Choosing the reagents for a substitution reaction Section 7.9

7.9 Designing Syntheses How do we use what we have learned to set up successful reactions? We must choose appropriate substrate, nucleophile, leaving group, solvent, etc. If you are working with a 1° substrate, the reaction will be SN2, so what are the best conditions? Nucleophile? Leaving Group? Solvent? Copyright © 2015 John Wiley & Sons, Inc. All rights reserved. Klein, Organic Chemistry 2e

7.9 Designing Syntheses If you are working with a 3° substrate, the reaction will be SN1, so what are the best conditions? Nucleophile? Leaving Group? Solvent? Copyright © 2015 John Wiley & Sons, Inc. All rights reserved. Klein, Organic Chemistry 2e

7.9 Designing Syntheses If you are working with a 2° substrate, the reaction could be SN1 or SN2, so what are the best conditions to get the stereochemistry you want, and WHY? Nucleophile? Leaving Group? Solvent? Copyright © 2015 John Wiley & Sons, Inc. All rights reserved. Klein, Organic Chemistry 2e

7.9 Designing Syntheses Some options and choices: Copyright © 2015 John Wiley & Sons, Inc. All rights reserved. Klein, Organic Chemistry 2e

7.9 Designing Syntheses Design a synthesis for the following molecule starting from R-2-chlorobutane Copyright © 2015 John Wiley & Sons, Inc. All rights reserved. Klein, Organic Chemistry 2e