Organic synthesis Flashcards

1
Q

Alkane to Halogenoalkane

A

Mechanism: Free radical sub
Reagent(s): X₂
Conditions: UV light

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2
Q

Halogenoalkane to alkene

A

Mechanism: elimination
Reagent(s): KOH or NaOH
Conditions: ethanolic. heat under reflux

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3
Q

alkene to halogenoalkane

A

Mechanism: e- addition
Reagent(s): HBr or HCl
Conditions: room temp

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4
Q

alkene to dihalogenoalkane

A

Mechanism: e- addition
Reagent(s): Br₂ or Cl₂
Conditions: room temp

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5
Q

Dihalogenoalkane to Diol

A

Mechanism: Nucleophilic sub
Reagent(s): KOH
Conditions: (aq) heat under reflux

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6
Q

alkene to poly(alkene)

A

Conditions: high pressure catalyst

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7
Q

Halogenoalkane to nitrile

A

Mechanism: Nucleophilic sub
Reagent(s): KCN in ethanol/ water mixture
Conditions: heat under reflux

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8
Q

Nitrile to primary amine

A

reduction:
LiALH4 dry ether
OR
2H₂ + Ni cat high temp and pressure

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9
Q

Primary amine to secondary, tertiary or quaternary ammonium salt

A

Mechanism: Nucleophilic sub
Reagent(s): 1y amine
Conditions:

excess Haloalkane = 4y main product

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10
Q

Halogenoalkane to primary amine

A

Mechanism: Nucleophilic sub
Reagent(s): alcoholic excess NH3
Conditions: heat under pressure

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11
Q

Halogenoalkane to alcohol

A

Mechanism: Nucleophilic sub
Reagent(s): NaOH or KOH (aq)
Conditions: heat under reflux

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12
Q

alkene to alcohol

A

Mechanism: e- addition (hydration)
Reagent(s): conc H2SO4 + steam
Conditions: (aq) 300C and high pressure 70 atm

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13
Q

alcohol to alkene

A

Mechanism: elimination (dehydration)
Reagent(s): excess hot conc H2SO4, hot Al2O3 cat (lab)
Conditions: 600K

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14
Q

1y alcohol to aldehyde

A

oxidation:
Reagent(s): Na2Cr2O7/H+
Conditions: heat

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15
Q

2y alcohol to ketone

A

oxidation
Reagent(s): Na2Cr2O7/H+
Conditions: heat

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16
Q

aldehyde to 1y alcohol

A

Mechanism: Nucleophilic addition
Reagent(s): NaBH4
Conditions: room temp

17
Q

ketone to 2y alcohol

A

Mechanism: Nucleophilic addition
Reagent(s): NaBH4
Conditions: room temp

18
Q

aldehyde or ketone to hydroxynitrile

A

Mechanism: Nucleophilic addition
Reagent(s): KCN or HCN + H2SO4
Conditions: room temp

19
Q

aldehyde to carboxylic acid

A

oxidation
Reagent(s): excess oxidising agent, Na2Cr2O7/H+
Conditions: heat under reflux

20
Q

alcohol to ester

A

esterification:
Reagent(s): carboxylic acid and H2SO4
Conditions: heat

21
Q

carboxylic acid to ester

A

esterification:
Reagent(s): alcohol + H2SO4
Conditions: Heat

22
Q

ester to carboxylic acid

A

Reagent(s): dilute H2SO4 catalyst + H2O
Conditions: reflux

23
Q

primary amine to secondary amide

A

Mechanism: Nucleophilic addition
Reagent(s): acyl chloride
Conditions: room temp

24
Q

secondary amide to acyl chloride or acid anhydride

A

Mechanism: Nucleophilic add elim
Reagent(s): primary amine
Conditions: room temp

25
Q

acyl chloride or acid anhydride to carboxylic acid

A

Mechanism: Nucleophilic add elim
Reagent(s): H2O
Conditions: room temp

26
Q

acyl chloride or acid anhydride to N-substituted amide

A

Mechanism: Nucleophilic add elim
Reagent(s): amine
Conditions: room temp

27
Q

acyl chloride or acid anhydride to primary amide

A

Mechanism: Nucleophilic add elim
Reagent(s): NH3
Conditions: room temp

28
Q

Benzene to Nitrobenzene

A

Mechanism: e- sub
Reagent(s): HNO3 + H2SO4

29
Q

eqn for formation of nitronium electrophile

A

HNO3 + 2H2SO4 –> NO2+ + 2HSO4- + H3O+

30
Q

Benzene to phenyl ethanone

A

Mechanism: e- sub
Reagent(s): Acyl chloride + ALCl3 cat

31
Q

eqn for formation of acylium electrophile

A

AlCl3 + CH3COCl –> [CH3CO]+ + [AlCl4]-

32
Q

Nitrobenzene to phenyl amine

A

reduction
Reagent(s): Sn + conc HCl then NaOH

33
Q

Phenylamine to N-methyl benzenamine

A

Mechanism: Nucleophilic sub
Reagent(s): CH3Cl

34
Q

N-methyl benzenamine to N-phenyl ethanomide

A

Mechanism: Nu add elim
Reagent(s): CH3COCl

35
Q
A

Mechanism: Nu add
Reagent(s):

36
Q
A

reduction
Reagent(s): LiALH4 OR 2H2 + Ni cat

37
Q
A

Mechanism: Nu add
Reagent(s): NaBH4 (reduction)

38
Q
A

esterification:
Reagent(s): H2SO4 + CH3COOH
Conditions: heat