= CH € ~—C = CHCH, ne ot 3,4, 4Trimethylpent-2-ene Q. 10:11. How will you bring about th (More stable, major product 5 loethene (Ili) Propene t ie following conversions ? (i) Ethanol to but-L-yne (ii) Ethane to v (¥) Ethanol to ethyl Rowse tt epFopane (i) Toluene to benzyl alcohol (x) Propene to propyne (i) 1-Chlorobuta ide (vil) Bromomethane to propanone (vil) But-1-ene to but-2-ene 10 M- octane, (Hr. Board 2011) (x) Benzene to biphenyl. Ams. (i) CH\CHOH Sl pte a ay? CH3CH)—Cl ' ros HCL st > 4 _— ‘Chloroethane (A) 4 HC =CH + NaNI Lig. NH,,196K HYCH By y Hy EHC CoNat 9 ene . Sod, acetylide (B) jy ¢ “aoe ye A+B —> CH,CH,—C=CH+NaCl : ac iw But-I-yne 2 Bil Go hy 520-610K KOH ale) 8 )T" Gi) CHy—CHy + Bry —5—> CH,CH,—Br — CH, = CH Ethane Bromoethane Ethene Yt CCl, ‘ SS Oe ‘4 SnICOs, BCH; —CHBr Kons, CH, = CHBr c ‘ae ted 1, 2-Dibromoethane Bromoethene 0 HBr, ROOR AgNOs.C3HGOWHLO Cay OH CH, (i) CHy—CH = CH, BOR, cHs—CH,—CHyBr SCH CH CHL} Propene 7 |-Bromopropane ‘ey FNitropropane bq rou CH; CH,CI 26 C1y/383 K, hv Ag. KOH, A @ ge Kel j| chloride: Benzyl alcohol Toluene Homy : .NH,196 BICC ys HCH NaNH liq. NH cH,—C= () CHy—CH=CH, > CHy—CH—CH, ae eee:Alentivey conversion of uz , : KOH (atc) but the yiel a tind SH FO" cous dehydrohalogenated to vin} Tequire a much stronger bas these steps, can, howeveh s0Ch 3 (vi) CH,CH,OH 0 oxide Ethanol : cHyMe Kenley, CHy it) CHs—Br Foyt O-4 a ceroitl ee ao ‘Mg OH)Br I Bromomethane Ch, Propanone , Se, Cho =r 196K |e” Na* Nabe py Altematively, HC = CH ty sou acetyide . Acetylene ¢ . 3K i 7 pit rss: 18808335, CH,—C—CH, H,O) _ (adn of Propanone KOH (ale). 4 ie CH cH, —CH-CHs =a CH;—CI ICH, ! But-2-ene - He (vit) CH,CH,CH = CH, Sram? CH; * (Major product) But-l-ene 2-Bromobutane (i) 2 CHjCH,CH,CH,CI + 2 Na __Dovether_,. CH,CH,CH,CH,—CH,CH,CH,CHs + 2.Na (Wurtz reaction) 04 1-Chlorobutane n-Octane eset 2Na, Dry ether, A OQ Con ee ORD 2000 Bromobenzene Biphenyl a Oe llTherefore, Gri 4 ae a nee reagents must be prepared under anhydrous conditions. . ie s of Freon-12, DDT, carbon tetrachloride and iodoform. E ns. Refer to Art. 10.10, pages 10/55-10/56. Q. 10.14. Write the structure of the major organic product in each of the foll () CH,CH,CH,Cl + Nat 2", (ii) (CH,),CBr + KOH (iii) CH,CH(Br)CH,CH; + NaOH ame, (iv) CH,CH,Br + KCN (v) CgHsONa + C,HsC1—> (vi) CHyCH,CH,0H + peroxide (vii) CH,CH,CH = CH, + HBr (viii) CH;CH = C(CH,), + HBr —> ; acetone, heat Ans. (i) CHjCH)CH,CI + Nal “Fasano CH,CH,CHpI + NaCl 1-Chloropropane 1-Iodopropane CH; ethanol, heat (Dehydrohalogenation) >-Bromo-2-methylpropane 2-Methylpropene water Br OH 2-Bromobu a Butan-2-ol (Hr, Board 2011) lowing reactions : ethanol, heat ——_—_ aq, ethanol soci, — (Br. Board 2011) \ —————_ oe —C= (ii) (CH,);CBr + KOH CH; Cc =CH,+ KBr +H,0 ne = a __water__, CH, -—CH-—CH C! NaBi (iii) CH,—¢CH CH,CH, + NaOH Fyarotysis Gy CH,CH, + NaBr QUESTIONS AND EXERCISES aeeavm? TEXOOLSeae ag-ethanol CH,CH2—CN + KBr Propanenitrile @v) CH CHAAR pe a CN Brom. oethane (Nucleophilic substitution) Mme 7 H. 6Hs07- Na* + Williamson 2 CoH;—Cl ——a H,—O—-O2Hs + Nach synthesis os a Phenetole Sod. phe noxide Ethyl! chloride t Nucleophilic CH,CH,CH2C! 4 HCIT + SOr OF 2) CH3CHjCH,OH + SOCI Propan-1-ol 2 ~ substitution 1-Chloropropane On i 4 CH3;CH,CH = CH, + HBr peor CH; CH,CH,CH2Br But-l-ene % (Anti—Mark.addn-) |-Bromobutane CH, - Mark.addn, @iii) CH,—CH =C—CH, + HBr Ma expect eo Br thylbutane 2-Methylbut-2-ene 2-Bromo-2-me| _-~ aA ceer ald@ 049, than lattice breaks, therefore, a Bet MT her WOM cone os an the corresponding o- and m= ime 100d 4 ts solubility iower han the correspon 008? angnol €0 but-2-yne OW the following conversions can be c2°7! we (Ht, iu Propene to propan-:9] fo 4-bromonitroberzey *, a premepropane to 2-bromopropane ) a propanenitrile ene to benzyl alcohol (wit) putane £0 3, 4-dimeth oplorol v ieee Alcohol to 2sphenylethanole aeld (x) 2 Sra promis wan niline to chlorobenzene (xi) Ef to 1-pro ropane (0 1-propangy tata Mth propene to 2edlore 2th PPP iy 7 Coro ee 'Ut-I-ene to n-butyl iodide sorabenen 1 p-nitropheno} my, lv) Tsopropyt alcohol to fodoform ont aretane to DUANE ide to isobuty| coy promeronane to Lbromopropane (gig setButy Drom’ 1 bonis zene to diphenyl (2x) Aniline to phenyl isocyanide. AqKOHLA, CH CH;CH,OH (i) CHCH = cH, __HBdpersxide CH,CH)CH:Br Hydrolysis) propio = -addn.) (Anti Mark 1 -Bromopropane By /CCl, oH (lS __y CH, = CHa ~(eiecirophilic addon > i) P/1,, 4 ® CHCH,OH 2", cHgCtsl Fayaonoeaa@— Bihene Propene Ethanol Todoethane nantigltN, | gt “C=C™ Nat NaNHy.lig.NHy | = CH Nat "C=C" Na FR,—CH, 196K Disodium acetylide Br Br _ (Dehydrohalogenation) 1, 2-Dibromoethane i eS CHC 8 C~ oy, CaN 4 (Nucleophilic substitution) But-2-yne Gi) CHCH,CHypr SOMOS _, CH,CH = CH am CH;—CHBr—CH, 1-Bromopropane Déodrohalogenation propene ‘MAM 2-Bromopropane (@) For toluene to benzyl alcohol, refer to Ans. to Q. 10.11 (iv), page 10/83. BryFeBry cone, HNO, + cone. S05 Ra qe NO hee TE ) ©? (Electophilic Cp (Wiration) ‘OgN: Br Benzene “™2SAintion) Bromobenzene 4-Bromonitrobenzene / (naj isomer) L .CH,OH CH,CI CH)CN PP) $0Ch 7" KCNIEIOH 1,0 7 3) nea ———_____» (50, =H (Nucleophiic substation, Benzyl aleotol Benzyl chloride ils cia cou 4 ea a) i wmso CH,COOH Ue “Gray” 2-Phenylethanoic acid(vii) CHACH,OH Ethanol 9 CH CHE —_KON, Bon -H,0 Todethane M#omhic subaiaany? CHCHACN A NI WeNosnie Propanenitie » (viii) YS fener s (Diacorsaiony cucu Aniline ca reaction) Henzenedinzonium chloride (Chlorobentene (i) 2CH,—CH—cH,¢ 3 H, t 20H +2Na Deter cH,cH, —CH—CH—CHCH, +2.NaCl cl (Wurtz reaction) 2-Chlorobutane cH cn, ch, 3,4-Dimethylhexane 1 @ CH—C=cn, —_, 2-Methyl-l-propene (Mark adn) CH, 1 CH. peat cl 2-Chloro-2-methylpropane : KCN, Et(OH-H,0 ie xi) CH,CH,Cl ————_, Ht THs Ge) CH;CH,C) aa? CHCHCN ezrin? CHsCH COOH Ethyl chloride S07") Propaneitile Propanoic acid HBr/RCOOR ee ee (ail) CHJCH,CH = CH, SEBO» CHyCH,CHsCHLB gin acl) But-l-ene 1-Bromobutane CH,CH,CH;CH,! n-Butyl iodide HBr, peroxide KOH (alc), & ——_ (ait) CHy—CH—CH, ~7pzparoalogeaiony a CHa “i= Mark. ai) i ne cl i 2-Chloropropane KOH (aq) of i 2, ORE te oy CHJCHCHBY cod CH,CH,CH, i 1-Bromopropane eee ce COONa +5 Nal +5 H;,0 we + CH,COONa + P 41, +6 NaOH 5 (xiv) CHy>—CH—CH, +41 ef OH Isopropyl alcohol H,0, {9 1S%NaOH, 433 K oe NO} C8 H3804 » = ore sh Oa Cl Gypaner al ‘p-Chloronitrabenzene (major isomer) on{