Reference Reaction Summary Tables
Reaction Summary Tables
Estimated reading time: 1 min
In this section
- Overview
- Substitution and Elimination (SN1, SN2, E1, E2)
- Addition to Alkenes and Alkynes
- Nucleophilic Addition to Aldehydes and Ketones
- Nucleophilic Acyl Substitution (Carboxylic Acid Derivatives)
- Enols, Enolates, and Carbon–Carbon Bond Formation
- Electrophilic Aromatic Substitution
- Addition vs. Substitution at Carbonyls — A Direct Comparison
- Cross-References
The main chapters deliberately favor patterns and mechanisms over reagent lists — the Common Mistakes sections in Chapters 7–17 repeatedly warn against memorizing tables in place of understanding why a reaction happens. This appendix is the reagent-level reference that goes with that reasoning: once a mechanism is understood, these tables are where to look up which specific reagents accomplish it.
How to use this appendix: each table gives the reaction name, typical reagents/conditions, the product, the key mechanistic pattern (which should already be familiar from the chapter body), and a common pitfall. Use it for exam review, not first-pass learning.
Substitution and Elimination (SN1, SN2, E1, E2)
Reasoning through these four questions, in order, resolves most substitution/elimination problems:
Addition to Alkenes and Alkynes
Aromatic rings do not undergo these reactions — see Electrophilic Aromatic Substitution, below, and the Chapter 9 Common Mistake on this point.
Nucleophilic Addition to Aldehydes and Ketones
Every reaction in this table follows the same general pattern introduced in Chapter 12: a nucleophile attacks the electrophilic carbonyl carbon, electron…
Nucleophilic Acyl Substitution (Carboxylic Acid Derivatives)
Unlike aldehydes and ketones, carboxylic acid derivatives have a leaving group attached to the carbonyl carbon. The tetrahedral intermediate formed by…
Enols, Enolates, and Carbon–Carbon Bond Formation
See Chapter 14 for the acidity argument (enolate resonance stabilization) and Appendix B’s section on carbonyl α-carbons for representative pKa values.
Electrophilic Aromatic Substitution
Addition vs. Substitution at Carbonyls — A Direct Comparison
This is one of the most frequently confused pairs in Organic Chemistry II. Both reactions begin identically — a nucleophile attacks the electrophilic…