) a el onGanic cHemistay Revision [STD xB. 1) DISTINGUISH BETWEEN THE FoiLowiNe: -o\\- ea ‘* Propanol and propanone + évgo amd eds! + Acetophenone and benzophenone ve + Phenol and benzoic acid Gg M¥g oma Colby + Benzoicacid and ethyibenzoate + Pentan-2-one and pentan-3-one * Benzaldehyde and acetophenone ‘+ Ethanal and propanal + Propanal and propanone : + Methylamine and dimethylamine + Secand tert amines + Aailing and benzylamine + Aniline and N methyl aniline 2) GIVE REASONS + CH,Ci2 haas high dipole moment than CHCIB and CCly ‘+ Dipole moment of cloro benzene is lower than that of cycichexyl chloride. + Ally halides are immiscible with water. + Grignard reagent should be prepared in anhydrous conditions. Chloroform should bestored in dark colour bottles, P- dichlorobenzene has high melting point and lower solubility than ortho and meta isomers ‘+ Haloarenes will undergo only electrophilic substitution reaction. * Vinyl chloride is unreactive in nucleophilic substitution reaction.\ | ‘+ Tert.buty| chloride reacts withaqueous NaOH by SNI mechanism while N- butylehloride reacts by SN2. * Though chlorine isan electron withdrawing group its an orthopara director. ‘+ The treatment of alkyl chloride with aquous KOH leads to the formation of alcoho! + Haloatkanes react with KCN to form alkyleyanide as main product while AgCN forms isocyanides. ‘+ Ethylalcohol is having high melting point and boiling point with ether, ‘+ ortho-nitrophenol is more acidic than ortho-methoxy phenol. + Phenol is having smaller dipole moment than methanol. + Why phenol do not undergo substitution reaction of the ~OH group like alcohol. Out of GsHyOH and H:0 which is stronger acid and why? + Phenol does not react with NaHCO,whereas COOH react + Cyclohexanone forms cyanodydrin in good yield but 2,2, cyclohexanone does not. imethy!* There are two-NH, group In semicarbazide but only one is involved in the formation of semicarbazone. + During the preparation of esters from a carboxylic acd and an alcohol water or ‘esters should be removed as soon as itis formed. * Aldehydes are more reactive than ketone. ‘ ‘+ pa value for aniline is high than that of methylamine, © Ethylamine is soluble in water where as aniline isnot. ‘* Methylamine in water reacts with ferric chloride to precipitate hydrated ferric oxide. * Although amino group is ortho and p directing in aromatic electrophilic substitution reaction ,aniline on nitration gives substantial amount of m-nitroaniline. Aniline does not undergo Friadel-erafts reaction. ‘© Gabriel pthalimide synthesising primary amines. ‘Amines are less acidic than alcohol of comparable molecular masses? ‘Why are aliphatic amines stronger base than aromatic amines? * Primary amines have higher tolling point than 3°amines? * Phenols are more acide than alcohol ‘+ -COOH is stronger than phenol. * Addition reaction at NaHSO, with'/C=0 is useful for purification of aldehyde. + 1amines with Hinsberg's reagent gives amide salt whichis soluble in alkall © Amines are basicin nature © Benzaldehydeis less reactive than propanol. * Preparation of ethers by acid dehydration of secondarylor)tertiary alcohol Is not 8 suitable method, + Acidity of alcohot increases 1°>2°>3° Go bond length in phenol is slightly less than methanol. 3). NAME THE REAGENTS TO BRING ABOUT FOLLOWING CONVERSION: © Hexan-ol to Hexan-al, ‘+ Cyclohexanol to cyclohexanone ‘* _p-fluorotoutene to p-fluorobenzaldehyde. © Ethan nitrile to ethanal + Allyl alcoho! to propenat © But-2-ene to ethanal. © Butan-1-ol to butanole acid, ‘* Oxidation of 1°alcoho! to carboxylic acid + Dehydration of propan-2-o1 to propene. © Butan-2-one to butan-2-ol. ‘+ Bromination of phenol to 2,4,6 tri bromophenol. + Benzyl alcohol to benzoic acd,ORGANIC CHEMISTRY WRITE ABOUT THE FOLLOWING REACTIONS WITH SUITABLE EXAMPLES: Williamson ether synthesis, ‘+ Carbylamine reaction., eke \o'> eLectro lyst s. + Dow's process # Riemer Tremen weachory ‘+ Gattermann-Koch eaction, + stepen’s reduction, = Etard reaction. + Wart reaction . Livexman's seat: 2 Lucan test : 3 Fu Friedel craga's aueghiakion, ANT + Fitz reaction + Aldol condensation + Crossaldol condensation © Decarrvonyladton + + Cannizeao reaction © DiQzolisaen. + Hvzreaction * Acebyladtun weaction. + Fridat crafts reaction = Clemensen reducer ‘+ Finklestein reaction © upelf cishex reductin. Sonora niBkecae eer '* Hoffmann bromamide reaction © * Gabriel phthalimide synthesis i uur on 'S.WRITE THE MECHANISM FOR THE FOLLOWING REACTIONS: + Formation of alcool rom akene + Formation of aene from alcohol + Formation of ether rom slchol + Formation of cyanohyin fom an aldehyde. '* Formation of 1° alcohol from chloro compound(SN,). ‘+ Formation of 3° alcohol from chloro compound(SN,) + Cevage of ethers using Hal 3 pes) : 4 ers. 2 Wuteor itl SRS tom wenckion ately de: 4.An acid (A) reacts with NH; and forms a compound(8),which on heating gives(C}.(C) on treatment wth @ry/NAOH ges ethy amine. Write the names otA8,C Witte allegGations Invobed '5.A compound (A) CsH,0, liberated CO; on reaction with sodium bicarbonate. exists in two forms neither of which is optically active.It yields compound(8) CHieO2 on hydrogenationcompound(8) can be separated into enantiomers. Write equation and structures from(A) and{6) and thelr isomers. 6. An organic compound(A) CaHs on heating with dil H;SO,/Hg™ gives a compound (8) Which ‘can be obtalned from berzene reacting with CHsco cl and any. Aclthe compound (8) when reacts with fodine and NaOH yielai( C) and a yellow compound (0) identify A,8,C,0 and show the 7 formatiod of 8 from A lil) GIVE ONE EQUATION TO SHOW THE ACTION OF THE FOLLOWING REAGENTS. (QD Neoulcad ' C8) sens \rage’ wy Felua- ch) Bralov- se) NaowlBra LY) Bry eely. @ pisar-w (YD atlautene- (2) Nooo Hr? CO _Nanses . &) Walpa\ Basen, w fas Wy] ow © © c ow iO C2) (@ ANY Qo a sa IV) ARRANG THE FOLLOWING IN THE INCREASING ORDER OF THE MENTIONED PROPERTIES. iw) Ze Seren Recent, CUZ Coroll, Cyd Coot’, CHU toot Coad ‘3 cremeon( pant) . Nase azine, beieiteo PRED, Seottro pend, PAE Gay : a rawvcadher, Cydg CORD, CBaniesent gn, Tease) eergen CoaDEe, SGCMBY, Anges CongBr CEM ae: a peclbem Eaters’ Tn anise Traces Aca, Cool, AAS CH, Cows, Clty! ' a crgewo, ERgcHon, CHOCHS | Cae C SAE Prepon 01 , Rtighlta, Cede NHB, Celbe Benraldehyde, Po fouludoldehyde-, P Calso8, CRY NY, Cals SHR Leading &S Acetaldehydt, GAcakone, Aj rend -vurryi Cerone, YC Pooky) methy) Ketone Creactiarty towards Wen Chany EADgNs, Gan | cers a, CEhaOhanty [_ Basic Srecagh Cals Ya, Rang) wu, (Cabedan, Cedsr¥a. Tesi e srrengt Sols ma, Ganslans, Catig wis T solubibty]wy 3) (e:5) A” @ &) x a) \y) ) yay Y / ‘CONVERT THE FOLLOWING: 1) propyl chloride to isopropyl chloride. bane: to bromobenzene.clmethy bromide to acetone.) ethylchloride to propanoicack.) Ethanol to But } yne.fl2chloro propane to L-propanol stert. Butyl bromide to iso butyl fest bromide.s}phenyt + ethane (styrene) to benzoic acid. Hi) propene to ‘Propan2 ol. !)methyl magnesium bromide to 2 methyl propan 2 ol) phe to bbenzoquinone.kjphenol to aspirin.) phenol to m- bromo phenol: m} acetaldehyde to But 2-en aLrn)Acetc acd to acetaldehyde. O}Butan 2-0 to butan-2 one placetaldehyde to ethane acetic acid to ethyl amine. ethyne to acetaldehyde. 5] acetophenone to 2 phenyl2 butanol) Ethanolc acd to Methanamine u)Hexanitrile to amino pentane.v)methanol to ethanolc acd. w}propencic acid to ethanolcacid xlanline to benzylalcohol (y) nitrobenzene to toluene. COMPLETE TRE Folrowine' yo o CeWg9, Len Ces ¥a > qu, Syof eho the .\ ho 1 CAA males g lyr? Sos] arevo¥s 2 cago + 4 4 ‘gro, a Bylo 57 nang ihe 7 Sorta, 2 o-sc esod 1 wal q tole. 7 ee 2 @ A WHOS, 9 4 7 a) ale Lor ABT Chackych cr, SO St Wer| peroxide 9 Ve Kol ? aigerycdg cra WES 9 TES v0" ° NoowlT2, Aveeno tcwZMge ——? 2 —s >? Nasty, AD curevy-C8 -CvO M BOD (e] Steetsq Neots 7 ® ; ; d “ cay A AN Ces SA\W8_ 56 ona, Veer 5 Wyler & #3 8% Sa a ;QAive -reanon: et amb: 2a, aved. Allyl aed wemaytie ‘rekowards the 8h). hamday ; ® Sry, a Dok ‘Teac With owen, ) why oo} ahtm Br es, gives GF OP BAF BL. water aye, Big. wR beumophenot. @® Cavs | ariuurto Fungi Vanuypmier | cy, ol = ‘ id ( Skeg enluride tO Prepamae axe © fe) 8] H a-cnwbotene bo B44, Asmara exon CH gamete -\-Prepenes He D-ehleror Bemmeahy) PTO ® Benryy alcohor bo a- phenyl eMramdcaatd G 140 CF! Abcohel 40 Lodofurm: ©) A-Trevme pega be \ Pewee Peon erevaby amide to Tacbuby ‘orem Bonric aud VO Bemraiiclehyde: Benreac ail FO ane Wiero bUnzylarchol: GD Benrens to Phemyeceticors et @® erqomone Yo prepens GD venowitile re Veen ci Aeretaad Weromateuns Yo Aimethyg) avoning (Wb) prepa ct Lav ethamcie 287 Ethamcicaud fo ohana @ genramide to bowen Bomrerc aust tO aniline Aine to B14 br pei beeen Purr eM EP (ayy 3B \etigl aniline Ante BEN rOMME. gay 4 nhinot oly ‘* Oxeove's proas> Rabies Sheu high venckvihy ro a Bromo bomen eet @® Benzene +O amine Qenzense sr NN, BL metal amitene ® ay, -a wee or" Vib: Baim a7