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EDEXCEL A2 Chemistry > organic 2 > Flashcards

organic 2 Flashcards

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1
Q

an aldehydes name ends in…

A

-al

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2
Q

where is the C=O bond on an aldehyde?

A

it always has the C=O bond on the 1st carbon of the chain

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3
Q

If there are two aldehyde groups then…

A

di is put before -al and an e is added to the stem.
e.g- pentanEDIAL

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4
Q

Ketones names end in

A

-one

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5
Q

If two ketone groups then…

A

di is put before -one and ane is added to the stem
e.g- pentanE-2,4-DIONE

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6
Q

The prefix oxo- should be used for compounds that contain…

A

a ketone group in addition to a carboxylic acid or aldehyde
e.g- 2-OXOpropanoic acid

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7
Q

Carboxylic acids have the ending…

A
  • oic acid
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8
Q

If there are carboxylic acid groups on both ends of the chain then it is called a…

A

-dioic acid

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9
Q

Nitriles end in …

A

-nitrile
e.g- butanenitrile

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10
Q

in nitriles, the C of the CN group counts as the…

A

first carbon in the chain

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11
Q

naming acyl chlorides…

A

add -oyl chloride to the stem
e.g- ethanOYL CHLORIDE

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12
Q

naming amides

A

add -amide to the stem
e.g- ethanamide

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13
Q

secondary and tertiary amides are named differently to show the two (or three) carbon chains…

A

The smaller alkyl group is preceded by an -N which plays the same role as a number in positioning a side alkyl chain
e.g- N-methylpropanamide

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14
Q

carbonyl compounds are compounds with….

A

a C=O bond.
- They can be either aldehydes or ketones

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15
Q

carbonyl compounds solubility in water

A
  • The smaller carbonyls are soluble in water because they can form hydrogen bonds with water.
  • Pure carbonyls cannot hydrogen bond, but bond instead by permanent dipole bonding.
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16
Q

The C=O bond is polarised because…

A

O is more electronegative than carbon.
- The positive carbon atom attracts nucleophiles.

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17
Q

what is the oxidising agent that causes alcohols and aldehydes to oxidise?

A

Potassium dichromate K2Cr2O7

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18
Q

oxidation of:
Primary alcohol →

A

aldehydes → carboxylic acid

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19
Q

oxidation of:
Secondary alcohol →

A

ketones

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20
Q

oxidation of:
Tertiary alcohols

A

Tertiary alcohols do not oxidise

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21
Q

can ketones be oxidised?

A

no

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22
Q

oxidation of aldehydes
- reaction

A

Reaction: aldehyde → carboxylic acid

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23
Q

oxidation of aldehydes:
reagent

A

Reagent: potassium dichromate (VI) solution and dilute sulfuric acid

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24
Q

oxidation of aldehydes:
conditions

A

Conditions: heat under reflux

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25
Q

Aldehydes can also be oxidised using…

A

Fehling’s solution or Tollen’s Reagent.
These are used as tests for the presence of aldehyde groups

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26
Q

observation during oxidation?

A

Observation: the orange dichromate ion (Cr2O7 2-) reduces to the green Cr 3+ ion

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27
Q

what does the silver mirror test for?

A

the presence of aldehyde groups

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28
Q

silver mirror test
reagent

A

Reagent: Tollen’s Reagent formed by mixing aqueous ammonia and silver nitrate

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29
Q

silver mirror test
conditions

A

conditions: heat gently

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30
Q

silver mirror test
reaction

A

Reaction: aldehydes only are oxidised by
Tollen’s reagent into a carboxylic acid and the silver(i) ions are reduced to silver atoms

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31
Q

silver mirror test
observation

A

observation: with aldehydes, a silver mirror forms coating the inside of the test tube.

KETONES RESULT IN NO CHANGE

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32
Q

fehlings solution test for aldehydes
reagent

A

Reagent: Fehling’s solution containing blue Cu 2+ ions.

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33
Q

fehlings solution test for aldehydes
conditions

A

conditions: heat gently

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34
Q

fehlings solution test for aldehydes
reaction

A

reaction: aldehydes are only oxidised by fehlings solution into a carboxylic acid and the copper ions are reduced to copper (l) oxide

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35
Q

fehlings solution test for aldehydes
observation

A

observation: blue Cu2+ ions in solution change to a red precipitate of Cu2O

KETONES DO NOT REACT

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36
Q

reduction of carbonyls
reagents

A

reagents: LiAlH4 (reducing agent), in dry ether

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37
Q

reduction of carbonyls
conditions

A

conditions: room temperature and pressure

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38
Q

reduction of carbonyls
type of reaction

A

type of reaction: reduction

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39
Q

LiAlH4 reduces carbonyls to…

A

alcohols

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40
Q

aldehydes are reduced to…

A

primary alcohols

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41
Q

aldehydes are reduced to…

A

primary alcohols

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42
Q

ketones are reduced to…

A

secondary alcohols

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43
Q

Addition of hydrogen cyanide to carbonyls forms…

A

hydroxynitriles

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44
Q

Addition of hydrogen cyanide to carbonyls
reaction

A

Reaction: carbonyl → hydroxynitrile

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45
Q

Addition of hydrogen cyanide to carbonyls
reagent

A

Reagent: HCN in presence of KCN

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46
Q

Addition of hydrogen cyanide to carbonyls
conditions

A

Conditions: Room temperature and pressure

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47
Q

Addition of hydrogen cyanide to carbonyls
mechanism

A

Mechanism: nucleophilic addition

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48
Q

When naming hydroxy nitriles the CN becomes part of the…

A

main chain

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49
Q

The extra KCN…

A

increases the concentration of the CN- ion nucleophile needed for the first step of the mechanism

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50
Q

the iodoform test
reagents

A

Reagents: lodine and sodium hydroxide

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51
Q

the iodoform test
conditions

A

Conditions: warm very gently

52
Q

the iodoform test
products

A

The product CHl3 is a yellow crystalline precipitate with an antiseptic smell

53
Q

what carbonyls will do the reaction in the iodoform test?

A

only carbonyls with a methyl group next to the C=O bond will do this reaction.
- ethanal is the only aldehyde that reacts.
- More commonly is methyl ketones.

54
Q

what is 2,4-dinitro phenylhydrazine used for?

A

2,4-DNP is used to identify if the compound is a carbonyl

55
Q

after using 2,4-DNP how can you distinguish between an aldehyde and ketone?

A

use tollens reagent

56
Q

2,4-DNP reacts with both…

A

aldehydes and ketones

57
Q

2,4-DNP test
product?

A

an orange precipitate

58
Q

how can you identify the carbonyl used with the 2,4-DNP test?

A

The melting point of the crystal formed can be used to help identify which carbonyl was used.
- Take the melting point of orange crystals product from 2,4-DNP.
- Compare melting point with known values in database

59
Q

acidity of carboxylic acids?

A

The carboxylic acid are only weak acids in water and only slightly dissociate, but they are strong enough to displace carbon dioxide from carbonates.

60
Q

solubility of carboxylic acids in water?

A

The smaller carboxylic acids (up to C4) dissolve in water in all proportions but after this the solubility rapidly reduces. They dissolve because they can hydrogen bond to the water molecules.

61
Q

Methods of preparing carboxylic acids…(3)

A
  • Full Oxidation of Primary Alcohols
  • Oxidation of Aldehydes
  • Hydrolysis of Nitriles
62
Q

Methods of preparing carboxylic acids
Full Oxidation of Primary Alcohols
reaction

A

Reaction: primary alcohol carboxylic acid

63
Q

Methods of preparing carboxylic acids
Full Oxidation of Primary Alcohols
reagent

A

Reagent: potassium dichromate(VI) solution and dilute sulfuric acid

64
Q

Methods of preparing carboxylic acids
Full Oxidation of Primary Alcohols
conditions

A

Conditions: use an excess of dichromate, and heat under reflux: (distil off product after the reaction has finished)

65
Q

Methods of preparing carboxylic acids
Full Oxidation of Primary Alcohols
observation

A

Observation: the orange dichromate ion (Cr2O7 2-) reduces to the green Cr 3+ ion

66
Q

Methods of preparing carboxylic acids
Oxidation of Aldehydes
reaction

A

Reaction: aldehyde → carboxylic acid

67
Q

Methods of preparing carboxylic acids
Oxidation of Aldehydes
reagent

A

Reagent: potassium dichromate (VI) solution and dilute sulfuric acid.

68
Q

Methods of preparing carboxylic acids
Oxidation of Aldehydes
conditions

A

Conditions: heat under reflux

69
Q

Methods of preparing carboxylic acids
Hydrolysis of Nitriles
reaction

A

Reaction: Nitrile → carboxylic acid

70
Q

Methods of preparing carboxylic acids
Hydrolysis of Nitriles
reagent

A

Reagent: dilute hydrochloric/ sulfuric acid.

71
Q

Methods of preparing carboxylic acids
Hydrolysis of Nitriles
conditions

A

Conditions: heat under reflux

72
Q

The Reactions of Carboxylic Acids

A
  • Reduction of carboxylic acids to alcohols
  • Reaction of carboxylic acid with phosphorous (V) chloride
  • Salt formation reactions of carboxylic acids
  • Oxidation of methanoic acid
73
Q

Reduction of carboxylic acids to alcohols
reagents

A

Reagents: LiAIH, In dry ether (reducing agent)

74
Q

Reduction of carboxylic acids to alcohols
conditions

A

Conditions: Room temperature and pressure

75
Q

Reduction of carboxylic acids to alcohols
product

A

product: primary alcohol

76
Q

Reaction of carboxylic acid with phosphorous (V) chloride
reaction

A

Reaction: carboxylic acid → acyl chloride + POCl3 + HCl

77
Q

Reaction of carboxylic acid with phosphorous (V) chloride
reagent

A

reagent: PCl5 (phosphorus (V) chloride

78
Q

Reaction of carboxylic acid with phosphorous (V) chloride
conditions

A

conditions: room temperature

79
Q

This reaction with PCIs (phosphorous(V)chloride) can be used as a test for…
what would you observe ?

A

carboxylic acids.
- You would observe misty fumes of HCl produced.

80
Q

This reaction with PCIs (phosphorous(V)chloride) can be used as a test for…
what would you observe ?

A

carboxylic acids.
- You would observe misty fumes of HCl produced.

81
Q

Salt formation reactions of carboxylic acids
what can carboxylic acids form salts with?

A
  • metals
  • alkalis
  • carbonates
82
Q

Salt formation reactions of carboxylic acids

acid + metal (Na) →

A

acid + metal (Na) → salt + hydrogen
2CH3CO2H + 2Na → 2CH3CO2-Na+ + H2

83
Q

Salt formation reactions of carboxylic acids
acid + alkali (NaOH) →

A

acid + alkali (NaOH) → salt + water
CH3CO2H + NaOH → CH3CO2-Na+ + H2O

84
Q

Salt formation reactions of carboxylic acids
acid + carbonate (Na2CO3) →

A

acid + carbonate (Na2CO3) → salt + water + carbon dioxide
2CH3CO2H + Na2CO3 → 2CH3CO2-Na+ + H20 + CO2

85
Q

The effervescence caused by production of CO2 with carboxylic acids with solid Na2CO3 or aqueous NaHCO3 can be used as a…

A

functional group test for carboxylic acids

86
Q

why can methanoic acid be oxidised but other carboxylic acids cannot?

A

Carboxylic acids cannot be oxidised by using oxidising agents but methanoic acid is an exception as its structure has effectively an aldehyde group

87
Q

how are esters formed from carboxylic acids?

A

Carboxylic acids react with alcohols, in the presence of a strong acid catalyst, to form esters and water. carboxylic acid + alcohol >< ester + water

88
Q

esters are named

A

backwards

89
Q

characteristics and uses of esters

A

Esters are sweet smelling compounds that can be used in:
- perfumes
- flavourings
- solvents for polar organic substances

90
Q

despite esters being polar, why can’t they form hydrogen bonds?
solubility in water?

A

there is no hydrogen bonded to a highly electronegative atom
they’re almost insoluble in water

91
Q

Esters can be hydrolysed and split up by either…

A

heating with
- acid or with sodium hydroxide

92
Q

hydrolysis of esters with acid
reagent

A

reagent: dilute HCl

93
Q

hydrolysis of esters with acid
conditions

A

conditions: heat under reflux

94
Q

hydrolysis of esters with acid
yield of products

A

does not give a good yield of the products

95
Q

hydrolysis of esters with sodium hydroxide
reagent

A

reagents: dilute sodium hydroxide

96
Q

hydrolysis of esters with sodium hydroxide
conditions

A

conditions: heat under reflux

97
Q

what’s more reactive, acyl chlorides or carboxylic acids?

A

Acyl chlorides are much more reactive than carboxylic acids

98
Q

acyl chlorides reaction with water
reaction

A

acyl chloride + water → carboxylic acid + HCl

99
Q

acyl chlorides reaction with water
reagent

A

reagent: water

100
Q

acyl chlorides reaction with water
condition

A

conditions: room temperature

101
Q

acyl chlorides reaction with water
observation

A

observation: Steamy white fumes of HCI are given off

102
Q

acyl chlorides reaction with alcohol
reaction

A

acyl chloride + alcohol → ester + HCl

103
Q

acyl chlorides reaction with alcohol
reagent

A

reagent: alcohol

104
Q

acyl chlorides reaction with alcohol
condition

A

condition: room temperature

105
Q

acyl chlorides reaction with alcohol
observation

A

Observation: Steamy white fumes of HCI
are given off

106
Q

acyl chloride reaction with ammonia
reaction

A

acyl chloride + ammonia → primary amide + NH4Cl

107
Q

acyl chloride reaction with ammonia
reagent

A

reagent: ammonia

108
Q

acyl chloride reaction with ammonia
conditions

A

conditions: room temperature

109
Q

acyl chloride reaction with ammonia
observations

A

Observation: white smoke of NH4Cl is given off

110
Q

acyl chloride reaction with primary amines
reaction

A

acyl chloride + primary amine → secondary amide + CH3NH3+Cl-

111
Q

acyl chloride reaction with primary amines
reagent

A

reagent: primary amine

112
Q

acyl chloride reaction with primary amines
conditions

A

conditions: room temperature

113
Q

there are 2 types of polymerisation. these are…

A

addition and condensation

114
Q

The two most common types of condensation polymers are…

A

polyesters and polyamides which involve the formation of an ester linkage or an amide linkage.

115
Q

In condensation polymerisation…

A

there are two different monomers that add together and a small molecule is usually given off as a side-product e.g. H2O or HCI

  • The monomers usually have the same functional group on both ends of the molecule e.g. di-amine, di carboxylic acid, diol, diacyl chloride.
116
Q

In condensation polymerisation…

A

there are two different monomers that add together and a small molecule is usually given off as a side-product e.g. H2O or HCI

  • The monomers usually have the same functional group on both ends of the molecule e.g. di-amine, di carboxylic acid, diol, diacyl chloride.
117
Q

what 2 reactions are used to form polyesters?

A

Carboxylic Acid + Alcohol → Ester + water

Acyl chloride + Alcohol → Ester + HCI

118
Q

If we have the same functional group on each end of molecule we can make…

A

polymers
e.g:
dicarboxylic acid + diol → poly(ester) + water

diacyl dichloride + diol → poly(ester) + HCI

119
Q

Using the carboxylic acid to make the ester or amide would need…

A

an acid catalyst

120
Q

terylene is…

A

a common polyester

121
Q

terylene is used for…

A

terylene fabric is used in clothing, tire cords

122
Q

Chemical reactivity of condensation polymers

A

polyesters can be broken down by hydrolysis and are therefore biodegradable

123
Q

Polyesters can be hydrolysed by…

A

acid and alkali

124
Q

With HCl, a polyester will be hydrolysed and split up into…

A

the original dicarboxylic acid and diol

125
Q

With NaOH an polyester will be hydrolysed and split up into…

A

the diol and dicarboxylic acid salt

EDEXCEL A2 Chemistry (19 decks)

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