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Determine the mechanistic pathway and product(s) for the reaction. Justify your responses using the four (4) criteria. Be specific with respect to configuration and major/minor product mixtures where appropriate. H3C CH3 Br CH3 H3C ONa DMSO ?

Determine the mechanistic pathway and product(s) for the reaction. Justify your responses using the four (4) criteria. Be specific with respect to configuration and major/minor product mixtures where appropriate. H3C CH3 Br CH3 H3C ONa DMSO ?

Organic Chemistry: A Guided Inquiry
Organic Chemistry: A Guided Inquiry
2nd Edition
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Andrei Straumanis
Chapter14: Elimination
Section: Chapter Questions
Problem 23E
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The Four Criteria referred to in directions are attached 

Determine the mechanistic pathway and product(s) for the reaction. Justify your responses using the four (4) criteria. Be specific with respect to configuration and major/minor product mixtures where appropriate. H3C CH3 Br CH3 H3C ONa ? DMSO
Transcribed Image Text:Determine the mechanistic pathway and product(s) for the reaction. Justify your responses using the four (4) criteria. Be specific with respect to configuration and major/minor product mixtures where appropriate. H3C CH3 Br CH3 H3C ONa ? DMSO
The Four Criteria 1. Leaving Group A. Meant to be a check for poor LGs, like OH, C, H and F = NO RXN B. Recall that LG-ability tracks with conjugate pKa where poor B-L bases are the best LGs 2. Nucleophile- Choosing between Sn and E A. Better Lewis than Bronsted-Lowry = Sn B. Better Bronsted-Lowry than Lewis= E C. Good/poor at both does both either quickly or slowly 3. Electrophile- Choosing between bi and unimolecular molecularity A. sterically unhindered E + make unstable carbocations= bi B. Sterically hindered E+ make stable carbocations- uni 4. Solvent- Most often used to decide secondary E+ and/or kinetics A. Nonpolar (LDF)- no effect on anything B. Polar aprotic (d/d)- encourage bimolecular pathways C. Polar protic (H-bonds)- encourage unimolecular pathways
Transcribed Image Text:The Four Criteria 1. Leaving Group A. Meant to be a check for poor LGs, like OH, C, H and F = NO RXN B. Recall that LG-ability tracks with conjugate pKa where poor B-L bases are the best LGs 2. Nucleophile- Choosing between Sn and E A. Better Lewis than Bronsted-Lowry = Sn B. Better Bronsted-Lowry than Lewis= E C. Good/poor at both does both either quickly or slowly 3. Electrophile- Choosing between bi and unimolecular molecularity A. sterically unhindered E + make unstable carbocations= bi B. Sterically hindered E+ make stable carbocations- uni 4. Solvent- Most often used to decide secondary E+ and/or kinetics A. Nonpolar (LDF)- no effect on anything B. Polar aprotic (d/d)- encourage bimolecular pathways C. Polar protic (H-bonds)- encourage unimolecular pathways
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-OAc can be used for Sn2 as well 

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