CHAPTER 18: E.A.S. REACTIONS
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1 CHAPTER 18: E.A.S. REACTNS ELECTRPHLC ARMATC SUBSTTUTNS (E.A.S.) GENERALTES Page 1
2 HALGENATN REACTN GENERAL REACTN (X = Cl, Br) MECHANSM APPLCATNS 2,4-D 2,4,5-T The mostly widely used herbicide in the world Another herbicide Agent range (defoliant used in Vietnam War): equal parts 2,4-D and 2,4,5-T. Much of health effects were due to dioxin in Agent range. Biosynthesis of Thyroxine1 (hormone secreted by the thyroid gland) HN HN HN enzyme H3N HN Tyrosine H H N Tyrosine H H H H H H N Thyroxine 1 Solomons, G., Fryhle, C.B., rganic Chemistry, 8th ed., Wiley, 2004, pp Page 2
3 NTRATN REACTN GENERAL REACTN MECHANSM APPLCATNS N 2 Underwear bomber Dec 25, 2009 HN 3 H 2 S 4 2 N N 2 Pentaerythritol tetranitrate The reason airport security uses full-body scanners. Page 3
4 SULFNATN REACTN GENERAL REACTN MECHANSM FY: You really only need H 2 S 4 because: 2 H 2 S 4 à S 3 + H HS 4 APPLCATNS S 3 (g) S H H 2 S 4 NaHC 3 S Micelle (dirt goes in the middle) H 2 N S 3 (g) H 2 S 4 H 2 N S H H 2 N N N NH 2 S NH2 Prontosil First antibiotic (1932) vertaken in popularity by penicillin in mid 1940 s. Sulfacetamide (Klaron, Plexion) Antibiotic for acne + rosacea Hyrochlorothiazide Diuretic for hypertension, congestive heart failure Ethoxzolamide Anticonvulsant for epilepsy, and treatment of glaucoma Page 4
5 FREDEL CRAFTS ALKYLATN / ACYLATNS (EAS RXNS) ALKYLATN REACTN CH 3 CH 2 X Charles Friedel (left, French) and James Craft (right, American), published this reaction in AlCl 3 X= Cl, Br They predate Nobel Prizes, which began in ALKYLATN MECHANSM WTH 1 RX R METHYL RX WTH 2 R 3 RX ALKYLATN VARATNS Page 5
6 SSUES WTH F.C. ALKYLATNS REARRANGEMENTS Product ratio with 1-chloropropane 2 VER-ALKYLATN CHEM 22 lab in Spring 2010: Br AlCl 3 2 Jones, M., Fleming, S.A., rganic Chemistry, 4 th ed., Norton, 2010, pp Page 6
7 ACYLATN REACTN X AlCl 3 X= Cl, Br ACYLATN MECHANSM APPLCATN Page 7
8 E.A.S. RXNS N SUBSTTUTED ARMATCS Least reactive Most reactive SUBSTTUENT S EFFECT N ELECTRN DENSTY F RNG ELECTRN WTHDRAWNG GRUPS (EWG) Through nductive Effects (effects felt through s bonds): Through Resonance Effects (effects felt through p bonds): ELECTRN DNATNG GRUPS (EDG) Through nductive Effects (s bonds): Through Resonance Effects (p bonds): Page 8
9 RATE EXPERMENTS GENERAL DEA RATE DATA Rates of Nitration 3 H CH 3 Cl CF 3 N 2 Relative Rate: Phenol Nitrobenzene 3 Rate of nitration of toluene from: Solomons, G., Fryhle, C.B., rganic Chemistry, 8 th ed., Wiley, 2004, pp Rate of nitration of chlorobenzene from pp Page 9
10 RTH, META, AND PARA DRECTRS EXPERMENTAL RESULTS Page 10
11 METHYL (,P DRECTR) CH 3 CH 3 CH 3 CH 3 CPh Cl Ph ortho: 9.3% meta: 1.5% para: 89.2% Product composition 4 AlCl 3 CPh CPh METHXY (,P DRECTR) Product composition 5 4 Jones, M., Fleming, S.A., rganic Chemistry, 4 th ed., Norton, 2010, pp Jones, M., Fleming, S.A., rganic Chemistry, 4 th ed., Norton, 2010, pp Page 11
12 NTR (M DRECTR) Product composition 6 RELATVE ENERGES F NTRATN 6 Jones, M., Fleming, S.A., rganic Chemistry, 4 th ed., Norton, 2010, pp Page 12
13 PRACTCE PRBLEM Which type of director (o,p or m) is the chloro group? Product composition 7 REACTNS N MNSUBSTTUTED RNGS rtho-para directors: Meta directors: 7 Jones, M., Fleming, S.A., rganic Chemistry, 4 th ed., Norton, 2010, pp Page 13
14 REACTNS N PLYSUBSTTUTED RNGS STRNGEST ACTVATR DRECTS SMETMES CNSDER STERCS PRACTCE Page 14
15 ARMATC SHFTS N NMR SPECTRA CHEMCAL SHFT + ELECTRN DENSTY a b a c c b d 2H 2H 1H 2H 1H 2H 1H N H PLYSUBSTTUTED RNGS CH 3 Resonance structures, considering methoxy group: Resonance structures, considering carbonyl group: Page 15
16 PRBLEM ü Use resonance structures to show why H d absorbs at a lower frequency (ppm) than H a. ü Assign the 1 H NMR spectrum to hydrogen atoms in the structure. SYNTHESS USNG E.A.S. REACTNS LMTATNS F PREVUS RXNS 1. Friedel Craft Reactions don t work on strongly deactivated rings (halobenzenes K). 2. Friedel Craft Reactions don t work with anilines. 3. Anilines react with Lewis acids (e.g. FeBr 3 ) and thus react unexpectedly. NH 2 Br 2, FeBr 3 Page 16
17 MPRTANCE F THE STEP RDER Design a synthesis to convert benzene into the compound shown below. Route 1: Route 2: NEW REACTNS (F SYNTHETC UTLTY) NTR REDUCTN FY Mechanism: Page 17
18 CLEMMENSEN REDUCTN FY Mechanism: REMVNG SULFNC ACD GRUP S 3 H H +, H 2 CH 3 Cl FY Mechanism: S H H + S H H 2 + S Page 18
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