CHEM<strong>360</strong> Report Book 2012-14Exp.17Experiment 17 Post Lab Questions:1. In Part C, what is the purpose of adding magnesium sulfate to the reaction mixture?2. In the discussion pertaining to the hydrolysis of 4-acetamidobenzoic acid, it wasargued that the presence of the electron-withdrawing carboxyl group in the paraposition could result in the occurrence of some nucleophilic displacement if thehydrolysis was carried out under acidic conditions and an elevated temperature.What would the product of such a nucleophilic displacement reaction?3. Write the balanced equation for the oxidation of 4’-methylacetanilide to 4-acetamidobenzoic acid as carried out in Part C of the synthesis.4. In Part E, what is the purpose of adding 100% ethanol to the reaction mixture? (useequations if necessary to answer this question)89
CHEM<strong>360</strong> 2012-14Table of ReagentsCompoundNameChemicalFormulaSolid (S) orLiquid (L)FormulaWeightMP or BP(C)Density(g/mL)Refract.IndexHazardousProperties*acetanilide CH 3 CONHC 6 H 5 S 135.17 113-115 Toxic, irritantacetanilide,4-methyl CH 3 CONHC 6 H 4 CH 3 S 149.19 149-151 Irritantacetanilide, p-nitro CH 3 CONHC 6 H 4 NO 2 S 180.16 216 Irritantacetanilide, o-nitro CH 3 CONHC 6 H 4 NO 2 S 180.16 94 1.419 Irritantacetanilide, m-nitro CH 3 CONHC 6 H 4 NO 2 S 180.16 154-156 Irritantacetic acid, glacial (17.4 M) CH 3 CO 2 H L 60.05 118.1 1.049 Corrosive, hygroscopicacetic acid, p-ethoxyphenyl C 2 H 5 OC 6 H 4 CH 2 CO 2 H S 180.2 87-90 Irritantacetic anhydride (CH 3 CO) 2 O L 102.09 140 1.082 1.3900 Corrosive, lachrymatoracetone CH 3 COCH 3 L 58.08 56.5 0.7899 1.3590 Flammable, irritantacetone, diethylamino (C 2 H 5 ) 2 NCH 2 COCH 3 L 129.2 64/16mm 0.832 1.4250 Irritantacetophenone C 6 H 5 COCH 3 L 120.15 202 1.030 1.5325 Irritantactivated carbon S (see charcoal)allyl alcohol (2-propen-1-ol) CH 2 =CHCH 2 OH L 58.08 96-98 0.854 1.4120 Highly Toxic, flammableammonia (14.8 M) NH 3 L 17.03 0.90 Corrosive, lachrymatorammonium hydroxide (14.8 M) NH 4 OH L 35.05 0.90 Corrosive, lachrymatoraniline C 6 H 5 NH 2 L 93.13 184 1.022 1.5860 Highly toxic, irritantaniline, 4-bromo BrC 6 H 4 NH 2 S 172.03 62-64 Toxic, irritantaniline, 4-chloro ClC 6 H 4 NH 2 S 127.57 72.5 Highly toxic, irritantaniline, o-ethyl CH 3 CH 2 C 6 H 4 NH 2 L 121.18 210 1.5590 Toxic, irritantaniline, 2-ethoxy CH 3 CH 2 OC 6 H 4 NH 2 L 137.18 231-233 1.051 1.5550 Irritant, light sens.aniline, 4-methyl CH 3 C 6 H 4 NH 2 L 107.16 196 0.989 1.5700 Toxic, irritantaniline, 3-nitro NO 2 C 6 H 4 NH 2 S 138.13 114 Highly toxic, irritantaspirin (see salicylic acid, acetate) CH 3 CO 2 C 6 H 4 CO 2 H S 180.16 138-140 Irritant, toxicbenzaldehyde C 6 H 5 CHO L 106.12 179.5 1.044 1.5450 Hi.toxic, cancer susp.agentbenzaldehyde, 4-methyl CH 3 C 6 H 4 CHO L 120.15 204-205 1.019 1.5454 Irritant (p-tolualdehyde)benzaldehyde,4-methoxy CH 3 OC 6 H 4 CHO L 136.15 248 1.119 1.5730 Irritant, (anisaldehyde)benzaldehyde, 4-nitro NO 2 C 6 H 4 CHO S 151.12 106 Irritantbenzene C 6 H 6 L 81.14 80.1 0.908 1.4990 Flamm., cancer susp.agentbenzene, bromo C 6 H 5 Br L 157.02 155-156 1.491 1.5590 Irritantbenzene, chloro C 6 H 5 Cl L 112.56 132 1.107 1.5240 Flammable, irritantbenzoate, ethyl C 6 H 5 CO 2 C 2 H 5 L 150.18 212.6 1.051 1.5050 Irritantbenzoate, methyl C 6 H 5 CO 2 CH 3 L 136.15 198-199 1.094 1.5170 Irritantbenzocaine,H 2 NC 6 H 4 CO 2 C 2 H 5 S 165.19 88-92 Irritant4-aminobenzoic acid, ethyl ester,benzoic acid C 6 H 5 CO 2 H S 122.12 122.4 Irritantbenzoic acid, 4-acetamido CH 3 CONHC 6 H 4 CO 2 H S 179.18 256.5 Irritantbenzoic acid, 4-amino H 2 NC 6 H 4 CO 2 H S 137.14 188-189 1.374 Irritantbenzoic acid, 3-chloro ClC 6 H 4 CO 2 H S 156.57 158 Irritantbenzoic acid, 4-chloro ClC 6 H 4 CO 2 H S 156.57 243 Irritantbenzoic acid, 3-hydroxy HOC 6 H 4 CO 2 H S 138.12 210-203 Irritantbenzoic acid, 4-hydroxy HOC 6 H 4 CO 2 H S 138.12 215-217 Irritantbenzoic acid, 2-methyl CH 3 C 6 H 4 CO 2 H S 136.15 103-105 See also o-toluic acidbenzoic acid, 4-methyl CH 3 C 6 H 4 CO 2 H S 136.15 180-182 See also p-toluic acidbenzoic acid, 4-nitro O 2 NC 6 H 4 CO 2 H S 167.12 239-241 Irritantbenzonitrile C 6 H 5 CN L 103.12 191 1.010 1.5280 Irritantbenzophenone (C 6 H 5 ) 2 CO S 182.22 49-51 Irritantbenzoyl chloride C 6 H 5 COCl L 140.57 198 1.211 1.5530 Corrosive, toxicbenzyl alcohol C 6 H 5 CH 2 OH L 108.14 205 1.045 1.5400 Irritant, hygroscopicbenzyl amine C 6 H 5 CH 2 NH 2 L 107.16 184-185 0.981 1.5430 Corrosive, lachrymatorbenzyl chloride C 6 H 5 CH 2 Cl L 126.59 179 1.1002 Hi.toxic, cancer susp.agentbiphenyl C 6 H 5 C 6 H 5 S 154.21 69-71 0.992 Irritantboric acid H 3 BO 3 S 61.83 1.435 Irritant, hygroscopicBrady’s Reagent (NO 2 ) 2 C 6 H 3 NHNH 2 L See hydrazine, 2,4-dinitrophenylbromine Br 2 L 159.82 58.8 3.102 Highly toxic, oxidizerbutanal CH 3 CH 2 CH 2 CHO L 72.11 75 Flammable, corrosive90
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