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Chemistry (Organic) > Carboxylic acids & derivatives > Flashcards

Carboxylic acids & derivatives Flashcards

1
Q

Which carbon is carbon 1 when naming a carboxylic acid

A

The carbon with the carboxyl group

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2
Q

What is the test for for carboxylic acids. State the reagent and observation
Write the full and ionic equation for the test for ethanoic acid

A

Reagent: Na2CO3
Observation: Effervescence due to CO2

2CH3COOH + Na2CO3 –> 2CH3COONa + CO2 + H2O
2H+ + CO32- —> CO2 + H2O

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3
Q

What is the general equation when a carboxylic acid reacts with a carbonate

A

carboxylic acid + carbonate –> Salt + water + carbon dioxide

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4
Q

What type of acid are carboxylic acids

A

Weak acids

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5
Q

What do carboxylic acids dissociate into

A

H+ and carboxylate ion

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6
Q

Write the equation for the reaction between ethanoic acid and sodium carbonate

A
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7
Q

What is the general equation for the reaction between a carboxylic acid and an alcohol

A

carboxylic acid + alcohol <—> Ester + water

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8
Q

What are the conditions for the reaction between a carboxylic acid and an alcohol to form an ester

A

Concentrated H2SO4 catalyst
Warm conditions

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9
Q

How do we name an ester

A

The first part is named from the alcohol used, and the second is named from the carboxylic acid

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10
Q

How do we name an ester with a methyl group

A

We number the carbons with carbon 1 being the carbon with the =O

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11
Q

Give 4 uses of esters

A

Perfumes
Food flavourings
Solvents
Plasticisers

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12
Q

Why are esters good solvents

A

They are polar so other polar solvents will dissolve well in them

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13
Q

Why can esters be used in making glues

A

They have a low boiling point and evaporate easily

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14
Q

What is the general equation for the hydrolysis of an ester in acidic conditions

A

Ester + water <—> carboxylic acid + alcohol

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15
Q

What is the general equation for the hydrolysis of an ester in alkaline conditions

A

Ester + sodium hydroxide —-> carboxylate salt + alcohol

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16
Q

What are the conditions for the hydrolysis of an ester in acidic conditions

A

Dilute H2SO4 catalyst
Hot conditions (reflux)

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17
Q

What are the conditions for the hydrolysis of an ester in alkaline conditions

A

Aqueous NaOH
Hot conditions (reflux)

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18
Q

Why is the hydrolysis of an ester in alkaline conditions to form a carboxylic acid preferred over acidic conditions and why may it not be preferred

A

Drawback: 2 step reaction so lower yield

Benefit: Both reactions are not reversible so goes to completion
(Both reactions being formation of carboxylate salt and turning the salt into a carboxylic acid)

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19
Q

Which way does equilibrium shift when we add water to the hydrolysis of an ester in acidic conditions

A

Equilibrium shifts right and so more of the product is produced

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20
Q

How do we turn a carboxylate salt from the hydrolysis of an ester in alkaline conditions into a carboxylic acid

A

Add dilute HCl

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21
Q

Write the general equation for the reaction between a carboxylate salt and HCl

A

Carboxylate salt + HCl —> Carboxylic acid + chloride salt

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22
Q

What are the conditions for the reaction between a carboxylate salt and HCl to form a carboxylic acid

A

Warm carboxylate salt
Dilute HCl

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23
Q

What is propane-1,2,3-triol also known as

A

Glycerol

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24
Q

What do we get when we react glycerol and fatty acids together

A

An ester

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25
Q

What is a saturated fatty acid

A

Long chain carboxylic acid with no double bonds

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26
Q

What is an unsaturated fatty acid

A

Long chain carboxylic acid with double bonds

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27
Q

Explain why vegetable oils are liquid at room temperature

A

They have unsaturated carbon chains that aren’t straight and so cant be packed close together, hence they have lower VDW forces, therefore have lower M.P’s and are liquids at room temp

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28
Q

What type of molecule are oils

A

Ester

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29
Q

What type of molecules are fats

A

Ester

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30
Q

Explain why animal fats are solid at room temperature

A

They have saturated hydrocarbon chains that are straight and uniform which means they can be packed close together and have much higher VDW forces. Therefore they have high M.P’s and are solid at room temp

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31
Q

Is this a fat or an oil ester?

A

Oil

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32
Q

Is this a fat or an oil ester?

A

Fat

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33
Q

What do we get when we react NaOH with a fat(ester)

A

Glycerol & soap

34
Q

What is the general equation for saponification

A

Fat + 3NaOH —> Glycerol + 3 Carboxylate salt (soap)

35
Q

What are the conditions for saponification

A

Warm conditions
NaOH

36
Q

What is the general equation for transesterification

A

Fat + 3Methanol —> glycerol + 3Biodiesel (methyl ester)

37
Q

What are the conditions for transesterification

A

KOH catalyst

38
Q

What is biodiesel

A

A mix of fatty acids made from methyl esters

39
Q

Give 3 advantages of biofuel

A

Non-toxic
Biodegradable
Burns cleaner than petrol (molecule already contains O atoms so less O2 needed from the air, so less incomplete combustion and less CO and C produced)

40
Q

Give 3 drawbacks of biofuel

A

May lead to deforestation
Sacrifice land that could be used to grow food
Slow due to time taken to grow the plant (e.g. rapeseed oil plant)

41
Q

What is the suffix for acyl chlorides

A

-COCl at end of molecule
-Oyl chloride

42
Q

How do we name acyl chlorides

A

Find the longest carbon chain then add -oyl chloride at the end (carbon with the acyl group is C1)

43
Q

What is the general equation for when an acyl chloride reacts with water

A

Acyl chloride + water —> carboxylic acid + HCl
RCOCl + H2O —> RCOOH + HCl

44
Q

What is the general equation for when an acyl chloride reacts with ammonia

A

Acyl chloride + ammonia —> Amide + HCl
RCOCl + NH3—> RCONH2 + HCl

45
Q

What is observed when an acyl chloride reacts with water

A

Vigorous reaction, white misty fumes of hydrogen chloride gas produced (must be done in fume cupboard)

46
Q

What is observed when an acyl chloride reacts with ammonia

A

Vigorous reaction, white misty fumes of hydrogen chloride gas produced (must be done in fume cupboard)

47
Q

What is the general equation for when an acyl chloride reacts with an alcohol

A

Acyl chloride + alcohol —> Ester + HCl

48
Q

What is observed when an acyl chloride reacts with an alcohol

A

Vigorous reaction, white misty fumes of hydrogen chloride gas produced (must be done in fume cupboard)

49
Q

What is the general equation for when an acyl chloride reacts with a primary amine

A

Acyl chloride + primary amine —> N-substituted amide + HCl

50
Q

What is observed when an acyl chloride reacts with a primary amine

A

Vigorous reaction, white misty fumes of hydrogen chloride gas produced (must be done in fume cupboard)

51
Q

Which bond breaks when an acyl chloride is attacked by a nucleophile

A

The C-Cl bond

52
Q

What bond breaks in water when it reacts with an acyl chloride or acid anhydride

A

one of the O-H bonds

53
Q

What bond breaks in an alcohol when it reacts with an acyl chloride or acid anhydride

A

the O-H bond

54
Q

What bond breaks in ammonia when it reacts with an acyl chloride or acid anhydride

A

one of the N-H bonds

55
Q

What bond breaks in an amine when it reacts with an acyl chloride or acid anhydride

A

one of the N-H bonds

56
Q

What does an acid anhydride consist of

A

Made from 2 carboxylic acids that are identical

57
Q

How do we name an acid anhydride

A

We name the carboxylic acid its made from
remove -acid and replace with - anhydride

58
Q

What is the general equation for when an acid anhydride reacts with a water

A

Acid anhydride + water –> 2carboxylic acid
(2 of the same carboxylic acid)

59
Q

Which bond breaks in an acid anhydride when it is attacked by a nucleophile

A

one of the C-O bonds

60
Q

What is the general equation for when an acid anhydride reacts with ammonia

A

Acid anhydride + ammonia –> Amide + carboxylic acid

61
Q

What is the general equation for when an acid anhydride reacts with an alcohol

A

Acid anhydride + alcohol —> Ester + carboxylic acid

62
Q

What is the general equation for when an acid anhydride reacts with a primary amine

A

Acid anhydride + primary amine —> N-substituted amide + carboxylic acid

63
Q

Write the equation for the reaction between ethanoyl chloride and ethanoic anhydride with water

64
Q

Write the equation for the reaction between ethanoyl chloride and ethanoic anhydride with methanol

A

CH3COCl + CH3OH —> CH3COOCH3 + HCl
(CH3CO)2O + CH3OH —> CH3COOCH3 + CH3COOH

65
Q

Write the equation for the reaction between ethanoyl chloride and ethanoic anhydride with ammonia

66
Q

Write the equation for the reaction between ethanoyl chloride and ethanoic anhydride with methylamine

67
Q

Write the general equation for the reaction between RCOCl and (RCO)2O with excess ammonia

A

Acyl chloride:
RCOCl + 2NH3 —> RCONH2 + NH4Cl

Acid anhydride:
(RCO)2O + 2NH3 —> RCONH2 + RCOO⁻NH4⁺

68
Q

Write the general equation for the reaction between RCOCl and (RCO)2O with excess methylamine

A

Acyl chloride:
RCOCl + 2CH3NH2 —> RCONHCH3 + CH3NH3Cl

Acid anhydride:
(RCO)2O + 2CH3NH2 —> RCONHCH3 + RCOO⁻CH3NH3⁺

69
Q

Name and outline the mechanism for the reaction between water and the acyl chloride CH3COCl. State what type of product is formed

A

R=H
Product: Carboxylic acid

70
Q

Name and outline the general mechanism for the reaction between an alcohol and the acyl chloride CH3COCl .

A

R= alkyl group
Product: ester

71
Q

Name and outline the mechanism for the reaction between ammonia and the acyl chloride: CH3COCl. State what type of product is formed

A

R=H
Product: amide

72
Q

Name and outline the general mechanism for the reaction between primary amine and the acyl chloride: CH3COCl

A

R= alkyl group
Product: N substituted amine

73
Q

What are the 2 tests for distinguishing between an acyl chloride and an acid anhydride.
For each state the reagent, observation and equation

A

Test 1:
Reagent: H2O
Observation with acyl chloride: Steamy misty fumes due to HCl
Observation with acid anhydride: no visible change
Equation with acyl chloride: RCOCl + H2O –> RCOOH + HCl

Test 2:
Reagent: AgNO3(aq)
Observation with acyl chloride: White ppt due to AgCl
Observation with acid anhydride: no visible change
Equations with acyl chloride: RCOCl + H2O –> RCOOH + HCl
HCl —> H+ + Cl-
Ag+ + Cl- —> AgCl

74
Q

How do we make aspirin

A

salicylic acid + ethanoic anhydride —> aspirin + ethanoic acid

75
Q

State 3 advantages of manufacturing aspirin from ethanoic anhydride over ethanoyl chloride

A

Cheaper
Safer by product (ethanoyl anhydride gives HCl gas whilst this method gives ethanoic acid which is less corrosive)
Doesn’t react violently with water

76
Q

What are the 2 main reasons why we manufacture aspirin from ethanoic anhydride over ethanoyl chloride

A

Cheaper
Safer by product

77
Q

State 3 advantages of manufacturing aspirin from ethanoyl chloride over ethanoic anhydride

A

Faster
Irreversible
Larger yield

78
Q

What is the functional group of an amine vs amide

79
Q

What type of link does an N substituted amine contain

A

Amide link

81
Q

What is the general equation for the reaction between an acyl chloride and excess amine

82
Q

What is the general equation for the reaction between an acid anhydride and excess amine

Chemistry (Organic) (15 decks)

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