VirtualChemist
It translates reactant Lewis formulas to machine readable format data, predicts and presents organic reaction mechanism, stereochemistry, and regiochemistry. Bug Fix (2021-04-18).
C3H5Br2
One isomer has a chiral center, another one does not.
C5H11Br
Some isomers have chiral centers, some does not.
C7H11O
It has two chiral centers.
methyl-cyclohexane
It has no chiral center.
C8H15OH
It has a chiral center.
C8H15OH
It has no chiral center.
C9H10O
It has a chiral center.
chlorohexane
Some isomers have one, some has two chiral centers.
CPI rule-1
Cahn-Ingold-Prelog sequence rules
CPI rule-2
Cahn-Ingold-Prelog sequence rules
isopropyl-methyl-ketone
Catalyst: acid or base. One step, two tautomers can be found.
2-methyl-propanamide
Catalyst: acid or base. Two tautomers can be found.
3-cyclohexene-1-one
(1). Catalyst: acid. Two tautomers are found. (2). Catalyst: base. Three tautomers are found.
Substrate: 3-methyl-2-penten-2-ol
Catalyst: acid or base. Two tautomers.
Substrate: 1-amino-2-methyl-1-butanol
Catalyst: acid/base. Two tautomers.
Substrate: 4-pyridone
Catalyst: acid. One tautomer.
Substrate: 4-hydroxypyridine
Catalyst: base. One Tautomer.
Substrate: 2-hydroxypyridone
Catalyst: base. One Tautomer.
Substrate: 2-pyridone
Catalyst: acid. One Tautomer.
Substrate: pyridine-2-thiol
Catalyst: base. One Tautomer.
Substrate: (S/R)2-bromobutane
(1). Reagent: CH3OK; Medium: CH3OH. (2). Reagent: CH3OH.
Substrate: (S/R)-2-chloro-1-methylcyclohexane
(1). Reagent: CH3OK; Medium: CH3OH. (2). Reagent: CH3OH.
Substrate: 1-bromopentane
(1). Reagent: NaOH; Medium: water. (2). Reagent: water.
Substrate: 2-bromo-2-methylpropane
(1). Reagent: CH3CH2OH.
Substrate: ter-butyl bromide
Reagent: CH3Ch2OH. The major reaction is solvolysis.
Substrate: (R/S)-1-bromo-2-methyl-cyclohexane
(1). Reagent: CH3OK, Medium: CH3OH. Major E2 product is ... (2). Reagent: CH3OH. Major SN1 product is (R/S) mixture.
Substrate: (R/S)-1-bromo-3-methyl-cyclohexane
(1). Reagent: CH3OK, Medium: CH3OH. Major E2 product is ... (2). Reagent: CH3OH. Major SN1 product is (R/S) mixture.
Substrate: 1-bromo-4-methyl-cyclohexane
(1). Reagent: CH3OK, Medium: CH3OH. Major E2 product is ... (2). Reagent: CH3OH. Major SN1 product is (R/S) mixture.
Substrate: (R/S)-1-bromo-5-ethyl-2-methyl-cyclohexane
(1). Reagent: CH3OK, Medium: CH3OH. Major E2 product is ... (2). Reagent: CH3OH. Major SN1 product is (R/S) mixture.
Substrate: 1-chloro-3-methyl-butane
Reagent: water. SN1/E1 competition
Substrate: (R/S)-1-phenyl-2-propanol
Reagent: H2SO4. Rearrangement, Zaitsev rule, (Z/E) products.
Substrate: (R/S)-2-phenyl-3-butanol
Reagent: HCl. Rearrangement, (R/S) products.
Substrate: 1-methyl-cyclohexanol
Reagent: HBr. Temperature effect on elimination-substitution competition.
Substrate: cyclohexyl-methyl-methanol
Reagent: HBr. Rearrangement, (R/S) products.
Substrate: 3-methyl-2-butanol
Reagent: HBr. Rearrangement, (R/S) products.
Substrate: 3-methyl-2-butanol
Reagent: HBr. Temperature effect on elimination-substitution competition
Substrate: (R/S)-4,4-dimethyl-3-pentanol
Reagent: H2SO4. Rearrangement, Zaitsev rule, (Z/E) products.
Substrate: (R/S)4-ethyl-4-methyl-3-pentanol
Reagent: H2SO4. Rearrangement, Zaitsev rule, (Z/E) products.
Substrate: 2, 2-dimethyl-1-pentanol
Reagent: HBr. Hindered primary alcohol SN1, rearrangement.
Substrate : 3, 3-dimethyl-1-pentanol
Reagent: HBr. primary alcohol SN2.
Substrate: (R/S)-2,3-dimethyl-cyclohexene
Reagent: HBr. Markovnikov rule, Br is axial in major stereoisomer.
Substrate: (R/S)-3,4-dimethyl-cyclohexene
Reagent: HCl. carbocation rearrangement, Markovnikov rule, (R/S)product, Cl is axial in major stereoisomer.
Substrate: 1-methyl-cyclohexene
Reagent: HBr. Markovnikov rule, Br is axial.
Substrate: 3-methyl-3-hexene
Reagent: HBr. Markovnikov rule, (R/S)product
Substrate: (R/S)-3-methyl-4-phenyl-1-butene
Reagent: HBr. carbocation rearrangement, Markovnikov rule, (R/S)product.
Substrate: (R/S)-1,3-dimethyl-cyclohexene
Reagent: HCl. Markovnikov rule, (R/S)product, Cl is axial in major stereoisomer.
Substrate: (Z/E)-1-phenylpropene
Reagent: HBr. regioselectivity, (R/S)product.
Substrate: 2-methyl-1-phenyl--1-propene
Reagent: HCl. regioselectivity, (R/S)product
Substrate: 2-butene
(1). Reagent: Cl2; (2). Reagent: Br2; (3). Reagent: I2. stereospecific anti-addition.
Substrate: phenyl ethylene
(1). Reagent: Cl2. (2). Reagent: Br2. (3). Reagent: I2. Size matters here.
Substrate: (s-cis/trans)-1,3-pentadiene
Reagent: HBr. Markovnikov rule, resonance, (R/S)product
Substrate: (E/Z)1,3,5-hexatriene
Reagent: HBr. Regioselectivity, resonance, (R/S)product.
Substrate: 2,5-dimethyl-2,4-hexadiene
Reagent: HBr, regioselectivity, resonance, (R/S)product
Substrate: (s-cis/trans)-1,3-pentadiene
Reagent: 2-propenal. Only s-cis- diene does Diels-Alder reaction, regioselectivity. However stereoselectivity?
Substrate: (s-cis/trans)2-methyl-1,3-butadiene
Reagent: 2-propenal. Only (s-cis)-dien does Diels-Alder reaction. regioselectivity. However stereoselectivity?
Substrate: (s-cis/trans)-1,3-butadienyl-methyl-ether
Reagent: 2-propenal, Only (s-cis)-diene does Diels-Alder reaction. regioselectivity. However, stereoselectivity?
Substrate: (s-cis/trans)-1,3-pentadiene
Reagent: acrylic acid. Only (s-cis)-diene does Diels-Alder reaction. Regioselectivity. However, stereoselectivity?
Substrate: (s-cis/trans)-1,3-butadiene
Reagent: butanedioic acid. Only (s-cis)-diene does Diels-Alder reaction. Both regioselectivity and stereoselectivity.
Substrate: 2-methyl-1,3-butadiene
Reagent: HBr. Regioselectivity
Substrate: 2-propenal
No reagent. Not very reactive but quite regioselective.
Substrate: isopropenyl-propenyl ketone
(1). Reagent: Cl2, Catalyst: acid. (2). Reagent: Cl2, Catalyst: base.
Substrate: isopropenyl-isopropenyl ketone
(1). Reagent: Br2, Catalyst: acid. (2). Reagent: Br2, Catalyst: base.
Substrate: propenyl-propenyl ketone
(1). Reagent: I2, Catalyst: acid. (2). Reagent: I2, Catalyst: base.
Substrate: cyclohexenyl-phenyl ketone
(1). Reagent: Grignard reagent (then water).
Substrate: cyclohexenyl-ethyl ketone
(1). Reagent: Organolithium (then water).
Substrate: pent-3-en-2-one
(1). Reagent: HBr.
Substrate: 4-methyl, hexe-3-en-2-one
(1). Reagent: methanol, Catalyst: acid.
Substrate: 4-methyl, pent-3-en-2-one
(1). Reagent: water, Catalyst: acid.
Substrate: pent-3-en-2-one
(1). Reagent: Br2. (2). Reagent: Br2, Medium: water. (3). Reagent: water, Catalyst: acid.
Substrate: pent-3-en-2-one
(1). Reagent: H2SO4.
Substrate: 2-methyl-5-hexenoic Acid
Reagent: Br2. Iodolactonization results in 6-membered rings, O and I are anti.
Substrate: 4-pentenoic acid
Reagent: I2. It produces 5-membered rings. O and I are anti.
Substrate: 3-methyl-5-hexenoic acid
Reagent: I2. It produces 6-membered rings. O and I are anti.
Substrate: Propanoic Acid
Reagent: (R/S)-1-methyl-1-propanol, Catalyst: acid. The stereochemistry of the alcohol is maintained.
Substrate: 2-methyl-propanoic Acid
Reagent: 2-methyl-1-propanol, Catalyst: acid. The esterification follows addition-elimination mechanism.
Substrate: (R/S)-4-hydroxy-pentanoic acid
Catalyst: acid. Intramolecular esterification yields lactone
Substrate: (R/S)-5-hydroxy-hexanoic acid
Catalyst: acid. Intramolecular esterification results in lactone.
Substrate: 4-hexenoic acid
Reagent: I2. Forming 5-membered ring and 6-membered ring. In one of the 6-membered ring, O and I are not Anti.
Substrate: 2-methyl-propanoic acid
Reagent: primary amine. Equilibrium favored at lower temperature.
Substrate: (R/S)-2-methyl-butanoic acid
Reagent: secondary amine. Equilibrium favored at lower temperature.
Substrate: Ethylbenzene or Toluene or Benzene or Benzaldehyde
Reagent: HNO3. Catalyst: acid. Nitration and substituent directing effect. Temperature is low at the last case.
Substrate: Ethylbenzene, Toluene or Benzene
Reagent: Br2 or Cl2. Catalyst: AlCl3. Lewis acid catalyzed halogenation.
Substrate: Ethylbenzene or Toluene or Benzene
Reagent: HOCl or HOBr or ICl. Halogenation.
Substrate: Ethylbenzene or Toluene or Benzene
Reagent: 1-bromobutane or 2-bromobutane. Catalyst: Lewis acid. Halogenation.
Substrate: Ethylbenzene or toluene or benzene
Reagent: 1-chloro-propane or 2-chloro-propane. Catalyst: Lewis acid. Reactivity order is F>Cl>Br>I.
Substrate: Ethylbenzene or Toluene or benzene
Reagent: 2-chloro-4-fluoro-hexane or 2-chloro-4-fluoro-pentane. Catalyst: Lewis acid. Friedel-Crafts alkylation. Reactivity order: F>Cl>Br>I.
Substrate: Ethylbenzene or Toluene or Benzene
Reagent: 2-chloro-5-fluoro-Hexane or 2-chloro-5-fluoro-heptane. Catalyst: Lewis acid. (entangled rings not done in 3D)
Substrate: ethylbenzene or toluene or benzene
Reagent: 2-propanol or 1-propanol or 2-butanol or 1-butanol or phenol. Catalyst: acid. Friedel-Crafts alkylation.
Substrate: Ethylbenzene or Toluene or benzene
Reagent: 3-methyl-butene or butane, propane or cyclohexene or 1-methylcyclohexene. Catalyst: acid. Friedel-Crafts alkylation.
Substrate: Ethylbenzene or Toluene or Benzene
Reagent: CH3Cl or CH2Cl2 or CHCl3 or CCl4. Catalyst: Lewis acid. C6H6 with CH3Cl gives PhCH3, with CH2Cl2 gives Ph2CH2, with CHCl3 gives PH3CH, with CCl4 gives PH3CCl.
The developer, Ming Yu, is a process engineer working in Canadian petrochemical industry. He attended schools in China and has degrees of BS, MS, and PhD all in chemical engineering. His earlier careers included thermodynamic calculations and engineering software development, his industrial experiences included plant design, operation, and technical services.