View
5
Download
0
Category
Preview:
Citation preview
Copyright © 2017 John Wiley & Sons, Inc. All rights reserved. Klein, Organic Chemistry 3e
Exam #2 Review
CHEM 20482
Basic Organic Chemistry II
March 18
Copyright © 2017 John Wiley & Sons, Inc. All rights reserved. Klein, Organic Chemistry 3e
Multi-step Reactions: Enolates
Copyright © 2017 John Wiley & Sons, Inc. All rights reserved. Klein, Organic Chemistry 3e
Multi-step Reactions: Enolates
Copyright © 2017 John Wiley & Sons, Inc. All rights reserved. Klein, Organic Chemistry 3e
Summary: Acid/Base Equilibrium
Copyright © 2017 John Wiley & Sons, Inc. All rights reserved. Klein, Organic Chemistry 3e
Aldol Additions
C2H4O C4H8O2
Copyright © 2017 John Wiley & Sons, Inc. All rights reserved. Klein, Organic Chemistry 3e
Aldol: Drawing Products
Copyright © 2017 John Wiley & Sons, Inc. All rights reserved. Klein, Organic Chemistry 3e
Claisen Condensations: Draw Products
Copyright © 2017 John Wiley & Sons, Inc. All rights reserved. Klein, Organic Chemistry 3e
Questions
Copyright © 2017 John Wiley & Sons, Inc. All rights reserved. Klein, Organic Chemistry 3e
Direct AlkylationKinetic vs. Thermodynamic Products
LDA – Sterically hindered
Kinetic product Thermodynamic product
Copyright © 2017 John Wiley & Sons, Inc. All rights reserved. Klein, Organic Chemistry 3e
Malonic and Acetoacetic Ester Synthesis
• Grignard reagents: 1,2 addition
• Gilman reagents and beta-dicarbonyls: conjugate addition
Copyright © 2017 John Wiley & Sons, Inc. All rights reserved. Klein, Organic Chemistry 3e
Conjugate Addition Reactions
• Overall, a 3-part process
(1) formation of enamine
(2) Michael addition
(3) hydrolysis
Copyright © 2017 John Wiley & Sons, Inc. All rights reserved. Klein, Organic Chemistry 3e
Stork Enamine Synthesis
Copyright © 2017 John Wiley & Sons, Inc. All rights reserved. Klein, Organic Chemistry 3e
Questions
Copyright © 2017 John Wiley & Sons, Inc. All rights reserved. Klein, Organic Chemistry 3e
Carboxylic Acid Derivatives
Copyright © 2017 John Wiley & Sons, Inc. All rights reserved. Klein, Organic Chemistry 3e
Patterns
Reduction
LiAlH4 gives primary alcohol for all except amides
Acyl Substitution
C-Cl, C-O, C-S, C-N bonds form and/or break
acid halide → anhydride → thioester → ester, carboxylic acid → amide
Uphill Reactions
- carboxylic acid + thionyl chloride (SOCl2)
- hydrolysis of amides (acid or base catalyzed)
Grignard
Commonly limited to esters and acid halides
Copyright © 2017 John Wiley & Sons, Inc. All rights reserved. Klein, Organic Chemistry 3e
Questions
Copyright © 2017 John Wiley & Sons, Inc. All rights reserved. Klein, Organic Chemistry 3e
Review of Reactions
Acidic conditionsmonohalogenation
Basic conditionsmultiple halogenations
Copyright © 2017 John Wiley & Sons, Inc. All rights reserved. Klein, Organic Chemistry 3e
Review of Reactions
Copyright © 2017 John Wiley & Sons, Inc. All rights reserved. Klein, Organic Chemistry 3e
Review of Reactions
Copyright © 2017 John Wiley & Sons, Inc. All rights reserved. Klein, Organic Chemistry 3e
Review of Reactions
Copyright © 2017 John Wiley & Sons, Inc. All rights reserved. Klein, Organic Chemistry 3e
Review of Reactions
Copyright © 2017 John Wiley & Sons, Inc. All rights reserved. Klein, Organic Chemistry 3e
Questions
Recommended