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SC CHEM 333 - SN1 Mechanism, Carbocations, & SN2 Mechanism

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Lecture 13Outline of Last Lecture I. Meso compoundII. Fischer ProjectionsIII. Properties of Stereoisomersa. EnantiomersCHEM 333 1st Editionb. Diasteriomersc. Nature is chiralIV. Nuclephilic Substitution Reactionsa. Nucleophile (Nuc/Nu)b. ElectrophileOutline of Current LectureI. Common NucleophilesII. Common Leaving GroupsIII. Two different subsitution mechanismsa. SN1i. Carbocations1. Inductive effects2. Hyperconjugationii. Stereochemistry1. Solvolysisb. SN2Current LectureI. Common NucleophilesII. Common Leaving Groups: Good leaving group leaves as a relatively stable, weakly basic moleculeIII. Two different subsitution mechanismsa. SN1Example:i. Carbocations: stabiity of C+. The more substituents, the more stable.Why is the stability like this? It is because of:1. Inductive effects: electron deficient carbon exerts an electron withdrawing effect that polarizes electrions from adjacent sigma bonds, therefore the more alkyl groups, the more stable2. Hyperconjugation: partial orbital overalp of a filled sigma bonding orbital with an adjacent empty orbital. Orbitals that are parallel next to each other can overlap, but orbitals that areperpendicular cannot.Example:ii. Stereochemistry: For SN1 reaction, start with a chiral starting material --> get equal amounts of both enantiomers1. Solvolysis: when solvent is the nucleophile in nucleophilic substitution reactions. Solvent is in excess and solvent takes proton off neautralize product.Example:b. SN2: two things reacting at oncei. Example:ii. Example: transition state is the middle state - cannot be isolated, is justa pathway with high energy. Simultaneous formation C-Nuc bond at same time as C-LG bond is


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SC CHEM 333 - SN1 Mechanism, Carbocations, & SN2 Mechanism

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