Organic Synthesis Flashcards

1
Q

Alkane > Halogenoalkane

A

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

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2
Q

Alkene > Halogenoalkane

A

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

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3
Q

Alkene > Dihaloalkane

A

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

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4
Q

Alkene > Alcohol

A

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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5
Q

1 Halogenoalkane > 1 Amine

A

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

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6
Q

1 Halogenoalkane > 2 Amine

A

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

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7
Q

1 Halogenoalkane > 1 Alcohol

A

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

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8
Q

1 2 or 3 Halogenoalkane > Alkene

A

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

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9
Q

1 Halogenoalkane > Nitrile

A

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

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10
Q

Alcohol > alkene

A

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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11
Q

Alcohol > halogenoalkane

A

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

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12
Q

2 Alcohol > Ketone

A

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

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13
Q

Aldehyde > carboxylic acid

A

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

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14
Q

Aldehyde > 1 Alcohol

A

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

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15
Q

Ketone > 2 Alcohol

A

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

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16
Q

Aldehyde/Ketone > hydroxynitrile

A

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

17
Q

Carboxylic acid > Aldehyde

A

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

18
Q

Carboxylic acid > 1 alcohol

A

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

19
Q

Carboxylic acid > ester

A

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

20
Q

Nitrile > 1 Amine

A

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

21
Q

Carboxylic acid > Ammonium salt

A

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

22
Q

Carboxylic acid > Sodium salt

A

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

23
Q

Acyl chloride > carboxylic acid

A

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

24
Q

Acyl chloride > Amide

A

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

25
Q

Acyl chloride > Ester

A

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

26
Q

Ester > carboxylic acid

A

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

27
Q

Acid anhydride > amide

A

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

28
Q

Acid anhydride > ester

A

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

29
Q

Benzene > nitrobenzene

A

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

30
Q

Nitrobenzene > phenylamine

A

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

31
Q

Benzene > Phenylethanone

A

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

32
Q

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

A

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

33
Q

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

A