Organic Named Reactions Flashcards by David B

How do you add a hydroxyalkyl to a ketone?

Aldol reaction

Aldehye + Ketone under basic or acidic conditions

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How do you convert a ketone to an ester and cyclic ketones to lactones?

Baeyer-Villiger Oxidation

Peracids (MCBPA) or hydrogen peroxide + lewis acid

Regiospecificity of the reaction depends on migratory ability - more e^- donating is faster

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How do you convert an aryl amine to aryl fluroides?

Balz-Schiemann

Diazonation with HBF₄ and NaNO₂ then thermal or photochemical decompsotion

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How do you convert an oxime to an amide?

Beckmann rearragement

H₂SO₄ conc and heat

Can be used as a ring expansion technique

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How do you convert a β-ethylamines bonded to an e- rich arenes to quinoline derivative?

Bischler-Napieralski Reaction

Forms 3,4-dihydroisoquinolines

Uses POCl₃ and heat in toluene

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How do you cause the disproportionation of non-enolizable aldehydes to carboxylic acids and alcohols?

Cannizzaro reaction

Uses KOH

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How do you aminate a subsituted pyridine?

Chichibabin reaction

Uses NaNH₂ / NH₃, heat and H₂O

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How do convert esters with α-hydrogen to a β-ketoester?

Clasien condensation

Sodium alkoxide then H₃O⁺

Driving force is formation of stabilised anion of β-ketoester

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How do you form a α,β-epoxy ester from a carbonyl compound?

Darzens condensation

Carbonyl + α-halo ester in presence of base

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How can you cause an intramolecular condensation of a diester?

Dieckmann condensation

Sodium alkoxide then acidic workup

Produces 5- or 6- membered cyclic β-keto ester

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How can you convert a cyclopropanones to carboxylic acid or derivatives?

Favorskii rearrangement

Base-catalysed

cyclopropanones themselves made from basic reaction of reaction of α-halo ketones

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How do you convert a carboxylic acid and alcohol to ester?

Fischer esterification

Equilibrium - lewis or bronstead acid catalysed

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How do you add a acyl group to a benzene or aryl ring?

Friedel-crafts acylation

Electrophilic aromatic substiution

Require lewis acid catalyst

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How do you add a alkyl group to a benzene or aryl ring?

Friedel-Crafts alkylation

Needs alkyl halide

Electrophilic aromatic substiution

Require lewis acid catalyst

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How do you convert a primary alkyl halide into a primary amine?

Gabriel synthesis

Pottasium phthalimide (^-NH₂ synthon, which is acidic) then base or hydrazine

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How do you formylate a benzene?

Gatterman-Koch

CO + HCl then add AlCl₃ and benzene

Not applicable to phenol / phenol ethers

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How do you convert a carboxylic acid to acyl bromides and α-bromo acids?

Hell-Volhard-Zelinsky reaction

Br₂ & PBr₃ catalyst

How do you convert a primary amide to form the corresponding primary amine?

Hofmann rearrangement

Br₂/Cl₂ and strongly basic NaOH (aq)

Goes via isocyanate intermediate

How do you convert a ketone/aldehyde to an α,β-unsaturated compounds?

Knoevenagel condensation - modification on aldol

Activated compound (e- withdrawing containing) with 2xH on a C with a weakly basic amine

How do you synthesise a substituted pyrrole?

Knorr pyrrole synthesis

α-amino-ketone and carbonyl with EWG α like an ester

Zinc and acetic acid catalysis

α-amino-ketone produced in situ with oxime via Neber

How do you convert a oxime to an α-amino-ketone?

Neber rearrangement

TsCl then base

Beckmann rearrangement is side reaction

How do you convert a primary halide to an aldehyde?

Kornblum oxidation

DMSO then Et₃N

via alkoxysulfonium ion

How do you convert a organic peroxide to corresponding ketone and alcohol?

Kornblum-DeLaMare rearrangement

Base (KOH/Et₃N) or Acid catalysis

How do you amino alkylate an acidic proton α to a carbonyl?

Mannich reaction

1°/2° amine or ammonia & formaldehyde

How do you cause a hydride shift from the α-carbon of an alcohol component to the carbonyl carbon of a second component ?

Meerwein-Ponndorf-Verley (MPV) reduction Aluminium alkoxide + alcohol + carbonyl Highly chemoselective ![]()

How do you convert 1°/2° alcohols to esters/thioesters?

Mitsonobu reaction DEAD/DIAD & Ph₃P with carboxylic acid ![]()

How can you cause a cationic [1,2]-sigmatropic rearrangements of a C in bicylic terpenes?

Nametkin rearrangement Acid catalysed Goes via non-classical carbocation

How do you synthesise a substituted furan?

Paal-Knorr Furan synthesis Cyclization of 1,4-dicarbonyl compounds using H⁺

How do you produce a pyrrole from 1,4-diketones?

Paal-Knorr pyrrole synthesis 1,4-diketones + 1° amine

How do you produce a substituted thiophene?

Paal-Knorr thiophene synthesis 1,4-diketones + P₄S₁₀

How do you isomerize 2,3-epoxy alcohols with inversion of config?

Payne rearrangment Basic conditions (aq) Causes migration of the epoxy group ![]()

How do you convert an aromatic aldehyde to an α,β-unsaturated aromatic acid?

Perkin reaction Aromatic aldehyde + Acid anhydride & Alkali salt ![]()

How do you convert α-silylcarbanions to alkenes?

Peterson Olefination Add carbonyl then either base or acid Base makes concerted syn elimination and acid causes anti elimination

How do you convert a β-arylenylamine to a tetrahydroisoquinoline?

Pictet-Spengler reaction Add aldehyde/ketone with acid catalyst Similar mechanism to mannich reaction Driving force is electrophilicity of the iminium ion ![]()

How do you convert a 1,2-diol to a carbonyl?

Pinacol rearrangement Acidic conditions Can be used as a ring-expansion or contraction reaction

How can you rearrange an alkyl sulfoxide to a α-acyloxy–thioether?

Pummerer rearrangement Acetic anhydride ![]()

How do you convert a α-halosulfones into E or Z alkenes?

Ramberg-Backland reaction Z from weak bases, E from strong bases ![]()

How do you condense aldehydes/ketones to β-hydroxy-esters?

Reformatsky reaction α-halo esters with Zinc in tolune then H₃O⁺ ![]()

How do you form a six-membered ring in a polycyclic compound?

Robinson annulation Ketone + methyl vinyl ketone with base ![]()

How do you form an oxazole?

Robinson-Gabriel synthesis 2-acylamino-ketone intermolecular reaction in acidic conditions ![]()

How do you convert an alkene to a cyclopropane?

Simmons-smith Reagents: CH₂I₂ + Zn