SynovAI Practice

Continuing education for synthetic chemists

Same exercises a master's student does, framed for an industry chemist's needs. Author-attributed content, spaced repetition, and CE credit on completion.

Use the modules below to drill the long-tail named reactions you need every quarter, verify your reasoning against the SynovAI model, and surface gaps before they show up in the lab.

Review queue

Loading your due reviews...

Featured modules

No CE modules have been published yet. Authors and editors can build one from the module authoring tool.

Browse by reaction class

Pick a transformation you want to keep sharp. Each cluster groups every CE-tagged exercise that teaches the named class.

Friedel-Crafts acylation

3 exercises

Esterification

2 exercises

Reduction

2 exercises

Amide formation

1 exercise

Aromatic nitration

1 exercise

Nucleophilic substitution (SN1/SN2)

1 exercise

Oxidation

1 exercise

Suzuki coupling

1 exercise

Featured targets

Each card is a target compound with one or more exercise types. Start with the primary CTA; the side options drill the same target through a different lens.

(-)-Menthol

Spot-the-flaw

Stereoretention during alkene hydrogenation

Takasago menthol process

Reading absolute configuration on polysubstituted cyclohexanols

By SynovAI Editorial · Last reviewed May 12, 2026

(R)-Limonene

Spot-the-flaw

Stereospecific cyclization in monoterpene biosynthesis

Limonene enantiomers and olfactory chirality

Reading R / S at a cyclohexene stereocenter

By SynovAI Editorial · Last reviewed May 12, 2026

[2+2] photocycloaddition: ethylene + ethylene

Mechanism arrows

photochemistry

cycloaddition

two-plus-two

By SynovAI Editorial · Last reviewed May 11, 2026

1,2-diphenylcyclobutane

Spot-the-flaw

Woodward-Hoffmann selection rules

[2+2] thermal vs photochemical

Frontier molecular orbital symmetry

By SynovAI Editorial · Last reviewed May 11, 2026

2-chlorobutane

Spot-the-flaw

Radical chain initiation

Why UV light or peroxide is required

Chain mechanism for halogenation

By SynovAI Editorial · Last reviewed May 11, 2026

2-methylbiphenyl

Spot-the-flaw

Suzuki coupling

Buchwald biaryl monophosphine ligands

Steric effects on cross-coupling

By SynovAI Editorial · Last reviewed May 11, 2026

2,4-D

Spot-the-flaw

Ortho/para directing effects of phenol OH

Electrophilic aromatic chlorination regiochemistry

2,4-D vs 3,5-D structural distinction

By SynovAI Editorial · Last reviewed May 11, 2026

2,4-D (2,4-Dichlorophenoxyacetic acid)

Build-from-disconnect

Williamson ether synthesis under aqueous base

Electrophilic aromatic chlorination (regioselectivity on phenol)

Acid + alkyl halide alpha-functionalization (chloroacetate as the synthon)

By SynovAI Editorial · Last reviewed May 11, 2026 · 1 citation

4-Aminophenol

Spot-the-flaw

Bamberger rearrangement of phenylhydroxylamine

Nitrenium ion intermediates

Distinguishing fused-ring inventions from real cationic intermediates

By SynovAI Editorial · Last reviewed May 12, 2026

Acetaminophen

Build-from-disconnect

Amide formation

Reduction

Para-substitution

By SynovAI Editorial · Last reviewed May 9, 2026 · 1 citation

Acrylic acid

Spot-the-flaw

Vapor-phase catalytic oxidation

Catalyst light-off temperature

Industrial process conditions for acrylic acid

By SynovAI Editorial · Last reviewed May 12, 2026

Adamantane

Spot-the-flaw

Lewis-acid carbocation rearrangement

Schleyer adamantane isomerization

Distinguishing Friedel-Crafts from skeletal rearrangement

By SynovAI Editorial · Last reviewed May 12, 2026

Addition: HCl + ethylene

Mechanism arrows

addition

hydrohalogenation

curly-arrows

By SynovAI Editorial · Last reviewed May 9, 2026

Adipic acid

Spot-the-flaw

Nitric acid oxidation of cyclohexanone to adipic acid

Industrial reactor conditions for ring-opening oxidation

Why cold nitric acid stops at alpha-hydroxy intermediates

By SynovAI Editorial · Last reviewed May 12, 2026

Aspirin

Build-from-disconnect

Walk-the-model

Esterification

Acetic anhydride chemistry

Salicylic acid

By SynovAI Editorial · Last reviewed May 11, 2026

Atazanavir hydroxyethylhydrazide fragment

Spot-the-flaw

Epoxide aminolysis regiochemistry

Hydroxyethylhydrazide isostere construction

Recognizing impossible quaternary-nitrogen adducts

By SynovAI Editorial · Last reviewed May 12, 2026

Atorvastatin (pyrrole core)

Spot-the-flaw

Statin syn-1,3-diol stereochemistry

(R,R) vs (S,S) for HMG-CoA reductase binding

Drawing and verifying stereocenters in late-stage intermediates

By SynovAI Editorial · Last reviewed May 11, 2026

Atrazine

Spot-the-flaw

Sequential SNAr on cyanuric chloride

Temperature staging for 1,3,5-triazines

Regiochemistry of the second and third Cl displacement

By SynovAI Editorial · Last reviewed May 12, 2026

Azidoacetic acid

Spot-the-flaw

SN2 with azide on primary alpha-halo acids

Distinguishing SN2 from Friedel-Crafts

C-N bond formation is not Friedel-Crafts

By SynovAI Editorial · Last reviewed May 12, 2026

Benzocaine

Build-from-disconnect

Spot-the-flaw

Fischer esterification (with chemoselectivity past an aromatic amine)

Aromatic nitro → amine reduction

Para-substituted benzene retro pattern

By SynovAI Editorial · Last reviewed May 11, 2026

Biotin

Spot-the-flaw

Biotin connectivity (side chain on the C2 of the thiophane)

Wittig olefination regiochemistry from the correct aldehyde

Why the wrong attachment point destroys streptavidin recognition

By SynovAI Editorial · Last reviewed May 12, 2026

Bisphenol A

Build-from-disconnect

Friedel-Crafts alkylation onto a phenol

Acid-catalyzed condensation with a ketone (carbocation chemistry)

Symmetric retrosynthesis (recognizing equivalent disconnections)

By SynovAI Editorial · Last reviewed May 11, 2026 · 1 citation

Bisphenol A

Spot-the-flaw

Friedel-Crafts alkylation vs acylation

Acid-catalyzed carbonyl condensation

Reading product structure to verify reaction class

By SynovAI Editorial · Last reviewed May 11, 2026

BODIPY 493/503 lipid dye

Spot-the-flaw

Pyrrole + aldehyde condensation to dipyrromethane

Distinguishing dipyrromethane from calix[4]pyrrole

Mechanistic plausibility of macrocyclic intermediates

By SynovAI Editorial · Last reviewed May 12, 2026

Butyl methyl ether

Spot-the-flaw

SN1 vs SN2 selection

Carbocation stability

Primary substrates strongly prefer SN2

By SynovAI Editorial · Last reviewed May 11, 2026

Caffeine

Build-from-disconnect

Spot-the-flaw

Walk-the-model

N-methylation regioselectivity on xanthine

Purine ring nitrogen labeling (N1, N3, N7)

Acidity ordering of heterocyclic NHs

By SynovAI Editorial · Last reviewed May 11, 2026

Spot-the-flaw Walk-the-model

Camphor

Build-from-disconnect

Spot-the-flaw

Bicyclic terpenoid (norbornane / bornane skeleton)

Alcohol → ketone oxidation

Wagner-Meerwein rearrangement (qualitative; the camphene → borneol step)

By SynovAI Editorial · Last reviewed May 11, 2026 · 1 citation

Celecoxib

Spot-the-flaw

Pyrazole regiochemistry from 1,3-diketones

Electronic vs steric control in pyrazole synthesis

Celecoxib vs its COX-1 selective regioisomer

By SynovAI Editorial · Last reviewed May 11, 2026

Chalcone

Spot-the-flaw

Claisen-Schmidt condensation mechanism

E vs Z selectivity in aldol dehydration

Why conjugated trans alkenes are thermodynamically favored

By SynovAI Editorial · Last reviewed May 12, 2026

Cinchonidine

Spot-the-flaw

Stereochemistry of cinchona alkaloids (C8/C9 assignment)

Cinchonidine vs C9-epi-cinchonidine

Enantioselectivity inversion of organocatalysts on epimerization

By SynovAI Editorial · Last reviewed May 12, 2026

Cortisone CD-ring fragment

Spot-the-flaw

Regiochemistry of Robinson annulation Michael addition

Why the kinetic enolate is alpha to the carbonyl, not gamma

Steroid ring-fusion stereochemistry

By SynovAI Editorial · Last reviewed May 12, 2026

Cubane

Spot-the-flaw

Photochemical [2+2] cycloaddition vs Friedel-Crafts

Eaton cubane synthesis

Why aromatic-ring chemistry does not apply to all-sp3 cages

By SynovAI Editorial · Last reviewed May 12, 2026

Cyclohexene

Spot-the-flaw

Diels-Alder [4+2] cycloaddition

Pericyclic vs cationic reaction families

Distinguishing Friedel-Crafts from concerted cycloaddition

By SynovAI Editorial · Last reviewed May 12, 2026

Dansyl chloride

Spot-the-flaw

Chlorosulfonation conditions on arenes

Anhydrous handling of sulfonyl chlorides

Why sulfonyl chlorides hydrolyze in water

By SynovAI Editorial · Last reviewed May 12, 2026

DBCO-amine (aza-dibenzocyclooctyne)

Spot-the-flaw

Distinguishing Suzuki coupling from base-mediated alkyne installation

Strained cyclooctyne synthesis (vic-vinyl dibromide elimination)

Reaction classes that can vs cannot form C-C triple bonds

By SynovAI Editorial · Last reviewed May 12, 2026

DDT (historical)

Spot-the-flaw

Suzuki coupling scope (aryl halide + aryl boronic acid)

Friedel-Crafts hydroxyalkylation in the classical DDT synthesis

When a Pd-coupling label cannot deliver the drawn bonds

By SynovAI Editorial · Last reviewed May 12, 2026

Desthiobiotin

Spot-the-flaw

Cyclic urea formation from a vicinal diamine plus phosgene equivalent

Distinguishing C-N bond formation from C-C coupling

Why Suzuki coupling cannot build a urea

By SynovAI Editorial · Last reviewed May 12, 2026

Diels-Alder: butadiene + ethylene

Mechanism arrows

cycloaddition

pericyclic

diels-alder

By SynovAI Editorial · Last reviewed May 11, 2026

Discodermolide C1-C7 fragment

Spot-the-flaw

Evans syn-aldol stereochemistry

Distinguishing syn-propionate from anti-propionate

Auxiliary chirality dictates the new C-C bond face

By SynovAI Editorial · Last reviewed May 12, 2026

E2: hydroxide + bromocyclohexane

Mechanism arrows

elimination

e2

curly-arrows

By SynovAI Editorial · Last reviewed May 9, 2026

Structure pending

EAS: nitration of benzene

Mechanism arrows

electrophilic-aromatic-substitution

eas

nitration

By SynovAI Editorial · Last reviewed May 11, 2026

Efavirenz

Spot-the-flaw

Asymmetric alkynyl-zinc addition to trifluoromethyl ketones

(R) vs (S) at the efavirenz quaternary carbinol

Reading absolute configuration on quaternary stereocenters

By SynovAI Editorial · Last reviewed May 12, 2026

epsilon-Caprolactam

Spot-the-flaw

Beckmann rearrangement of cyclohexanone oxime

Strong-acid activation of oximes for [1,2]-alkyl migration

Why dilute HCl cannot drive the Beckmann

By SynovAI Editorial · Last reviewed May 12, 2026

Estrone

Spot-the-flaw

Estrone A-ring numbering (C1, C2, C3, C4)

Selective demethylation of methyl ether at C3

Why the C1-hydroxy steroid is not estrone

By SynovAI Editorial · Last reviewed May 12, 2026

Ethylene oxide

Spot-the-flaw

Silver-catalyzed direct epoxidation of ethylene

Choosing the correct oxidant for heterogeneous catalysis

Why H2O2 over-oxidizes on Ag and O2 is the right choice

By SynovAI Editorial · Last reviewed May 12, 2026

Fluorescein

Spot-the-flaw

Friedel-Crafts mechanism on resorcinol (C-acylation, not O-acylation)

Xanthene formation by intramolecular SEAr

Telling productive intermediates from wrong-connectivity ones

By SynovAI Editorial · Last reviewed May 12, 2026

Fluorophosphonate serine warhead

Spot-the-flaw

Hydrolytic instability of P-F bonds

Anhydrous fluoride sources (DAST, AgF, anhydrous KF in DMF)

Why activity-based probes need to be assembled dry

By SynovAI Editorial · Last reviewed May 12, 2026

Fluoxetine

Spot-the-flaw

CF3 directing effects in SNAr

Para vs meta substitution on activated phenols

SAR sensitivity of fluoxetine to regiochemistry

By SynovAI Editorial · Last reviewed May 11, 2026

Fmoc-Cl

Spot-the-flaw

Anhydrous chloroformate synthesis

Why chloroformates hydrolyze in aqueous base

Distinguishing Schotten-Baumann amide coupling from chloroformate prep

By SynovAI Editorial · Last reviewed May 12, 2026

Furfural

Spot-the-flaw

Pentose dehydration mechanism

Beta-dicarbonyl intermediates in sugar chemistry

Distinguishing fused-ring inventions from real open-chain intermediates

By SynovAI Editorial · Last reviewed May 12, 2026

Gefitinib

Spot-the-flaw

SNAr vs Buchwald-Hartwig amination on activated heterocycles

When a transition-metal catalyst is unnecessary

Process chemistry purity considerations

By SynovAI Editorial · Last reviewed May 11, 2026

Geraniol

Build-from-disconnect

Spot-the-flaw

Allylic alcohol from carbonyl reduction

Isoprene rule / terpene biogenetic disconnection

E / Z assignment on the allylic alkene (E by IUPAC, "trans" in older texts)

By SynovAI Editorial · Last reviewed May 11, 2026 · 1 citation

Glutathione

Spot-the-flaw

L vs D cysteine assignment

CIP priorities flipped on cysteine (R is the L isomer)

Why D-cysteine glutathione is not enzymatically equivalent

By SynovAI Editorial · Last reviewed May 12, 2026

Glyphosate

Spot-the-flaw

Kabachnik-Fields / phosphonomethylation reaction

Distinguishing C-C from C-P bond formation

Why Friedel-Crafts cannot operate on a non-aromatic substrate

By SynovAI Editorial · Last reviewed May 12, 2026

Structure pending

Heck reaction: Pd-catalyzed alkene arylation

Mechanism arrows

organometallic-catalysis

cross-coupling

heck-reaction

By SynovAI Editorial · Last reviewed May 11, 2026

Ibuprofen

Build-from-disconnect

Spot-the-flaw

Walk-the-model

Friedel-Crafts acylation

Carbonyl reduction

Catalytic carbonylation (BHC route)

By SynovAI Editorial · Last reviewed May 11, 2026

Spot-the-flaw Walk-the-model

Imatinib

Spot-the-flaw

SNAr on chloropyrimidines

Acid catalysis in pyrimidine SNAr

Imatinib (Novartis) process chemistry

By SynovAI Editorial · Last reviewed May 11, 2026

Iodoacetamide

Spot-the-flaw

Finkelstein halide exchange mechanism

When a cyclic intermediate is consistent with mechanism vs invented

SN2 displacement on alpha-halo amides

By SynovAI Editorial · Last reviewed May 12, 2026

Isosorbide

Spot-the-flaw

Stereospecific intramolecular etherification

Conservation of sorbitol stereocenters during dehydration

Distinguishing isosorbide from isomannide and isoidide

By SynovAI Editorial · Last reviewed May 12, 2026

Lactide (PLA monomer)

Spot-the-flaw

Transesterification thermodynamics

Lactide production conditions (heat + vacuum + tin catalyst)

Why aqueous conditions favor the open-chain hydroxy acid

By SynovAI Editorial · Last reviewed May 12, 2026

Levulinic acid

Spot-the-flaw

Wittig reaction scope and products

Acid-catalyzed routes to levulinic acid from sugars

When a "Wittig" label cannot be the real mechanism

By SynovAI Editorial · Last reviewed May 12, 2026

Lidocaine

Build-from-disconnect

Spot-the-flaw

Amide formation from an acyl chloride + hindered aniline

SN2 on an alpha-halo amide by a secondary amine

Two-step convergent synthesis (acyl chloride is the linker)

By SynovAI Editorial · Last reviewed May 11, 2026 · 1 citation

Longifolene

Spot-the-flaw

Wittig methylenation does not invert ring stereocenters

Longifolene absolute configuration

Reading stereo on bicyclic terpene frameworks

By SynovAI Editorial · Last reviewed May 12, 2026

Losartan

Spot-the-flaw

Tetrazole formation by NaN3 + nitrile cycloaddition

Distinguishing real vs fabricated reaction sequences

Losartan (Merck / DuPont) process

By SynovAI Editorial · Last reviewed May 11, 2026

Metformin

Spot-the-flaw

Biguanide formation from cyanoguanidine

Activation energy for amine + nitrile-type addition

Melt vs aqueous conditions in industrial chemistry

By SynovAI Editorial · Last reviewed May 11, 2026

Methyl salicylate

Build-from-disconnect

Fischer esterification

Chemoselectivity: carboxylic acid OH vs phenol OH

Why phenols are poor nucleophiles for esterification under acid catalysis

By SynovAI Editorial · Last reviewed May 9, 2026 · 1 citation

Methyl salicylate

Spot-the-flaw

Spot-the-flaw

Fischer esterification

Acid vs base catalysis

Chemoselectivity of carboxylic acid OH vs phenol OH

By SynovAI Editorial · Last reviewed May 12, 2026

N-Ethylmaleimide

Spot-the-flaw

Anhydride to imide via dehydrative cyclization

Why aqueous base does not deliver an imide

Maleimide hydrolytic stability

By SynovAI Editorial · Last reviewed May 12, 2026

Structure pending

NaBH4 reduction: acetone to isopropanol

Mechanism arrows

reduction

hydride-transfer

carbonyl-chemistry

By SynovAI Editorial · Last reviewed May 11, 2026

Naproxen

Build-from-disconnect

Spot-the-flaw

Spot-the-flaw

Walk-the-model

Friedel-Crafts acylation on activated naphthalene (methoxy directing effect)

Carbonyl reduction

Catalytic carbonylation (BHC-style alpha-aryl propionic acid disconnection)

By SynovAI Editorial · Last reviewed May 12, 2026

Spot-the-flaw Spot-the-flaw Walk-the-model

Nicotinamide

Spot-the-flaw

Nitrile hydration mechanism

Iminol-amide tautomerism

Distinguishing sp3 hemi-orthoamide invented species from real intermediates

By SynovAI Editorial · Last reviewed May 12, 2026

Nitrobenzene

Spot-the-flaw

Directing effects of strong meta directors

Regiochemistry of dinitration of nitrobenzene

Deactivated arene EAS gives meta substitution

By SynovAI Editorial · Last reviewed May 12, 2026

Omeprazole

Spot-the-flaw

Selective sulfide to sulfoxide oxidation

Overoxidation to sulfone with excess peroxide

Omeprazole Pyne / Sharpless processes

By SynovAI Editorial · Last reviewed May 11, 2026

Oseltamivir

Spot-the-flaw

Three contiguous stereocenters on the oseltamivir cyclohexene

(3R,4R,5S) vs (3S,4S,5R) enantiomer activity

Reading absolute stereochemistry on a substituted cyclohexene

By SynovAI Editorial · Last reviewed May 11, 2026

Structure pending

PCC oxidation: ethanol to acetaldehyde

Mechanism arrows

oxidation

chromium-chemistry

alcohol-oxidation

By SynovAI Editorial · Last reviewed May 11, 2026

Phenol (cumene process)

Spot-the-flaw

Friedel-Crafts alkylation directing effects

Alkyl groups as ortho/para directors

Polyalkylation control in the cumene process

By SynovAI Editorial · Last reviewed May 12, 2026

Praziquantel

Spot-the-flaw

Pictet-Spengler closes onto the arene, not onto a tethered carbamate oxygen

Mechanistic plausibility check on intermediates

Tetrahydroisoquinoline synthesis logic

By SynovAI Editorial · Last reviewed May 12, 2026

Pregabalin

Spot-the-flaw

Lipase-mediated kinetic resolution

(S) vs (R) pregabalin activity

Tracking absolute configuration through a nitrile reduction

By SynovAI Editorial · Last reviewed May 11, 2026

Procaine

Build-from-disconnect

Spot-the-flaw

Ester formation between an aromatic acid and an alcohol with a basic amine

Aromatic nitro reduction

Para-substituted benzene retro pattern

By SynovAI Editorial · Last reviewed May 11, 2026 · 1 citation

Propargylamine

Spot-the-flaw

Wittig reaction scope (alkene formation from aldehydes / ketones)

Classical SN2 amination routes to primary amines

When the drawn reaction class cannot deliver the drawn bonds

By SynovAI Editorial · Last reviewed May 12, 2026

Prostaglandin F2alpha

Spot-the-flaw

Prostaglandin numbering (C8, C12, C13)

Wittig reaction targets the carbon bearing the aldehyde, not a neighbor

Distinguishing the upper (omega) and lower (alpha) chain attachment points

By SynovAI Editorial · Last reviewed May 12, 2026

Pyrethrin I (analog)

Spot-the-flaw

Cyclopropane cis vs trans diastereomers

Cu-carbene cyclopropanation stereochemistry

Chrysanthemic acid configuration

By SynovAI Editorial · Last reviewed May 12, 2026

Structure pending

Radical chlorination: Cl2 + methane

Mechanism arrows

radical-chain

radical-mechanism

fishhook-arrows

By SynovAI Editorial · Last reviewed May 11, 2026

Reserpine yohimbinoid core

Spot-the-flaw

Pictet-Spengler uses indole C2 as the nucleophile

Distinguishing fused vs bridged bicyclic closures

Topology of the indoloquinolizidine framework

By SynovAI Editorial · Last reviewed May 12, 2026

Rhodamine B

Spot-the-flaw

Friedel-Crafts C-acylation vs N-acylation on aminophenols

Xanthene formation mechanism

Why N-acylation kills the downstream cyclization

By SynovAI Editorial · Last reviewed May 12, 2026

Salicylic acid

Build-from-disconnect

Walk-the-model

Kolbe-Schmitt carboxylation

Ortho-selectivity via chelated six-membered TS

Sodium phenoxide as a nucleophile

By SynovAI Editorial · Last reviewed May 11, 2026

Salicylic acid

Spot-the-flaw

Kolbe-Schmitt carboxylation

Phenoxide chemistry vs Friedel-Crafts on phenol

CO2 reactivity under different activations

By SynovAI Editorial · Last reviewed May 11, 2026

Sildenafil

Spot-the-flaw

Chlorosulfonation of electron-rich arenes

Functional-group compatibility under forcing conditions

Sildenafil process chemistry (Pfizer route)

By SynovAI Editorial · Last reviewed May 11, 2026

Sitagliptin

Spot-the-flaw

Rh-Josiphos asymmetric hydrogenation of enamines

(R) vs (S) enantiomer activity at DPP-4

Reading absolute configuration on beta-amino amides

By SynovAI Editorial · Last reviewed May 11, 2026

Structure pending

SN1: t-butyl chloride + water

Mechanism arrows

SN1 mechanism

Carbocation intermediates

Stepwise vs concerted

By SynovAI Editorial · Last reviewed May 9, 2026

SN2: hydroxide + methyl bromide

Mechanism arrows

nucleophilic-substitution

sn2

curly-arrows

By SynovAI Editorial · Last reviewed May 9, 2026

Stilbene

Spot-the-flaw

Wittig olefination

Distinguishing C=C formation (Wittig) from C-C alkyl arene formation (Friedel-Crafts)

Mechanistic class hygiene

By SynovAI Editorial · Last reviewed May 12, 2026

Structure pending

Suzuki coupling: Pd-catalyzed biaryl formation

Mechanism arrows

organometallic-catalysis

cross-coupling

oxidative-addition

By SynovAI Editorial · Last reviewed May 11, 2026

Taxol C13 side chain

Spot-the-flaw

Sharpless asymmetric aminohydroxylation regiochemistry

Why N goes to the benzylic carbon of methyl cinnamate

Distinguishing 2,3-isoserine regioisomers

By SynovAI Editorial · Last reviewed May 12, 2026

Terephthalic acid

Spot-the-flaw

Methyl directing effects in Friedel-Crafts

Selectivity for p-xylene over m-xylene

Why m-xylene oxidation gives isophthalic acid, not terephthalic

By SynovAI Editorial · Last reviewed May 12, 2026

tert-Butyl chloride

Spot-the-flaw

Mitsunobu reaction scope (works on 1 and 2 alcohols)

SN1 substitution at tertiary alcohols with HCl

Why steric crowding blocks Mitsunobu at tertiary centers

By SynovAI Editorial · Last reviewed May 12, 2026

Thiabendazole

Spot-the-flaw

Benzimidazole formation regiochemistry

o-Phenylenediamine + carboxylic acid closes at C2

C5 vs C2 substitution on benzimidazole

By SynovAI Editorial · Last reviewed May 12, 2026

Trimethoprim

Build-from-disconnect

Spot-the-flaw

Knoevenagel-like condensation of an aromatic aldehyde with a cyanoacetate equivalent

Guanidine-driven 2,4-diaminopyrimidine ring closure

Heterocycle retrosynthesis (recognizing the diaminopyrimidine bone graft)

By SynovAI Editorial · Last reviewed May 11, 2026 · 1 citation

Tropinone (Robinson)

Spot-the-flaw

Bredt's rule for small bridged bicyclics

Robinson tropinone Mannich condensation

Cis vs trans ring fusion in [3.2.1] bicyclics

By SynovAI Editorial · Last reviewed May 12, 2026

Vanillin

Build-from-disconnect

Spot-the-flaw

Reimer-Tiemann formylation

Ortho/para direction by OMe and OH groups

Why CHO lands ortho to OH on guaiacol (steric + electronic preference)

By SynovAI Editorial · Last reviewed May 11, 2026

Structure pending

Wittig: benzylidene ylide + benzaldehyde

Mechanism arrows

wittig

olefination

ylide

By SynovAI Editorial · Last reviewed May 11, 2026

Your concept tree

Practice stale concepts

Looking for the student version?

Same exercises, classroom framing

Author content for your team

Admin tools for instructors

Content authored by SynovAI Editorial unless otherwise marked. CE credit hours are advisory; check with your CE provider for accreditation.