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Alevel Chemistry OCR A > Module 6: Carbonyls, Carbocylic Acid, Acyl And Esters > Flashcards

Module 6: Carbonyls, Carbocylic Acid, Acyl And Esters Flashcards

1
Q

Carbonyls
What are carbonyl compounds

A

Aldehydes and ketones

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2
Q

Carbonyls
What is the carbonyl functional group

A

C=O

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3
Q

Carbonyls
Where is the carbonyl group in aldehydes

A

At end of chain

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4
Q

Carbonyls
What is aldehydes suffix

A

-al

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5
Q

Carbonyls
Where is the carbonyl group in ketones

A

In middle of group

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6
Q

Carbonyls
What is the suffix for ketones

A

-one

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7
Q

Carbonyls
How are carbonyls made

A

Oxidising alcohols

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8
Q

Carbonyls
What is used to oxidise alcohol s

A

Oxidising agent acidified potassium dichromate H+/K2Cr2O7

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9
Q

Carbonyls
How do you form an aldehyde

A

Partially Oxidise a primary alcohol in distillation

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10
Q

Carbonyls
How do you form a ketone

A

Fully oxidise a secondary alcohol in reflux

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11
Q

Testing for carbonyl compounds
What is used to test

A

2,4-DNP

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12
Q

Testing for carbonyl compounds
What does 2,4-DNP detect

A

Prescience of carbonyl functional group in aldehydes and ketones

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13
Q

Testing for carbonyl compounds
What is observed when 2,4-DNP in presence of carbonyl

A

Yellow-orange precipitate is formed

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14
Q

Testing for carbonyl compounds
How is 2.4-DNP used in practical

A

Dissolved in methanol and sulfuric acid as asa a solid is very hazardous and explosive

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15
Q

Testing for carbonyl compounds
What is 2,4-DNP

A

2,4-dinitrophenylhydrazine

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16
Q

Testing for carbonyl compounds
Practical method for testing carbonyls

A
  1. Add 5cm 2,4-DNP solution to clean test tube this is in excess
  2. Use pippete add 3 drops of unknown compound and leave to stand
  3. Is no yellow crystals form add few drops of sulfuric acid
  4. A yellow orange precipitate indicates presence of group
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17
Q

Testing for carbonyl compounds can 2,4-DNP test for carboxylic acid

A

No

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18
Q

Testing for carbonyl compounds
How can you identify compounds using 2,4-DNP

A

Orange precipitate is a derivative of carbonyl compounds each different produces a crystalline precipitate with a different melting point so can measure melting point and compare to known

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19
Q

Testing for carbonyl compounds
How can you distinguish between aldehyde and ketone

A

Using tollens reagent

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20
Q

Testing for carbonyl compounds
What does the tollens reagent use to distinguish

A

Fact that an aldehyde can be easily oxidised to a carboxylic acid and a ketone cannot

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21
Q

Testing for carbonyl compounds
What is tollens reagent

A

Clear solution of silver nitrate in aqueous ammonia

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22
Q

Testing for carbonyl compounds
What happens to tollens reagent in prescience of aldehyde

A

Silver mirror is formed

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23
Q

Testing for carbonyl compounds
Practicals for tollens reagent

A
  1. In clean test tube add 3cm^3 aqueous silver nitrate
  2. Add aqueous silver hydroxide to test tube until a brown precipitate of silver oxide is formed, Ag2O
  3. Add dilute ammonia solution until brown precipitate just dissolves to form a clear colourless solution this is tollens
  4. Pour 2 cm depth of unknown solutions to clean test tube
  5. Add equal volume of tollen
  6. Leave test tube to stand in beaker of warm water about 50’C for 10-15 mins then observe if silver mirror formed
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24
Q

Testing for carbonyl compounds
Ionic equation for use of tollens

A

Ag(NH3)2+ (aq) + e- —> Ag(s) + 2NH3 (aq)

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25
Q

Reactions of carbonyls
How can you change carbonyls ack to alcohols

A

Reduction

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26
Q

Reactions of carbonyls
What is used to reduce carbonyls (general)

A

Reducing agent

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27
Q

Reactions of carbonyls
What symbol represents reducing agent

A

[H]

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28
Q

Reactions of carbonyls
What are aldehydes reduced to

A

Primary alcohol

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29
Q

Reactions of carbonyls
Equation for reducing aldehyde

A

RCHO + 2[H] —> RCH2OH

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30
Q

Reactions of carbonyls
What are ketones reduced to

A

Secondary alcohol

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31
Q

Reactions of carbonyls
Equation for reducing ketone

A

RCOR’ + 2[H] —> RCHOHR’

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32
Q

Reactions of carbonyls
What reducing agent is often used

A

NaBH4 dissolved in water with methanol
(Sodium borohydride

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33
Q

Reactions of carbonyls
What kind of reaction is reduction

A

Nucleophilic additons

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34
Q

Reactions of carbonyls
Why is reduction nucleophilic addition

A

Nucleophile attacks molecule and extra group is added

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35
Q

Reactions of carbonyls
Description of mechanisms for recution

A

Reducing agent supplied hydride ions H- which has a lone pair of electrons so its a nucleophile and can attack the delta positive carbon on carbonyl group
Electron pair from C=O moves onto o making it -ve
Lone pair of oxygen removes proton from water and over there is addition of hydrogen

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36
Q

Reactions of carbonyls
What ions the other common reaction

A

Hydrogen cyanide

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37
Q

Reactions of carbonyls
What does hydrogen cyanide and carbonyls produce

A

Hydroxynitrile molecules (with -OH and -CN group )

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38
Q

Reactions of carbonyls
What type fo reaction is carbonyl and hydrogen cyanide

A

Nucleophilic addition

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39
Q

Reactions of carbonyls
What is hydrogen cyanide so what’s does it do in water

A

Weak acid so partially dissolves to form H+ and CN- ion s

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40
Q

Reactions of carbonyls
Partial dissociation of HCN

A

HCN <=> H+ + CN-

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41
Q

Reactions of carbonyls
Mechnaism for reaction with HCN

A

CN- ion attacks slightly positive carbon atom and donates a pair of electrons to it both electrons from double bond transfer to oxygen
H+ bond to oxygen to form hydroxyl group

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42
Q

Reactions of carbonyls
What is true for HCN

A

Highly toxic gas

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43
Q

Reactions of carbonyls
How is HCN used in laboratories

A

Solution of acidified hydrogen cyanide in fume cupboard

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44
Q

Reactions of carbonyls
For reduction what is the condition

A

Aqueous or alcoholic

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45
Q

Reactions of carbonyls
What is the condions of HCN

A

Reflux

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46
Q

Reactions of carbonyls
Equation for HCN with ethanal

A

CH3CHO + HCN —> CH3CH(OH)CN

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47
Q

Reactions of carbonyls
What is the reaction with HCN useful for

A

Adding an extra C atom to a chain as CN can then be converted to carboxylic acid or amines

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48
Q

Reactions of carbonyls
What is the reaction with HCN useful for

A

Adding an extra C atom to a chain as CN can then be converted to carboxylic acid or amines

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49
Q

Carboxylic acid
What is the functional group

A

-COOH

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50
Q

Carboxylic acid
What are carboxylic acids

A

Weak acids

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51
Q

Carboxylic acid
What happens to carboxylic acid in water

A

Partially dissociate into carboxylate ions and H+ ions

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52
Q

Carboxylic acid
Where does the equilibrium lie in the dissociation

A

Towards left as most of molecules don’t dissociate

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53
Q

Carboxylic acid
What are they often used as

A

In organic synthesis as starting materials or intermediates to make more useful compunds

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54
Q

Carboxylic acid
What is the name of the functional group

A

Carboxyl group

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55
Q

Carboxylic acid
What type of imf can they form

A

Hydrogen bonds

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56
Q

Carboxylic acid
Whycan they form hydrogen bonds

A

C=O and O-H bond polar and Lone electron pair on oxygen to hydrogen also to water molecules

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57
Q

Carboxylic acid
Are they soluble

A

Yes

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58
Q

Carboxylic acid
Why are they soluble

A

Form hydrogen bonds to water molecules

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59
Q

Carboxylic acid
What happens to solubility at number of carbon atoms increase and why

A

Solubility decreases as non polar carbon chain has a greater effect on the overalll polarity fo the molecule

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60
Q

Carboxylic acid
Why are carboxylic acids more soluble then alcohol

A

Can form two hydrogen bonds for every one molecule with a carboxyl group

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61
Q

Carboxylic acid
Are they strong acuds

A

No weak

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62
Q

Carboxylic acid
What happens when dissolved in water

A

Partially dissociate

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63
Q

Carboxylic acid
Partial dissociation of methanoic acid

A

HCOOH(aq) <==> H+(aq) + HCOO-(aq)

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64
Q

Carboxylic acid reactions
What type of reactions do they undergo with what

A

Redox reactions with metals
Neutralisation reactions with bases

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65
Q

Carboxylic acid reactions
In redox and neutralisation reactions what do they form

66
Q

Carboxylic acid reactions
Name of salt they form

A

Carboxylate salts

67
Q

Carboxylic acid reactions
What is the ion called they form.

A

Carboxylate ion

68
Q

Carboxylic acid reactions
What do aqueous solution react with metals to form

A

Carboxylate salt and hydrogen gas

69
Q

Carboxylic acid reactions
What would you observe with redox reaction with metal

A

Metal disappearing and effervescence as hydrogen gas released

70
Q

Carboxylic acid reactions
Reaction for propanoic acid and magnesium

A

Mg(s) + 2 CH3CH2COOH(aq) —> (CH3CH2COO)2Mg(aq) + H2(g)

71
Q

Carboxylic acid reactions
What do the form from reacting with metal oxide

A

Metal carboxylate salt and water

72
Q

Carboxylic acid reactions
Reaction for Ethanoic acid and calcium oxide

A

CaO(s) + 2 CH3COOH(aq) —> (CH3COO)2Ca(aq) + H2O(l)

73
Q

Carboxylic acid reactions
What dot form from reaction with alkali

A

Salt + water

74
Q

Carboxylic acid reactions
Ionic equation for acid and alkali

A

H+(aq) + OH-(aq) —> H2O

75
Q

Carboxylic acid reactions
Observation for reaction with alkali

A

May not see reaction as for an aqueous solution of salt

76
Q

Carboxylic acid reactions
What is formed from reaction with carbonate

A

Metal carboxylate salt + water + CO2 gas

77
Q

Carboxylic acid reactions
Observation for reaction with carbonate

A

If carboxylic acid is in excess, solid carbonate would disapppear and effervescence from co2

78
Q

Carboxylic acid test
What is used to test for carboxylic acids

A

Neutralisation reaction with carbonates

79
Q

Carboxylic acid test
Why can they reaction with carbonates be used to test for it

A

Only common organic compounds sufficiently acidic enough to react with carbonates

80
Q

Carboxylic acid test
What is the carbonate test specifically useful to distinguish from

A

Phenol as they’re not acidic enough you react with carbonates

81
Q

Esters
What is the functional group

82
Q

Esters
What is the name made up of

A

Alcohol sections is first part eg ethanol becomes ethyl
Carboxylic acid derivative is the second part eg Ethanoic acid becomes ethanoate

83
Q

Esters
What s the name of the Esther from propanol and butanoic acid

A

Propyl butanoate

84
Q

Esters
What is a carboxylic acid derivative

A

Something that can be made from carboxylic acid eg acrylic chloride

85
Q

Esters
What type of reaction si esterification

A

Equilibrium

86
Q

Esters
What is esterificaiton

A

Making esters from carboxylic avid and alcohol

87
Q

Esterification
What are the reactants

A

Alcohol + carboxylic acid

88
Q

Esterification
What are the conditions

A

Reflux and conc acid catalyst (conc H2SO4 or H3PO4)

89
Q

Esterification
What does it produce

A

Ester and water

90
Q

Esterification
Where do the oxygens on the ester come from

A

C=O oxygen comes from carboxylic avid
C-O-C exogenous comes from alcohol
Other oxygen and 2 H form H2O

91
Q

Esterification
What type of reaction is this an example of and why

A

Condensation as molecules combine by releasing a smaller molecule

92
Q

Esterification
What does conc H2SO4 acts as and why

A

Dehydrating agent as removes water

93
Q

Esterification
What does the conc H2SO4 do for equilibrium

A

Removes water causing POE to move to right increasing yield of ester and water

94
Q

Esterification
What does the reaction being reversible mean

A

Product need to be separated as formed

95
Q

Esterification
How can you separate smaller esters as formed and why

A

Warm and distil them off a more volatile than other compounds

96
Q

Esterification Esterification
How can you separate larger esters and formed and why

A

Harder to form so best to heat them under reflux and use fractional distillation

97
Q

Esterification
Equation for ethanol and Ethanoic acid

A

CH3CH2OH + H3CCOOH <==> CH3CH2OOCCH3 + H2O

98
Q

Esterification
Wgat are two other ways to form esters

A

From alcohols and acid anhydrides
From alcohols and acrylic chlorides

99
Q

Esterification
What are acid anhydrides

A

Made from two carboxylic acids

100
Q

Esterification
Equation for two Ethanoic acids

A

2 H3CCOOH —> CH3C(=O)O(O=)CCH3 + H2O

101
Q

Esterification
Conditions for acid anhydrides + alcohol

102
Q

Esterification
What is the products of acid anhydrides + alcohols

A

Ester + carboxylic acid

103
Q

Esterification
How are the ester and carboxylic acdi separated

A

By fractional distillation

104
Q

Esterification
Equation for Ethanoic anhydride + methanol

A

H3CC(=O)O(O=)CCH3 + CH3OH —> H3CC(=O)OCH3 + CH3COOH

105
Q

Esterification
What is the products from acrylic chloride and alcohol

A

Ester + hydrogen chloride

106
Q

Esterification
Equation for ethyl chloride + methanol

A

CH3C(=O)Cl + CH3OH —> CH3C(=O)OCH3 + HCl

107
Q

Hydrolysis of ESters
What are the two types of hydrolysis

A

Acid hydrolysis
Base hydrolysis

108
Q

Hydrolysis of ESters
What is used in both hydrolysis

109
Q

Hydrolysis of ESters
What does acid hydrolysis split ester into

A

Carboxylic Acid and alcohol

110
Q

Hydrolysis of ESters
Conditions for acid hydrolysis s

A

Reflux with dilute acid such as HCl or H2SO4

111
Q

Hydrolysis of ESters
Equation for acid hydrolysis of ethyl ethanoate

A

CH3C(=O)OCH2CH3 + H2O <=> CH3COOH + CH3CH2OH

112
Q

Hydrolysis of ESters
Is acid hydrolysis reversible

113
Q

Hydrolysis of ESters
What is the problems of acid hydrolysis

A

Reversible reaction so will start to return to reactants

114
Q

Hydrolysis of ESters
What is used to pushy equilibrium to products

A

Need to add lots of water

115
Q

Hydrolysis of ESters
What is produced in base hydrolysis

A

Carboxylate salt + alcohol

116
Q

Hydrolysis of ESters
What are the conditions for base hydrolysis

A

Reflux with dilute alcohol

117
Q

Hydrolysis of ESters
Is base hydrolysis reversible

118
Q

Hydrolysis of ESters
Equation for ethyl ethanoate + NaOH

A

CH3C(=O)OCH2CH3 + NaOH —> CH3COO- Na+ + CH3CH3OH

119
Q

Hydrolysis of ESters
After base hydrolysis how can the carboxylic avid be reformed and what will be formed

A

Add HCl to products mixture
The carboxylic acid + metal chloride salt

120
Q

What are the two carboxylic acid derivative need to know

A

Acyl chlorided
Acid anhydrides

121
Q

Acyl chlorides
What is the functional group

122
Q

Acyl chlorides
What is the general formula

A

CnH2n+1COCl

123
Q

Acyl chlorides
What do they all end in

A

-oyl chloride

124
Q

Acyl chlorides
What is import about the functional group

A

Two dipoles on carbon from C=O bond and C-Cl

125
Q

Acyl chlorides
What is the slightly positive carbon atom susceptible for attach from

A

Nucleophiles

126
Q

Acyl chlorides
Why are they susceptible to attack from nucleophiles

A

Positive carbon due to 2 electron with drawing groups

127
Q

Acyl chlorides
What type of reactions do they undergo

A

Nucleophilic Addition elimination

128
Q

Acyl chlorides
What is their relative reactivity

A

Much more reactive then carboxylic acids and acid anhydrides

129
Q

Acyl chlorides
How do you form them

A

Chlorinations of carboxylic acids

130
Q

Acyl chlorides
What does chlorination of carboxylic acids involve

A

Replacing -OH with -Cl

131
Q

Acyl chlorides
What two reagents could possible be used for chlorinations of carboxylic acids

A

Thionyl chloride (SOCl2) to phosphorus pentachloride (PCl5)

132
Q

Acyl chlorides
What conditions are needed for chlorination of carboxylic acid

A

Dry conditions

133
Q

Acyl chlorides
What is produced in chlorinations of carboxylic acid using thionyl chloride

A

Acyl chloride + SO2 + HCl

134
Q

Acyl chlorides
What is the equation for Ethanoic acid and thionyl chloride

A

CH3COOH + SOCl2 —> CH3COCl + SO2 + HCl

135
Q

Acyl chlorides
What are the four nucleophiles they react with

A

Water
Alcohol
Ammonia
Amine

136
Q

Acyl chlorides
What is produced in reaction with water

A

Carboxylic acid + HCl(g)

137
Q

Acyl chlorides
Equation for ethanoyl chloride and water

A

CH3COCl + H2O —> CH3COOH + HCl(g)

138
Q

Acyl chlorides
What is produced in reaction with alcohol

A

Ester and HCl

139
Q

Acyl chlorides
Equation for ethanoyl chloride and ethanol

A

CH3COCl + CH3CH2OH —> CH3COOCH2CH3 + HCl(g)

140
Q

Acyl chlorides
What is produced with ammonia

A

Primary amide and HCl

141
Q

Acyl chlorides
What is reaction of ethanoyl chloride and ammonia

A

CH3COCl + NH3 —> CH3CONH2 + HCl

142
Q

Acyl chlorides
What is produced with amine

A

Secondary amide and HCl

143
Q

Acyl chlorides
Equation for ethanoyl chloride and methyl amine

A

CH3COCl + CH3NH2 —> CH3CONHCH3 + HCl(g)

144
Q

Acyl chlorides
What is always produced in Acyl chloride reactions

145
Q

Acyl chlorides
What is observed in Acyl chloride reactions and what is this useful for

A

White fumes from gas HCl useful to identify Acyl chlorides

146
Q

Acyl chlorides
Why are Acyl chlorides not always used (2)

A

HCl produced which is corrosive
Extremely exothermic and releases lots of heat

147
Q

Acyl chlorides
Why are Acyl chlorides sometimes chosen to be used

A

More reactive so less energy needed and cheaper

148
Q

Acyl chlorides
At what temp for these reactions occur

149
Q

Acid anhydrides
What is the functional group

A

R-C(=O)O(O=)C-R

150
Q

Acid anhydrides
How do you name them

A

-anoic anhydride

151
Q

Acid anhydrides
Relative reactivity

A

Less reactive

152
Q

Acid anhydrides
What does produce with water

A

2 carboxylic acid

153
Q

Acid anhydrides
Equation for Ethanoic anhydride with water

A

CH3COOOCCH3 + H2O —> 2CH3COOH

154
Q

Acid anhydrides
What is produced with alcohol

A

Ester and carboxylic acid

155
Q

Acid anhydrides
Eqatuoin for Ethanoic anhydride and ethanol

A

CH3COOOCCH3 + CH3CH2OH —> CH3COOCH2CH3 + CH3COOH

156
Q

Acid anhydrides
What is produced with ammonia

A

Primary amide and carboxylic acid

157
Q

Acid anhydrides
What is equation for Ethanoic anhydride and ammonia

A

CH3COOOCCH3 + NH3 —> CH3CONH2 + CH3COOH

158
Q

Acid anhydrides
What is rpdocued with amine

A

Secondary amide and carboxylic acid

159
Q

Acid anhydrides
Equation for Ethanoic anhydride and methyl amine

A

CH3COOOCCH3 + CH3NH2 —> CH3CONHCH3 + CH3COOH

160
Q

Acid anhydrides
Why might these be prefered over Acyl chloride

A

Less reactive so less exo producing less heat
Doesn’t proceed HCL only carboxylic acids

161
Q

Acid anhydrides
Why is carboxylic acid preferred to be reduced then HCl

A

Are weak acids so less corrosive due to being more soluble as they’re dimers

Alevel Chemistry OCR A (17 decks)

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