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Year 2 - Chem > Organic Named Reactions > Flashcards

Organic Named Reactions Flashcards

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1
Q

How do you add a hydroxyalkyl to a ketone?

A

Aldol reaction

Aldehye + Ketone under basic or acidic conditions

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2
Q

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

A

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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3
Q

How do you convert an aryl amine to aryl fluroides?

A

Balz-Schiemann

Diazonation with HBF4 and NaNO2 then thermal or photochemical decompsotion

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4
Q

How do you convert an oxime to an amide?

A

Beckmann rearragement

H2SO4 conc and heat

Can be used as a ring expansion technique

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5
Q

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

A

Bischler-Napieralski Reaction

Forms 3,4-dihydroisoquinolines

Uses POCl3 and heat in toluene

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6
Q

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

A

Cannizzaro reaction

Uses KOH

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7
Q

How do you aminate a subsituted pyridine?

A

Chichibabin reaction

Uses NaNH2 / NH3, heat and H2O

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8
Q

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

A

Clasien condensation

Sodium alkoxide then H3O+

Driving force is formation of stabilised anion of β-ketoester

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9
Q

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

A

Darzens condensation

Carbonyl + α-halo ester in presence of base

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10
Q

How can you cause an intramolecular condensation of a diester?

A

Dieckmann condensation

Sodium alkoxide then acidic workup

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

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11
Q

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

A

Favorskii rearrangement

Base-catalysed

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

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12
Q

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

A

Fischer esterification

Equilibrium - lewis or bronstead acid catalysed

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13
Q

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

A

Friedel-crafts acylation

Electrophilic aromatic substiution

Require lewis acid catalyst

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14
Q

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

A

Friedel-Crafts alkylation

Needs alkyl halide

Electrophilic aromatic substiution

Require lewis acid catalyst

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15
Q

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

A

Gabriel synthesis

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

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16
Q

How do you formylate a benzene?

A

Gatterman-Koch

CO + HCl then add AlCl3 and benzene

Not applicable to phenol / phenol ethers

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17
Q

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

A

Hell-Volhard-Zelinsky reaction

Br2 & PBr3 catalyst

18
Q

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

A

Hofmann rearrangement

Br2/Cl2 and strongly basic NaOH (aq)

Goes via isocyanate intermediate

19
Q

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

A

Knoevenagel condensation - modification on aldol

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

20
Q

How do you synthesise a substituted pyrrole?

A

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

21
Q

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

A

Neber rearrangement

TsCl then base

Beckmann rearrangement is side reaction

22
Q

How do you convert a primary halide to an aldehyde?

A

Kornblum oxidation

DMSO then Et3N

via alkoxysulfonium ion

23
Q

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

A

Kornblum-DeLaMare rearrangement

Base (KOH/Et3N) or Acid catalysis

24
Q

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

A

Mannich reaction

1°/2° amine or ammonia & formaldehyde

25
Q

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

A

Meerwein-Ponndorf-Verley (MPV) reduction

Aluminium alkoxide + alcohol + carbonyl

Highly chemoselective

26
Q

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

A

Mitsonobu reaction

DEAD/DIAD & Ph3P with carboxylic acid

27
Q

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

A

Nametkin rearrangement

Acid catalysed

Goes via non-classical carbocation

28
Q

How do you synthesise a substituted furan?

A

Paal-Knorr Furan synthesis

Cyclization of 1,4-dicarbonyl compounds using H+

29
Q

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

A

Paal-Knorr pyrrole synthesis

1,4-diketones + 1° amine

30
Q

How do you produce a substituted thiophene?

A

Paal-Knorr thiophene synthesis

1,4-diketones + P4S10

31
Q

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

A

Payne rearrangment

Basic conditions (aq)

Causes migration of the epoxy group

32
Q

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

A

Perkin reaction

Aromatic aldehyde + Acid anhydride & Alkali salt

33
Q

How do you convert α-silylcarbanions to alkenes?

A

Peterson Olefination

Add carbonyl then either base or acid

Base makes concerted syn elimination and acid causes anti elimination

34
Q

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

A

Pictet-Spengler reaction

Add aldehyde/ketone with acid catalyst

Similar mechanism to mannich reaction

Driving force is electrophilicity of the iminium ion

35
Q

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

A

Pinacol rearrangement

Acidic conditions

Can be used as a ring-expansion or contraction reaction

36
Q

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

A

Pummerer rearrangement

Acetic anhydride

37
Q

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

A

Ramberg-Backland reaction

Z from weak bases, E from strong bases

38
Q

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

A

Reformatsky reaction

α-halo esters with Zinc in tolune then H3O+

39
Q

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

A

Robinson annulation

Ketone + methyl vinyl ketone with base

40
Q

How do you form an oxazole?

A

Robinson-Gabriel synthesis

2-acylamino-ketone intermolecular reaction in acidic conditions

41
Q

How do you convert an alkene to a cyclopropane?

A

Simmons-smith

Reagents: CH2I2 + Zn

Year 2 - Chem (23 decks)

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