15. SULPHONIC ACIDS Aromatic sulphonic acids: i. These may be detected by fusion with alkali as follows.

Mix about 0.5gm.of the substance, 3gm. of potassium hydroxide and 5 drops of water in a nickel crucible. Heat the crucible carefully, with occasional stirring, so that the mixture melts and remains in the molten state for about 0 minutes. !ool the melt, add about 5 ml. of water and stir the contents to dissol"e the mass #warm, if necessary$. %cidify the solution & '() gas is e"ol"ed which may be detected by means of a filter paper strip impregnated with acidified potassium dichromate solution. ii. Treat the compound with phosphorus pentachloride and then with phenol in alkaline medium. % crystalline deri"ati"e is obtained.

.!l %r&'(3H %r5()!l

!*H5&(H

%r'()&(&!*H5 &H!l The abo"e formed sulphonyl chloride also reacts with ammonia to form crystalline sulphonamide. %r'o)!l + ,H) %r'(),H) +H!'ulphonamide

16. HIOU!"AS i. Meat a small amount of the substance with ) ml. of a/. ,a(H to boiling for about 30 seconds. !ool and add one drop of !() 0ead acetate&dark brown or black colour. 1,H.!'.,1.1 + 23(H 3)' + #!H3!(($) pb ii. )1,H) + 3)!(3 + 3)' + H)( black precipitate + )!H)!((3

Take a small amount of the compound in a test tube, add to it an alcoholic solution of yellow mercuric oxide, and warm & a black precipitate of mercuric sulphide will or formed. 1,H.!'.,H + Hg( 1,H.!(.,H1 + Hg'

iii.

4use #melt$ a small amount of the compound in a test tube, cool and dissol"e the product in water. %dd a/. ferric chloride solution & a blood red colour will be de"eloped. 1#. H$D!OCA!%ONS %lthough hydrocarbons ha"e no general test, they can be detected by the following tests.

i.

-odine test5 6issol"e 0.) gm. (r )&3 drops of the substance in 5 ml. of ben7ene. To this add 5 ml. of "ery dilute solution of iodine in ben7ene and shake8 solution remains "iolet.

ii.

4riedel & !raft condensation test5 #(nly for aromatic hydrocarbons$. Take 0.5 gm. anhydrous %29f3 in a dry test tube. Heat the test&tube when. %&fc.l:sublimes to deposit on the upper end of the tube. ,ow add )&3 drops of a mixture of e/ual amounts of the substance and chloroform. %llow this solution to come in contact with aluminum chloride & appearance of red, orange, blue or green colour due to the formation of triphen;lmethane dyes indicates aromatic hydrocarbons. <sters. . 'ubstance + drop of Hpn + ,a(H =0fe>&dropwise while warming the?'ebrpink& edor disharges

). Hydroxamic a test r 'ubstaance + ms@AsBic soln of hydroxylamineCHcl. 3 61(.'$ + 4<A 61(.' (4 Meth. 'oln of 3(H, boil, cool, add a drop offe>rD acidiE Fffci. ( .urple G wine colour HB esEg0!onfurmed

Part II D"!I&A I&"S AND H"I! P!"PA!A IONS a'l( o) d(ri*ati*(s o) th( *arious class(s o) compounds S.No Class o) compounds . %cids ). 3. 2. 5. *. K. L. M. 0. .henols %lcohols %ldehydes and 3etones !arbohydrates %mines ,itro compounds %mides, -mides and %nilides 'ulphonic acids Hydrocarbons Suita'l( d(ri*ati*(s %mides, %nilides, esters,bromo deri"IB %cetates, Jen7oates, etc %cetates, Jen7oates, ).2 6initrophenylhydra7lsHeE .henyl hydra7ones, (ximes etc (sa7ones, %cetates,etc. %cetyl, Jen7oyl, Jromo, etc. .olynitro, %mino and its deri"ati"es. Hydrolysis to acids, ,itro, picrates, etc. 'ulphonamides, 'ulphanilides. ,itro

D"!I&A I&"S O+ CA!%O,$LIC ACIDS i. %mide5 'hake the solution of 0.5 gm. &(f the acid with .5 ml. of phosphorus pentachloride or thionyl chloride till the "igorous reaction ceasesN. Aarm the solution gently and then cool it. ,ow add cautiously nearly Ml.(iwe of concentrated ammonia solution, and when the "igorous reaction ceases, stir, cool and filter the product #acid amide$. Aash the acid amide with cold water, crystalli7e from water and dry.. ii. %nilide or .&Toluidide5 'hake the solution of 0.5 mgda!the acid with .5 ml. of &2>OtyNor 'eOiP till the "igorous reaction ceases. Aarm the solution gently and then cool it. %dd nearly one ml. of aniline or p&toluidine #as the case may be$ and shake the reaction mixture "igorously. -f necessary, warm and then cool. 4ilter off

the anilide or p&toluidide, wash it with cold water and crystalli7e it with alcohol and dry. %nilities or pEpluidide5 may also be obtained directly from the acid itself. (ne gram of the acid is relluxed gently under a "ery low flame for half an hour with nearly two grams of the aniline or p&toluidine in a completely dry test tube. !ool the reaction mixture, filter off the product and wash the anilide or p&toluidide with acid. !rystalli7ation may be accomplished by means of alcohol. iii. i". <ster5 1epeat as in acids 4or aromatic acids5 Mix about lg of the substance with 5ml of3f@Qin glacial acetic acid slowly,with constant stirring till yellow color de"elops. 'hake well for 0& 5 mts pour it into 50ml of water with stiring.filter the yellow crystals,wash with water and recrystallise from dil %c(H. D"!I&A I&"S O+ ANH$D!ID"S i. %mide5 Treat the compound with 0ml. of concentrated ammonia solution in a glass stopper llask until a solid is formed, filter off the deri"ati"e, wash with water and recrystallise from water or dilute alcohol.

ii.

%nilide5 #for monobasic acids$5 Meat a mixture of

ml. of aniline and

gm. (f

the anhydride almost to boiling. !ool, add 3 ml. of water and stir the contents with a glass rod. 1ecrystallise the product #anilide$ from water or a/ueous ethanol. #1!($)( + !*H5,H)&&&&&&&&&&&>1!(,H!*H5 + 1!((H D"!I&A I&"S O+ PH"NOLIC H$D!O,$ -!OUP Jen7oate5 6issol"e .0 gm. of the phenol #orCsuspend .0 gm. w@2he amine$ in 5 ml. of acetone and add ).5 ml. of ben7oyl chlorideE %dd 0 ml. of a/. ,a(H gradually with cooling and shaking, then add further 20 ml. of ,a(H solution. 'topper the tube or the flask and shake "igorously #if the flask or tube becomes hot it must be cooled under tap Aater$ till the odour of ben7oyl chloride has disappeared

#which nearly takes )0 minutes$. The final solution should be alkaline to litmus. %cetate deri"ati"e5 Take g of the phenolic compound in a clean and dry test

tube8 add ).5ml of acetic anhydride and a drop of cone, sulphuric acid. !ork the tube, shake it "igorously for 2&5mts and then transfer the mixture to 5ml of cold water, 'tir the contents with a glass rod till the oil solidifies. 4ilter, wash with water and recrystallise from hot water.

D"!I&A I&"S O+ ALCOHOLS i. %cetate5 Take one gm. prthe alcohol, (y&feEanRf fused sodium acetate and 5 ml. of acetic anhydride in a conical flask. 'hake and heat the mixture on a water bath for S2 hours. Transfer the warm solution into K5 ml. of ice cold water with "igorous shaking. 3eep the solution for some time and filter the product. Aash with water and crystalli7e from alcohol. !H3!((,0 1(H + #!H3!($)(&&&&&&&&&&&&&&&T1(!(!H3 + !H3!((H ii. Jen7oate5 Take - ml. of the alcohol, 0ml. of acetone, 5 ml of ben7oyl chloride and 50ml. of a/ueous sodium hydroxide solution in a small flask. !ool, cork and shake the flask "igorously till the odour of ben7oyl chloride disappears. 4ilter off the solid compound. Aash well with water and crystalli7e from alcohol. 6<1-U%T-U<' (4 %06<HV6<' %,6 3<T(,<' O.im( 4or aldehydes and aliphatic ketones5 6issol"e 0.5 gm. of hydroxylamine hydrochloride and 0.5 gm. of the carbonyl compound, heat the mixture on the water bath, add ethanol dropwise with shaking until a clear solution is obtained. !ontinue refluxing until a sample of the reaction mixture gi"es a clear solution on adding to a little ),sodium hydroxide solution #lto ) hours$. !ool the product when the deri"ati"e will crystalli7e out, recrystallistion may be done with ethyl alcohol, a/ueous ethanol

or petrol !H( + Wipmi&&&&&&&&T! H ,(H + H)0 (xime 4or aromatic and some eyeMM ketones5 6issol"eE&gm. of the ketone and 0.* gm. of hydroxylamine hydrochloride in a mixture of 3 ml of ethanol and ml. of water. %dd CmiimtosrN !ool the reaction mixture, add about )0 ml.?Gr water and shake, filter the unchanged ketone #if any$ and acidify the filtrate with dil. <feT #test with blue litmus$. 4ilter off the oxime. .henylhydra7one5 -t should be ;pptet4 that phenylhydra7ones of only the aromatic carbonyl compounds are crystalline in nature while those of aliphatic carbonyls are either oils or possess low m.p 4orEaromatic carbonyl compounds, dissol"e 0.5 gm. of phenylhydra7ine 0NX D hydrochloride and YdTgin. of sodium acetate in 5 ml of water. %dd 0.) to 0.2 gm. of the compound dissol"ed in alcohol to the resulting solution. 'hake the mixture and warm the solution on a water & bath for 0& 5 arts., cool and filter of the deri"ate..1ecrystallise the phenlhydra7one from dilute ethanol, water or ben7ene, NE ! H ( + H),.H,!*H'&&&&&&&&&3! H ,.H,!*H5 D"!I&A I&"S O+ CA!%OH$D!A "S i. (sa7one5 Take 0.5 gm of the powdered in a sugar clean test&tube. -n another test& tube dissol"e 0.2 gm. of phenylhydra7ine hydrochloride and.0.* gm. #Ecrystalline sodium acetate in 2 mlG;9f cold water and add this solution to.sugar8 0oosely cork the test tube, immerse it in a boiling water&bath with periodical shaking, !ool the solution, filter the osa7one precipitate and recrystallise it from 50Z alcohol. DD% i$&>E ii. %cetate5 6issol"e 0.5 mg. of the carbohydrate, 0.5 gm of powdered anhydrous soduirn[ acetate and 3 ml of acetic anhydride in 5 ml. of glacial acetic acid by refluxing on ewater bath. 4urther heat the solution for a period of two hours. .our cautiously the hot reaction mixture in )5m0Gcold water and stir the solution "igorously to decompose the excess of acetic anhydride. 4ilter off the product,

wash with cold water and recrystallise from alcohol. D"!I&A I&"S O+ P!I/A!$ AND S"CONDA!$ A/IN"S 0i1 Ac(t2l d(ri*ati*(. 4or primary amines5 'uspend 0.5 ?irf of the amine in 0. 5 ml. of water and add 0.5 m0, of glacial acetic acid and 0.5 mol. of acetic anhydride dropwise with shakiflt -f the mixture does not warm spontaneously, it is heated cautiously o"er a small flame for 5 minutes. !oolN the reaction mixture, if the oil does not solidify, stir with a glass rod and cool in an ice bath. -f on deri"ati"e separates, the acid in aewtraiist with saturated sodium carbonate solution. 4ilter off the acetyl deri"ati"e and recrystallise from water or a/ueous ethyl alcohol. G 4or mononitroanilines5 Take mg. of the compound and 5 ml. (facetic

anhydride in a 00ml.wide mouthed flask fitted with a reflux condenser. Heat the content to boiling for some time #) minutes for m&and p&nitro and 0 minutes for a iE& nitroaniline$, after refluxing, add )0ml. of boiling water2EEse\of para compound, solid material separates out on the addition of waterE pssol"e it by gradually adding acetic acid with stirring and boil the contents in order to dissol"e the oily material. !ool, filter off the product and recrystallise from dil. %cetic acid 4or secondary amines5 Aarm a mixture of 0.5 gm. of the amine and 0.5 gm. of acetic anhydride on the water&bath for 5& 0 i]tsN. !ool, add 3 ml. of water and stir the mixture until the deri"ati"e is solidified. -t should be noted that sometimes the amine is resistant to acetylating, for which sulphuric acid #as catalyst$ may pro"e ad"antageous. (ne drop of concentrated sulphuric acid is dissol"ed in ml. ;pnacetic anhydride, and one drop of this solution is added to the reaction mixture before warming on the water bath. ii$ Jen7oyl deri"ati"e5 'uspend about 0.5 gm. of the compound in 0ml. of 5Z sodium hydroxide solution in a small conical flask. %dd dropwise lml. of ben7oyl chloride, the flask should be well stoppered and shaken "igorously between additions of the reagent. The reaction mixture should be kept cool throughout the addition. 4inally, shake the reaction mixture "igorously for 5& 0 minutes and filter off the

product. Aash the deri"ati"e with water and recrystallise from alcohol. D"!I&A I&"S O+ NI !O CO/POUNDS Nitro d(ri*ati*(: ,itration with concentrated nitric acid5 %dd nearly gm. of the compound

portion wise with shaking to 5 ml. of concentrated nitric acmpTfST)$ at room temperature #cool under tapEin case the reaction mixture tends to become warm$. 'tir the mixture for 0 minutes and add some crushed ice when the product will be crystalli7ed out either on standing or on scratching the sides of the test&tube with a glass rod. 4ilter off the product, wash with water and recrystallise. D"!I&A I&"S O+ A/ID"S3 I/ID"S AND ANILID"S #i$ Hydrolysis5 Take 0.5 gm. of the compound and excess of )5Z sodium hydroxide solution in a conical flask fitted with reflux condenser. 1eflux the contents until all ammonia has been dri"en off #it takes about half an hour$ and then cool. %dd concentrated hydrochloric acid drop wise till the reaction mixture is strongly acidic and the acid separates out as a deri"ati"e. 4ilter and recrystallise from alcohol. 1!(,H) + H)(&&&&&&&&&&&&&&T1!((H + ,H3 1!(,H1 + H)(&&&&&&&&&&&&&&T1!((H + 1 ,H) #ii$ :anthylamide5 %dd about 0.5 gm. of the substance to nearly K ml. of KZ solution of xanthydrol in glacial acetic acid. 'hake the contents well and then allow to stand for 0 minutes. -f solid deri"ati"e is not obtained, heat the contents on a water bath for about half an hour and then cool when solid xanthylamide is obtained. 4ilter it off and recrystallise from acetic acid. D"!I&A I&"S O+ SULPHONIC ACIDS i. 'ulphonamide5 Take gm. of the dry sulphonic acid and mix it with ) gm. of

phosphorous pentachloride. Heat the mixture on an oil bath at 50^! for about 30 minutes. Ahen the reaction seems to be completed, cool the contents and treat with 5ml. of cold water. 'tir and wash the sulphonyl chloride twice with cold&

water by decantation. ,ow add 5ml. of the concentrated ammonia solution, with stirring. Heat the reaction mixture on a water&bath for 5 to 0 minutes and then cool. The amide will start crystalli7ing out, if not, e"aporate the solution to dryness on the water&bath. 1ecrystallise the deri"ati"e from water or a/ueous alcohol. ii. 'ulplianilmide5 .repare the sulphonyl chloride as abo"e in #i$ method. 6issol"e it in acetone and treat with 0.5 ml. of pure aniline dissol"ed in acetone together with )5ml. .@2HN,a(H solution. 'hake the mixture for 0 minutes, extract with ether to remo"e excess of aniline. %cidy the product ;EaArand feereystaHi'5 from dil. %lcohol,

D"!I&A I&"S O+ H$D!OCA!%ONS i. ,itration of halogeno hydrocarbons5 Take ml.Epr gm. of the compound in a

dry test&tube, add to it .5inl. concH,(3 and .5ml. !onDH)'(2. .lace the test& tube in gently boiling water for 5 minutes with occasional shaking. !ool, add 0ml. of water and shake. .iker off the product, wash with cold water and crystalli7e from alcohol. ii. .icrate5 6issol"e 0.5g of the compound #amine,phenolar aromatic hydrocarbon$ in minimum amount of ethanol. %dd to it nearly 3ml of a saturated solutionof picric acid in ethanol. Aarm the reaction mixture for one minute and then cool it slowly.4ilter off the picrate.1ecrystallise the picrate of amines and phenols from alcohol. !,oHL + !*H)#,()$3 (H _&&&&&&&&&T !ioHL!*H)#,#`$3 (H

Part III LIS O+ O!-ANIC CO/POUNDS AND H"I! D"!I&A I&"S

m.pt5M2^, a&,aptho !olored crystalline solid. 'lightly soluble in water. 1eadily soluble in ,a(H, alcohol, ether etc,,,. . ,o colour with neutral 4e!-3 M;& )*>but gi"es white ppt.

). shake a small amounl of the compound with mixture ha"ing e/ual "olume of $a and 3l and add excess of ,a(H&"iolet colour, rapidly darkening and followed by a precipitate. 3. Take a small amount of the compound in test tube and add to it )ml. of s/3,a(H solution and one drop #Echloroform. Aarm&a blue colour. This test is also gi"en by J&naphthol. 2. Take a small amount of the compound in a test tube, add to it ) ml. of ,a(H, a drop of carbon tetrachloride and a pinch of copper powder. Aarm the contents& blue colour #distinction from J&naphthol$. 6eri"ati"es5 i. ii. iii. i". ". "i. Jen7oate M... 5*^ .icrateM... LM^ %cetate M... 5*^ 6ibromo Mc;;Q 05^ .&,itroben7yl ether M... 20^ 6initroben7oateM...) K^.

.&Tosyl M... LL^ .inksih white crystalline solid. (dourless 'oluble in HsD, ether, alcohol and chloroform.

. Aith neutral a/. 4e!`D sol. -t gi"es blue "iolet colour ). Heat c.c. o the a/ueous solution of the original compound with mE of ,a(H solution and a drop of chloroform till a definite red of "iolet red colour is produced. ,ow fill up the test&tube with water_a red solution appearing "iolet&red on shaking, gi"ing no fluorescence on dilution indicates resorcinol, while a "iolet&red solution changing to deep red, yielding a green fluorescence indicates orcino0 3. Heat a mixture of small amount #rice&grain$ of phthalic anhydride and twice this bulk of the original compound with ) drops of conc& kR''Etintil the mixture appears red&brown in colour. !ool and add a few drops of water followed by ,a(H solution gradually and with shaking until the mixture is alkaline, fskefoutiml. of this solution in a test&tube and ?pll up the latter with water & a yellow&green fluorescence indicates resorcinol. AaterHapC 2. ,o ppt, with lead acetate solution 5. %pply general tests of polyhydric phenols. D(ri*ati*(s: i. ii. iii. i". ". "i. 6iben7oate M... K^

6iben7enesulphonate M... *M^ 6i&p&toluenesulphonale M...L00 3,5&diitroben7oate M...)( 0 .&Tosyl M...L00 6ibromo M...- )^

m.pt5 ))^, p,apththol .ink&brown coloured crystalline solid ha"ing Drrit odour. 'oluble in ,a(H, ether, alcohol and ben7ene8 sparingly soluble in water. . ,o colour with neutral 4e!l3 ). Aith titanic acid in conE. H)'(2 gi"es red colour. 3. -ts solution in ,a(H when warmed with chloroform gi"es a blue coleu #,ote that if YL*<3 is replaced by !!0t no colour is obtained$.

2. .hthalein test & faint green colour with some fluorescence. 5. .erform Test ,o`hnentioned irEnapthol #M.. M2^$. D(ri*ati*(s: 4 i. ii. iii. i". ". "i. %cetate M... K0^ Jen7oaeM... 0K. (ucrateM.. 5*^ .&Toluenesulphonate M... )5C 3,5&6initroben7oateM;aE2O&c ..Tosyl M.. )5^ CA!%O,$LIC ACIDS 33^ !innamic acid,. shining cream Yekrarfl crystals sparingly soluble in water and chloroform. 'oluble in alcohol and ether. . Take ) ml. of the neutral solution of the compound, add an eual "olume of.D dI@.3Mn02 solution and shake&purple colour of permanganate is discharged with the appearance of brown ppt. and bitter&almond like odour of ben7aldehyde. ). ?fe3e ) ml. of the neutral solution o@acid and add ) ml. of alkaline 3Mi(H2 solution. Heat and filter. !ool the fiku'e while crystals of ben7oic acid are obtained.

D(ri*ati*(s: i. ii. iii. i". ". "i. amide M...-2K0 %nilideM... 53> p&ToluidieM... *L^ 6ibromo M... )03^ p&,itraoben7yl ester M.. !sJTM... K5^E) K^

0 N (xalic acid #Hydrated$, #!((H$))H)( r 'oluble in water. . Take about ) ml. of the a/. soluion of oxalic acid, add ) ml of glacial acetic acid and )&3 drops of a/. !a!Hxsolution &white ppt. insoluble in acetic acid but soluble in dil. H!). %dd 5 drops of cone> 2fe'0.# to a small amount of ??>e compound in a dry test&tube and warm the contents gently by rotating the end of the tube o"er a small flame and turn the mouth of the tube periodically to the flameEcharacteristic blue flame of carbon monoxide.$ U&?tf;fo 3tEEot r ? 3. Heat the a/. 'owfion oy&the compound wach acidic X3EBln!hBpurple colour of 3Mn(os discharged. D(ri*ati*(s: 4 i. ii. iii. amide#di$M..2 M^d %nilide #di$ M...)250 .&Toluidide M...)*K0 X _N

) ^ Jen7oic acid Ahite shining cystals, sparingly soluble in cold water but fairly in soluble hot water, alcohol ben7ene, acetone. !H!-3, and !!?0 Juffppt. with neutral a/ueous

4e!-3 solution. 6eri"ati"es5 #i$ %mide M... )L^ #ii$ .&ToluidideM... 5L^E #iii$ %nilideM... *2^ fEctiQ 35^ %cetyl salicylic acid #%spirin$ EE E!((H Take 0.) gm.of.acid and )ml. of dil. ,a(H in a test tube. Joil the contents for 5 minutes. !ool, add dil. H!l&white precipice fer salicylic acid will be obtained 6eri"ati"es5 #i$ amide M... 3L^ #ii$ anilideM.. 3*^ #iii$ salicylic acid M... 55^ #i"$ .& ,itroben7yf eserM... 20^ L5^ succinic acid, !((H !H)!H)!((H, soluble in water, alcohol and acetone 'paringly soluble in ether. # $ Mix a rice&grain of the original compound with double.he amount of resorcinol and ) drops of cone. H)'(2. Yently heat the contents until the mixture attains a red brown colour, cool, ad a few drops of water followed by a/. ,a(H till the solution becomes alkaline. Take out fluorescence$ #)$ 6eri"ati"es5 %mides M.p&)*0 ^ c 8 %nilides&M..&))L ^ c M5Nc, .lithalic acid $ soluble in hot water and !H!-) 'paringly soluble in ether. )$ Mix. % rice grain for the substance with double the amount of phenol in a dry test&tube. %dd ) drops of cone. H)'(2 and heat gently till the mixture attains red& ml. of this solution into another test tube and fill he later with water & ygllow& grcon fill the lattew"itfc'?fter yyellow green

brown colour. !ool, add few drops of wateGfbllowed by gradual addition of a/. ,a(H solution with shaking till the solution becomes alkaline&red colour due 2 phenolphthalein formation8 the colour is discharged on adding as acid. 3$ Mix a rice grain of the substance with double the amount of resorcinol %dd ) drops of coaer Y;>@sC H)'(2 and heat gently till the mixture attains red brown colourfi!ool, add few drops of water and then s/. ,a(H till the solutionEe&semes alkaline. Take out ml. of this alkaline solution in another test&tube and fill up the later with water tyellow green fluorescence, y 6eri"ati"es5 #i$ %mide#di$M... ))0^ #ii$ %nilide#di$M..)50^ #iii$ .&Toluidide#di$M... )0 ^ #b 30^ .hthalic anhydride `b $ -nsoluble in cold water but dissol"es readily in hot water with decomposition. 'oluble in feii72ne and alcohol )$ 1esponds tests mentioned under phthalic acid. 3$ Yi"es fluorescence test 6eri"ati"es5 #i$ Aith 7inc dust and acetic acid gi"es phthalide M... K3^ #ii$ %mide M... 2M^ #iii$ %nil M... ) 0^ #i"$ #%mlicaciiM... K0N %0-.H%T-! HV61(:V %!-6' #!((H$!H)!((H, 3/. At. K0 # $ 'oluble in water and alcohol but less in ether #)$ Aarm a small amount of the acid with con@ H)'(2 e"olution of !( and 00^ !itric %cid H!((H. !H)!

!() takes place and the mixture turns into yellow solution without charring. Heat the abo"e solution for one minute, cool dilute with water, add sodium hydroxide solution followed by sodium nitroprusside solution Rnfeense red colour changing to "iolet on adding YH;!((H. #3$ Ahite crystalline precipitate on boiling the neutral solution with calcium chloride solution #note that no ppt. is formed in cold$ #2$ Jlue colour with p&naphthol in concentrated sullphuric acid #5$ .erform test #2$ mentioned on 1 0M& 0.

#*$ %nd few drops of %g,!c3 solution to the a/ueous solution of thecompound fa white ppd$ in ,H)(H and keep the test tube in boiling water batl#@a sil"er mirror is deposited on the walls of test&tubeNe 6eri"ati"es5 #i$ %cetylM.. 5^

#ii$ %mide#tri$M..) 0^d #iii$ %nilide#tri$m... LM^ K0 Tartaric acid, H((!.!H#(H$.!H#(H$.!((H, </.wt.K5 # $ 'oluble in water and alcohol, 0ess soluble in ether. #)$ !harring along with effer"escences of !( and !0) on heating with concentrated sulphuric acid #3$ 1educes ammonical sil"er nitrate solution #see test ,o. #*$ in citric acid$.. c #2$ To acid solution in water, add one drop ofI@e'Y2 solution, shake and add one drop of IH)0) solution and then ) ml. of ,a(H solution Eintense "iolet colourQ$ #5$ To acid solution and cobalt nitrate solution followed by excess of sodium

hydroxide solution&no colour in cold, blue colour on warming, again colourless wrcooling. #*$ Yreen colour with `? &napthol in cone. 'ulphuric acid the colour changes to orange on dilution. , f% > f[ b K$ Take 3 ml. o&he cetrtrl gnHirUn el.Che aeid, add glacial !H3!((H.y L$ To the a/ueous solution add 5Z solution of ammotmum "anadate, acidify it with dil. !HE!((H&!range coloi% M$ Heat 0.) gm. of acid, 0.) gm. of resorcinol ad ) m`. of cone, H)'(2 in a test tubeRyiolet red colour appearsG 6eri"ati"es5 #i$ %mide #di$ M. -M5Nd. #ii$ %nilide #di$ M...)*2^d. #iii$ %cetyl M... )*^ .H<,(0-! %!-6' </. At 3L. !((H 5LG'alicy lie acid. $ !olourless needle type crystals. 'paringly 'oluble in water b>r dissol"es in hot water, alcohol, ether and ben7ene. )$ 'hake a small amount of the compound with cold water and then add a drop of neutral a/.ferric chloride solution & "iolet colour. 3$ Take a small amount of the compound in a dry test tube, add about 0 drops of methyl alcohol and 0 drops of cone.IH)'(T. Heat the contents gently, cool and pour these contents into a dish ha"ing 5 ml. of wateiGodour of oil of wintergreen #methyl salicylate$.E 2$ %dd ml. of cone. H,(f to a small amount #0.)gm.$ of the acid. .lace the cter of a/. !a!l) solution

and shake "igorouslywiea"y, write crystallie ppt. soluble on boiling with;;nl. of

test&tube in a boiling water&bath for 5 minutes8 remo"e it and dilute with water. Take

out )ml. of this yellow if and dilute with water. Take out )ml. of this yellow solution #plicric acid$E5afce alkaline with a/. ,a(H and add ) drops of ammonium sulphide. .lace the test tube again in a boiling water&bath forth minuter&deep red colour owing to formation of alkali salt of picramic acid $ 6eri"ati"es5 #i$ %mideEpl 3M^ #ii$ %mlideHfc;f 'JTm.pl2*^ #"$ %cpylm.p. 35^ 32^ #iii$ .&Toluidide m.p . 5*^ #i"$

L0 Uanillin 'lightly soluble in water. 'oluble in organic sol"ents like ether, chloroform ben7ene, etc 1e to "iolet colour with 4e!-) E OQ@& UE 6eri"ati"es5 #i$ ),2 & 6initrophenylhydra7one m.p. )K0^ #ii$ .henylhydra7one m.p 30^ #iii$ ),2 6initrophenylhyda7one m.p)*0^ #i"$ (ximen>p, LL^

Jen7iflT .ale yellow. -nsoluble in water. .lace a pellet of 3(H in a dry porcelain dish laced on a heated Aater bath. ,ow place ) rice grains of the compound on the 3(H pellet and carefully pour and ml. of absolute alcohol from the side of the dishEaeep "iolet coloury <"aporate the YOHitettis&to&drynessr&remo"e any imdicogC-"ed 3(H, ml of cone. HEsoE [[ )[ 6eri"ati"es #i$ 6iphenyihydra7one m.p ))5^ #ii$ ),2 6introphenylthdra7one #di$ m.p LM^ #iii$ (xime #di m.p. )3K^$ #i"$ 'emicarba7one #di$ m.p )23^

Jen7oin Vellow although pure bon7okt is colourless insoluble in water. 'paringly soluble in ether. 'oluble in alcohol. $ Take a small amount of the compound and add to it Z.mb of 4ehlingCs solution #e/ual "olumes of ,o.l and ,o.)$ and seconds & red ppt. of!u)( )$ Take about 0.5 gar. of the original compound in a dry test&tube, add to it .)5 ml. of conI@ H,(3 #%"oidE?arge amount of H,(3 which may cause nitrating of ben7oin$. .lace the. test&tube in boiling water bath for about 0 minutes. !ool add 0ml, of water ml. of water Joil the contents for 30

and shake dhc [ & till&ifee red oil solidifies, 4ilter off the;plc yettow productyoen7il$, wash with cold water . X....... gQ>.hI. Ecbbo]B IQ>oduI> HEE"Ci and crystalli7e from alcohol G !%1J(HV61%T<' 2*. 6extrose #d&glucose$, !H)(H.#!H(H$2.!H( $ soluble in water and hot alcohol -nsoluble in ben7enes and ether. )$ 1educes fchHtng solution, BeibnCs reagent and JarfoedCs reagent X3$ Yi"es rapid furfural test, ..2) 2$ %pply test ,o #2$ mentioned under maltose usttig twice the amount of lead acetateGa salmon&pink or rose&pink colour ? 6eri"ati"es #i$ (sa7one m.p )05^ formed on wanning for 2L minutes #ii$ .enta&acetate m.pE& )^ J & 32^ #iii$ (xime m.p 3K^

Ahite shining crystalline solid with characteristic odour. -nsoluble in water but soluble in

alcohol, ben7ene and ether. 'ublimes readily. 6eri"ati"es5 . !haracteristic odour. ). compound + !H!-3 + dry %-!-3 &&&&&&#'reen colour. #i$ ,aphthalene picrate, m.p. 2M^5 place a small amount of the powered

naphthalene in a test&tube and dissol"e it inC;0ml.of cold ben7ene. %dd ) ml.of saturated solution of picric acid in ben7ene and snake, filter off the precipitate8 wash with few drops of cold ben7ene and dry. #ii$ (xidation with conc.H)'(2 in presence of Hg'!B2 gi"es phthalic acid,m.p.lM5^. '-M.0< %M-6<' %,6 -M-6<' 6. %cetamide,!H3!(,H) 'oluble in water and alcohol8 insoluble in either, 6eri"ati"es5 #i$ .icratem.p. 0K^. #ii$ %nilidem.p.i5^. #iii$ :anthylamide m.p.)25^. <. Jen7amide !*H&!(,H) 'paringly soluble in cold water, soluble in hot water, alcohol and ben7ene, sparingly soluble in either. #i$ Mix a small amount of the substance with three times its bulk of dry soda lime. .lace this mixture into an ignition tube and heal&a better almond odour of ben7onitrile. #u$ Hydrolysis is ben7ene aofd,m.p.l) ^5 take 0.5 gm.of the compound l(ml.of a/. ,a(H and some porcelain pieces in a 00 ml.flack fitted with a reflex condenser. 1oil #he contents under reflex condenser for l(mts. !ool and acidity with

cone. M!-. !oel and filter off the product Aash with cold and crystalli7e from water. 6eri"ati"es5 #i$ anilide m.p. *0^ #ii$ :anthylamide m.p. ))3^ 3)^ urea, H).,.!(.,H) . soluble in water, in excess of alcohol8 insoluble in either. ). Jiuret test5 Heat,then cool the compound and then dissol"e in warm a/.,a(H sol. %dd to ) drops of "ery "ery dil. 'olution of !u'!m&&&&&&T .ink colour changing to "iolet and finally deep blue. 3. :anth & hydrol test5 !ompound + 55Z !H3!((H +Eml. of 5Z solution ofxanlh&hydrol im methyl alcohol > the immediate formation of ppt. indicates the presence of urea. 2. Aith sodium hypobromite solution _&Jrisk effer"escences of ,) and !() 5. 6issol"e a small amount of urea in dil. H!0 by heating. !ool, add about 3ml of ,a,dp&b solution add shake. .ass the "apours of this test & tube to another tube ha"ing 3 ml of baryta water. ,ow close the mouth of the baryta water tube with thumb and shake well &baryta water turns milky. *. irea nitrate m.p. *305 Heat a small amount of urea with water until a clear solution is obtained. !ool.add ) ml. of cone. H,(3and again cool. 4ilter off the product, wash with cold water and dry. 6eri"ati"es #i$ (xalate m.p. K ^ #ii$ Aith aniline hydrochloride it forms phenyl urea m.p. 2K^ #iii$ ,,,f&6iacety`m.p 5)^

#i"$ ,.,C&6iben7onyl m.p ) L&))0^d. %M-,( %!-6' #%0-.H%T-!$ )3) d&Ylyeine, H),.!H). !((H . 'oluble in 2 parts of water, insoluble in alcohol and ether. ). %dd one or two drops of 4e!E to the a/ueous solution of the compound& %ed colourG 3. 6issol"e a small amount of the substance in water add to it ) ml. of a/. !opper sulphate solution & blue colour #"ery much deeper than the a/.!u'!c2 solution$. 2. Take ) ml. of the a/tteus solution of the compound, add to it ) drops of phenolphthalein solution, ) drops of a/. ,a(H and ) &3 ml. of neutrali7ed alcohol & disappearance of red colour. 6eri"ati"es5 p #i$ .reparation of ben7oyl deri"ati"e #hippuric acid$, m.p. LK^5 .lace gm.

&(f the compound, 3 gm.c0ff solid ,aH!#B3 and about )0 or!of water in a 00 c>e& tiask. 'hake the contents well and then add .5 ml of ben7oyl chloride. 'hake the wtctifcbd flask "igorously till the odour of ben7oyl chloride disappears. 4ilter off !ool, filter off the product, wash well with cold water and dry. Aash the solid product by stirring it with 0ml. of ben7ene taken in a flask. 4ilter off the product, wash with bene7ene and crystallise from water.

. 'oluble in excess water, sparingly soluble in ether.

). %lkaline solution darkens rapidly in air. 3. .urple colour with 4e!;3 or %g,fl'0 2. 6issol"e a rice grain of the substance in )0 ml. of water. Take out nearly 5 ml. of this solution and add to it ml. of a/. ,a(H followed by ml. of saturated a/. .henol solution. 'hake the contents&deep blue colour within minute.

5. Take a small amount of the substance in test and add to it ) ml. of dichromate mixture. Heat the contents to boiling Gpungent odour of ben7o/uinoneT$ t *. 6issol"e a small amount c 2hc substance in 5 ml. of dil. &H!f cither on shaking or on warming. !ool it, add 5 ml. eene. 'odium hypochlorite solution #,a(H +dE) water$ and shake & yellow ppt. #/uinone chloromide, ni.p. L5^$. 6eri"ati"es5 i. 6iacetyl deri"ati"e, m.p. 50^. To a small amount of the substance add 3 ml. of acetic anhydride and heat the contents to boiling forE0minute with occasional shaking. !ool, add 5 ml. of water and shake. 4ilter off the deri"ati"e, wash with cold water and dry. fcrc;f ii. Monoacetfy m.p *L^. iii. Monoben7oylm.p) *N. i". 6iben7oyl m.p. )32^. TH-(i1<%' r>A.Thiourea, H),.!'.,H) >N I^ "E^^c . 'oluble in cold water sparingly soluble in ether and alcohol. ). Joil a small amount of the substance with ,a(H_,H3 is e"ol"ed. To the solution add 5 ml. water and a drop of 4e!d3 @a blood red colour due to formation of ferric thiocyanate is formed.$ 3. 6issol"e a small amount of the compound by hea'hg with ) ml. of dil. %cetic acid. To the hot solution add ) ml. of potassium 4erro cyanide solution Egreen colour changing to blue.$

2. Heat a small amount of the compound a small flame until the solid melts. !ontinue heating for 5 seconds. 6issol"e the residue by shaking with ) ml. of water and then add ) c>e. a/. 4e!i3. 4ill the test&tube with water and shake Gdeep red solution.$ 5. -ts solution in ,a(H gi"es black precipitate with lead acetate.> G 6eri"ati"es8 #i$ (n heating with ben7yl chloride in alcohol it gi"es ben7yliso & thiourea hydrochloride m.p K2^. #ii$ :anthylm.p. 3*^. #iii$ Thiourea hydrochloride, m.p 3*^.

Ahite. 'paringly soluble in cold & water but soluble in hot water. . %dd a pinch of substance to a solution of sodium bicarbonate & effer"escences of carbon, dioxide are e"ol"ed. ). (n dia7otisation followed by coupling with alkaline g&napthol, it forms an orange&red dye. 3. 6issol"e a small amount of the substance in )^Dc of water by warming. To the hot solution add bromine water with shaking until the solution gi"es the yellow ppt. 2. Heat a small amount of the compound with ) c.c of potassium dichromate&

sulphuric acid mixture to boilingGpungent odour$ 5. Heat the compound with soda &2ime &#characteristic odourG 6eri"ati"es5 #i$ ),2,*&Tribromo m.p. M^.

#ii$ p&,itroaniline #obtained by treatment with cone. H,(3$. M... 2L^. #iii$ 'ulphonamide, m.p. )00^. #i"$ 'ulphonanilide m.p.)00^. !H( E %06<HV6<' KM^ Jen7aidehyde, !H( #o$ (dour of bitter almond. 'paringly soluble in water. 6eri"ati"es5 . oxime m.p. 35^. ). .henylhydra7one m.p. 5L^ 3. ),2 & 6initrophenylhydra7one m.p. ) 2^ tEf 3<T(,<' 5*^ %cetone, !H3!(!H3. Miscible with water. &> Eo #i$ Awhfli + ,a(H in cold gi"es iodoform m.p 6eri"ati"es5 . .henylhydra7one m.p. 2)^ M^.

). ),2 & 6initrophenylhydra7one m.p )L^. 3. 'emicarba7one m.p. LK^. L0^ Methyl ethyl ketone. !H3!(!)H5. Miscible with water. 6eri"ati"es5 . ),2&6initrophenylhydra7one m.p. ). 'emicarba7one m.p. 35^. j.& %1(M%T-! .1-M%1V %M-,<' ff$f L3> %nine, RHs,Hi 'oluble in 0 "ol. (f cold water but freely soluble in organic sol"ents. . Aith bleaching powder it gi"es purple colour. ). <"il odour of phenylisocyanate on warming with ale. 3(H and !HOp. 6eri"ati"es5 #i$ %cetylm.p. 3^. 5^

#ii$ Jen7yolm.p *0^ #iii$ Tribromo m.p L^

#i"$ %7o & p& naphthol8 m.p. 3 ^ Ri<'T-(,' . Ahat is the principle in"ol"ed,in the detection aromaticityQ ). Ahich types of compounds will gi"e positi"e reaction with neutral 4erric chlorideQ

3. Ahat is carbylamine reactionQ 2. Ahat is dia7oti7ationQAhich compound will undergo dia7otisationQ 5. %7o dye test&explainQ *. Ahat happens when monocarboxyllic acids are treated with 4erric chlorideQ K. How will you confirm the presence of 6icarboxylic acidQ L. How can you detect the presence of unsaturationQ M. ,ame some acidic organic compounds. j 0. ,ame some basic organic compounds. . ,ame some neutral organic compounds. ). ,ame some aliphatic and aromatic primary amines., 3. How can you distinguish aldehydes from ketonesQ 2. Ahat is Molisch reagentQ 5. Ahat is TollenCs reagentQ *. ,ame some carbonyl reagents. K. ,ame some easily oxidi7able compounds. L. ,ame some compounds which can reduce the carbonyl reagents. M. Ahat happens when aldehydes are oxidi7ed with 3MH02Q )0. Ahy phenol,naphthol are acidic in natureQ ) . Ahy ammonia is basic in natureQ )). Ahat happens if an ester is hydrolysedQ

)3. Ahat is esterificationQ )2. !onfirmatory test for urea )5. -dentification tests for amino acid. .art -U .1<.%1%T-(,' EG<xercise ,o.-. .reparation of %cetanilide from %niline by acetyiation. 1e/uirements. %nline& ).5 ml %cetylating %cetic anhydride &),5 ml Mixture Ylacial acetic acid&).5 ml .1-,!-.0<5 !hemical reaction.

%mines can readily be acetylated to solid acetyl deri"ati"es using acetylating mixture.#%cetic b! acid bxD mixed due to the high cost ofacetic anhydride$.This reaction is an eg for ,ucleophilic substitution rEacuku0priiline acts as nucleophile and the lone pair elecrons fln the nitrogen atom N&&&&&&&&&&&&&&&&&&&& r>5>'c'dta attacks the carhonyl group of aceticanhydridEand th^ TfE;uftroc product i.s %cetanilide. .rocedure5 Take ).5 ml. of the aniline. ).5 ml. ofacetic anhydride and ).5 ml. of glacial acetic acid in a )50ml. conical flask, 'cake the reaction mixture thoroughly

and then repux it gently for 5 minutes using air condenser. .our the hot mixture with constant stirring to )00 ml. of ice cold water in a beaker. 4ilter the product and wash wfctrr water. 1ecrystalise the curde acetanilide either from boiling water or dilute acetic acid #)0 ml. of jUN acid 20 ml. of water$. %ppearance5 Ahite shining Hakes Vield5 2.5gms. M...5 5^c

Ri<'T-(,' . <xplain the mechanism in"ol"ed in aceElEon. ). Ahich acfcias the nucleophileQ 3. E'n aniline is. ,ucleophilicQ 2. -ndicate the anilide linkage. 5. Afesf aniline is aromaticQ bG<xerchcisc, ). To prepare %spirin #acetyl salicylic acid$ from 'alicylic acid by acefylation. 1e/uirements5 'alicylic acid 5 gms. %cetic anhydride K ml. !ong. 'ulphuric acid 3&5 drops. !hemical reaction5

.1-,!-.0<5 'alicylic acid is a phenolic acid.The phenolic group can easily be acetylated using acetic anhydride.This is an eg of ,ucleophilic substitution reaction. .henolic hydroxyl group of salicylic acid acts as ;pucleophile and the lone pair of electrons on the oxygen atom attacks the carbonyl group of acetic anhydride to form %spirin. .rocedure. Take all the three chemical compounds in the gi"en proportions in a )50 ml. flask. 'hake the mixture thoroughly and warm the reaction mixture at 50 & *0^xBn a water & bath with continuous stirring. %llow the reaction mixture to cool and add nearly )5 ml. of&water, stir thoroughly and filter the product. 1ecrystallise the product from 50Z alcohol or 50Z acetic acid or hot water. %ppearance !olourless needles Vield 5 gms. M.. 3*& 3K^! Ri<'T-(,' . <xplain the mechanismQ ). Ahich is the nucleophileQ 3. ise of %spirin 2. -dentification tests for aspirin <xercise ,o.3. To prepare ),2,* & Tribromoaniline from %nilineEby bromination. 1e/uirements %niline )ml.

Ylacial acetic acid 5 ml. Jromine in glacial acetic acid 3 ml in 0 ml of -ce glacial acetic acid !hemical reaction5

@ .1-,!-.0<5 Jen7ene does not react appreciably with Jk but the presence of acti"ating groups like&,H)en the ring can acti"ate the substitution, can easily form bromo drri"ati"es,when treated with a solution of J>@ in acetic acid. This is an eg of <lectrophilic substitution reaction.'ince& ,H)N is an ortho,para director the incoming bromonium ion#<?/oEropliile$ is directed to form symmetrical tribromo aniline. .rocedure. Take ) ml. of aniline and .5 ml. of glacial acetic acd in a conical flask. .lace the Jask in ice bath and add to it L.2 ml. of bromine water in 0 ml. of glacial acetic acid dropwise with constant stirring through a burette or separating funnel. .our the reaction mixture to a beaker ha"ing excess# 00ml$ of water. 4ilter the product, wash with water and reeryste'tse from alcohol or.rectified spirit. %ppearance !olourless shining Eong needles Vield 5 gm. M. .. )0^! Ri<'T-(,' . <xplain the mechanism of reaction

). Ahich is the electrophileQ 3. Ahat type of group is&,H)Q 2. <xplain how ben7ene is morcstao?cQ bsU( <xereise ,o.2 To prepare p&Jromoaeetanilide from %eetanilide by termination. 1e/uirements5 %eetanilide ) gm. Ylacial acetic acid 5 nil. Jromine in glacial acetic acid 3 ml. of bromine in 0 ml. of glacial acetic acid. !hemical 1eaction5

.1-,!-.0<5 The anilide group present in aeetanilide. is a moderate acti"ating group which directs the incoming bromonium ion to ortho and para positions..ractically only a little amount of ortho product is formed because of steric hindrance of the bulky functional group.The formed ortho product is remo"ed during recrystallisation because it is completely soluble in alcohol or rectified spirit. This reaction is also an eg&for <lectrophilic substitution.E .rocedure. 6issol"e ) gm. (f the aeetanilide in 5 ml. ofglacial aeet4'icid in )50ml. flask. %dd 3 ml. of bromine dissol"ed in 0 ml. glacial acetic acid from a burette ;D a separating funnel to the aeetanilide solution drop by drop with continuous

stirring. %llow the reaction mixture to stand for half an hour. .our the contents to a beaker ha"ing )50 ml. cold water. 4ilter the product, wash with cold water, dry and recrystallise from alcohol or rectified spirit. %ppearance Ahite crystalline compound Vield ).5 gm. M... *K^! Ri<'T-(,' . <xplain the mechanism of reaction. ). Ahich is the electrophileQ <xercise ,o.5 To prepare .henyla7o & p> & naptho@from %niline by dia7oti7ation followed by coupling reaction. 1e/uirements. %niline?. )ml !one. Hydrochloric acid 2 ml 'odium nitrite g

p&,apthol .M5 g 'odium hydroxide 0Z -ce .1-,!-.0<5 %niline is an aromatic primary amine which can undergo dia7otisation to form ben7ene dia7onium chloride in presence of sodium nitrite and con trf. This in turn undergoes coupling reaction with )&napihthtrftelefm phenyl a7o)& naphthol. .1(!<6i1<5 6issol"e .)ml of aniline in 2ml of con H!; and Lml of water ml

in a conical flask?6ia7otise by addition of solution of fg of sodium nitrite in 5ml of water..repare the solution of .M5g of )&naphthol in ml of 0Z ,%(H in a )50ml beaker,@ool the solution to 0D*dy immersion in ice bath or by direct addition ofl0cf5g of crushed ice.'tuyhe naphtho;l solution "igorously and add the cooled 6ia7onium chloride solution "ery slowly.1ed colour >b de"elops and red crystals erfphenyl a7o )&naphthol separates out.Ahen all the solution has been added aHawthe mixture to stand in ice bath for ?0mts with stirring. 4ilter the solution,wash well with water and drain thoroughly.1ecrystallf 7e the product from glacialacetic acid. %ppearance 6eep shining red crystals Vield 3.5 g M.. 3 c Ri<'T-(,' . <xplain 6ia7otisation. ). How does nitrous acid is generatedQ 3. Ahy nitrous acid should be generated in situQ <xercise ,o5 * 6etermination of Mixed Melting .oint %imrTo determine the mixed melting point of the following mixtures and to report on the purity of #-$ and to report whether the product is formed in# )$ . Jen7oic acid D )&,aphthol

). %spiringffld %nilide of %spirin .1-,!-.0E.resence of impurity generally decreases the melting point.so if two compounds ha"ing "ery close melting points are mixed the melting point of the mixture will considerably be lower than that of either.of the two compouns.'o the melting point determination helps to ascertain whether the compound is pure or not. -n some cases the melting point of the compound is "ery close to its deri"ati"e.so it becomes "ery difficult to ascertain by means of melting point that whether the product is formed or not.-n such cases, the deri"ati"e should be mixed with the original compound and the mixture should be sub;ected `p melting point determination. -f the melting point of the mixture is "ery low than that of either of the components it is ascertained that the deri"ati"e is formed, because if the deri"ati"e were pet been formed the mixture will ha"e the same melting point as the original compound. .1(!<6i1<8 !lose one end of the capillary tube, by holding it in the edge of a flame.continuously rotating till it is sealed.-ntroduce nearly 0.5g of the completely dried and finely powdered compound by thrusting the open end of the capillary tube into a small heap of the compound,and tapping, ?aie sealed end of the tube on the bench..ladeEie capillary tube inside the electrically heated melting point apparatus and note down the melting point.6etermine the melting point of pure Jen7oic acid D )&,aphlhol and mixture of the two by placing the tubes beside each other inside the apparatus.6etermine the melting point of %spirin and the product expected to be %nilide of aspirin and for the mixture of the two compounds. 1eport5Melting point of Jen7oic acid H Melting point of )&,aphthol H Melting point of Jen7oic acid D )&,aphthol H Hence the gi"en sample is .i1<G-M.i1< H Melting point of %spirin H Melting point of %nilide of %spirin H Melting point of mixture H

<xercise ,o K5 'tereo Models of (rganic !ompounds s;E; %im5 To construct the bail and stick stereo models of Methane, <thane, %cetylene, %cetone and % Jen7ene and comment on the shape, structure, bond angle, bond length etc. .1-,!-.0<5 !arbon atom can exist in three hybridi7ed states depending on the number of atoms attached to it. !arbon atom is '.f hybridi7ed if attached to 2 atoms or groups. !arbon atom is 'r? hybridi7ed if it is attached to 3 atoms or groups. !arbon atom is '. hybridi7ed if it is attached to ) atoms or groups. 'lfy hybridi7ed carbon is tetrahedral in shape8'.E hybridi7ed carbon is trigonal in shape and '. hybridi7ed carbon is planar. 'o depending on the number of atoms attached to the carbon rtem the stereo model can be build for better understanding of the molecular geometry. .1(!<6i1<5 !arbon atom is black colored and hydrogen atom is white coloured. Ahite sticks are used to represent the bonds between the atoms. Three different carbon atoms are a"ailable to pro"ide tetrahedral, trigonal and planar arrangement. 'elect the

carbon atom according to the number of atoms attached to it. Juild the model by inserting the sticks into the holes pro"ided in the corresponding atom. 4inally report the shape, Molecular orbital picture of the molecule, type of hybridi7ation of carbon, ,umber of sigma bonds and pi bonds, bond length and bond angle. Ri<'T-(,' .Molecular formula for Methane, <thane, ). 'tate of hybridi7ation of carbon in Methane, <thaneEand %cetylene. 3. Ahat is the "alency of carbon, oxygen, nitrogen, hydrogenQ 2. 6efine "alency. 5. 6efine bond angle, bond length. *. 6efine orbital, molecular orbital. K. Ahy acetylene is more reacti"eQ L. Ahy bond length in alkenes, alkynes is, less than alkanesQ M. 6efine atomic weight, molecular weight. </ui"alent weight and atomic number. 0. -i.%! name for %cetylene. 6iben7al acetone by !laisenCs & 'chmidt condensation %-M

To prepare diben7al acetone by claisenCs & 'chmidt condensation .1-,!-.0< %romatic aldehydes condense with aliphatic ketones or with mixed alkyl& aryl ketones in the presence of a/ueous alkali to form a, ;R& unsaturated ketones. -n the preparation of diben7alacetone ) molecules of ben7aldehyde condenses withE[ molecule of diben7al acetone. This reaction is called claisenCs condensation.. .1(!<6i1< . -n a 50ml conical flash place a cold solo of 5.0g of ,a(H pellets in 50ml of H)( and 20ml of alcohol. ). Ahilst swirling the contents of the flash, add a mixture of 5. ml of pure, redistilled !*H5!H( and .Mml of %.1. acetone. 'hake fre/uently and maintain the temperature at )0&)5c for 5min by immersion of the flas3in a bath of cold H)0. 3. 4ilter off the precipitated diben7al acetone at the pump and wash it in cold water to eliminate the alkali as completely as possible. 2. !rude precipitate is recrystalli7ed for ethyl acetate or 1ectified spirit. .ure diben7al acetone h% yellow crystal solidk s ,(T< 'ufficient alcohol is employed to dissol"e the ben7aldehyde and to retain the initially formed ben7al acetone in solution until it has had time to react with the second molecule of ben7aldehyde. .reparation of Jen7anilide %im To prepare and submit Jen7anilide .rinciple %cylation of an %romatic G) amine may be readily achie"ed by using an acid chloride.

fin general, Jen7oyiation of aromatic,amines finds less application than acetylation in preparati"e work, but the process is often employed for the identification D characteri7ation of amines. ? ft b N\EEE -n the schoyen & Jaumen Method of Jen7oy;ation, the amine, or its salt is dissol"ed #or$ suspended in a slight excess of L & 5 Z ,a(H D soln a small excess of ben7oyl chloride is then added D the mixture "igorously shaken in a stoppered "essel hJen7oy`ation proceeds smoothly D the sparingly soluable ben7oyl deri"ati"e separates as a&seiklfr @iE: j .rocedure 'uspend g GR mlpf the substance in )0 ml of 5Z ,a(H soln in a Aell &

corked boiling tube #or$ small concial flask, D add ) ml of Jen7oyl chloride 0.5 ml at a time with constant shaking, XoooU and cooling in water if necessary shake "igorously for 5& 0 min until the ce2Fr&of ben7oyl chloride has disappeared. Make sure that the mixture has an %lkaline 1eaxn. 4ilter off the solid ben7oyl deri"ati"e$ wash it with a little cold water D 1ecrystallise it from ethanol #or$ dil ethah6l. fV,TH<'-' (4 J<,a..H<,(,l(:-M< %im To prepare and submit Jen7ophenone (xime. .rinciple Jen7pphenone condenses with Hydroxyfamine in the presence of excess of ,a(H soln to yield the oxime.

#c*h5$) co + h)noh +Dmm #!*H5$) !H,&(H + Ap+fih(. .rocedure -n a 00ml 1J 4lask filed c a 1eflux condenser place 5 gm of Jen7ophenone, 3 gm of Hyproxylamine Hcl, 0ml of ethanol D ) ml of H;E(, To the resulting mixture now add with shaking D.in portions 5.* gm of solid ,a(H taking care that the reaxn does not become too "igorous ?n so cool the flask under tap waterk. %fter the addition of ,a(H is complete heat the flask under 1eflux&for 0 min. cool and pour the contents of the flask in a beaker containing a soln of 5 ml of cone. Hcl in 50 ml H'(. 4ilter the ppt92 (xime D wash with cold water. 1ecrystalli7erthe product from methanol. M..HB 20] 2)^! Vield H 5 gms.