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Cpt 3 Solomons reaction mechanisms

Cpt 3 Solomons reaction mechanisms - Chapter3...

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Created by Professor William Tam & Dr. Phillis Chang Ch. 3 - Chapter 3 Chapter 3 An Introduction to Organic An Introduction to Organic Reactions and Their Reactions and Their Mechanisms Mechanisms Acids and Bases Acids and Bases
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Ch. 3 - 1. Reactions and Their Mechanisms Almost all organic reactions fall into  one of four categories: Substitutions Additions Eliminations Rearrangements
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Ch. 3 - Substitutions Characteristic reactions of  saturated compounds such as  alkanes and alkyl halides and of  aromatic compounds (even  though they are unsaturated) In a substitution,  one group  replaces   another
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Ch. 3 - Examples H 3 C Br Na OMe MeOH H 3 C OMe Na Br + + Br Br + + H Br H Br h ν + CH 3 Cl AlCl 3 + H Cl H CH 3
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Ch. 3 - Additions Characteristic of compounds  with multiple bonds In an addition  all parts of the  adding reagent appear in the  product; two molecules become  one
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Ch. 3 - Examples Br Br + C C H H H H CCl 4 C C Br H H H H Br Cl Cl + HC CH CCl 4 C C Cl H Cl Cl H Cl 2
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Ch. 3 - Eliminations In an elimination  one molecule  loses the elements of another  small molecule Elimination reactions give us a  method for preparing  compounds with double and  triple bonds
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Ch. 3 - Examples C C H H CH 3 CH 3 C C H H H CH 3 CH 3 Br NaOMe MeOH heat + MeO H Na Br + C C C C H H Br H H Br NaNH 2 heat + 2 2 Na Br + H H H NH 2
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Ch. 3 - Rearrangements In a rearrangement   a molecule  undergoes a reorganization of its  constituent parts Examples C C H 3 C H 3 C CH 3 CH 3 H C C C H H H CH 3 H 3 C H 3 C
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Ch. 3 - 1 1A. 1A. Homolysis and Heterolysis of  Homolysis and Heterolysis of  Covalent Bonds Covalent Bonds Homolysis A B radicals homolytic bond cleavage + A B
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Ch. 3 - 1 Heterolysis A B ions A B heterolytic bond cleavage + A B + A B
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Ch. 3 - 1
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