A amides carboxylic acids hydrolysis may be acid or

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A. Amides → Carboxylic Acids (Hydrolysis) May be acid or base catalyzed. Base catalyzed is slow due to poor leaving group.
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176 B. Amides → Amines (Reduction) Will form an amine. Poly amides and Polyesters Step Growth Polymers.
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177 A. Polyamides (nylons!) Wallace Carothers at DuPont. B. Polyesters Other important and current polymers.
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178 Spectroscopic Data NMR 1) Protons on carbons appear around 2.0-2.5 ppm 2) N-H protons of 1 o and 2 o amides appear around 7.5-8.5 ppm 3) In 13 C-NMR , C=O appears around 160-180 ppm for carboxylic acid derivatives. It occurs around 200 ppm for aldehyde and ketones. IR 1) Have a strong C=O absorption between 1600 and 1850 cm -1 . Acid Anhydrides have two absorptions in the carbonyl region. 2) Acid chlorides have absorptions around 1800 cm -1 3) 1 o amides have two N-H stretches around 3200-3400 cm -1 4) 2 o amides have one N-H stretch around 3200-3400 cm -1
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179 O O O Cl O O O N O Cl O NHCOPh O O Practice Quiz for Chapter 21 1. Give the IUPAC name for the following compounds. a) b) c) d) e) f) g)
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180 2. Draw the structures of the following compounds. a) vinyl formate b) tert-butyl acetate c) cyclohexanecarboxamide d) benzoic propanoic anhydride e) octyl butanoate f) 3-methylhexanoyl chloride
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181 NH 2 O N O 3. Using IR spectroscopy, determine how you would distinguish between the following compounds. 4. Determine the structure of the compound based on its spectroscopic data. a) C 4 H 7 N IR: 2250 cm -1 NMR: 1.8, t, 3H 1.7, m, 2H 2.4, t, 2H b) C 8 H 14 O 3 IR: 1810 cm -1 and 1770 cm -1 NMR: 1.25, d, 12H 2.65, septet, 2H c) C 10 H 12 O 2 IR: 1740 cm -1 NMR: 1.2, t, 3H 2.4, quartet, 2H 5.1, s, 2H 7.1-7.5, m, 5H
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182 5. Predict the products of the following reactions. No reaction is a possible answer.
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183 O O O O O O O Ph O O Ph O O OH O Cl O 6. Which of the following substrates cannot be used as an immediate precursor to synthesize an ester?
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