CHEM 20482 Basic Organic Chemistry II March 18

Copyright © 2017 John Wiley & Sons, Inc. All rights reserved. Klein, Organic Chemistry 3e

Exam #2 Review

CHEM 20482

Basic Organic Chemistry II

March 18


Multi-step Reactions: Enolates


Multi-step Reactions: Enolates


Summary: Acid/Base Equilibrium


Aldol Additions

C2H4O C4H8O2


Aldol: Drawing Products


Claisen Condensations: Draw Products


Questions


Direct AlkylationKinetic vs. Thermodynamic Products

LDA – Sterically hindered

Kinetic product Thermodynamic product


Malonic and Acetoacetic Ester Synthesis

• Grignard reagents: 1,2 addition

• Gilman reagents and beta-dicarbonyls: conjugate addition


Conjugate Addition Reactions

• Overall, a 3-part process

(1) formation of enamine

(2) Michael addition

(3) hydrolysis


Stork Enamine Synthesis


Questions


Carboxylic Acid Derivatives


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


Questions


Review of Reactions

Acidic conditionsmonohalogenation

Basic conditionsmultiple halogenations


Review of Reactions


Review of Reactions


Review of Reactions


Review of Reactions


Questions

CHEM 20482 Basic Organic Chemistry II March 18

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