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CHEM 104 Experiment 7: Organic Synthesis – Portage Learning Lab Report

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This document is a lab report for Portage Learning CHEM 104 Experiment 7 on organic synthesis. Three syntheses are performed: (1) Synthesis of aspirin (acetylsalicylic acid) from salicylic acid and acetic anhydride with sulfuric acid catalyst – includes heating, water addition to hydrolyze excess anhydride, ice water precipitation, suction filtration, Fe³⁺ test (phenolic groups – salicylic acid gives deep purple, aspirin gives no color change), melting point determination (133.8°C), and percent yield calculation (54.4% – actual 1.42 g, expected 2.61 g). (2) Synthesis of urea from potassium cyanate and lead nitrate to form lead cyanate precipitate, followed by reaction with ammonium hydroxide and heating, then evaporation to obtain urea crystals – melting point 133.2°C, percent yield 75.5% (actual 1.76 g, expected 2.33 g), with urea infrared spectrum analysis. (3) Synthesis of salicylic acid from methyl salicylate (oil of wintergreen) via reaction with sodium hydroxide (saponification) followed by acidification with sulfuric acid to lower pH to 1–2, causing precipitation of salicylic acid – melting point 155.8°C, percent yield 74.8% (actual 1.04 g, expected 1.39 g). Historical notes include Felix Hoffman Jr. synthesizing aspirin in 1893, Bayer naming it aspirin (analgesic, antipyretic, anticoagulant, anti-inflammatory), Frederick Wöhler synthesizing urea in 1828. Suitable for college organic chemistry students learning organic synthesis, recrystallization, percent yield, melting point analysis, and functional group tests.

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CHEM 104 EXPERiMENT 7;ORGANiC SYNTHESiS
i i i i i




i
PORTAGE LEARNiNG EXAM i i i




Name:i
i

Date:i
i

Experimenti #:i 7i
i

Title:i Organici Synthesisi
i

Purpose:i Thei purposei ofi thisi labi wasi toi determinei thei processi ofi synthesizingi variousi carbon-i
containingi organici productsi includingi aspirin,i urea,i &i salicylici acid.i Ini doingi so,i wei werei alsoi ablei
toi calculatei thei percenti yieldi ini eachi ofi thesei experiments.i
i

Procedure:i
i

Parti 1:i Synthesisi ofi aspirini
1. Placedi 2.0i gi ofi salicylici acidi &i placedi iti ini ai flaski
2. 5.0i mLi ofi acetici anhydridei wasi theni addedi toi thei flaski &i mixedi
3. 5i dropsi ofi sulfurici acidi wasi addedi toi thei flask,i whichi actsi asi ai catalysti (helpsi thei reactioni toi
takei place)i &i causesi ai yellowi colori changei
4. Usingi ai Bunseni burner,i heati thei flaski ini ai beakeri ofi wateri fori 15i minutesi
5. Duringi thei heati time,i wei expecti thati onei ofi thei acetyli groupsi toi replacei Hi
6. Mosti ofi thei solidi ini thei flaski dissolvedi duringi thei heatingi processi
7. Addi ai couplei mLi ofi wateri whilei thei flaski solutioni isi stilli hoti toi usei upi anyi unreactedi acetici
anhydridei
8. Allowi thei flaski toi cooli fori ai fewi minutesi
9. Addi 40.0i mLi ofi icei wateri toi thei flaski andi mix,i thisi causesi ai precipitatei toi formi (whitei solidi –i
that’si thei aspirin)i
10. Cooli thei flaski ini ai beakeri ofi icei wateri
11. Whilei cooling,i scratchi thei bottomi ofi thei flaski toi helpi inducei crystallizationi ofi thei solidi
12. Nowi wei needi toi isolatei thei whitei solidi ini thei flaski byi utilizingi suctioni filtrationi
13. Suctioni filtrationi isi performedi byi attachingi thei flaski toi ai wateri aspirator,i whichi sucksi thei airi
outi ofi thei flaski &i filtersi thei aspirini fromi thei solutioni
14. Confirmi thei synthesisi ofi aspirationi byi takingi ai tubei &i placingi salicylici acidi &i ai fewi dropsi ofi
Fe3+i toi thei tube,i producingi ai dark/deepi purplei colori sincei phenolici groupsi arei present;i
however,i aspirini doesn’ti havei ai phenolici groupi (wei usedi alli ofi themi upi ini thei reaction)i soi
therei willi bei noi colori changei wheni thei dropsi arei addedi
15. Determinei thei meltingi pointi ofi thei synthesizedi aspirini byi usingi ai meltingi pointi apparatusi 16.i
Weighi thei driedi aspirini &i theni calculatei thei %i yieldi
i

Parti 2:i Synthesisi ofi Ureai
1. Preparei 2i solutionsi ofi potassiumi cyanatei andi leadi nitrate,i mixingi themi toi createi leadi cyanatei
(whichi willi theni bei preparedi toi makei urea)i
2. Wheni mixed,i noticei thei whitei precipitatei thati isi formedi
3. Cooli thisi solutioni ini ai beakeri ofi icei wateri fori 15i minutesi
4. Afteri cooled,i wei filteredi thisi solutioni toi obtaini thei leadi cyanatei precipitatei (whitei stuffi oni thei
bedi ofi thei filter)i
i
i




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