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chem - [6] organic chemistry and analysis > [26.4] carboxylic acid derivatives > Flashcards

[26.4] carboxylic acid derivatives Flashcards

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1
Q

what is a carboxylic acid derivative?

A

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

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2
Q

what are 4 derivatives of carboxylic acids?

A
  • esters
  • acyl chlorides
  • acid anhydrides
  • amides
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3
Q

what is esterification?

A

the reaction of an alcohol with a carboxylic acid to form an ester

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4
Q

esterification: reagents, conditions, product, naming

A
  • reagents: carboxylic acid + alcohol
  • conditions: reflux and concentrated sulfuric acid cataylst
  • products: ester + water
  • naming: -yl from alcohol, -oate from CA
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5
Q

what can esters be prepared from?

A
  • carboxylic acids
  • acyl chlorides
  • acid anhydrides
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6
Q

describe the reactivity of esters

A

unreactive compared to acids and acyl chlorides

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7
Q

describe the isomerism of esters

A

structural isomers of CAs

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8
Q

acid hydrolysis of esters

A
  • reverse of esterification
  • heated under reflux
  • dilute HCl (aq) acts as a catalyst (doesn’t go in equation)
  • reversible reaction
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9
Q

alkaline hydrolysis of esters

A
  • heated under reflux
  • NaOH (aq)
  • forms COOH + alcohol but metal ions present (aq) so carboxylate salt produced
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10
Q

what do all carboxylic acid derivatives contain?

A
  • an acyl group (R-C=O)
  • an electronegative atom or group of atoms
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11
Q

naming acyl chlorides

A
  • named from ‘parent’ CA
  • remove the -oic acid
  • replace with -oyl chloride
  • structure: C=O and Cl attached to C

eg. ethanoic acid = ethanoyl chloride

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12
Q

making acyl chlorides

A
  • carboxylic acid + thionyl chloride (SOCl₂)
  • R-COOH + SOCl₂ -> R-COCl + SO₂ (g) + HCl (g)
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13
Q

conditions for making acyl chlorides

A
  • acyl chlorides must be kept dry as they react with water
  • reaction should be carried out in a fume cupboard as products are harmful
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14
Q

reactions of acyl chlorides

A
  • good starting material as it can make lots of functional groups
  • acyl chloride group makes it very reactive
  • no need for catalyst
  • Cl and O are electron-withdrawing, increasing the positivty of C and susceptibility to nucleophilic attack
  • corrosive and produce harmful gases (HCl)
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15
Q

what 4 reactions can acyl chlorides undergo to form?

A
  • esters
  • carboxylic acids
  • primary amides
  • secondary amides
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16
Q

reaction of acyl chlorides to form esters

A
  • acyl chloride + alcohol -> ester + HCl (g)
  • room temperature
  • irreversible reaction
  • HCl - misty fumes observed
17
Q

reaction of acyl chlorides to form carboxylic acids

A
  • acyl chloride + water -> carboxylic acid + HCl (g)
  • vigourous at room temperature
  • HCl - misty fumes observed
18
Q

reaction of acyl chlorides to form primary amides

A
  • acyl chloride + ammonia (NH₃) -> (1) amide + NH₄Cl
  • does produce HCl but HCl + excess NH₃ -> NH₄⁺Cl⁻
  • violent reaction producing white smoke
19
Q

reaction of acyl chlorides to form secondary amides

A
  • acyl chloride + primary amine -> N-amide + CH₃NH₃⁺Cl⁻
  • violent reaction producing a white solid mixture
  • does produce HCl but HCl + excess primary amine -> CH₃NH₃⁺Cl⁻
20
Q

why is using acyl chlorides to make esters preferable to COOH + alcohol?

A
  • irreversible so better yield
  • no need for catalyst: happens ar room temp
  • reacts with phenol (COOH too weak)
21
Q

reactions of acid anhydrides compared to reactions of acyl chlorides

A
  • react in a similar way to acyl chlorides but are less exothermic, less corrosive and safer
  • cheaper
  • less reactive than acyl chlorides (less electron-withdrawing effect) so reactions are slower
  • requires gentle heating
  • instead of HCl as a product, makes R-COOH
22
Q

describe the structure and naming of acid anhydrides

A
  • symmetrical molecule
  • O in middle, C=O attached to either side
  • -R attached to C
  • to name, basically split molecule in half and see which parent CA eg. ethanoic anhydride
23
Q

reaction of acid anhydrides to form esters

A
  • acid anhydride + alcohol -> ester + carboxylic acid
  • CA is safer than HCl
24
Q

reasons why use of acid anhydrides is favoured over corresponding acyl chlorides

A

acyl chlorides are:

  • difficult to hand as they react very readily with water so need to be used in water-free conditions
  • react to produce corrosive HCl

acid anhydrides are:

  • cheaper to produce
  • no as moisture sensitive
  • less corrosive
  • produce carboxylic acids, which are safer than HCl

chem - [6] organic chemistry and analysis (14 decks)

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