(3S)-3-methylpentan-1-ol
(3S)-3-methylpentan-1-oic acid
(3S, 4S, 6S)-3,6-dimethyloctan-4-ol,
(3S, 4R, 6S)-3,6-dimethyloctan-4-ol,
(3R, 4S, 6S)-3,6-dimethyloctan-4-ol,
and
(3R, 4R, 6S)-3,6-dimethyloctan-4-ol
(3S)-3-methylpentan-1-amine
3-methylpentane
(3S)-3-methylpentan-1-oic acid
Major products: (E)-(3S, 7S)-4-carboaldehyde-3,7-dimethylnon-4-ene
and
(Z)-(3S, 7S)-4-carboaldehyde-3,7-dimethylnon-4-ene
Minor products: (E)-(3S, 4S, 7S)-4-carboaldehyde-3,7-dimethylnon-5-ene,
(Z)-(3S, 4S, 7S)-4-carboaldehyde-3,7-dimethylnon-5-ene,
(E)-(3S, 4R, 7S)-4-carboaldehyde-3,7-dimethylnon-5-ene,
and
(Z)-(3S, 4R, 7S)-4-carboaldehyde-3,7-dimethylnon-5-ene
No Reaction
(3S)-2-methylhexan-3-ol
and
(3R)-2-methylhexan-3-ol
Complex Products
3-methyl-4-(1-methylethyl)heptan-4-ol
(3R, 4R)-3-methyl-4-(1-methylethyl)heptan-4-ol,
(3R, 4S)-3-methyl-4-(1-methylethyl)heptan-4-ol,
(3S, 4R)-3-methyl-4-(1-methylethyl)heptan-4-ol,
and
(3S, 4S)-3-methyl-4-(1-methylethyl)heptan-4-ol
(3S)-2-methylhexan-3-amine
and
(3R)- 2-methylhexan-3-amine
Major product: prop-2-yl butanoate
Minor product: propyl 2-methylpropanoate
(6S)-6-hydroxy-5,5-dimethyl-6-(1-methylethyl)nonan-4-one,
(6R)-6-hydroxy-5,5-dimethyl-6-(1-methylethyl)nonan-4-one,
4-ethyl-2-methyl-5-(1-methylethyl)oct-4-en-3-one (from Aldol adduct),
And other minor alkene products
No Reaction
(1S, 6S)-6-ethyl-2,2-dimethylcyclohexan-1-ol
and
(1R, 6S)-6-ethyl-2,2-dimethylcyclohexan-1-ol
Complex Products
(6S)-6-ethyl-2,2-dimethyl-1-(1-methylpropyl)cyclohexan-1-ol
(note that the molecule has two other chiral centers, each of these centers could be either R or S configuration)
(1S, 6S)-6-ethyl-2,2-dimethylcyclohexan-1-amine
and
(1R, 6S)-6-ethyl-2,2-dimethylcyclohexan-1-amine
(3S)-3-ethyl-1,1-dimethylcyclohexane
Major and minor complex products
Racemic mixture of complex products
No Reaction
Phenylmethanol
Benzoic acid
(1R, 2R)-2-methyl-1-phenylbutan-1-ol,
(1R, 2S)-2-methyl-1-phenylbutan-1-ol,
(1S, 2R)-2-methyl-1-phenylbutan-1-ol,
and
(1S, 2S)-2-methyl-1-phenylbutan-1-ol
Phenylmethanamine
(benzyl amine)
Toluene or methylbenzene
benzoic acid
No Reaction
No Reaction
(2S)-1-phenylpropan-2-ol
and
(2R)-1-phenylpropan-2-ol
Benzoic acid
(2R, 3S)-2,3-dimethyl-1-phenylpentan-2-ol,
(2S, 3S)-2,3-dimethyl-1-phenylpentan-2-ol,
(2R, 3R)-2,3-dimethyl-1-phenylpentan-2-ol,
and
(2S, 3R)-2,3-dimethyl-1-phenylpentan-2-ol
(2S)-1-phenylpropan-2-amine
and
(2R)-1-phenylpropan-2-amine
Propylbenzene
Major product: benzyl ethanoate
Minor product: methyl 2-phenylethanoate
(E)-4-methyl-3,5-diphenylpent-3-en-2-one
and
(Z)-4-methyl-3,5-diphenylpent-3-en-2-one
Sodium 2-phenylethanoate and triiodomethane (CHI3)
2-cyclopentylethan-1-ol
2-cyclopentylethanoic acid
(2R, 3R)-1-cyclopentyl-3-methylpentan-2-ol
(2R, 3S)-1-cyclopentyl-3-methylpentan-2-ol
(2S, 3R)-1-cyclopentyl-3-methylpentan-2-ol
and
(2S, 3S)-1-cyclopentyl-3-methylpentan-2-ol
2-cyclopentylethan-1-amine
1-ethylcyclopentane
2-cyclopentylethanoic acid
(E)-2,4-dicyclopentylbut-2-en-1-al,
(Z)-2,4-dicyclopentylbut-2-en-1-al,
And
Other minor alkene products possible from the aldol adduct
No Reaction
(2R)-3,3-dimethylpent-4-en-2-ol
and
(2S)-3,3-dimethylpent-4-en-2-ol
2,2-dimethyl-3-oxobutanoic acid and carbonic acid (HOCOOH)
(note that carbonic acid will spontaneously decompose into water (H2O) and carbon dioxide (CO2))
(4S, 5R)-3,3,5-trimethylhept-1-en-4-ol,
(4S, 5S)-3,3,5-trimethylhept-1-en-4-ol,
(4R, 5R)-3,3,5-trimethylhept-1-en-4-ol,
and
(4R, 5S)-3,3,5-trimethylhept-1-en-4-ol
(2R)-3,3-dimethylpent-4-en-2-amine
And
(2S)-3,3-dimethylpent-4-en-2-amine
3,3-dimethylpent-1-ene
Major product: (2,3-epoxy-1,1-dimethylpropyl) ethanoate
Minor product: methyl 3,4-epoxy-2,2-dimethylbutanoate
(E)-3,3,6,7,7-pentamethylnona-1,5,8-trien-4-one,
(Z)-3,3,6,7,7-pentamethylnona-1,5,8-trien-4-one
And
Other minor alkene products possible from aldol adduct
CHI3 precipitate likely
(Complex Products will also form)
(2S, 4S)-2,4-dimethyl-2-(1-methylethyl)hexan-1-ol
(2S, 4S)-2,4-dimethyl-2-(1-methylethyl)hexan-1-oic acid
(3R, 4S, 5S, 7S)-3,5,7-trimethyl-5-(1-methylethyl)nonan-4-ol
(3R, 4R, 5S, 7S)-3,5,7-trimethyl-5-(1-methylethyl)nonan-4-ol
(3S, 4S, 5S, 7S)-3,5,7-trimethyl-5-(1-methylethyl)nonan-4-ol
and
(3S, 4R, 5S, 7S)-3,5,7-trimethyl-5-(1-methylethyl)nonan-4-ol
(2S, 4S)-2,4-dimethyl-2-(1-methylethyl)hexan-1-amine
(5S)-2,3,3,5-tetramethylheptane
(2S, 4S)-2,4-dimethyl-2-(1-methylethyl)hexanoic acid
No Reaction
No Reaction
Organo-metallic reactions with carbonyl groups
Grignard mechanism (Can the stereochemistry change?)
Low Temperature in Step 2 minimizes Elimination
Oxime formation from an Aldehyde and Hydroxylamine
(E) and (Z) notations
Reduction of Oximes to Amines
Clemmensen Reduction:
Aldehydes → Alkanes
Peroxy-carboxylic acids
Baeyer-Villiger Oxidation:
Migratory Aptitudes
pKa and Acid/base Reactions
pKa of α-hydrogens
Le Chatelier's Principle
Aldol Addition and Condensation
Uncontrolled Temperatures Favor the Dehydration of the Alcohol to the Alkene
Elimination Favors Increasing Conjugation
Iodoform Reaction (what group is needed?)
Ketones typically resist further oxidation
Organo-metallic reactions with carbonyl groups
Grignard mechanism (Can the stereochemistry change?)
Low Temperature in Step 2 minimizes Elimination
Oxime formation from an Aldehyde and Hydroxylamine
(E) and (Z) notations
Reduction of Oximes to Amines
Clemmensen Reduction:
Ketones → Alkanes
Peroxy-carboxylic acids
Baeyer-Villiger Oxidation:
Migratory Aptitudes
pKa and Acid/base Reactions
pKa of α-hydrogens
Le Chatelier's Principle
Aldol Addition and Condensation
Uncontrolled Temperatures Favor the Dehydration of the Alcohol to the Alkene
Elimination Favors Increasing Conjugation
Iodoform Reaction (what group is needed?)
Ketone can be oxidized, causing a ring opening
Organo-metallic reactions with carbonyl groups
Grignard mechanism (Can the stereochemistry change?)
Low Temperature in Step 2 minimizes Elimination
Oxime formation from an Aldehyde and Hydroxylamine
(E) and (Z) notations
Reduction of Oximes to Amines
Clemmensen Reduction:
Ketones → Alkanes
Peroxy-carboxylic acids
Baeyer-Villiger Oxidation:
Migratory Aptitudes
pKa and Acid/base Reactions
pKa of α-hydrogens
Le Chatelier’s Principle
Aldol Addition and Condensation
Uncontrolled Temperatures Favor the Dehydration of the Alcohol to the Alkene
Iodoform Reaction (what group is needed?)
Organo-metallic reactions with carbonyl groups
Grignard mechanism (Can the stereochemistry change?)
Low Temperature in Step 2 minimizes Elimination
Oxime formation from an Aldehyde and Hydroxylamine
(E) and (Z) notations
Reduction of Oximes to Amines
Clemmensen Reduction:
Aldehydes → Methyl
Peroxy-carboxylic acids
Baeyer-Villiger Oxidation:
Migratory Aptitudes
Iodoform Reaction (what group is needed?)
Oxidative cleavage of benzene by KMnO4 (potassium permanganate)
Organo-metallic reactions with carbonyl groups
Grignard mechanism (Can the stereochemistry change?)
Low Temperatures in Step 2 minimize Elimination
Oxime formation from an Aldehyde and Hydroxylamine
(E) and (Z) notations
Reduction of Oximes to Amines
Clemmensen Reduction:
Ketones → Alkanes
Peroxy-carboxylic acids
Baeyer-Villiger Oxidation:
Migratory Aptitudes
pKa and Acid/base Reactions
pKa of α-hydrogens
Le Chatelier’s Principle
Aldol addition and condensation
Elimination Favors Increasing Conjugation
Uncontrolled Temperatures Favor the Dehydration of the Alcohol to the Alkene
Iodoform Reaction (what group is needed?)
What observation signifies a positive Iodoform Test?
Organo-metallic reactions with carbonyl groups
Grignard mechanism (Can the stereochemistry change?)
Low Temperature in Step 2 minimizes Elimination
Oxime formation from an Aldehyde and Hydroxylamine
(E) and (Z) isomers
Reduction of Oximes to Amines with LAH (Lithium aluminum hydride)
Clemmensen Reduction:
Aldehydes → Alkanes
Peroxy-carboxylic acids
Baeyer-Villiger Oxidation:
Migratory Aptitudes
pKa and Acid/base Reactions
pKa of α-hydrogens
Le Chatelier’s Principle
Aldol Addition and Condensation
Elimination Favors Increasing Conjugation
Uncontrolled Temperatures Favor the Dehydration of the Aldol Adduct to the conjugated enal condensation product
Iodoform Reaction (what group is needed?)
KMnO4 (potassium permanganate) oxidation dependence on temperature
Automatic dissociation of carbonic acid to water and carbon dioxide
Organo-metallic reactions with carbonyl groups
Grignard mechanism (Can the stereochemistry change?)
Low Temperature in Step 2 minimizes Elimination
Oxime formation from an Aldehyde and Hydroxylamine
(E) and (Z) notations
Reduction of Oximes to Amines
Clemmensen Reduction:
Ketones → Alkanes
Peroxy-carboxylic acids
Baeyer-Villiger Oxidation:
Migratory Aptitudes
Epoxide formation from alkenes
pKa and Acid/base Reactions
pKa of α-hydrogens
Le Chatelier’s Principle
Aldol Addition and Condensation
Uncontrolled Temperatures Favor the Dehydration of the Alcohol to the Alkene
I2 (iodine) and NaOH (Sodium hydroxide) can also react with the double bond (similar to Br2 (bromine) and NaOH (Sodium hydroxide))
Organo-metallic reactions with carbonyl groups
Grignard mechanism (Can the stereochemistry change?)
Which stereo-centers are preserved?
Low Temperature in Step 2 minimizes Elimination
Oxime formation from an Aldehyde and Hydroxylamine
(E) and (Z) notations
Reduction of Oximes to Amines
Clemmensen Reduction:
Aldehydes → Methyl
Changes to the number of chiral centers
Peroxy-carboxylic acids
Baeyer-Villiger Oxidation:
Migratory Aptitudes
Iodoform Reaction (what group is needed?)
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