PREPARING ACETANILIDE FROM ANILINE and ACETIC ANHYDRIDE 1. Determine how much aniline you have.

You will need at least 0.05 mole (0.05 mole X 93.12 gr/mole !."" grams# then !."" grams / 1.022 g m$%1 !.5" m$& You don't need (X)*+$Y !.5" m$s, %% -ust something in that range# .ut you do need to /now the (X)*+ amount you use, in order to determine 0ercent yields later.. 12 you have 345( than 0.05 mole, -ust use what you have# .ut determine e6actly the num.er o2 grams, and num.er o2 moles you start with. 2. 7lace the aniline into a 250 .ea/er with a.out 125 m$s o2 water. 8tir in a.out !.3 m$ o2 conc 9*l to o.tain a :*$()5: solution . +his converts the aniline into its hydrochloride salt. )dd a .it more 9*l i2 needed to dissolve any oil dro0lets, .ut avoid a large e6cess. 1t is dou.t2ul that your solution will .e "HIGHLY COLORED", so 2orget the charcoal treatment. 3. 7re0are a.out 25 m$s o2 an a;ueous (water& sodium acetate solution :using a 20 0ercent e6cess:< (0.05 mole = 0.01 mole 0.0" moles o2 sodium acetate< +hen 0.0" mole X 13".0> grams / mole >.1" grams IF you had started with 0.05 moles o2 aniline !. 1? +9( 944D, measure out (0.05 mole = 20@ e6cess& 0.0" moles o2 acetic anhydride< 0.0" mole X 102.09 grams /.mole ".12 grams o2 acetic anhydride. +hen ".12 grams / 1.0>2 grams / m$ 5."" m$ o2 acetic anhydride IF you had started with 0.05 moles o2 aniline. GET YOUR STIRRING ROD READY, AND STAND BY . . .OR, you may opt to u ! t"! t#$$#n% "ot&p'at! (#t" t"! ma%n!t#) t#$ *a$. 5. +ITH CONTINUOUS STIRRING, add the acetic anhydride IN ONE PORTION to the aniline hydrochloride solution, FOLLO+ED IMMEDIATELY .y the sodium acetate solution IN ONE PORTION. . . ,. -!!p t#$$#n% .o$ a m#nut! o$ t(o to %#/! t"! $!a)t#on a )"an)! to )om! to )omp'!t#on. A. *ool the mi6ture .y immersing the .ea/er in an ice slurry# %% then collect the 0roduct on Buchner 2unnel with suction. 12 necessary, remove the magnetic stir%.ar. +hen, trans2er the dam0 0roduct B)*C into its .ea/er, and stir in a .it o2 ice cold water. 5e%2ilter on Buchner, washing the 0roduct with ice%cold water (you are removing the acetic acid .y%0roduct&. >. +he 0roduct may .e le2t o0en to dry until the ne6t la. 0eriod. 12 you wish, you may come in sometime during the 2ew days to determine the m.0., mass, and 0ercent yield. 9. +RITE YOUR DATA IN YOUR NOTEBOO- FIRST, t"!n com0lete the $a.oratory 5e0ort Dorm and turn in your 0roduct along with your $a. 5e0ort Dorm. 12 you can get this done sometime during the ne6t wee/ BEFORE your ne6t la. 0eriod, your la. instructor can return the acetanilide to you, and there will .e no delay in the 0re0aration o2 the 0%chloroacetanilide. IT +OULD BE INTERESTING IF NO ONE STARTED +ITH E0ACTLY 1.12 MOLE OF ANILINE . . . +HY NOT ACCEPT THE CHALLENGE AND USE A DIFFERENT AMOUNT SO YOU CAN DO YOUR O+N CALCULATIONS . . .