310-11 - 1 CH 310 N T Th 2-3:30 LECTURE 11 Textbook...

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Unformatted text preview: 1 CH 310 N T Th 2-3:30 LECTURE 11 Textbook Assignment: Chapter 16 (cont’d) Homework (for credit): POW 5 posted- Today’s Topics: Reactions with amines: imines & enamines Notice & Announcements: Exam 1– Available in Chem Office Office Hrs: are T & Th 9:30-11 and 1-2 PM for rest of the semester Organic Lecture Series Organic Lecture Series Organic Lecture Series Organic Lecture Series 2 Aldehydes Aldehydes And And Ketones Ketones Organic Lecture Series Organic Lecture Series Organic Lecture Series Organic Lecture Series 3 Drawing Mechanisms Drawing Mechanisms • Use double-barbed arrows to indicate the flow of pairs of e- • Draw the arrow from higher e- density to lower e- density i.e. from the nucleophile to the electrophile • Removing e- density from an atom will create a formal + charge • Adding e- density to an atom will create a formal - charge • Proton transfer is fast (kinetics) and usually reversible 2 Organic Lecture Series Organic Lecture Series Organic Lecture Series Organic Lecture Series 4 Addition of Nitrogen Nucleophiles Addition of Nitrogen Nucleophiles • Ammonia, 1°aliphatic amines, and 1°aromatic amines react with the C=O group of aldehydes and ketones to give imines imines (Schiff bases) • Water is removed by Dean-Stark trap or chemical dehydration (e.g. molecular sieves) CH 3 CH H 2 N H + CH 3 CH=N H 2 O + + Acetaldehyde Aniline An imine (a Schiff base) O An imine (a Schiff base) Ammonia Cyclohexanone + + N H 3 H 2 O O N H H + Organic Lecture Series Organic Lecture Series Organic Lecture Series Organic Lecture Series 5 Addition of Nitrogen Addition of Nitrogen Nucleophiles Nucleophiles Formation of an imine occurs in two steps Step 1: carbonyl addition followed by proton transfer Step 2: loss of H 2 O and proton transfer to solvent C O H 2 N-R H H C O:- N-R O H N-R H C + + O H H H H C O H N-R N-R H C O H H O H H C N-R O H H H An imine + + + + + + H 2 O Organic Lecture Series Organic Lecture Series Organic Lecture Series Organic Lecture Series 6 – a value of imines is that the carbon-nitrogen double bond can be reduced to a carbon- nitrogen single bond + Dicyclohexylamine Cyclohexanone (An imine) Cyclohexylamine O N N H-H 2...
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310-11 - 1 CH 310 N T Th 2-3:30 LECTURE 11 Textbook...

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