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Octet

Browse reaction mechanisms, conditions, solvents, and selectivity notes.

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83Reactions

63Reagents

25Groups

109Reference rows

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Reaction

Acetal Formation

Remove water

Formula: ROH (excess), acid catalyst
SMILES: CC=O -> CC(OC)OC

Carbonyl

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Reaction

Acetoacetic Ester Synthesis

Makes substituted ketones (methyl ketones), Decarboxylation of β-keto acid, Can alkylate twice, Partner: malonic ester synthesis (makes acids)

Formula: NaOEt, R-X, then H₃O⁺/heat
SMILES: CCOC(=O)CC(=O)C -> CCC(=O)C

Substitution

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Reaction

Acid-Catalyzed Ester Hydrolysis

Aqueous acid, reflux

Formula: H₂O, H₂SO₄ or HCl
SMILES: CC(=O)OCC -> CC(=O)O.CCO

Carbonyl

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Reaction

Acyl Chloride Formation

SOCl₂ most common - gaseous byproducts escape, Acyl chlorides very reactive - use quickly, React with alcohols → esters, amines → amides

Formula: SOCl₂, or PCl₃, or PCl₅
SMILES: CC(=O)O -> CC(=O)Cl

Carbonyl

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Reaction

Alcohol Dehydration

Concentrated acid, heat

Formula: H₂SO₄, H₃PO₄
Detail: E1 / > 140°C
SMILES: CC(C)(C)O -> CC(C)=C

EliminationE1Zaitsev product (more substituted alkene)

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Reaction

Alcohol to Alkyl Bromide (PBr₃)

OH is poor leaving group - PBr₃ activates it, Works for 1° and 2° alcohols, Alternative: SOCl₂ for chlorides

Formula: PBr₃
SMILES: CCO -> CCBr

SubstitutionInversion (SN2 mechanism)

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Reaction

Alcohol to Alkyl Chloride (SOCl₂)

Byproducts are gases - easy purification, Pyridine added to neutralize HCl, Works well for 1° and 2° alcohols

Formula: SOCl₂, pyridine (optional)
SMILES: CCO -> CCCl

Substitution

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Reaction

Aldol Addition

Low temperature for addition (warm for condensation)

Formula: NaOH (dilute), LDA
SMILES: CC=O -> CC(O)CC=O

Carbonyl

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Reaction

Aldol Condensation

Condensation = addition + elimination of water, Heat favors elimination (entropy), Product is α,β-unsaturated carbonyl

Formula: NaOH, heat
SMILES: CC=O -> CC=CC=O

Carbonyl

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Reaction

Amide Formation from Acyl Chloride

Use 2 eq amine (one acts as base) or add Et₃N, Most stable carboxylic acid derivative, Peptide bonds are amide bonds

Formula: CH₃NH₂, excess amine or with base
SMILES: CC(=O)Cl -> CC(=O)NC

Carbonyl

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Reaction

Anti Dihydroxylation (Epoxide Opening)

Acid-catalyzed: opens at more substituted carbon, Base-catalyzed: opens at less substituted carbon

Formula: H₃O⁺/H₂O, or NaOH/H₂O
SMILES: CC1OC1C -> CC(O)C(O)C

AdditionAnti addition (OHs on opposite faces)

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Reaction

Anti-Markovnikov HBr Addition (Radical)

Peroxide initiator (light or heat)

Formula: HBr, ROOR (peroxide)
SMILES: CC=C -> CCCBr

AdditionAnti-Markovnikov: Br on less substituted carbon

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Reaction

Appel Reaction

ROH → RX conversion, CBr₄ for bromides, CCl₄ for chlorides, CI₄ for iodides, Mild conditions, Alternative to PBr₃, SOCl₂

Formula: CBr₄, PPh₃
SMILES: CCO -> CCBr

Substitution

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Reaction

Baeyer-Villiger Oxidation

Ketone → Ester (oxygen inserted), Migratory aptitude: H > 3° > 2° ≈ aryl > 1° > methyl, Aldehydes give formate esters, Cyclic ketones → Lactones

Formula: mCPBA, CF₃CO₃H, peracetic acid
SMILES: CC(=O)c1ccccc1 -> CC(=O)Oc1ccccc1

Oxidation

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Reaction

Beckmann Rearrangement

Acidic conditions, heat

Formula: H₂SO₄, PCl₅, SOCl₂
SMILES: CC(c1ccccc1)=NO -> CC(=O)Nc1ccccc1

Rearrangement

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Reaction

Birch Reduction

-33°C (liquid ammonia)

Formula: Na or Li, NH₃(l), ROH
SMILES: c1ccccc1 -> C1=CCC=CC1

Reduction

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Reaction

Cannizzaro Reaction

Strong base, no α-hydrogens

Formula: NaOH (conc.), KOH
SMILES: c1ccccc1C=O -> c1ccccc1CO.c1ccccc1C(=O)[O-]

Oxidation

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Reaction

Catalytic Hydrogenation

H₂ gas, metal catalyst

Formula: H₂, Pd/C or Pt or Ni
Detail: Reduction
SMILES: CC=CC -> CCCC

AdditionReductionSyn addition

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Reaction

Claisen Condensation

Ester equivalent of aldol, Product is β-keto ester, Requires at least 2 α-hydrogens (for irreversible step)

Formula: NaOEt, EtOH
SMILES: CC(=O)OCC -> CC(=O)CC(=O)OCC

Carbonyl

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Reaction

Claisen Rearrangement

Thermal (150-200°C)

Formula: Heat
SMILES: C=CCOC=C -> C=CCC(=O)C

Pericyclic

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Reaction

Clemmensen Reduction (C=O → CH₂)

Heat

Formula: Zn(Hg), HCl (conc.)
SMILES: c1ccc(C(=O)C)cc1 -> c1ccc(CC)cc1

Reduction

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Reaction

Cope Rearrangement

Thermal (150-200°C)

Formula: Heat
SMILES: C=CCC=CC -> CC=CCC=C

PericyclicChair-like transition state preferred

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Reaction

Curtius Rearrangement

Heat or UV light

Formula: Heat or photolysis
SMILES: CC(=O)N=[N+]=[N-] -> CN=C=O

Rearrangement

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Reaction

Dess-Martin Oxidation

Very mild oxidation - many functional groups tolerated, Stops at aldehyde (no over-oxidation), Room temperature, neutral conditions, Expensive but selective

Formula: DMP (Dess-Martin periodinane)
Detail: CH₂Cl₂
SMILES: CCO -> CC=O

Oxidation

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Reaction

DIBAL Reduction (Ester → Aldehyde)

-78°C, 1 equivalent

Formula: DIBAL-H (diisobutylaluminum hydride)
SMILES: CC(=O)OC -> CC=O

Reduction

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Reaction

Diels-Alder Reaction

Heat or pressure

Formula: Heat (or Lewis acid catalyst)
SMILES: C=CC=C.C=C -> C1CC=CCC1

PericyclicSyn addition on both components. Endo product kinetically favored.

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Reaction

Dissolving Metal Reduction (Alkyne → trans-Alkene)

-33°C (liquid ammonia)

Formula: Na or Li, NH₃ (liquid)
Detail: Reduction
SMILES: CC#CC -> C/C=C/C

AdditionReductionAnti addition → trans-alkene

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Reaction

E1 Elimination

Polar protic solvent, heat

Formula: Weak base or heat
Detail: E1 / Water or alcohol
SMILES: CC(C)(C)Br -> CC(C)=C

EliminationE1No stereospecificity (unlike E2)Zaitsev: more substituted alkene favored

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Reaction

E2 Elimination

Strong base, heat

Formula: KOtBu, NaOEt, NaOH (conc.)
Detail: E2 / t-BuOH or EtOH
SMILES: CC(Br)CC -> CC=CC

EliminationE2Anti-periplanar geometry required. E/Z depends on which H is removed.Zaitsev: more substituted alkene favored (with most bases)

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Reaction

Enamine Formation

Remove water (Dean-Stark)

Formula: R₂NH (2° amine), acid catalyst
SMILES: CC(=O)CC -> CC(=CN(C)C)C

Carbonyl

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Reaction

Epoxidation (with mCPBA)

mCPBA = meta-chloroperoxybenzoic acid, Concerted mechanism, stereospecific, cis-alkene → cis-epoxide; trans-alkene → trans-epoxide

Formula: mCPBA, MMPP, peracetic acid
Detail: CH₂Cl₂
SMILES: CC=CC -> CC1OC1C

AdditionSyn addition (stereochemistry of alkene preserved)

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Reaction

Fischer Esterification

Reflux, remove water

Formula: MeOH, H₂SO₄ (cat.)
SMILES: CC(=O)O -> CC(=O)OC

Carbonyl

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Reaction

Friedel-Crafts Acylation

Acylium ion resonance-stabilized → NO rearrangement, Product is deactivated → only monosubstitution, Better control than alkylation, Clemmensen/Wolff-Kishner removes C=O if needed

Formula: CH₃COCl, AlCl₃
Detail: Electrophilic Aromatic Substitution
SMILES: c1ccccc1 -> c1ccccc1C(=O)C

AromaticElectrophilic Aromatic Substitution

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Reaction

Friedel-Crafts Alkylation

Carbocation can rearrange!, Product more reactive than starting material → polyalkylation, Does NOT work on deactivated rings (nitrobenzene), AlCl₃ catalyst

Formula: (CH₃)₂CHCl, AlCl₃
Detail: Electrophilic Aromatic Substitution
SMILES: c1ccccc1 -> c1ccccc1C(C)C

AromaticElectrophilic Aromatic Substitution

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Reaction

Gabriel Synthesis

Makes pure PRIMARY amines (no over-alkylation), Only works with 1° (and some 2°) halides (SN2), Alternative to direct alkylation of ammonia, Hydrazine releases amine, forms phthalhydrazide

Formula: R-X (1° alkyl halide), then N₂H₄ or NaOH/heat
SMILES: O=C1c2ccccc2C(=O)N1 -> CCN

Substitution

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Reaction

Grignard Addition to Carbonyl

Anhydrous ether, then acid workup

Formula: CH₃MgBr, then H₃O⁺
SMILES: CC=O -> CC(C)O

Carbonyl

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Reaction

Halogenation of Alkene

Bromonium ion intermediate explains anti stereochemistry, In water: halohydrin forms instead, Test for unsaturation: Br₂/CCl₄ decolorizes, Mechanism shown for Br₂; Cl₂ works analogously via chloronium ion

Formula: Br₂ (or Cl₂)
Detail: Electrophilic Addition / CCl₄ or CH₂Cl₂
SMILES: CC=CC -> CC(Br)C(Br)C

AdditionElectrophilic AdditionAnti addition (trans-dihalide from cis-alkene)

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Reaction

Halogenation of Benzene

Lewis acid catalyst required for benzene, Phenol and aniline react without catalyst (activated), Halogens are ortho/para directors but deactivating

Formula: Br₂, FeBr₃ (or AlBr₃)
Detail: Electrophilic Aromatic Substitution
SMILES: c1ccccc1 -> c1ccccc1Br

AromaticElectrophilic Aromatic Substitution

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Reaction

Halohydrin Formation

Water is nucleophile, not halide, Product can be converted to epoxide with base, Mechanism shown for Br₂; Cl₂ works analogously

Formula: Br₂/H₂O (or Cl₂/H₂O)
SMILES: CC=CC -> CC(O)C(Br)C

AdditionAnti additionOH on more substituted carbon (Markovnikov-like)

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Reaction

Heck Reaction

Aryl halide + Alkene → Substituted alkene, Generally gives trans (E) product, Nobel Prize 2010 (Heck), No organometallic partner needed (unlike Suzuki)

Formula: Alkene, Pd(OAc)₂, base (Et₃N), phosphine ligand
SMILES: c1ccccc1Br -> c1ccccc1/C=C/C

Coupling

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Reaction

Hell-Volhard-Zelinsky Reaction

α-Bromination of carboxylic acids, Goes through acid bromide intermediate, Br₂/P or Br₂/PBr₃, Product useful for further substitution

Formula: Br₂, PBr₃ or P
SMILES: CCC(=O)O -> CC(Br)C(=O)O

Substitution

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Reaction

Henry Reaction (Nitroaldol)

Like aldol but with nitroalkane, Product: β-nitro alcohol, Can dehydrate to nitroalkene, NO₂ can be converted to many groups (amine, carbonyl, etc.)

Formula: R-NO₂, base (NaOH, Et₃N)
SMILES: CC=O -> CC(O)C[N+](=O)[O-]

Addition

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Reaction

Hofmann Elimination

Heat

Formula: Ag₂O/H₂O then heat, NaOH, heat
Detail: E2
SMILES: CC(C)C[N+](C)(C)C -> C=CC(C)C

EliminationE2Hofmann: less substituted alkene (opposite of Zaitsev)

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Reaction

Hofmann Rearrangement

Aqueous base

Formula: Br₂, NaOH
SMILES: CC(=O)N -> CN

Rearrangement

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Reaction

Hydroboration-Oxidation

THF solvent, 0°C for BH₃, then oxidation

Formula: BH₃·THF, then H₂O₂/NaOH
Detail: Syn Addition
SMILES: CC=C -> CCCO

AdditionSyn AdditionSyn addition (H and OH end up on same face)Anti-Markovnikov: OH ends up on less substituted carbon

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Reaction

Hydrohalogenation (HX Addition)

Carbocation stability determines regiochemistry, Rearrangements possible with carbocation intermediate, Follows Markovnikov's rule, Mechanism shown for HBr; HCl and HI work analogously

Formula: HBr (or HCl, HI)
Detail: Electrophilic Addition
SMILES: CC=C -> CC(C)Br

AdditionElectrophilic AdditionMarkovnikov: H adds to carbon with more H's, X to more substituted carbon

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Reaction

Jones Oxidation (Alcohol → Carboxylic Acid)

Strong oxidizing agent, 1° alcohol → carboxylic acid (through aldehyde), 2° alcohol → ketone, 3° alcohol → no reaction

Formula: CrO₃/H₂SO₄/acetone, Jones reagent
SMILES: CCO -> CC(=O)O

Oxidation

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Reaction

KMnO₄ Oxidative Cleavage

Heat, aqueous

Formula: KMnO₄ (hot, concentrated)
SMILES: CC=CC -> CC(=O)O.CC(=O)O

Oxidation

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Reaction

LiAlH₄ Reduction

Very strong reducing agent, Reduces: aldehydes, ketones, esters, acids, amides, nitriles, Ester → 2 alcohols; Amide → amine, Violently reacts with water - use anhydrous!

Formula: LiAlH₄
Detail: Et₂O or THF (anhydrous!)
SMILES: CC(=O)OC -> CCO.CO

Reduction

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Reaction

Lindlar Reduction (Alkyne → cis-Alkene)

Lindlar catalyst is "poisoned" - stops at alkene, Lead (Pb) deactivates catalyst to prevent over-reduction, For trans-alkene, use dissolving metal reduction

Formula: H₂, Lindlar catalyst (Pd/CaCO₃/Pb)
Detail: Reduction
SMILES: CC#CC -> C/C=C\C

AdditionReductionSyn addition → cis-alkene

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Reaction

Malonic Ester Synthesis

Makes substituted acetic acids, Can alkylate twice for disubstituted, Decarboxylation: β-keto acid loses CO₂, Partner: acetoacetic ester synthesis (makes ketones)

Formula: NaOEt, R-X, then H₃O⁺/heat
SMILES: CCOC(=O)CC(=O)OCC -> CCC(=O)O

Substitution

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Reaction

Mannich Reaction

Three-component reaction: C-H acid + aldehyde + amine, Product is β-amino carbonyl (Mannich base), Important in alkaloid synthesis, Mannich base can undergo elimination to enone

Formula: HCHO, R₂NH (or NH₃), acid catalyst
SMILES: CC(=O)C -> CC(=O)CCN(C)C

Addition

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Reaction

Michael Addition

Conjugate (1,4) addition to α,β-unsaturated carbonyl, Soft nucleophiles prefer conjugate addition, Hard nucleophiles prefer 1,2-addition to C=O

Formula: Nucleophile (enolate, CN⁻, amine, thiol)
Detail: Conjugate Addition
SMILES: CC(=O)C=C -> CC(=O)CCC#N

CarbonylConjugate Addition

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Reaction

Mitsunobu Reaction

Converts alcohol to other groups with INVERSION, Nucleophiles: azides, phthalimide, carboxylic acids, phenols, pKa of nucleophile must be < 15, Great for stereochemistry manipulation

Formula: DEAD or DIAD, PPh₃, Nucleophile (pKa < 15)
SMILES: CC(C)O -> CC(C)N3

SubstitutionInversion of configuration (like SN2)

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Reaction

NaBH₄ Reduction (Aldehyde/Ketone → Alcohol)

Mild reducing agent, Reduces: aldehydes, ketones, Does NOT reduce: esters, amides, carboxylic acids, alkenes, Chemoselectivity useful in synthesis

Formula: NaBH₄
Detail: MeOH or EtOH
SMILES: CC=O -> CCO

Reduction

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Reaction

Negishi Coupling

Organozinc + Halide → Coupled product, More functional group tolerant than Grignard, Nobel Prize 2010 (Negishi), Works well for sp³-sp² coupling

Formula: R-ZnX (organozinc), Pd catalyst
SMILES: c1ccccc1Br -> c1ccccc1CC

Coupling

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Reaction

Nitration of Benzene

Heat

Formula: HNO₃, H₂SO₄
Detail: Electrophilic Aromatic Substitution
SMILES: c1ccccc1 -> c1ccccc1[N+](=O)[O-]

AromaticElectrophilic Aromatic Substitution

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Reaction

Olefin Metathesis

Swaps alkene partners (2 RCH=CH₂ → RCH=CHR + CH₂=CH₂), Ring-closing metathesis (RCM) makes rings, Ring-opening metathesis polymerization (ROMP), Nobel Prize 2005 (Grubbs, Schrock, Chauvin), Mechanism: metal-carbene via metallacyclobutane (Chauvin mechanism)

Formula: Grubbs catalyst (Ru-based)
SMILES: C=CC -> CC=CC

Coupling

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Reaction

Oxymercuration-Demercuration

Markovnikov product without carbocation rearrangement, Mercurinium ion intermediate prevents rearrangement, Alternative to acid-catalyzed hydration

Formula: Hg(OAc)₂/H₂O, then NaBH₄
Detail: Electrophilic Addition
SMILES: CC=C -> CC(C)O

AdditionElectrophilic AdditionAnti additionMarkovnikov: OH on more substituted carbon

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Reaction

Ozonolysis

-78°C

Formula: O₃, then Zn/H₂O or DMS
SMILES: CC=CC -> CC=O.CC=O

Oxidation

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Reaction

PCC Oxidation (1° Alcohol → Aldehyde)

Mild oxidizing agent - stops at aldehyde, For carboxylic acid, use Jones or KMnO₄, Also oxidizes 2° alcohol → ketone, Anhydrous conditions required

Formula: PCC (pyridinium chlorochromate)
Detail: CH₂Cl₂
SMILES: CCO -> CC=O

Oxidation

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Reaction

Pinacol Rearrangement

Acidic conditions, heat

Formula: H₂SO₄, H₃PO₄
SMILES: CC(O)(C)C(O)(C)C -> CC(=O)C(C)(C)C

Rearrangement

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Reaction

Reductive Amination

One-pot: Carbonyl + Amine → Amine, NaBH₃CN: selective for iminium (works at pH ~6), NaBH(OAc)₃: milder, better functional group tolerance, Avoids over-alkylation problem of direct alkylation

Formula: R-NH₂, then NaBH₃CN or NaBH(OAc)₃
SMILES: CC=O -> CCNC

Reduction

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Reaction

Reformatsky Reaction

Like Grignard but for α-bromo esters, Zn less reactive than Mg - ester survives, Product: β-hydroxy ester, Useful when Grignard would attack the ester

Formula: α-Bromo ester, Zn, aldehyde or ketone
SMILES: BrCC(=O)OCC -> CC(O)CC(=O)OCC

Addition

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Reaction

Robinson Annulation

Michael addition + Aldol condensation = ring formation, Makes 6-membered rings with enone, Key step in steroid synthesis, One of most important ring-forming reactions

Formula: MVK (methyl vinyl ketone), base
SMILES: CC(=O)CC(=O)C -> CC1=CC(=O)CCC1

Carbonyl

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Reaction

Saponification (Base-Catalyzed Ester Hydrolysis)

Aqueous base, reflux

Formula: NaOH, KOH
SMILES: CC(=O)OCC -> CC(=O)[O-].CCO

Carbonyl

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Reaction

Sharpless Asymmetric Epoxidation

Requires allylic alcohol (OH directs reaction), D-tartrate → attacks from "front" (mnemonic), L-tartrate → attacks from "back", Nobel Prize 2001 (Sharpless)

Formula: TBHP (t-BuOOH), Ti(OiPr)₄, Tartrate ester (D or L)
SMILES: C/C=C/CO -> CC1OC1CO

AdditionEnantioselective: D-(-)-tartrate or L-(+)-tartrate controls face of attack

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Reaction

Simmons-Smith Cyclopropanation

Alkene → Cyclopropane, Delivers :CH₂ (carbene equivalent), Stereospecific: cis-alkene → cis-disubstituted cyclopropane, OH group directs addition (hydroxyl-directed)

Formula: CH₂I₂, Zn-Cu couple (or Et₂Zn)
SMILES: CC=CC -> CC1CC1C

AdditionSyn addition - cyclopropane stereochemistry reflects alkene geometry

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Reaction

SN1 Solvolysis

Polar protic solvent, heat

Formula: H₂O
Detail: SN1 / Water or aqueous ethanol
SMILES: CC(C)(C)Br -> CC(C)(C)O

SubstitutionSN1Loss of stereocontrol (planar carbocation attacked from either face → racemization if chiral center)

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Reaction

SN2 with Azide

Polar aprotic solvent

Formula: NaN₃
Detail: SN2
SMILES: CCBr -> CCN=[N+]=[N-]

SubstitutionSN2

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Reaction

SN2 with Cyanide

Polar aprotic solvent

Formula: NaCN, KCN
Detail: SN2 / DMSO or DMF
SMILES: CCI -> CC#N

SubstitutionSN2Inversion of configuration

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Reaction

SN2 with Hydroxide

Polar aprotic solvent

Formula: NaOH, KOH
Detail: SN2 / DMSO, DMF, or acetone
SMILES: CCBr -> CCO

SubstitutionSN2Inversion of configuration (Walden inversion)N/A - single site of attack

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Reaction

SN2 with Tosylate Leaving Group

Polar aprotic solvent

Formula: NaN₃
Detail: SN2
SMILES: CCOS(=O)(=O)c1ccc(C)cc1 -> CCN=[N+]=[N-]

SubstitutionSN2

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Reaction

Sonogashira Coupling

Aryl halide + Terminal alkyne → Aryl alkyne, Cu activates alkyne for transmetalation, Room temperature, mild conditions, Used heavily in pharmaceutical synthesis

Formula: Terminal alkyne, Pd catalyst, CuI (co-catalyst), amine base
SMILES: c1ccccc1Br -> c1ccccc1C#CC

Coupling

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Reaction

Stille Coupling

Very functional group tolerant, Stannanes are stable but TOXIC (Sn), Being replaced by Suzuki in many applications, Still used for complex molecule synthesis

Formula: R-SnBu₃ (organostannane), Pd catalyst
SMILES: c1ccccc1Br -> c1ccccc1C=C

Coupling

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Reaction

Strecker Synthesis

Classic amino acid synthesis, Aldehyde → α-Amino acid, Racemic product (non-stereoselective), One of oldest named reactions (1850)

Formula: NH₃, HCN, then H₃O⁺
SMILES: CC=O -> CC(N)C(=O)O

Addition

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Reaction

Sulfonation of Benzene

Reversible reaction (unlike other EAS), Sulfonation blocks position (protecting group strategy), Desulfonation: H₂O/H⁺, heat

Formula: SO₃, H₂SO₄ (fuming)
Detail: Electrophilic Aromatic Substitution
SMILES: c1ccccc1 -> c1ccccc1S(=O)(=O)O

AromaticElectrophilic Aromatic Substitution

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Reaction

Suzuki-Miyaura Coupling

Most widely used cross-coupling reaction, Boronic acids are air-stable, non-toxic, Nobel Prize 2010 (Suzuki), Works with aryl, vinyl halides/triflates

Formula: PhB(OH)₂ (aryl boronic acid), Pd(PPh₃)₄, base (Na₂CO₃)
SMILES: c1ccccc1Br -> c1ccccc1c2ccccc2

Coupling

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Reaction

Swern Oxidation

-78°C

Formula: (COCl)₂ (oxalyl chloride), DMSO, Et₃N
SMILES: CCO -> CC=O

Oxidation

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Reaction

Syn Dihydroxylation (OsO₄)

OsO₄ is toxic and expensive - use catalytic with NMO, Alternative: cold, dilute KMnO₄ (also syn)

Formula: OsO₄, cat. OsO₄ with NMO
SMILES: CC=CC -> CC(O)C(O)C

AdditionSyn addition (both OHs on same face)

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Reaction

Williamson Ether Synthesis

Best method for making ethers, Use 1° or methyl halides (SN2 mechanism), Bulky alkoxide + 3° halide → elimination instead!, Unsymmetrical ethers: put smaller group on halide

Formula: R-X (alkyl halide), alkoxide
SMILES: C[O-] -> COC

Substitution

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Reaction

Wittig Reaction

Converts C=O to C=C, Ylide made from: Ph₃P + R-X, then base, Stereochemistry controlled by ylide type (stabilized vs unstabilized)

Formula: Ph₃P=CH₂ (ylide)
SMILES: CC=O -> CC=C

Carbonyl

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Reaction

Wolff-Kishner Reduction

High temperature, ethylene glycol

Formula: NH₂NH₂ (hydrazine), KOH, heat
SMILES: c1ccc(C(=O)C)cc1 -> c1ccc(CC)cc1

Reduction

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