310-20 - Organic Lecture Series CH 310 N LECTURE 20...

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Organic Lecture Series 1 CH 310 N LECTURE 20 Textbook Assignment: Chap 18 finish- Homework (for credit): POW 6 posted (Due Mar 7) Today’s Topics: Nucleophilic Acyl Substitution Reactions Notice & Announcements: “Hospitalist - New Trends in Medicine” Antonio Gamboa, M.D. - Hospitalist Mike Romaine, M.D. - Hospitalist Reuben Tovar, M.D. - Hospitalist Organic Lecture Series 2 The The “big picture big picture
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Organic Lecture Series 3 hydrolysis reactions- Organic Lecture Series 4 –Step1: protonation of the carbonyl oxygen gives a resonance-stabilized cation intermediate RC O NH 2 O HH H O CN H 2 R H O H 2 R H C O 2 R H H 2 O Resonance-stabilized cation intermediate + + + + + + Reaction with H Reaction with H 2 O O - Amides Amides
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Organic Lecture Series 5 – Step 2: addition of water (a nucleophile) to the carbonyl carbon (an electrophile) followed by proton transfer gives a TCAI – Step 3: collapse of the TCAI and proton transfer RC OH CO H R NH 3 H C O 3 + R 4 + + + O + O H Reaction with H Reaction with H 2 O O - Amides Amides Organic Lecture Series 6 Hydrolysis of an amide in aqueous base Hydrolysis of an amide in aqueous base requires 1 mole of base per mole of amide – reaction is driven to completion by the irreversible formation of the carboxylate sale CH 3 CNH O NaOH H 2 O 3 - Na + O H 2 N Aniline Sodium acetate N- Phenylethanamide ( Phenylacetamide, Acetanilide) + + heat Reaction with H Reaction with H 2 O O - Amides Amides
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Organic Lecture Series 7 hydrolysis reactions- Organic Lecture Series 8 • The cyano group is hydrolyzed in aqueous acid to a carboxyl group and ammonium ion – protonation of the cyano nitrogen gives a cation that reacts with water to give an imidic acid
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This note was uploaded on 04/24/2011 for the course CH 56255 taught by Professor Colapret during the Spring '11 term at University of Texas.

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310-20 - Organic Lecture Series CH 310 N LECTURE 20...

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