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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 (reflux)

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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

Aqueous 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
What is a saturated fatty acid
Long chain carboxylic acid with no double bonds
26
What is an unsaturated fatty acid
Long chain carboxylic acid with double bonds
27
Explain why vegetable oils are liquid at room temperature
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
28
What type of molecule are oils
Ester
29
What type of molecules are fats
Ester
30
Explain why animal fats are solid at room temperature
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
31
Is this a fat or an oil ester?
Oil
32
Is this a fat or an oil ester?
Fat
33
What do we get when we react NaOH with a fat(ester)
Glycerol & soap
34
What is the general equation for saponification
Fat + 3NaOH ---> Glycerol + 3 Carboxylate salt (soap)
35
What are the conditions for saponification
Warm conditions NaOH
36
What is the general equation for transesterification
Fat + 3Methanol ---> glycerol + 3Biodiesel (methyl ester)
37
What are the conditions for transesterification
KOH catalyst
38
What is biodiesel
A mix of fatty acids made from methyl esters
39
Give 3 advantages of biofuel
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
Give 3 drawbacks of biofuel
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
What is the suffix for acyl chlorides
-COCl at end of molecule -Oyl chloride
42
How do we name acyl chlorides
Find the longest carbon chain then add -oyl chloride at the end (carbon with the acyl group is C1)
43
What is the general equation for when an acyl chloride reacts with water
Acyl chloride + water ---> carboxylic acid + HCl RCOCl + H2O ---> RCOOH + HCl
44
What is the general equation for when an acyl chloride reacts with ammonia
Acyl chloride + ammonia ---> Amide + HCl RCOCl + NH3---> RCONH2 + HCl
45
What is observed when an acyl chloride reacts with water
Vigorous reaction, white misty fumes of hydrogen chloride gas produced (must be done in fume cupboard)
46
What is observed when an acyl chloride reacts with ammonia
Vigorous reaction, white misty fumes of hydrogen chloride gas produced (must be done in fume cupboard)
47
What is the general equation for when an acyl chloride reacts with an alcohol
Acyl chloride + alcohol ---> Ester + HCl
48
What is observed when an acyl chloride reacts with an alcohol
Vigorous reaction, white misty fumes of hydrogen chloride gas produced (must be done in fume cupboard)
49
What is the general equation for when an acyl chloride reacts with a primary amine
Acyl chloride + primary amine ---> N-substituted amide + HCl
50
What is observed when an acyl chloride reacts with a primary amine
Vigorous reaction, white misty fumes of hydrogen chloride gas produced (must be done in fume cupboard)
51
Which bond breaks when an acyl chloride is attacked by a nucleophile
The C-Cl bond
52
What bond breaks in water when it reacts with an acyl chloride or acid anhydride
one of the O-H bonds
53
What bond breaks in an alcohol when it reacts with an acyl chloride or acid anhydride
the O-H bond
54
What bond breaks in ammonia when it reacts with an acyl chloride or acid anhydride
one of the N-H bonds
55
What bond breaks in an amine when it reacts with an acyl chloride or acid anhydride
one of the N-H bonds
56
What does an acid anhydride consist of
Made from 2 carboxylic acids that are identical
57
How do we name an acid anhydride
We name the carboxylic acid its made from remove -acid and replace with - anhydride
58
What is the general equation for when an acid anhydride reacts with a water
Acid anhydride + water --> 2carboxylic acid (2 of the same carboxylic acid)
59
Which bond breaks in an acid anhydride when it is attacked by a nucleophile
one of the C-O bonds
60
What is the general equation for when an acid anhydride reacts with ammonia
Acid anhydride + ammonia --> Amide + carboxylic acid
61
What is the general equation for when an acid anhydride reacts with an alcohol
Acid anhydride + alcohol ---> Ester + carboxylic acid
62
What is the general equation for when an acid anhydride reacts with a primary amine
Acid anhydride + primary amine ---> N-substituted amide + carboxylic acid
63
Write the equation for the reaction between ethanoyl chloride and ethanoic anhydride with water
64
Write the equation for the reaction between ethanoyl chloride and ethanoic anhydride with methanol
CH3COCl + CH3OH —> CH3COOCH3 + HCl (CH3CO)2O + CH3OH —> CH3COOCH3 + CH3COOH
65
Write the equation for the reaction between ethanoyl chloride and ethanoic anhydride with ammonia
66
Write the equation for the reaction between ethanoyl chloride and ethanoic anhydride with methylamine
67
Write the general equation for the reaction between RCOCl and (RCO)2O with excess ammonia
Acyl chloride: RCOCl + 2NH3 —> RCONH2 + NH4Cl Acid anhydride: (RCO)2O + 2NH3 —> RCONH2 + RCOO⁻NH4⁺
68
Write the general equation for the reaction between RCOCl and (RCO)2O with excess methylamine
Acyl chloride: RCOCl + 2CH3NH2 —> RCONHCH3 + CH3NH3Cl Acid anhydride: (RCO)2O + 2CH3NH2 —> RCONHCH3 + RCOO⁻CH3NH3⁺
69
Name and outline the mechanism for the reaction between water and the acyl chloride CH3COCl. State what type of product is formed
R=H Product: Carboxylic acid
70
Name and outline the general mechanism for the reaction between an alcohol and the acyl chloride CH3COCl .
R= alkyl group Product: ester
71
Name and outline the mechanism for the reaction between ammonia and the acyl chloride: CH3COCl. State what type of product is formed
R=H Product: amide
72
Name and outline the general mechanism for the reaction between primary amine and the acyl chloride: CH3COCl
R= alkyl group Product: N substituted amide
73
What are the 2 tests for distinguishing between an acyl chloride and an acid anhydride. For each state the reagent, observation and equation
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
How do we make aspirin
salicylic acid + ethanoic anhydride ---> aspirin + ethanoic acid
75
State 3 advantages of manufacturing aspirin from ethanoic anhydride over ethanoyl chloride
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
What are the 2 main reasons why we manufacture aspirin from ethanoic anhydride over ethanoyl chloride
Cheaper Safer by product
77
State 3 advantages of manufacturing aspirin from ethanoyl chloride over ethanoic anhydride
Faster Irreversible Larger yield
78
What is the functional group of an amine vs amide
79
What type of link does an N substituted amine contain
Amide link
80
81
What is the general equation for the reaction between an acyl chloride and excess amine
82
What is the general equation for the reaction between an acid anhydride and excess amine
83
What is the most common form of drying agent (when we have a general organic sample and want to remove H2O)
Sulfates (Calcium sulfate most common)
84
Explain why an impure sample of aspirin melts over a range of values and has a lower MP
Lower MP because impurities disrupt the regular crystal structure of the solid. Range as other compounds present of different MPs
85
What is saponification essentially
Base hydrolysis of an ester

Chemistry (Organic) (16 decks)

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