12.1 Master One-Step Syntheses!!

Chapter 12. Synthesis! ! "

Junha Jeon !
Department of Chemistry ! University of Texas at Arlington ! Arlington, Texas 76019 ! " ! Chem 2321, Fall 13 !

! Substitution! ! ! Elimination! ! ! Addition! ! ! Radical!

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Master One-Step Syntheses!!

" Solving one-step syntheses:! 1." Analyze the structures of the reactant and product.! 2." Assess HOW the functional groups have changed.! 3." Use the reactions and mechanisms you have learned to determine appropriate reagents and conditions.! 4." Check your answer by working out the mechanism.!

Master One-Step Syntheses!! ! Substitution! ! ! Elimination! ! ! Addition! ! ! Radical!

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Case Study!!

12.2 Functional Group (FG) Transformations: Transposition of FG!

Functional Group Transformations: Transposition of FG!

E1/E2!

Markovnikov!

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Functional Group Transformations: Transposition of FG!

Functional Group Transformations: Transposition of FG!

Functional Group Transformations: Transposition of FG!

Functional Group Transformations: Transposition of FG!

Why not acid-catalyzed hydration?!

Functional Group Transformations: Transposition of FG!

Functional Group Transformations: Transposition of FG!

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Functional Group Transformations: Transposition of FG!

Functional Group Transformations: Transposition of FG!

Functional Group Transformations: Transposition of FG!

Functional Group Transformations: Transposition of FG!

12.3 Reactions That Change the Carbon Skeleton! " There are many important molecules that have complex carbon skeletons.! " The ability to design syntheses that produce a desired carbon skeleton is highly prized.! " Some reactions will INCREASE the number of carbons in the molecule.! " Some reactions will DECREASE the number of carbons in the molecule.!

Reactions That Change the Carbon Skeleton: C-C Bond Formation!

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Reactions That Change the Carbon Skeleton: C-C Bond Cleavage!

12.4 How To Approach a Synthesis Problem! ! Is there a change in the carbon skeleton?! ! ! Is there a change in the identity or location of the functional group?! !
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How To Approach a Synthesis Problem!

How To Approach a Synthesis Problem!

How To Approach a Synthesis Problem!

How To Approach a Synthesis Problem!

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12.5 Retrosynthesis (Retrosynthetic Analysis)! " For more challenging, complex multi-step syntheses, it is often helpful to work backwards (retro) in our analysis, although the same basic analysis is performed.! !

Retrosynthesis!

Retrosynthesis!

Retrosynthesis!

Retrosynthesis!

Retrosynthesis!

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Retrosynthesis!

Retrosynthesis!

12.6 Practical Tips for Increasing Prociency!

! Organizing a synthetic Toolbox of Reactions! ! Creating your own synthesis problems! ! ! Multiple correct answers!

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