is optical » The presenct carbanion bY ubsttution reactions. (il Long Answer Questions seit jolowing questions are of 5 marke. qu @ Among all the isomers of molecular formula C,H,Br, identify [CBSE 2019 (56/2/1)\ (a) the one isomer which is optically active. (6) the one isomer which is highly reactive towards S2. (© the two isomers which give same product on dehydrohalogenation with alcoholic KOH. (i) Give IUPAC name of the following organic compounds: wae aT . a pink av a cy eo @ . © (CH,),CCH,Br lk ( I i : 0 @ CH;—CH,—CH —CH, ~~ (@) CH; —CH;—CHy—CH,—Br YA il 1-Bromobutave 2-Brombnaaal 4-94. HO)-19) cH; CH ape ity © CHy— cichovn0e gabe glia gat 7a) ateoy pect CHs—Br and CHs Is te se Peaed . ioe he 2+ Bromo 2-methylpropane (i) (a) 2, Hoa 7 ’) 2-chloro, cyclopent-I-ene-L-carboxylic acid dy cay ; @) Writ 2, 2-dimethyl propane 4 BS ‘ite equation for preparation of 1-iodobutane from 1- ‘ne rnepsen ore omega a _ ve towards eli zs ©) Give TUPAC name of elimination reaction and why? a7 7) efi meee cu, i é x ; be(ii) What are enantiomers? Draw the structures of the possible enantiomers . Ans. ()) @)’ CHyCH,CH,CHi GI Nall?" CH CH] CH} Gi () 2-Bromo-2-methylbutane is more reactive as it gives more substituted alke (0) 4-Bromo-4-methylpent-2-ene Stereoisomers which are non-superimposable mirror images of each oth ciel obi 19 STR @) Mirror CH; CH ie I CH,—=CH i i i a7 oxen, HjCH,C : Enantiomers of 3-methylpent-1-ene