Figure Library
Reaction schemes, mechanisms, and diagrams for organic and general chemistry. Filter by course, topic, or reaction type, then click any figure for the full-size version and its walkthrough.
Organic
Imine and Enamine Formation from Ketones
Cyclohexanone reacts with a primary amine to give an imine and with a secondary amine to give an enamine.
Organic
Markovnikov Addition of HBr to an Alkene
HBr adds to methylenecyclopentane through the more stable tertiary carbocation, giving the Markovnikov product 1-bromo-1-methylcyclopentane.
Organic
Oxidation of Primary and Secondary Alcohols
Primary alcohols oxidize to aldehydes and then carboxylic acids; secondary alcohols oxidize to ketones.
Organic
Radical Chlorination Mechanism
The initiation, propagation, and termination steps of radical chlorination of an alkane.
Organic
Inductive Effects on Acidity
Fluorine pulls electron density away from the negative charge of the conjugate base, which is why fluoroacetic acid is more acidic than acetic acid.
Fun Stuff
From Cotton to Guncotton
Nitration with HNO3 and H2SO4 replaces cellulose's hydroxyl groups with nitrate esters, putting fuel and oxygen in one molecule.
Organic
Enamine Formation Mechanism
Steps 1–4 of enamine formation: protonation of the carbonyl, addition of the secondary amine, and formation of the carbinolamine.
Organic
Anti-Markovnikov HBr Addition with Peroxides
With peroxide as a radical initiator, HBr adds to methylenecyclopentane so that Br ends up on the less substituted carbon.
Organic
Malonic Ester Synthesis: Overall Reaction
Overall transformation in the malonic ester synthesis: enolate formation, alkylation, then hydrolysis and decarboxylation to a substituted carboxylic acid.
Organic
Assigning R/S: The Single Swap Method
When group 4 is in the plane of the page, swap two groups, assign the configuration, then reverse it.
Organic
Resonance Effects on Acidity: Phenoxide
The negative charge of phenoxide spreads around the ring by resonance, stabilizing the conjugate base and making phenol more acidic.
Organic
Oxymercuration: Forming the Mercurinium Ion
Mercury(II) acetate ionizes to electrophilic +HgOAc, which bridges the alkene π bond to form a mercurinium ion intermediate.
Organic
1,2- vs 1,4-Addition to 1,3-Butadiene
Resonance in the allylic carbocation explains why HBr addition to a conjugated diene gives both 1,2- and 1,4-products.
Organic
Substitution and Elimination Flow Chart
A decision chart for predicting SN1, SN2, E1, or E2 based on the substrate and the strength of the nucleophile or base.
Organic
Spin-Spin Splitting and the n+1 Rule
How the possible spin alignments of neighboring protons split a signal into a quartet, explaining the n+1 rule.
General
Reading a Graduated Cylinder
Reading a graduated cylinder correctly and recording the estimated digit, the basis for counting significant figures.