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OCR Chemistry A > Organic Synthetic Routes > Flashcards

Organic Synthetic Routes Flashcards

1
Q

Alkane -> Haloalkane

A 
X2
UV light
Free-radical substitution
1)Initiation-
Cl2->2Cl• (UV light) 
2)Propagation-
Cl•+CH4->CH3•+HCl
Cl2+CH3•->CH3Cl+Cl• 
3)Termination-
Cl•+Cl•->Cl2 
CH3•+CH3• -> C2H6• etc..
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2
Q

Alkene -> Dihaloalkane

A

Reagents: Halogen
Mechanism: Electrophilic Addition

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3
Q

Alkene -> Haloalkane

A

Reagents: HX (e.g. HBr)
Mechanism: Electrophilic addition

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4
Q

Haloalkane -> Amine

A

Reagents: Excess ethanolic ammonia
Conditions: Heat
Mechanism: nucleophilic substitution

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5
Q

Haloalkane -> Nitrile

A

Reagent: NaCN/ KCN ; ethanol
Conditions: reflux
Mechanism: nucleophilic substitution

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6
Q

Nitrile -> Amine

A

Reagents: H2, Ni catalyst
Conditions: High temp. and pressure
Mechanism: catalytic hydrogenation

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7
Q

Alkene -> Alcohol

A

Reagents: Steam, Phosphoric acid catalyst
Conditions: 300°C and 60-70 atm
Mechanism: Hydration

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8
Q

Alcohol -> Alkene

A

Reagents: conc. phosphoric acid
Conditions: 170°C
Mechanism: Elimination

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9
Q

Alcohol -> Haloalkane

A

Reagents: NaX, Sulfuric acid catalyst
Mechanism: Nucleophilic substitution

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10
Q

Haloalkane -> alcohol

A

Reagents: NaOH or H2O
Conditions: reflux
Mechanism: Nucleophilic substitution

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11
Q

Alcohol -> Ester

A

Reagents: Carboxylic Acid/ Acyl Chloride/ Acid Anhydride & Conc. Sulfuric Acid
Conditions: Reflux (w/ carboxylic acid)
Mechanism: Esterification

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12
Q

Ester- Acid Hydrolysis

A

Reagents: Water
Products: carboxylic acid and alcohol
Conditions: Reflux & dilute Sulfuric acid catalyst
Mechanism: Hydrolysis

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13
Q

Ester- Base Hydrolysis

A

Reagents: dilyte NaOH
Products: Carbooxylate salt and Alcohol
Conditions: Reflux
Mechanism: Hydrolysis (or saponification)

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14
Q

Alcohol -> Aldehyde

A

Reagents: Primary alcohol & K2Cr2O7/H+ i.e. acidified potassium dichromate & Sulfuric acid
Conditions: Distil
Mechanism: Oxidation
Observation: Orange -> Green

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15
Q

Alcohol -> Carboxylic Acid

A

Reagents: Primary alcohol & acidified potassium dichromate & Sulfuric acid
Conditions: Reflux
Mechanism: Oxidation
Observation: Orange -> Green

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16
Q

Alcohol -> Ketone

A

Reagents: Secondary Alcohol & Acidified potassium dichromate & sulfuric acid
Conditions: reflux
Mechanism: oxidation

17
Q

Aldehyde/Ketone -> Alcohol

A

Reagents: NaBH4 then water
Mechanism: Nucleophilic addition / Reduction

18
Q

Aldehyde/Ketone -> Hydroxynitrile

A

Reagents: HCN (made ‘in situ’ w/ NaCN and H2SO4)
Conditions: Alkaline, Reflux
Mechanism: nucleophilic addition
NaCN +H2SO4 ->HCN

19
Q

Hydroxynitrile -> Amine

A

Reagents: H2 and Ni catalyst
Conditions: High temp. and pressure
Mechanism: catalytic hydrogenation

20
Q

Hydroxynitrile -> Carboxylic

A

Reagents: dilute HCl
Conditions: reflux
Mechanism: Acid Hydrolysis
nitrile + 2H2O + HCl -> carboxylic acid + NH4Cl

21
Q

Nitrile -> Carboxylic Acid

A

Reagents: dilute HCl
Conditions: Reflux
Mechanism: Acid Hydrolysis
nitrile + 2H2O + HCl -> carboxylic acid + NH4Cl

22
Q

Carboxylic Acid -> Acyl Chloride

A

Reagents: SOCl2 (thionyl chloride)

Equation:
CH3COOH + SOCl2 -> CH3COCl + SO2 + HCl

23
Q

Acyl Chloride -> Carboxylic Acid

A

Reagents: cold H2O

24
Q

Acyl Chloride -> Primary Amide

A

Reagents: NH3
Mechanism: Nucleophilic addition-elimination reaction

25
Q

Acyl Chloride- > Secondary Amide

A

Reagents: Amine
Mechanism: Nucleophilic addition-elimination reaction

26
Q

Benzene -> Halobenzene

A

Reagents: Halogen, AlCl3 catalyst
Conditions: warm
Mechanism: Electriphilic Substitution

27
Q

Benzene -> Phenylketone

A

Reagents: Acyl chloride + AlCl3 catalyst
Conditions: reflux, 50’C, dry inert solvent
Mechanism: Friedal-Crafts acylation

28
Q

Benzene -> Alkyl Benzene

A

Reagents: Haloalkane + AlCl3 catalyst
Conditions: reflux
Mechanism:Friedal- Crafts Alkylation

29
Q

Benzene -> Nitrobenzene

A

Reagents: Conc. HNO3 & conc. H2SO4
Conditions: warm
Mechanism: Electrophilic Substitution

Equation: C6H6 + HNO3 → C6H5NO2 + H2O
Electrophile Regenerated:
CONC H2SO4 + CONC HNO3
H2SO4 + HNO3 → HSO4(-) + NO2(+) + H2O

30
Q

Nitrobenzene -> Phenylamine

A

Reagents: 1. Tin & conc. HCl 2. NaOH
Conditions: reflux
Mechanism: Reduction

31
Q

Phenol -> 2,4,6-Tribromophenol

A

Reagents: Bromine Water
Mechanism: Electrophilic substitution

32
Q

Phenol -> 2-nitrophenol or 4-nitrophenol

A

Reagents: Diltue HNO3
Mechanism: Nitration or electrophilic substitution

33
Q

Phenol -> Phenylester

A

Reagents: Acyl Chloride
Mechanism: electrophilic substitution

34
Q

Phenol -> Sodium Phenoxide

A

Reagents: NaOH
Mechanism: Neutralisation

OCR Chemistry A (5 decks)

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