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Chemistry A Level Pearson's Edexcel > Organic Synthesis Reactions > Flashcards

Organic Synthesis Reactions Flashcards

1
Q

Halogenoalkane -> alcohol + ppt

Hint:
- Reagents and conditions
- Reaction type

A

+AgNO3 in ethanol
Heat

Nuclephilic substitution
(water acts as nucleophile)

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2
Q

Halogenoalkane -> nitriles

Hint:
- Reagents and conditions
- Reaction type

A

+KCN in ethanol
HUR
Nucleophilic substitution

(cyanide ion acts as a nucleophile)
(method of increasing C chain length)

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3
Q

Combustion (alkanes)

Hint:
- Complete and incomplete reaction equation
- Reagents

A

Complete:
alkane + oxygen(excess) -> carbon dioxide + water

Incomplete:
alkane + oxygen(insufficient) -> carbon/carbon monoxide + water

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4
Q

Free Radical Substitution

Hint:
- Reaction (overall)
- Reagents and conditions

A

Alkane + halogens -> halogenalkane

UV light + X2

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5
Q

Alkene -> Alkane

Hint:
- Reagents and conditions
- Reaction type

A

+Hydrogen
Solid nickel catalyst
150*C

Reduction hydrogenation

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6
Q

Alkenes -> dihalogenoalkanes

Hint:
- Reagents and conditions
- Reaction type
- Colour change

A

+X2 and RTP

Electrophilic addition

Halogen colour -> colourless

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7
Q

Alkenes -> alcohols

Hint:
- Reagents and conditions
- Reaction type

A
  • solid H3PO4 catalyst
  • 300*C and 60-70atm
  • electrophilic addition
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8
Q

Alkene -> diol

Hint:
- Reagents and conditions
- Colour change
- Reaction type

A
  • KMnO4 (aq)
  • dilute H2SO4
  • RTP
  • purple to colourless
  • oxidation / electrophilic addition
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9
Q

Halogenoalkanes -> amines

Hint:
- Reagents and conditions
- Reaction type

A
  • excess NH3 in ethanol
  • heat under pressure in sealed tube
  • nucleophilic substitution

(furher substitution may occur)
(ammonia molecule acts as a nucleophile)

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10
Q

Halogenoalkanes -> alkenes

Hint:
- Reagents and conditions
- Reaction type

A
  • KOH in ethanol
  • Heat under reflux
  • Elimination
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11
Q

Alcohol combustion

Hint:
- Reaction equation

A

Alcohol + oxygen -> water + carbon dioxide

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12
Q

Alcohol -> ketone (acidic)

Hint:
- Type of alcohol
- Reagents and conditions
- Colour change
- Reaction type

A
  • 2* alcohol
  • [O] -> K2Cr2O7
  • dilute H2SO2
  • Heat under reflux then distill out
  • Oxidation
  • Orange to green
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13
Q

Alcohol -> halogenoalkane

Hint:
- Reagents and conditions (for each halogen)
- Reaction type

A
  • Chloro -> +PCl5
  • Iodo -> Red phosphorus + 3/2 I2
  • Bromo -> KBr + 50% conc H2SO4
  • Substitution
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14
Q

Alcohol -> aldehyde (acidic)

Hint:
- Type of alcohol
- Reagents and conditions
- Colour change
- Reagents

A
  • 1* alcohol
  • [O] -> K2Cr2O7
  • dilute H2SO4
  • Oxidation
  • Orange -> green
  • Warm gently and distill out as it forms
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15
Q

Aldehyde -> carboxylic acid (acidic)

Hint:
- Reagents and conditions
- Reaction type
- Colour change

A
  • [O] -> K2Cr2O2
  • dilute H2SO2
  • Heat under reflux
  • Oxidation
  • Orange to green
  • Distil out acid
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16
Q

Alcohol -> carboxylic acid (acidic)

Hint:
- Alcohol type
- Reagents and conditions
- Reaction type
- Colour change

A
  • 2[O] -> K2Cr2O7
  • Dilute H2SO4
  • Heat under reflux
  • Orange -> green
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17
Q

Alcohol -> alkenes

Hint:
- Reagents and conditions
- Reaction type

A
  • H3PO4 catalyst
  • Warm under reflux
  • Elimination
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18
Q

Alkene -> polymer

Hint:
- Reagents and conditions
- Reaction type

A
  • Addition polymerisation
  • High temp + pressure
    (exact conditions depends on alkene)
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19
Q

Halogenoalkane -> alcohol

Hint:
- Reagents and conditions
- Reaction type

A
  • KOH
  • Heat under reflux
  • Nucleophilic substitution
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20
Q

Acyl chloride + alcohol -> ester

Hint:
- Side product
- Advantages
- Reaction type

A
  • HCl
  • Esterification
  • Fast and irreversible therefore high yield
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21
Q

Acyl chloride -> cab rboxylic acid

Hint:
- Reagents and conditions
- Side product and hazard

A
  • water
  • HCl
  • very acidic as two acids are produced (HCl + COOH)
22
Q

Carboxylic acid + alcohol -> ester

Hint:
- Reaction type
- Reagents and conditions

A
  • Condensation esterification
  • conc H2SO4 catalyst
23
Q

Carboxylic acid -> acyl chloride

Hint:
- Products
- Respective observations
- Reagents
- Reaction type

A
  • PCl5
  • Products HCl and POCl3 (HCl in the form of steamy white fumes + effervescence)
  • Substitution
24
Q

Nitrile -> carboxylic acid

Hint:
- Reagents and conditions
- Reaction type
- Reaction equation

A
  • R-CN + 2H2O -> carboxylic acid or carboyxlate salt
  • Heat under reflux w/:
    NaOH -> salt
    dilute HCl -> acid
  • Produces ammonia/ammonium dependent on conditions
  • Nitrile hydrolysis/Substitution
25
Q

Acyl chloride -> amide

Hint:
- Side products
- Reagents and conditions
- Reacton type

A
  • ammonia
  • HCl produced
  • Condensation
26
Q

Acyl chloride -> N-substituted amide

Hint:
- Reagents and conditions
- Side products

A
  • amine
  • produces HCl
27
Q

Ester -> carboxylic acid + alcohol (acidic)

Hint:
- Reagents and conditions
- Disadvantages

A
  • H2O
  • H+ catalyst (dilute HCl(aq))
  • Heat under reflux
  • Sow and reversible therefore no yield
28
Q

Aldehyde -> carboxylate (Fehling’s/Benedict/s)

Hint:
- Reagents and conditions
- Colour change
- Reaction type

A
  • Fehling’s/Benedict’s solution (alkaline Cu2+ ions)
  • Blue solution -> red precipitate
  • alkaline oxidation
29
Q

Aldehyde -> carboxylate (Tollens’)

Hint:
- Reagents and conditions
- Observations
- Reaction type

A
  • Alkaline Ag+ (aq)
  • Forms silver mirror
  • Alkaline oxidation
30
Q

Ester -> carboxylic acid + alcohol (alkanline)

Hint:
- Reagents and conditions
- Advantage

A
  • NaOH
  • Warm
  • Fast, irreversible and therefore has a high yield
  • Add HCl after to turn the carboxylate salt formed into a carboxylic acid
31
Q

Polyester formation

Hint:
- Reaction pairs
- Respective reaction type and products

A
  • Dicarboxylic acid + diol -> water
  • Diacyl chlroide + diol -> HCl
  • Hydroxycarboxylic acid -> water
  • Hydroxyacylchloride -> HCl
  • Condensation esterification polymerisation
32
Q

Aldeyde/ketone -> nitrile

Hint:
- Reagents and conditions (+explanation)
- Reaction type

A
  • HCN + KCN
  • KCN needed to generate nucleophile and HCN needed to turn C=O -> C-OH
  • Nucleophilic substitution
33
Q

Aldehyde -> 1* alcohol

Hint:
- Reagents and conditions
- Reaction equation
- Reaction type

A

Aldehyde + 2[H] -> 1* alcohol

[H] -> Lithal: lithium aluminium tetrahydride (solvent: dry ether)

-then dilute HCl (aq)
-reduction

34
Q

Ketone -> 2* alcohol

Hint:
- Reagents and conditions
- Reaction equation
- Reaction type

A

Ketone + 2[H] -> 2* alcohol

[H] -> Lithal: lithium aluminium tetrahydride (solvent: dry ether)

-then dilute HCl (aq)
-reduction

35
Q

Carboxylic acid -> 1* alcohol

Hint:
- Reagents and conditions
- Reaction equation
- Reaction type

A

Carboxylic acid + 4[H] -> 1* alcohol

[H] -> Lithal: lithium aluminium tetrahydride (solvent: dry ether)

-then dilute HCl (aq)
-reduction

36
Q

Iodoform reaction

Hint:
- Reagents and conditions
- Observations
- Reaction equation (+ product structure)
- Possible reactants

A

iodine + methyl ketone or methyl 2* alcohol -> iodoform

  • I2 (aq) w/ NaOH (aq)
  • warm
  • iodoform [RCOO-]
  • pale yellow ppt + antiseptic smell
37
Q

Nitrile -> amine

Hint:
- Reaction type (2)
- Reagents and conditions (2)

A
  • Reduciton via hydrogenation
  • LiAlH4 + acidic conditions
    OR
  • Catalytic hydrogenation
  • H2 w/ nickel catalyst
38
Q

Friedel-Crafts Acylation

Hint:
- Reaction equation
- Reagents and conditions

A

Benzene + R-COCl -> Benzene-C-RO + HCl

  • Acyl chloride
  • Warm w/ AlCl3 catalyst
39
Q

Phenol -> tribromophenol

Hint:
- Reagents and conditions

A
  • Br2
  • no heat, no catalyst
40
Q

Halogenoalkane -> amine

Hint:
- Reaction type
- Reaction equation
- (explanation for low yield)

A
  • Nucleophilic substitution
  • RX + 2NH3 -> R-NH3 + NH4+ +X-
  • Substitution can occur w/ all hydrogens on the amine because the product is still a nucleophile due to the lone pair on the nitrogen
41
Q

Amine + Cu2+

Hint:
- Reaction equation

A

[Cu(H2O)6]2+ + 2 R-NH2 -> [Cu(H2O)4(OH)2] + 2 R-NH3+

42
Q

Amine -> salt

Hint:
- Reaction equation
- Salt produced

A

R-NH2 + HCl -> R-NH3+
- Ammonium salt produced

43
Q

Amine -> amide

Hint:
- Reaction equation
- Structure of possible products

A

Amine + acyl chloride -> amide/N-sub amide
Amide -> R-CONH2
N-sub amide -> R-CONHR

44
Q

Friedel-Crafts Alkylation

Hint:
- Reaction equation
- Reagents and conditions

A

Benzene + R-Cl -> Beneze-R + HCl

  • Warm w/ R-Cl + AlCl3 catalyst
45
Q

Benzene combustion

Hint:
- Reaction equation
- Observation + explanation

A

Benzene + O2 -> CO2/C + H2O

  • Sooty flame
  • Because easier to produce elementary carbon
46
Q

Grignard reagents

Hint:
- Reagents and conditions
- Side product
- Reaction type
- Possible reactions

A

R-MgBr + H+ -> MgBr+
- Nucleophilic addition
- R-MgBr in dry ether

Possible Reactions:
1. Methanol -> 1* alcohol
2. Aldehyde -> 2* alcohol
3. Ketone -> 3* alcohol
4. CO2 -> carboxylic acid

47
Q

Polyamide produciton

Hint:
- Reaction pairs

A

Diamines + diacyl chloride
Amine carboxylic acid
Dicarboxylic acid + diamines
Amine acyl chloride

48
Q

Benzene -> benzene nitrate

Hint:
- Reagents and conditions
- Mechanism steps

A
  • Conc H2SO4 catalyst
  • Conc HNO3
  • Warm but T < 50*C
  • Mechanism:
    1. Generate electrophile
    2. Substitution
    3. Cleaning up
49
Q

Amine -> base

Hint:
- Reaction equation
- Explanation

A

R-NH2 + H2O -> R-NH3+ + OH-

  • Amine acts as base due to lone pair on nitrogen accepting H+
50
Q

Benzene -> bromobenze

Hint:
- Mechanism steps
- Reagents and conditions

A
  • Warm w/ Br2 + AlBr3 catalyst
  • Mechanism:
    1. Generate electrophile
    2. Substitution
    3. Cleaning up

Chemistry A Level Pearson's Edexcel (17 decks)

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