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Organic Chemistry Year 13 > 6.1.3 Carboxylic Acids and Esters > Flashcards

6.1.3 Carboxylic Acids and Esters Flashcards

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1
Q

what is a carboxylic acid

A
  • contains the carboxyl functional group
  • carbonyl (C=O) and hydroxyl (OH) functional group
  • COOH
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2
Q

what are carboxylic acids often used for

A
  • useful on their own
  • or as starting materials for other compounds
  • e.g. aspirin is made from salicylic acid
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3
Q

how do you name carboxylic acids

A
  • the carboxyl group is indicated via the -oic acid suffix
  • always placed on carbon 1
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4
Q

how would you name a carboxylic acid with a 4 carbon main chain and a methyl group coming off carbon 3

A

3-methylbutanoic acid

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5
Q

are carboxylic acids soluble, and why

A
  • YES
  • because both the C=O and O-H bonds are polar
  • so can form hydrogen bonds with the water
  • if drawing, remember dipoles
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6
Q

which carboxylic acids are soluble

A
  • a carboxylic acid with up to 4 C atoms
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7
Q

what happens to the solubility as the number of carbon atoms in a carboxylic acid increases

A
  • as the number of carbon atoms increases
  • the solubility decreases
  • as the non-polar carbon chain has a grater effect on the overall polarity of the molecule
  • when comparing, always refer to the RATIO of carbons against COOH group
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8
Q

what is special about dicarboxylic acids and solubility

A
  • have 2 polar carboxyl groups COOH to form hydrogen bonds
  • so are usually solid at room temperature
  • but readily dissolve
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9
Q

what type of acids are carboxylic acids

A

weak acids
- so only partially dissociate and release H+ ion
- e.g. HCOOH(aq) ⇌ H+(aq) + HCOO-(aq)

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10
Q

what is the basic way in which carboxylic acids act in acid reactions

A
  • undergo redox reactions with metals
  • and neutralisation reactions with bases, e.g. alkalis, metal oxides and carbonates
  • FORM CARBOXYLATE SALTS
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11
Q

show how the carboxyl group forms a carboxylate ion

A

R-COOH → R-COO-

  • carboxylate is used to name the ions formed
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12
Q

how do carboxylic acids react with metals

A
  • in an aqueous solution
  • forming hydrogen gas and a carboxylate salt
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13
Q

what would you be able to observe when a carboxylic acid reacts with a metal

A
  • metal disappears
  • effervescence as hydrogen gas evolves
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14
Q

what is important to remember when constructing equations to show the redox and neutralisation of carboxylic acids

A
  • need to balance out the transfer of protons
  • e.g. the monoprotic carboxylic acid and the base, whether monoprotic too or diprotic
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15
Q

how would you show the equation between propanoic acid and magnesium

A

2CH3CH2COOH(aq) + Mg(s) → (CH3CH2COO-)2Mg2+(aq) + H2

  • as propanoic acid is monoprotic
  • and Mg is diprotic (2+)
  • so need to balance out the charges
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16
Q

how do carboxylic acids react with metal oxides

A

carboxylic acid + metal oxide → salt + water

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17
Q

what is the equation for ethanoic acid reacting with calcium oxide

A

2CH3COOH(aq) + CaO → (CH3COO-)2Ca2+(aq) → H2O

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18
Q

how do carboxylic acids react with alkalis

A

carboxylic acid + alkali → salt + water

  • you may not see any reaction taking place at all, as 2 solutions are reacting to form an aqueous salt
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19
Q

how would you show ethanoic acid reacting with sodium hydroxide

A

CH3COOH(aq) + NaOH(aq) → CH3COO-Na+(aq) + H2O (l)

  • ionically, is the neutralisation equation:
  • H+ + OH- → H2O
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20
Q

how do carboxylic acids react with carbonates

A

carboxylic acid + carbonate → salt + water + carbon dioxide

  • if the carboxylic acid is in excess, you should see any solid carbonate fully disappear
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21
Q

equation for ethanoic acid and sodium carbonate

A

2CH3COOH(aq) + Na2CO3(aq) → 2CH3COO-Na+ + H2O + CO2

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22
Q

how can you test for the carboxyl group

A
  • can test via the neutralisation of carboxylic acids by carbonates
  • as they are the only common organic compound acidic enough to react with carbonates
  • especially useful when distinguishing between phenols
  • as they aren’t acidic enough to react
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23
Q

what is a derivative of carboxylic acid

A

a compound that can be hydrolysed to form the parent carboxylic acid

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24
Q

what is the common series of atoms present in all derivatives of carboxylic acids

A
  • the ACYL GROUP
  • made of R-C=O (and then another line coming off the carbon
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25
Q

what are the 4 derivatives of carboxylic acids and what group is present coming off the 4th carbon bond

A

1) esters: OR (COO)
2) acyl chlorides Cl (COCl)
3) acid anhydrides (RCOO)
4) amides CONH2 (NH2)

26
Q

what are esters

A

contain the functional group COO
- where C=O and C-O
- sweet smelling liquids

27
Q

how are esters named

A
  • named after their parent carboxylic acid they’re derived from
    1) remove the -oic acid suffix from the parent carboxylic acid
    2) replace suffix with -oate
    3) the alkyl chain attached to the O coming off the COO group is used as the first word
28
Q

how could you name CH3COOCH3

A
  • methyl ethanoate
  • ETHANoate off the ethanoic acid
  • METHyl off the CH3 at the end
29
Q

what are acyl chlorides

A

contain COCl
- where C=O and C-Cl

30
Q

how are acyl chlorides named

A
  • named after the parent carboxylic acid from which they are derived
    1) remove the -oic acid off the parent acid
    2) replace with -oyl chloride
31
Q

how would you name CH3CH2COCl

A

propanoyl chloride

  • PROPANoyl off the carboxylic acid
  • chloride from the Cl
32
Q

what are acid anhydrides

A
  • formed via the removal of water from 2 carboxylic acid molecules
  • the 2 OH groups combine, releasing water and leaving a O in the middle to join the 2 C=O
33
Q

how do you name acid anhydrides

A
  • whichever carboxylic acid has been combined with itself
  • use as the prefix
  • remove the acid from the end and replace with anhydride
34
Q

what is the esterification equation

A

alcohol + carboxylic acid → ester (+ water)

35
Q

what is esterification overview

A
  • an alcohol is warmed with a carboxylic acid with a small amount of sulfuric acid acting as a catalyst
36
Q

how does propanoic acid react with ethanol

A

CH3CH2COOH + CH3CH2OH → CH3CH2COOCH2CH3 + H2O

  • propanoic acid + ethanol → ethyl propanoate + water
37
Q

how do you make esters in a lab

A

1) add equal volumes (2cm3) of your carboxylic acid and alcohol to a boiling tube
2) add a few drops of sulfuric acid
3) place the beaker in hot water at 80 degrees C and leave for 5 minutes
4) pour contents into beaker containing sodium carbonate (aq) and you should see oily drops of ester in the mixture as well as being able to distinguish the sweet smell

  • you add Na2CO3(aq) to act as a weak base neutralise any left over carboxylic acid left in the mixture, removing the smell of it so ester is easier to detect
38
Q

what is hydrolysis

A

the chemical breakdown of a compound in the presence of water / in an aqueous solution

39
Q

with what can esters be hydrolysed

A
  • either an acid
  • or alkali
40
Q

what is acid hydrolysis of esters

A
  • the opposite of esterification
  • ester + water → carboxylic acid + alcohol
  • the H+ can be given to a species, but none present as both the Os have Hs on them, so no specific product
41
Q

how is the acid hydrolysis of esters carried out

A

1) the ester is heated under reflux with dilute aqueous acid
2) the ester is broken down by water, with acid acting as a catalyst
3) produced carboxylic acid and alcohol

  • OH of water goes to the methyl chain attached to the C-O’s O and the O goes to the O of the C-O
42
Q

write equation for the acid hydrolysis of methyl-2-hydroxybenzoate

A

OH⌬COOCH3 + H2O → OH⌬COOH + CH3OH

  • forming 2-hydroxybenzoic acid and methanol
43
Q

what is alkaline hydrolysis of esters

A
  • known as saponification
  • is irreversible
  • ester is heated under reflux with aqueous hydroxide ions to form a carboxylate salt and alcohol
  • the OH- ion needs to gain a H+ in order to form water, and can gain this from the H present in the carboxylic acids COOH
44
Q

how would methyl ethanoate react under acid hydrolysis

A

H3C-C-OO-CH3 + OH-(aq) → H3C-C-OO- + CH3OH

  • forms an ethanoate ion and methanol
  • for a specific alkali used, would form that carboxylate salt
45
Q

how would you prepare acyl chlorides

A
  • prepared from the parent carboxylic acid by a reaction with thionyl chloride SOCl2
  • does also form SO2 and HCl, but these get evolved as gases, leaving just the acyl chloride behind
  • MUST BE IN A FUME CUPBOARD, as forms harmful products
46
Q

how can you form propionyl chloride

A
  • reaction of propanoic acid with thionyl chloride
  • e.g. CH3CH2COOH + SOCl2 → CH3CH2COCl + SO (g) + HCl(g)
47
Q

why are acyl chlorides useful reactants in organic synthesis

A
  • they are very reactive
  • and can be easily converted into carboxylic acid derivatives, such a esters and amides, both with good yields
48
Q

how do acyl chlorides react

A
  • react with nucleophiles
  • via losing the chloride ion
  • but still retain the C=O bond
49
Q

how do acyl chlorides react with alcohols

A

form esters (and HCl as a product)
- e.g. ethanoyl chloride + propan-1-ol → propyl ethanoate
- e.g. H3C-COCl + CH3CH2CH2OH → CH3COOCH2CH2CH3 + HCl

50
Q

how do acyl chlorides react with phenols

A
  • form esters
  • carboxylic acids alone aren’t reactive enough to react with phenols
  • but acyl chlorides, and acid anhydrides are
  • as they are much more reactive
  • so form phenyl esters WITH NO CATALYST NEEDED
51
Q

how could I form phenyl ethanoate using an acyl chloride

A
  • ethanoyl chloride + phenol →phenyl ethanoate + HCl
  • H3C-COCl + HO-⌬ → H3C-COO-⌬ +HCl
52
Q

how do acyl chlorides react with water

A

form carboxylic acids
- via a violent reaction taking place
- produces dense, steamy hydrogen chloride fumes

53
Q

how could I form ethanoic acid from an acyl chloride

A
  • ethanoyl chloride + water → ethanoic acid + HCl
  • H3C-COCl + H2O → H3C-COOH + HCl
54
Q

how do acyl chlorides react with ammonia and amines

A
  • form amides O=C-N
55
Q

how do ammonia and amines act when reacting with acyl chlorides

A
  • act as nucleophiles
  • as can donate the lone pair of electrons on the :N atom to an electron deficient species
56
Q

what is the reaction between acyl chlorides and ammonia

A
  • form primary amides
  • primary as: the nitrogen is attached to ONE carbon atom (CNH2)
57
Q

what is the reaction between ethanoyl chloride and ammonia

A

ethanoyl chloride + ammonia → ethanamide + ammonium chloride
- H3C-COCl + 2NH3 →H3C-CONH2 + NH4Cl

58
Q

how do primary amines react with acyl chlorides

A
  • react in the same way, forming a secondary amide
  • where the nitrogen atom is attached to 2 carbons
59
Q

how does ethanoyl chloride react with methylamine

A

ethanoyl chloride + methylamine → N-methylethanamide + methylammonium chloride
- H3C-COCl + 2CH3NH2 → H3C-CO-NH-CH3 + CH3NH3+Cl-

60
Q

how do acid anhydride react

A
  • in a similar way to acyl chlorides with alcohols, phenols, ammonia and amides
  • but are LESS reactive than acyl chlorides
61
Q

why might you choose acid anhydride in lab work rather than acyl chlorides

A
  • where acyl chloride might be too reactive
62
Q

how would ethanoic anhydride react with phenol

A

forms phenylethanoate + ethanoic acid

Organic Chemistry Year 13 (10 decks)

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