NineBasicRxnMechWade5

NineBasicRxnMechWade5 - C Lg C H Base C C Lg HB 252-257...

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REACTION MECHANISM Many basic reactions are studied in a two-semester Organic Chemistry course. Probably 80% of these reactions can be described by one of the nine basic mechanisms given in the following table. The remaining reactions occur by simple variations of one of the nine basic mechanisms, by some uncommon mechanism, or an unknown pathway. Table of the Nine Basic Mechanisms No. Name Reaction Steps pages in Wade 5th Edition I Radical Substitution II Electrophilic Addition III Radical Addition initiation propagation termination (one of many) A A ROOR hv or heat A A + H 3 C H + H 3 C H-A H 3 C H 3 C H 3 C-CH 3 C C E Nu C C E C C E C Nu C E 315-316 319-320 initiation propagation termination (one of many) A B ROOR hv or heat A B + A H 3 C H 3 C H 3 C-CH 3 C C C C A | | C A | | A B C B + A + Nu + Nu H 3 C A A A H 3 C A A +
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IV Substitution Nucleophilic Unimolecular, S N 1 and Elimination Unimolecular, E1 V Substitution Nucleophilic Bimolecular,S N 2 VI Elimination Bimolecular, E2 VII Electrophilic Aromatic Subst. No. Name Reaction Steps pages in Wade 5th Edition C C H C C H C Nu C H Nu C Lg C H Lg 238-245 C C H a) S N 1 b) E1 Base C C + HB 248-251 Nu R Lg backside attack Nu R + Lg 225-237
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Unformatted text preview: C Lg C H Base C C Lg + + HB 252-257 leaving groups are anti-coplanar E E H 722-723 E H Base + HB E page 2 + VIII Nucleophilic Addition IX Nucleophilic Substitution a) Acyl S N 2 b) Aryl S N 2 Mechanism Effect on Degree of unsaturation on carbon at the reaction site Catalyst required Reagent Required E + Nu-base I Radical Substitution II Electrophilic Addition III Radical Addition IV S N 1 and E1 V S N 2 VI E2 VII Electrophilic Aromatic Substitution VIII Nucleophilic Aromatic Substitution IX Acyl S N 2 / Aryl S N 2 None Decreases Decreases Decreases None / Increases None None None Increases hv or ROOR Lewis acid Lewis acid hv or ROOR * * * * * * Hints to Recognize which of the Nine Basic Mechanism is Appropriate No. Name Reaction Steps pages in Wade 5th Edition C O 797-800 Nu C O Nu C O H Nu Nu C OH Nu Nu + Nu C Lg O Nu C O Lg * Lg W Nu Nu Lg W Nu Lg W 921-922 750-754 Nu W + Lg page 3...
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This note was uploaded on 02/13/2011 for the course CHEM 2344 taught by Professor Slack,wu during the Spring '11 term at University of Houston.

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NineBasicRxnMechWade5 - C Lg C H Base C C Lg HB 252-257...

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