Native tools

Octet

Organic chemistry tools generated from the bundled source payload and run locally in the browser.

OverviewLocal data

Structure drawer

SmilesDrawer offline renderer / 272 structures
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Functional group

Alkane

Saturated hydrocarbons with only C-C single bonds. Least reactive functional group.

CCCC

Mechanism walkthrough

Substitution / 3 drawable steps
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Step 1Bromoethane: C-Br bond is polarized, carbon is electrophilic
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Step 2Hydroxide ion approaches from the backside (180° from leaving group)
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Step 3Concerted: C-O bond forms as C-Br bond breaks. Br⁻ leaves.

Functional groups

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AlkaneHydrocarbons / CₙH₂ₙ₊₂
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AlkeneHydrocarbons / CₙH₂ₙ
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AlkyneHydrocarbons / CₙH₂ₙ₋₂
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AlcoholOxygen / R-OH
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AldehydeOxygen / R-CHO
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KetoneOxygen / R-CO-R'
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Carboxylic AcidOxygen / R-COOH
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EsterOxygen / R-COO-R'
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EtherOxygen / R-O-R'
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EpoxideOxygen / Cyclic ether (3-membered)

Reagents

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Sodium BorohydrideReducing / NaBH₄
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Lithium Aluminum HydrideReducing / LiAlH₄
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DIBAL-HReducing / (i-Bu)₂AlH
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H₂/Pd (Catalytic Hydrogenation)Reducing / H₂ + Pd/C
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Lindlar CatalystReducing / Pd/CaCO₃/Pb
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Dissolving Metal (Na/NH₃)Reducing / Na + NH₃(l)
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Clemmensen ReductionReducing / Zn(Hg) + HCl
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PCC (Pyridinium Chlorochromate)Oxidizing / C₅H₅NH⁺CrO₃Cl⁻
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Jones ReagentOxidizing / CrO₃/H₂SO₄/H₂O
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Potassium PermanganateOxidizing / KMnO₄

Reference lookup

pKa: HIpKa -10Strongest common acid
pKa: HBrpKa -9
pKa: HClpKa -7
pKa: H₂SO₄pKa -3First proton
pKa: HNO₃pKa -1.4
pKa: H₃O⁺pKa -1.7Hydronium ion
pKa: HSO₄⁻pKa 2Second proton of H₂SO₄
pKa: HFpKa 3.2Weak due to strong H-F bond
pKa: RCOOH (carboxylic acid)pKa 4-5Resonance-stabilized anion
pKa: Acetic acid (CH₃COOH)pKa 4.76
pKa: Benzoic acidpKa 4.2
pKa: H₂CO₃pKa 6.4Carbonic acid
pKa: H₂SpKa 7
pKa: NH₄⁺pKa 9.2Ammonium ion
pKa: HCNpKa 9.2Hydrogen cyanide
pKa: Phenol (ArOH)pKa 10Resonance into ring stabilizes anion
pKa: RSH (thiol)pKa 10-11More acidic than alcohol
pKa: RNH₃⁺pKa 10-11Protonated amine