Cpt 3 Solomons acids and bases

Cpt 3 Solomons acids and bases - Chapter3...

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Created by Ch. 3 - 1 Chapter 3 An Introduction to Organic Reactions and Their Mechanisms Acids and Bases
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Ch. 3 - 2 2. Acid–Base Reactions v Many of the reactions that occur in organic chemistry are either acid–base  reactions themselves or they involve an acid–base reaction at some stage v Two classes of acid–base reactions are fundamental in organic chemistry Brønsted–Lowry Lewis  acid–base reactions
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Ch. 3 - 3 2A. Br ø nsted Lowry Acids and  Bases v Brønsted–Lowry  acid–base reactions involve the transfer of protons v Brønsted–Lowry   acid   is a substance that can  donate (or lose) a proton v Brønsted–Lowry   base   is a substance that can  accept (or remove) a proton
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Ch. 3 - 4 v Example + H O H H Cl O H H H Cl + Base (H+ acceptor) Acid (H+ donor) Conjugate Acid of  H2O Conjugate Base of  H Cl
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Ch. 3 - 5 2B. Acids and Bases in Water v Hydronium ion (H3O+)  is the strongest acid that can exist in water to any  significant extent: Any stronger acid will simply transfer its proton to a water  molecule to form hydronium ions v Hydroxide ion (HO-)  is the strongest base that can exist in water to any  significant extent: Any base stronger than hydroxide will remove a proton from  water to form hydroxide ions
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Ch. 3 - 6 v Total ionic reaction 2 H O H O H H H Cl + Na H O + + + Na Cl Spectator ions v Net reaction 2 H O H O H H H + H O
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Ch. 3 - 7 3. Lewis Acids and Bases v Lewis  Acids  are electron pair acceptors v Lewis  Bases  are electron pair donors + Cl H δ + δ - NH 3 Cl H NH 3 + Lewis  Acid (e  pair acceptor) Lewis  Base (e  pair donor)
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Ch. 3 - 8 Lewis  Acid (e  pair acceptor) Lewis  Base (e  pair donor) + Cl Al δ + δ - NH 3 Cl Cl δ - δ - Al NH 3 Cl Cl Cl v In Lewis acid–base theory, the attraction of oppositely charged species is  fundamental to reactivity
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Ch. 3 - 9 6. The Strength of Brønsted–Lowry Acids and Bases:  Ka  and  pKa v In contrast to strong acids such as HCl and H2SO4, acetic acid is a much  weaker acid + O H H H O H 3 C O H H 2 O O H 3 C O + At 25oC, in a 0.1 M acetic acid solution,  only about 1% of the acetic acid  molecules ionize
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Ch. 3 - 10 + O H H H O H 3 C O H H 2 O O H 3 C O + v Equilibrium constant ( Keq ) 6A. The Acidity Constant,  Ka Keq  = [CH3CO2 ] [H3O ] [CH3CO2H][H2O]
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Ch. 3 - 11 Ka  =  Keq  [H2O] = [CH3CO2 ] [H3O ] [CH3CO2H] v For dilute aqueous solutions, the concentration of water is essentially constant 
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This note was uploaded on 01/16/2012 for the course PSYCH 373 taught by Professor Marthafaircloth during the Spring '09 term at Campbell.

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Cpt 3 Solomons acids and bases - Chapter3...

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