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Chemistry > Organic Reactions > Flashcards

Organic Reactions Flashcards

1
Q

Alkene to Alkane
Type of reaction - reagents - conditions

A

Addition - H2 (g), Ni catalyst, 150 degrees

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2
Q

Alkane to CO2 and H2O

Type of reaction - reagents - conditions

A

complete combustion - N/A - excess oxygen

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3
Q

Alkane to halogneoalkane Type of reaction - reagents - conditions

A

Free radical substitution - halogen gas - UV light

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4
Q

Halogenoalkane to alkene

Type of reaction - reagents - conditions

A

Elimination - ethanolic NaOH - reflux

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5
Q

Alkene to halogenoalkane Type of reaction - reagents - conditions

A

Electrophilic substitution - X-H - N/A

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6
Q

Alkene to Dihalogenoalkane Type of reaction - reagents - conditions

A

Electrophilic addition - X2 - N/A

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7
Q

Alkene to alcohol
Type of reaction - reagents - conditions

A

Electrophilic addition - stream, conc H3PO4 - 100 degrees (for steam)

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8
Q

Alcohol to Alkene (2 methods)

Type of reaction - reagents - conditions

A
  1. Elimination - conc. H3PO4 - 180. degrees
  2. Elimination - Al2O3 - heat
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9
Q

Alkene to diol

Type of reaction - reagents - conditions

A

N/A - acidified potassium permanganate (KMnO4) - N/A

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10
Q

Alkane to Alkene (2 types)

Type of reaction - products - conditions

A
  1. Thermal Cracking - Alkenes and alkanes - 400 < T < 900, 7000 kPa
  2. Catalytic Cracking - branched alkanes, cycloalkanes and aromatic hydrocarbons - zeolite catalyst, 450, slight pressure
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11
Q

Halogenoalkane to grignard reagent

Type of reaction - reagents - conditions

A

N/A - Mg in dry ether - reflux

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12
Q

Halogenoalkane to 1 amine

Type of reaction - reagents - conditions

A

Nucleophilic substitution - XS NH3 in ethanol - sealed tube, heat

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13
Q

Halogenoalkane to nitrile

Type of reaction - reagents - conditions

A

Nuc Sub - aq/ethanolic mix of KCN - reflux

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14
Q

Nitrile to carboxylic acid (2 ways)

Type of reaction - reagents - conditions

A
  1. Hydrolysis - Dilute HCl - reflux
  2. Hydrolysis - aq NaOH then acid - reflux
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15
Q

Nitrile to 1 amine (2 ways)

Type of reaction - reagents - conditions

A
  1. Reduction - LiAlH4 in dry ether - N/A
  2. Reduction - H2 - Ni, 150
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16
Q

Halogenoalkane to Alcohol

Type of reaction - reagents - conditions

A

Nuc sub - aqueous NaOH or KOH - warm

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17
Q

Alcohol to Halogenoalkane

Type of reaction - reagents - conditions

A
  1. Chlorination - PCl5 - room temp
  2. Bromination - 50% conc H2SO4, KBr - reflux
  3. Iodination - damp red P, I2 - warm
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18
Q

Alcohol to acid/ aldehyde/ ketone

Type of reaction - reagents - conditions

A

Oxidation- acidified K2Cr2O7 - reflux or distill depending on required product

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19
Q

Ketone/ aldehyde/ acid to alcohol

Type of reaction - reagents - conditions

A

Reduction - LiAlH4 in dry ether - N/A

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20
Q

What can LiAlH4 reduce and what are the conditions for its use

A

Polar double bonds - dry ether

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21
Q

Alcohol to ester

Type of reaction - reagents - conditions

A

Condensation (esterification) - carboxylic acid, conc H2SO4 - reflux

22
Q

Ester hydrolysis in acid

Type of reaction - reagents - conditions - products

A

Hydrolysis - water, HCl - reflux - equilibrium mix of ester, acid and alcohol

23
Q

Ester hydrolysis in alkali

Type of reaction - reagents - conditions - products

A

Hydrolysis - water, NaOH - reflux - carboxylate ion and alcohol

24
Q

Acid to acyl chloride

Type of reaction - reagents - conditions - other products

A

Substitution - PCl5 - N/A - POCl3 + HCl

25
Q

Acyl chloride to carboxylic acid

Type of reaction - reagents - conditions

A

Nuc sub - water - N/A

26
Q

Acyl chloride to ester

Type of reaction - reagents - conditions

A

Nucleophilic addition elimination
- alcohol - N/A

27
Q

Acyl chloride to amide (primary)

Type of reaction - reagents - conditions

A

Nucleophilic addition elimination
- ammonia - N/A

28
Q

Acyl chloride to secondary amide

Type of reaction - reagents - conditions

A

Nucleophilic addition elimination- primary amine - N/A

29
Q

Describe the first and second steps of Nucleophilic addition elimination of water and ethanoyl chloride

A
  1. Lone pair on O attacks delta+ C and double bond breaks with electrons going to O (addition)
  2. H lost from OH2 group, double bond reforms and Cl eliminated (elimination)
30
Q

How are polyesters formed (3 ways)

Type of reaction - reagents - conditions

A

Polymerisation - diol, dicarboxylic acid- reflux, H2SO4

Polymerisation - diol, diacyl chloride - N/A
Polymerisation - hydroxyl group and a carboxylic acid group on either end of the molecule

31
Q

Why are ester polymers biodegradable

A

The ester linkage is susceptible to hydrolysis

32
Q

Two reactants to make polyamides

A

Diamine and dicarboxylic acid

33
Q

3 pieces of evidence against the kekule structure

A
  1. All bond lengths are the same
  2. Enthalpy of hydrogenation is a less negative value than expected if it was 3 double bonds
  3. Benzene doesn’t undergo addition reactions
34
Q

What species attacks benzene rings

A

Electrophile

35
Q

Why don’t benzene react via addition

A

As they don’t want to lose the stability of the delocalised ring

36
Q

How to form a nitro group

Type of reaction - reactants - how both reaction steps happen

A

Acid base - nitric acid and sulphuric acid
1. Nitric acid acts as base and H2NO3+ forms
2. Dissociation into water and nitronium ion

37
Q

Benzene to Nitrobenzene

Type of reaction - reactants - conditions

A

Electrophilic substitution - nitric acid and benzene - 50 degrees and conc. H2SO4

38
Q

Why is nitration of benzene done at 50 degrees

A

Higher gives multiple substitutions and lower reduces rate of reaction too much

39
Q

What’s the electrophile in friedel-crafts acylation

A

Acylium ion

40
Q

How is an acylium ion formed

A

Acyl chloride + AlCl3 —> AlCl4- + acyclium ion

41
Q

Acyl group substitution onto benzene ring

Type of reaction - reactants - conditions

A

Electrophilic substitution - acyl chloride, AlCl3 - anhydrous

42
Q

Bromination of benzene

Type of reaction - reactants - conditions

A

Electrophilic substitution - Br2, FeBr3 catalyst - catalyst made in situ

43
Q

How is the catalyst formed in bromination of benzene
Reactants and equation

A

Iron fillings and bromine

2Fe + 3Br2 —> 2FeBr3

44
Q

What’s the Electrophile in Bromination of benzene

A

Bromonium Br+

45
Q

What kind of group is the OH in phenol and why

A

2,4,6 Activating - adds electron density to the ring

46
Q

Phenol + bromine water
Characteristics of product

A

2,4,6-tribromophenol - white ppt with antiseptic smell

47
Q

Phenol nitration

Type of reaction - reactants - conditions

A

Electrophilic substitution - dilute nitric acid - 50 degrees

48
Q

How do phenols behave differently to alcohols

A

They are weak acids (less so than carboxylic acids)

49
Q

Why can phenol behave as an acid

A

Delocalisation from the ring can stabilises A-

50
Q

How is friedelcrafts alkylation different to acylation

A

A Halogenoalkane is used rather than an acyl chloride

Chemistry (14 decks)

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