Organic Synthesis Flashcards by Lewis Wadsworth

Alkane > Halogenoalkane

Reagents: Cl2
Conditions: UV light
Mechanism: Free-radical substitution
Type of reaction: Substitution

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Alkene > Halogenoalkane

Reagents: HX
Conditions: N/A
Mechanism: Electrophilic addition
Type of reaction: Addition

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Alkene > Dihaloalkane

Reagents: Halogen (Br2)
Conditions: N/A
Mechanisms: Electrophilic addition
Type of reaction: Addition

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Alkene > Alcohol

Reagents: H2O
Conditions: Conc H2SO4 or conc H3PO4
300 degrees
7 MPa
Mechanisms: Electrophillic addition
Type of reaction: Addition followed by hydrolysis

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1 Halogenoalkane > 1 Amine

Reagents: Conc NH3
Conditions: Excess NH3 dissolved in ethanol
Mechanism: Nucleophillic substution
Type of reaction: Substitution

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1 Halogenoalkane > 2 Amine

Reagents: 1 Amine
Conditions: Amine dissolved in ethanol
Mechanism: Nucleophilic substitution
Type of reaction: Substitution

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1 Halogenoalkane > 1 Alcohol

Reagents: NaOH (aq)
Conditions: Heat under reflux
Mechanism: Nucleophilic substitution
Type of reaction: Substiution

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1 2 or 3 Halogenoalkane > Alkene

Reagents: KOH (dissolved in ethanol)
Conditions: Heat under reflux
Mechanism: Elimination
Type of reaction: Elimination

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1 Halogenoalkane > Nitrile

Reagents: Potassium cyanide (dissolved in ethanol)
Mechansm: Nucleophilic substiution
Type of reaction: substitution

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Alcohol > alkene

Conc H2SO4 or conc H3PO4 (or Al2O3 catalyst)
Conditions: 170 degrees for acid dehydration
Mechanism: Elimination
Type of reaction: Elimination dehyration

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Alcohol > halogenoalkane

Reagent: HX
Conditions: Heat under reflux
Type of reacton: Substitution

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2 Alcohol > Ketone

Reagents: Acidified potassium dichromate (VI) solution
Conditions: Heat under reflux
Type of reaction: Oxidation

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Aldehyde > carboxylic acid

Reagents: Acidified potassium dichromate (VI) solution
Conditions: Heat under reflux
Type of reaction: Oxidation

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Aldehyde > 1 Alcohol

Reagents: NaBH4
Conditions: Aqueous solution
Mechanism: Nucleophilic addition
Type of reaction: Reduction

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Ketone > 2 Alcohol

Reagents: NaBH4
Conditions: Aqueous solution
Mechanism: Nucleophilic addition
Type of reaction: Reduction

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Aldehyde/Ketone > hydroxynitrile

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Reagents: KCN followed by a dilute acid
Conditions: N/A
Mechanism: Nucleophilic addition
Type of reaction: Addition

Carboxylic acid > Aldehyde

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Reagents: LiAlH4
Conditions: In dry ether
Mechanism: Nucleophilic addition
Type of reaction: Reduction

Carboxylic acid > 1 alcohol

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Reagents: LiAlH4
Conditions: In dry ether
Mechanism: Nucleophillic addition
Type of reaction: Reduction

Carboxylic acid > ester

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Reagents: Alchol
Conditions: conc sulfuric acid
Mechanism: Nucleophillic addition elimination
Type of reaction: Elimination or condensation

Nitrile > 1 Amine

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Reagents: LiAlH4
Conditions: In dry ether
Mechanism: Nucleophilic addition
Type of reaction: Reduction

Carboxylic acid > Ammonium salt

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Reagents: Ammonia solution
Conditions: Room temp
Mechanism: N/A
Type of reaction: Neutralisation

Carboxylic acid > Sodium salt

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Reagents: NaOH (aq)
Conditions: Room temp
Mechanism: N/A
Type of reaction: Neutralisation

Acyl chloride > carboxylic acid

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Reagents: H2O
Conditions: Room temp
Mechanism: Nucleophilic addition-elimination
Type of reaction: Hydroylsis

Acyl chloride > Amide

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Reagents: Ammonia
Conditions: Acid chloride added to conc ammonia
Mechanism: Nucleophilic addition-elimination
Type of reaction: Substitution

Acyl chloride > Ester

Reagents: Alcohol added to acid chloride Conditions: Room temp Mechanism: Nucleophilic addition-elimination Type of reaction: Esterification or elimination

Ester > carboxylic acid

Reagents: Dilute hydrochloric acid Conditions: Heat under refluc Mechanism: N/A Type of reaction: Hydrolysis

Acid anhydride > amide

Reagents: Conc NH3 Conditions: Room temp Mechanism: N/A Type of reaction: N/A

Acid anhydride > ester

Reagents: Alcohol Conditions: Room temp Mechanism: N/A Type of reaction: Elimination or condensation

Benzene > nitrobenzene

Reagents: conc HNO3 or conc H2SO4 Conditions: Low temp Mechanism: Electrophilic substitution Type of reaction: Substiution

Nitrobenzene > phenylamine

Reagents: Sn conc HCl Conditions: Heat under reflux and add NaOH Mechanism: N/A Type of reaction: Reduction

Benzene > Phenylethanone

Reagents: CH3COCl Conditions: AlCl3 catalyst with CH3COCl Mechanism: Electrophilic substitution Type of reaction: Substituiton

Why do chemists aim to design processes that do not require a solvent and use non- hazardous starting materials

Limit the potential for accidents and environmental damage Solvents are often flamable and toxic and have to be disposed off after (waste)

Why do chemists want reactions with high atom economy and percentage yeilds?

Organic Synthesis Flashcards

(33 cards)