CHM1C3 Introduction to Chemical Reactivity of Organic Compounds Prof Jon A Preece Teaching Resources Username:

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Presentation transcript:

CHM1C3 Introduction to Chemical Reactivity of Organic Compounds Prof Jon A Preece Teaching Resources Username: Undergradchem Password: Preece57nano

Prof Preece’s Powerpoint Lecture Presentations and answers to questions can be found at… Username: Undergradchem Password: Preece57nano Teaching Resources Queries on course after reading around the subject to Be Specific with the problem(s) in your . Give me three times when you are free to see me. I will you back with a time to see me.

Content of Course Part 1.Resonance and Inductive Effects Part 2. Organic Acids and Bases Part 3.Nucleophilic Substitution Reactions at sp 3 Carbon Centres Part 4. Elimination Reactions Part 5. Hybridisation

Part 0 CHM1C3 Some Organic Chemistry Tools Line formulae Lone pair electrons Bonding pair electrons Curly arrows Prof Preece Office 301 E:

Revision: Line Formula Primary Carbons Secondary Carbons Tertiary Carbons Quartenary Carbons Methyl group Methylene group Methyne group

Revision: The Line and Electrons two centre two electron bond

Revision: Lone Pair of Electrons Line Formulae Lone Pair Lewis Formulae Pairs of bonding electrons in two centre two electron bonds 3D Formulae Tetrahedral structure sp3 hybridised nitrogene

Electrons and Charges Across The Periodic Table Group 3 (B 2s 2 2p 1 ) Group 4 (C 2s 2 2p 2 ) Group 5 (N 2s 2 2p 3 ) Group 6 (O 2s 2 2p 4 ) Group 7 (F 2s 2 2p 5 )

How We Represent Structures in Reaction Mechanisms Group 3 (B 2s 2 2p 1 ) Group 4 (C 2s 2 2p 2 ) Group 5 (N 2s 2 2p 3 ) Group 6 (O 2s 2 2p 4 ) -ve charge = a lone pair of electrons -ve charge = not a lone pair of electrons Group 7 (F 2s 2 2p 5 )

Reaction Mechanisms And Curly Arrows

Lone pairs acting as nucleophiles VERY IMPORTANT: Curly-arrow starts at lone pair of electrons (the –ve Charge) VERY IMPORTANT: Curly-arrow starts at bonding pair of electrons An substitution reaction Lone pair attacks non-proton atom VERY IMPORTANT: Curly-arrows always starts at bonding or non-bonding pair of electrons

Lone pairs acting as bases VERY IMPORTANT: Curly-arrow starts at lone pair of electrons VERY IMPORTANT: Curly-arrows always starts at bonding or non-bonding pair of electrons An Elimination reaction H + and Cl - have been eliminated from EtCl VERY IMPORTANT: Curly-arrow starts at bonding pair of electrons

Lone pairs acting as bases two centre two electron bond Lone pair VERY IMPORTANT: Curly-arrow starts at lone pair of electrons An acid-base reaction Lone pair attacks a proton VERY IMPORTANT: Curly-arrows always starts at lone pair of electrons An Electrophile An empty 1s-orbital

Lone pairs acting as nucleophiles An addition reaction Lone pair attacks a non-proton atom VERY IMPORTANT: Curly-arrows always starts at lone pair of electrons VERY IMPORTANT: Curly-arrow starts at lone pair of electrons An Electrophile An empty 2p-orbital Sextet of electrons around sp 2 B centre Octet of electrons around sp 3 B centre Lewis acid B