Lab 12 Preparation of Aspirin and Oil of Wintergreen

Lab 12 Preparation of Aspirin and Oil of Wintergreen - K...

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Unformatted text preview: K Section EXPERIMENT 12 THE PREPARATION OF ASPIRIN AND OIL OF WIN TERGREENzAN ORGANIC SYNTHESIS EXPERIMENT PRE-LABORATORY QUESTIONS 1 The following preparatory questions should be answered before coming to lab. They 5 E are intended to introduce you to several ideas that are important to aspects of the z ; experiment. You must turn in your work to your instructor before you will be : : allowed to begin the experiment. 2 1. The two compounds you are synthesizing in this experiment, acetylsalicylic acid (aspirin) and methylsalicylate (oil of Wintergreen), are examples of organic compounds called esters. a. Define ester. ~ flied i a” «‘1’ a MM *0 5% as s,» écx’ : . .1 kg. :9 \( Oil '0‘ w , H ( ;%List 3 common esters and the odors of'these compounds. , , ‘ Abra-WV“ " V ~ v ,f x... . M97 . @‘g/ i 451 iéwiilflig- 1 9M ‘ i‘ ’z‘; V3 éfliw‘}i r "y w II M (A? “we L f», ‘ ‘3’ ‘ L." Ex: ‘ ( + \> (flew/U; 4?? #33:: aw /. (7/? vvz _ fl / W ' \ I OH 0. Write the equation for the reaction of phenol ‘ s with acetic acid (CH3COOH), and name the products. (343* , ‘ I 'o O \ l I / \ Q I ——‘.§ \ i 4' /\ o H I / ’ A / if} '7' k 'L Q Chem1515~Academic Year 2010/2011 2. Define the following: i a. anti-inflammatory was A .g cm . .n V, - i a w (9 We ML 0V“ 01 WM, ; o r, .A f m M f“ L V M Li; w‘gfi_-La; 3/1? W»va 9m m 3”'r\a‘l”\l‘O/\ b. antipyretic Olr M3 5.3%" ugly“ng r g - c. analgesic 0 if MC _ 0 _ HCOOH CH3CH2CH2COOH O *0 /OH 4. Write the names and formulas of a) the most common ingredient found in engine coolant é/yCon prwcfié, ~D~H \ I E -.' H ‘ ' u . u b) alcohol found 1n moonshme that can cause blindness Walekww’ (NC/OH) f4 Chem1515—Academic Year 2010/201 1 1 2—2 Section C G RESULTS PART ONE: PREPARATION OF ASPIRIN Mass of salicylic acid /, 6% 2 2‘ Observation durmg synthe51s reaction ,1 - o i ax: 1%, , , , New Appearance of aspirin crystals c a? .7 a, f . Mass of 50 mL beaker Mass of 50 ml beaker plus aspir_in Mass of as irin crystals PART TWO : PREPARATION OF OIL OF WINTERGREEN Observation durin s nthesis reaction V I g y [if £5.45 PART THREE: ANALYSIS OF COMMERCIAL ASPIRIN TABLETS BY TITRATION Concentration of standardized NaOH = a / M Tablet # l Tablet # 2 Mass of tablet ’ , g 1529 Initial volume of NaOH " O W“: L. Q m L— Final volume of NaOH /4' 2/ /?' g M L mLofNaOHadded i y M; SIGN -OUT: All equipment is put away, and the student bench is clean and dry. TA M N ~ Date ,9!” Cheml 5 l SfiAcademic Year 2010/201 1 12—7 CALCULATIONS PART ONE : PREPARATION OF ASPIRIN Theoretical yield of aspirin, C9H804 Experimental yield of aspirin, % 2.37? 2,16 “x00 "/5 1 PART THREE: ANALYSIS OF COMlVIERCIAL ASPIRIN TABLETS BY TITRATION r_Mass of acetylsalicylic acid in tablet #1 3 (,IM)(Io/QZL) -_~, ,oo/QZ ‘m/ Na 04‘- : ,QQI7'? ,fl/‘Q” M l K M9,,- lmf i I i—Mass of acetylsalicylic acid in tablet #2 t: .0019; WQW :_ ’34,} 0 flit? W) 1:, Percent of acetylsalicylic acid in tablet #1 55723 ‘0 __ 0 7 W7 x/00/; m /0 Percent of acetylsalicylic acid in tablet #2 I??? 0: cf 3, a, , "* 735:9 84 r k t [0,3194 ww/ Cheml 5 l S—Academic Year 2010/2011 12kg POST LABORATORY QUESTIONS 1. Michael A. Young weighs out 5.32 g. of salicylic acid in a 50 mL flask and adds mL (/3/ aim> of acetic anhydride (density = 1.080 g/mL). Determine the maximum (theoretical) number of grams of acetylsalicylic acid ‘he can prepare. ' ’3 .If a 1 a ,M /1 ‘3 r I J i yi'\ Vifltfiwz‘ 45*, gigjwz; x 3,52Qq V} )W p I \i F 3.5—— ‘f '51 was . [by V141,; 5 5/ a 0 MA“, \QTT‘WWM 7; 2. If Michael obtained 4.86 g. of aspirin, what is his % yield? Briefly, explain why he might have obtained this amount of product. 9 a b ('r “i m at” 3 v 949% t; . ’> Z» a s at flag- .’ {20923, (4:: Com f5! VL 3° [flea/«M: Cw“ 5;, V1.5; r: 433:1}. gag-£3 T s 3. The solubility of aspirin (acetylsalicylic acid ) at 25 °C is 150 g/300 mL. Calculate the molar concentration of acetylsalicylic acid in solution at this temperature. What density assumption can help you in solving this problem? . r . f ,1 L, , , _ a “’25 V ., , w. «14"‘1 w} .. v 4». {fig 33/113523 4 £31.; 1:313 5' “'9’ “ ‘ " ‘" V ; ' f i {5; we 44.; // LO /0a’§~.éwc« X /2‘MJ "‘ F K * 3396M", //, /0i’+'?'31 it; / m hi": ’ 4‘ >4 :5; fl ‘73 q . , ( {J ,iidia'm‘i Chem1515——Academic Year 2010/2011 4. If Ka for acetylsalicylic acid at this temperature is 3.3"): 104, calculatethe pH of the A solution in question #3 (1.0 gram acetylsalicylic acid per 300 mL of water). MW ‘3 I E 5 4 i! in a Wm i y ' O A .4 w / 9' Mn. K2" {@254’7/ [/4754 f , 7ft _ “t? m => 2w Cheml 5 1 S—Academic Year 2010/2011 12__10 ’\ ...
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Lab 12 Preparation of Aspirin and Oil of Wintergreen - K...

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