26.4 Carboxylic avid derivatives Flashcards

1
Q

What are the 4 derivatives of carboxylic acids

A

ester
acyl chlorine
acid anhydride
amide

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2
Q

How do you name an ester

A
  1. suffix is ____oate
  2. the alkyl chain attached to the oxygen atom of COO group is added to the first word in the name
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3
Q

How do you name a acyl chloride

A

suffix is ____oyl chloride

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4
Q

How is a acid anhydride formed

A

-removal of water from 2 carboxylic acid molecules

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5
Q

What is esterification?

A

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

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6
Q

What are the reagents and conditions required for esterification of a carboxylic acid?

A

Alcohol, conc. H2SO4 (esterfication)

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7
Q

What is the use of H2SO4 (sulfuric acid) in esterification

A

acts as a catalyst

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8
Q

What is produced from the reaction of propanoic acid with ethanol

A

propanoic acid + ethanol = ethyl propanoate + water

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9
Q

What does anhydride mean

A

with water

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10
Q

Definition of hydrolysis

A

the chemical breakdown of a compound in the presence of water or in aqueous solution

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11
Q

What are the reagents and conditions required for acid hydrolysis?

A

Dilute aq acid, reflux

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12
Q

What is formed during acid hydrolysis of esters?

A

-Ester broken down by water with the acid acting as the catalyst
-Carboxylic acid and alcohol formed

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13
Q

What is the role of dilute aqueous acid in acid hydrolysis?

A

Acts as a catalyst

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14
Q

What are the reagents and conditions required for alkaline hydrolysis?

A

aq hydroxide ions (or NaOH, KOH), reflux

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15
Q

What is formed from alkaline hydrolysis?

A

-carboxylate ion
-alcohol

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16
Q

What is the equation for reaction of methyl ethanoate and sodium hydroxide?

A
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17
Q

How are acyl chlorines prepared?

A

Directly from carboxylic acid by reaction with SOCl2 (thionyl chloride)

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18
Q

What are the precautions for the preparation of acyl chlorines

A

-volatile so should be carried out in a fume cupboard
-fume cupboard as products are harmful

19
Q

What are the precautions for the preparation of acyl chlorines?

A

-Volatile so should be carried out in a fume cupboard
-Fume cupboard as products are harmful

20
Q

What is the equation for the preparation of acyl chlorine from propanoic acid?

21
Q

How do acyl chlorine’s react with nucleophiles?

A

-losing the chlorine ion whilst retaining the C=O double bond

22
Q

What do acyl chlorine’s react with alcohols to form?

A

Esters and HCl

23
Q

What is the equation for the reaction of acyl chlorine with propan-1-ol?

24
Q

What is produced when acyl chlorines react with phenols?

A

Phenyl esters

25
What is produced when acid anhydrides react with phenols?
Phenyl esters
26
What are the observations when acyl chlorines react with water?
-violent reaction -evolution of dense steamy hydrogen chloride fumes -carboxylic acid formed
27
What is formed when acyl chlorines react with water?
Carboxylic acid, HCl
28
What is the equation for the reaction of ethanoyl chloride with water
29
What is the equation for the esterification of propanoic acid?
30
What is the equation for the acid hydrolysis of methyl 2-hydroxybenzonate?
31
What are the products of acid hydrolysis?
Alcohol, carboxylic acid
32
What is the equation for the alkaline hydrolysis of methyl ethanoate?
33
What are the products of the reaction of acyl chlorides with alcohols?
Ester, HCl
34
What is the equation for reaction of ethanoyl chloride with phenol?
35
What forms from the reaction of acyl chlorides with ammonia?
Primary amide and ammonium chlorine
36
What happens when acyl chlorides react with with ammonia and amines?
The ammonia (NH3) and amines act as nucleophiles by donating the lone pair of electrons on the nitrogen atom to an electron deficient species
37
What is the equation for the reaction of ethanoyl chloride with ammonia?
38
What is formed when an acyl chloride reacts with a primary amide?
Secondary amide, ammonium chloride
39
What is the equation for the reaction of ethanoyl chloride and methylamine?
40
What are reactions with acid anhydrides like?
-Similar to how acyl chlorides react with alcohols, phenols, water. ammonia and amines -But are less reactive than acyl chlorides, useful for laboratory preparations where acyl chlorides are too reactive
41
What is the equation for the reaction of ethanoic anhydride with phenol?
42
What is the mechanism of reaction between acyl chlorides with H2O?
43
What is the name of the mechanism of reaction between acyl chlorides with H2O?
Nucleophilic addition-elimination