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Organic Chemistry — Reaction Mechanisms

Electron-pushing and named reactions in organic chemistry

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arrow_pusher_ap 26 terms Mar 10, 2026
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Terms 26

1
Nucleophile
Electron-rich species that donates electrons to electrophile; attacks positive centers
2
Electrophile
Electron-poor species that accepts electrons; attacked by nucleophiles
3
SN1 Reaction
Unimolecular nucleophilic substitution; two-step; forms carbocation intermediate; racemization
4
SN2 Reaction
Bimolecular nucleophilic substitution; one-step; backside attack; inversion of configuration
5
E1 Elimination
Unimolecular elimination; carbocation intermediate; forms more substituted alkene (Zaitsev)
6
E2 Elimination
Bimolecular elimination; one-step; anti-periplanar requirement; strong base required
7
Zaitsev's Rule
More substituted (more stable) alkene is the major product of elimination
8
Markovnikov's Rule
In addition to alkene, H adds to carbon with more H already; positive charge on more stable carbon
9
Carbocation Stability
Tertiary > secondary > primary > methyl; hyperconjugation and inductive effects
10
Carbanion Stability
Opposite of carbocation; primary > secondary > tertiary; electron-withdrawing groups stabilize
11
Radical Reaction
Involves species with unpaired electron; initiation, propagation, termination steps
12
Electrophilic Addition
Addition to alkene by electrophile; follows Markovnikov's rule
13
Electrophilic Aromatic Substitution (EAS)
Electrophile replaces H on benzene ring; preserves aromaticity; e.g. nitration, halogenation
14
Nucleophilic Aromatic Substitution (NAS)
Requires ring with strong electron-withdrawing groups; Meisenheimer complex intermediate
15
Diels-Alder Reaction
Concerted [4+2] cycloaddition between diene and dienophile; forms 6-membered ring
16
Aldol Condensation
Carbonyl compound with alpha-H reacts with another carbonyl; forms β-hydroxy carbonyl; dehydration gives enone
17
Grignard Reaction
RMgX (organomagnesium) acts as nucleophile attacking carbonyl; adds carbon chain
18
Fischer Esterification
Carboxylic acid + alcohol → ester + water; acid-catalyzed; reversible
19
Hydrolysis
Breaking bonds with water; ester hydrolysis under acidic or basic (saponification) conditions
20
Stereochemistry
Spatial arrangement of atoms; enantiomers, diastereomers, meso compounds
21
Enantiomers
Non-superimposable mirror images; same connectivity, opposite R/S configuration
22
Diastereomers
Stereoisomers that are not mirror images; differ in configuration at some but not all stereocenters
23
R/S Configuration
Cahn-Ingold-Prelog rules; priority of substituents determines R (clockwise) or S (counterclockwise)
24
Aromatic Compound
Cyclic, planar, fully conjugated; 4n+2 π electrons (Hückel rule); benzene is prototype
25
Resonance Structures
Alternative Lewis structures; true structure is hybrid; stabilizes molecules and ions
26
Leaving Group Ability
Better leaving groups are weaker bases; I⁻ > Br⁻ > Cl⁻ >> F⁻; crucial for SN and E reactions