Chemistry 2213: Visual Cheat Sheet for Carboxylic Acids and Derivatives
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Purpose - This document contains the reactions related to the unit “Carboxylic acids” and
“Derivatives of carboxylic acids”
How to use this review - Before the exam, we recommend that you attempt to familiarize
yourself with all the reactions covered in the Organic Chemistry 2213 course. This document is a
visual cheat sheet summarizing the reaction details and electron movements for the reactions
taught in the last two units of the course.
Most of the reactions will have supplementary notes to describe in-detail the specifics of the
reaction.
We wish you the best of luck on your exams!
Disclaimer: This visual assumes that you have thoroughly reviewed your material. This cheat
sheet is a way for us to provide all the mechanisms in one area so you can avoid flipping through
your notes.
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1
Carboxylic Reactions
Acid-Base Reactions
Note:
●
Production of a weaker base and acid
●
Equilibrium reaction, does not react all the way
Reduction of Primary Alcohols
Note:
●
LiAlH4 is a strong reducing agent
2
Decarboxylation of beta-keto acids
Note:
●
Carbonyl must be in the beta position
Decarboxylation of beta dicarboxylic acid
3
Fischer Esterification
Mechanism:
Note:
● Acid Dependant Carbonyl Activation
● Nucleophilic Attack on carbocation carbon
● H2O leaving Group Ejection by Oxygen “Nucleophile”
4
Lactone Formation (Cyclic Esterification)
Acid-Chloride Formation
Mechanism:
5
Acid Derivative Reactions
Anhydride Hydrolysis
Note:
● 2nd most
reactive
● Anhydrides also react rapidly with water, but slower than acid halides. No catalyst is
needed, but one can be helpful
● Result is a carboxylic acid byproduct
6
Anhydride Hydrolysis: Carboxylation
Ester Hydrolysis: Carboxylation
Note:
●
●
●
●
Require catalyst: heat + acid or base
Tetrahedral carbonyl addition intermediate formed
In base: product is carboxylic acid salt + alcohol
○ Saponification, provides good yields because salt precipitates
In acid: product is carboxylic acid + alcohol
7
Amide Hydrolysis: Carboxylation
Note:
●
●
●
Amides are very stable
○ Thus require higher temperature and stronger acid or base to hydrolyze
In acid: liberated amine react with acid to form salt
In base: base reacts with acid product to form salt
8
Conversion to other Acid Derivatives
Acid chloride
Note:
● Two moles are required
9
Esters to Amide: Amidification
Note:
●
●
●
●
Nucleophilic acyl substitution
2nd weakest acid derivative (only makes amides)
Amine can be NH3, RNH2, or R2NH
Need 2 equivalents of amine
10
Esters to Alcohols
Note:
●
2 nucleophilic attacks for each Grignard reagent (carbonyl reforms)
●
Produces 3° alcohol
●
Stop after 1st step using Gilman reagent to make ketone
Reduction of esters
11
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