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Organic Reactions > Organic Synthesis > Flashcards

Organic Synthesis Flashcards

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Organic Chemistry 101 flashcards
1
Q

Alkanes –> Halogenoalkanes

A

Mechanism: Free Radical Substitution

Reagent: Chlorine/Bromine

Conditions: UV Light

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2
Q

Alkene –> Alkane

A

Addition/ Reduction

Reagent: Hydrogen

Conditions: Ni catalyst

N.B. CANNOT use LiAlH4 as it is a source of hydride ions, which will be repelled by electron rich double bond.

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3
Q

Alkene –> Dihalogenoalkane

A

Mechanism: Electrophilic Addition

Reagent: Bromine/ Chlorine (dissolved in organic solvent)

Conditions:Room temperature

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4
Q

Alkene –> Halogenoalkane

A

Mechanism Electrophilic Addition

Reagent: HCl/HBr

Conditions: Room temperature

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5
Q

Alkene –> Bromoalcohol

A

Addition

Reagent: Bromine water

Observation: brown to colourless

Test for carbon double bond

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6
Q

Alkene –> Bromoalcohol

A

Addition

Reagent: Bromine water

Observation: brown to colourless

Test for carbon double bond

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7
Q

Alkene –> Diol

A

Oxidation

Reagent: KMnO4 in acidified solution

Conditions: Room temperature

Observation: purple colour of MnO4- ions decolourises

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8
Q

Alkene –> Alcohol

A

Hydration

Reagent: water

Conditions: High T (300-600), High pressure (70 atm) and conc H3PO4 acid catalyst

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9
Q

Alkene –> Polymer

A

Addition Polymerisation

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10
Q

Halogenoalkane –> Alcohol (2)

A

Hydrolysis

Reagent; Water

Add silver nitrate which will react with halid leaving group to to produce silver halide ppt –> identification test

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11
Q

Halogenoalkane –> Alcohol (1)

A

Mechanism: Nucleophilic Substitution

Reagent: KOH/NaOH

Conditions: AQUEOUS solution, heat under reflux

Primary undergo SN2 mechanism and tertiary undergo SN1 mechanism

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12
Q

Halogenoalkane –> amine

A

Mechanism: Nucleophilic substitution

Reagent: Ammonia, dissolved in ethanol

Conditions: Heat under pressure in sealed tube

N.B. If ammonia added in aqueous solution, alcohol forms

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13
Q

Halogenoalkane –> Alkene

A

Mechanism: Elimination

Reagents: KOH/NaOH

Conditions: In ETHANOL; heat

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14
Q

Alcohol –> Chloroalkane

A

PCl5

observations: misty fumes

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15
Q

Alcohol –> Bromoalkane

A

KBr and 50% conc H2SO4

will produce HBr in situ to prevent its escape

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16
Q

Alcohol –> Iodoalkane

A

Red phosphorus and iodine (PI3 produced in situ)

Can’t use KI and H2SO4 as sulphuric acid will oxidise hydrogen halides to other products.

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17
Q

Alcohol –> Aldehyde

A

Oxidation

Reagent: K2Cr2O7 (acidified by dilute sulphuric acid)

Conditions: Use limited amount of dichromate, warm gently and distil out aldehyde as it forms.

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18
Q

Alcohol –> Carboxylic Acid

A

Oxidation

Reagent: K2CrO7 (acidifed with dilute sulphuric acid)

Conditions: use an EXCESS of dichromate and heat under reflux (distil off product after reaction)

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19
Q

Secondary alcohol –> Ketone

A

Oxidation

Reagent: K2CrO7 (acidified with dilute sulphuric acid)

Conditions: Heat under reflux

20
Q

Alcohol –> Alkene

A

Acid catalysed elimination

Reagents: Concentrated phosphoric acid

Conditions: warm under reflux

Role of reagent: deyhdrating agent/catalyst

21
Q

Aldehyde –> Carboxylic acid

A

Oxidation

Reagent: K2CrO7 (acidified with dilute sulphuric acid)

Conditions: Heat under reflux

22
Q

Aldehydes –> Primary alcohols

A

Reduction

Reagent: LiAlH4 in dry ether

Conditions: Room temperature and pressure

23
Q

Ketones–> Secondary alcohols

A

Reduction

Reagent: LiAlH4 in dry ether

Conditions: Room temperature and pressure

24
Q

Carbonyl –> Hydroxynitrile

A

Mechanism: Nucleophilic addition

Reagent: HCN (in presence of KCN- catalyst)

Conditions: Room re and pressure

25
Q

Iodoform reaction (test for methyl group adjacent to carbonyl group)

A

Reagents: NaOH and I2

Conditions: warm gently

Observations: yellow crystalline precipitate with antiseptic smell

26
Q

Nitrile –> Carboxylic acid

A

Hydrolysis

Reagent: dilute HCl/ H2SO4

Conditions: Heat under reflux

27
Q

Carboxylic acid –> Alcohol

A

Reduction

Reagents: LiAlH4 in dry ether

Condition: Room temperature and pressure

28
Q

Carboxylic acid –> Carboxylate salt

A

Three methods:

  1. Add metal (Na)
  2. Add alkali (NaOH)
  3. Add carbonate (Na2CO3)
29
Q

Carboxylic acid –> Acyl chloride

A

Reagent: PCl5

Conditions: Room temperature

Observations: Misty fumes (HCl)

30
Q

Carboxylic acid –> Ester

A

Add alcohol

Conditions: strong acid catalyst (H2SO4), heat under reflux

Reaction is reversible. Low yield.

31
Q

Ester –> Carboxylic acid + alcohol

A

Two ways for this hydrolysis:

  1. with acid
    Reagent: dilute HCl
    Conditions: Heat under refluc
    This is a reversible reaction.
  2. with NaOH
    Reagent: dilute NaOH
    Conditions: Heat under reflux
    Reaction goes to completion! :)
32
Q

Acyl chloride –> Carboxylic acid

A

Reagent: water
Condition: room temperature

Observations: Steamy white fumes of HCl

33
Q

Acyl chloride –> ester

A

Reagent: alcohol
Conditions: room temperature

Observation: Steamy white fumes of HCl

Reaction not reversible so preferred method to make ester :)

34
Q

Acyl chloride –> Primary Amide

A

Reagent: Ammonia
Conditions: Room temperature

Observation: White smoke of NH4Cl given off

35
Q

Acyl chloride –> Secondary amide

A

Reagent: Primary amine

Conditions: room temperature

36
Q

Polyester formation

A
  1. Dicarboxylic acid + diol –> polyester + water

2. Diacyl chloride + diol –> polyester + HCl

37
Q

Benzene –> Bromobenzene

A

Mechanism: Electrophilic Substitution

Reagents: Bromine

Conditions: Aluminium (III) Bromide catalyst

38
Q

Benzene –> Nitrobenzene

A

Mechanism: Electrophilic substitution

Reagents: Conc nitric acid in the presence of conc sulphuric acid (catalyst)

Electrophile is NO2+
Equation to form electrophile:
HNO3 + 2H2SO4 –> NO2+ + 2HSO4- + H3O+

39
Q

Benzene –> Cyclohexane

A

Hydrogenation

Reagents: Hydrogen

Conditions: Ni catalyst at 200 T and 30 atm

Reactions: Addition and reduction

40
Q

Benzene–> Alkylbenzene

A

Mechanism: Electrophilic Substitution

Reagents: Chloroalkane in the presence of anhydrous aluminium chloride catalyst

Conditions: Heat under reflux

41
Q

Benzene –> Phenyl ketone

A

Mechanism: Electrophilic substitution

Reagents: Acyl chloride in presence of anyhydrous aluminium chloride catalyst

Conditions: Heat under reflux

42
Q

Phenol –> 2,4,6-tribromophenol

A

Reagents: Bromine water

Conditions: Room temperature

43
Q

Amine –> Ammonium salt

A

Acid : HCl/H2SO4

addition of NaOH to an ammonium salt will convert it back to amine

44
Q

Primary amine –> secondary amine

A

Reagent: Halogenoalkane

45
Q

Halogenoalkane –> nitrile

A

Reagents: KCN in ETHANOL

Conditions: heat under reflux

46
Q

Nitrile –> Amine

A

Reagents : LiAlH4 in dry ether

47
Q

Nitrobenzene –> aromatic amines

A

Reduction

Reagents: Sn and HCl

Conditions: heating

Organic Reactions (1 decks)

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