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Pitt CHEM 0320 - Electron Donating and Electron Withdrawing Groups
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I. Types of Dienes best for Diels AlderII. Types of Dienophiles best for Diels AlderI. Types of Dienes best for Diels Aldera. Dienes must be substituted with net electron donating groupsi. AKA “Resonance donating” or RD1. Resonance: Possible when the attaching atom of the substituent has a lone pair OR is part of the pi system itselfb. “Net” accounts for the fact that a substituent could be both RD and Iwi. However, the effect of one substituent can take precedence over the other effect of that substituent, and therefore there is a “net” resonance donating or net inductive withdrawing effect.c. Strong electron donating groups always have an attaching atom with at least one lone pairi. Strong electron donating groups are NOT bonded to carbonylsa. CarbonylsWEAKEN electron resonance donation abilityb. It is possible that a real structure can put a positive charge on an electronegative atomi. When there is positive character at one or two atoms in the real structure (resonant structure), resonance donation can be considered moderate1. Attaching atoms have at least one lone pair but also AND bonded to an electron withdrawing carbonyl(weaken resonance donation ability)b. For examples of Electron withdrawing groups and electron donating groups:i. Refer to green handout titled, “Electronic influence of substituents and directly bonded to a pi system”CHEM 0320 1st Edition Lecture 5Outline of Last Lecture I. Behavior of Conjugated Diene in D-ClII. Kinetic Control at LOW TemperatureIII. Thermodynamic Control at HIGH Temperature or Long TimeIV. Diels-Alder ReactionV. Stereochemistry of Diels-Alder ReactionOutline of Current Lecture I. Types of Dienes best for Diels Alder II. Types of Dienophiles best for Diels Alder Current LectureI. Types of Dienes best for Diels Alder a. Dienes must be substituted with net electron donating groups i. AKA “Resonance donating” or RD1. Resonance: Possible when the attaching atom of the substituent has a lone pair OR is part of the pi system itselfb. “Net” accounts for the fact that a substituent could be both RD and Iwi. However, the effect of one substituent can take precedence over the other effect of that substituent, and therefore there is a “net” resonance donating or net inductive withdrawing effect. c. Strong electron donating groups always have an attaching atom with at least one lone pairi. Strong electron donating groups are NOT bonded to carbonyls a. CarbonylsWEAKEN electron resonance donation ability b. It is possible that a real structure can put a positive charge on an electronegative atom i. When there is positive character at one or two atoms in the real structure (resonant structure), resonance donation can be considered moderate1. Attaching atoms have at least one lone pair but also AND bonded to an electron withdrawing carbonyl(weaken resonance donation ability)II. Dienophiles must be substituted with net electron withdrawing groups These notes represent a detailed interpretation of the professor’s lecture. GradeBuddy is best used as a supplement to your own notes, not as a substitute.a. AKA “Inductive withdrawing” groups or Iwi. Induction: Nearby electronegative atoms stabilize uneven electron distribution by shifting electron density through sigmabonds due to electronegative differencesii. Inductive withdrawing effect is ALWAYS there 1. Resonance donation ability is not always there. b. For examples of Electron withdrawing groups and electron donating groups: i. Refer to green handout titled, “Electronic influence of substituents and directly bonded to a pi


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Pitt CHEM 0320 - Electron Donating and Electron Withdrawing Groups

Type: Lecture Note
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