Organic Synthesis Flashcards

(47 cards)

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
Iodoform reaction (test for methyl group adjacent to carbonyl group)
Reagents: NaOH and I2 Conditions: warm gently Observations: yellow crystalline precipitate with antiseptic smell
26
Nitrile --> Carboxylic acid
Hydrolysis Reagent: dilute HCl/ H2SO4 Conditions: Heat under reflux
27
Carboxylic acid --> Alcohol
Reduction Reagents: LiAlH4 in dry ether Condition: Room temperature and pressure
28
Carboxylic acid --> Carboxylate salt
Three methods: 1. Add metal (Na) 2. Add alkali (NaOH) 3. Add carbonate (Na2CO3)
29
Carboxylic acid --> Acyl chloride
Reagent: PCl5 Conditions: Room temperature Observations: Misty fumes (HCl)
30
Carboxylic acid --> Ester
Add alcohol Conditions: strong acid catalyst (H2SO4), heat under reflux Reaction is reversible. Low yield.
31
Ester --> Carboxylic acid + alcohol
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
Acyl chloride --> Carboxylic acid
Reagent: water Condition: room temperature Observations: Steamy white fumes of HCl
33
Acyl chloride --> ester
Reagent: alcohol Conditions: room temperature Observation: Steamy white fumes of HCl Reaction not reversible so preferred method to make ester :)
34
Acyl chloride --> Primary Amide
Reagent: Ammonia Conditions: Room temperature Observation: White smoke of NH4Cl given off
35
Acyl chloride --> Secondary amide
Reagent: Primary amine Conditions: room temperature
36
Polyester formation
1. Dicarboxylic acid + diol --> polyester + water | 2. Diacyl chloride + diol --> polyester + HCl
37
Benzene --> Bromobenzene
Mechanism: Electrophilic Substitution Reagents: Bromine Conditions: Aluminium (III) Bromide catalyst
38
Benzene --> Nitrobenzene
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
Benzene --> Cyclohexane
Hydrogenation Reagents: Hydrogen Conditions: Ni catalyst at 200 T and 30 atm Reactions: Addition and reduction
40
Benzene--> Alkylbenzene
Mechanism: Electrophilic Substitution Reagents: Chloroalkane in the presence of anhydrous aluminium chloride catalyst Conditions: Heat under reflux
41
Benzene --> Phenyl ketone
Mechanism: Electrophilic substitution Reagents: Acyl chloride in presence of anyhydrous aluminium chloride catalyst Conditions: Heat under reflux
42
Phenol --> 2,4,6-tribromophenol
Reagents: Bromine water Conditions: Room temperature
43
Amine --> Ammonium salt
Acid : HCl/H2SO4 addition of NaOH to an ammonium salt will convert it back to amine
44
Primary amine --> secondary amine
Reagent: Halogenoalkane
45
Halogenoalkane --> nitrile
Reagents: KCN in ETHANOL Conditions: heat under reflux
46
Nitrile --> Amine
Reagents : LiAlH4 in dry ether
47
Nitrobenzene --> aromatic amines
Reduction Reagents: Sn and HCl Conditions: heating