Carboxylic Acids Flashcards

1
Q

EsterAcid hydrolysis
Reagent
What it forms
Equation

A

Heat with aqueous acid HCl

Forms a carboxylic acid and alcohol

Eater + water —> (H+/heat) acid + alcohol

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2
Q

Converting carboxylic Acids to acid chlorides

A

Reflux with either phosphorus pentachloride PCl5 or sulfur dichloride oxide SOCl2

NUCLEOPHILIC substitution

Anhydrous conditions- because otherwise the acid chloride will hydrolyse back to the acid

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3
Q

What are the products in making acid chlorides using phosphorus pentachloride?

A

Acid chloride

POCl3

HCL

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4
Q

What are the products in converting acid chlorides with sulfur dichloride oxide SOCl2

A

Acid chloride

SO2

HCl

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5
Q

Why is SOCL2 preferred when converting carboxylic acids to acid chlorides?

A

Because only gaseous co-products are formed. The product in PCl5 (POCl3) is a liquid which means you’d have to separate the acid chloride which is also a liquid- this would be difficult

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6
Q

Ester Alkaline hydrolysis

A

Heat with NaOH (aq)
Forms sodium salt of acid and alcohol

2- obtain a Carboxylic acid by adding strong hydrochloric acid to the sodium salt as sodium salts are fairly soluble

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7
Q

Hydrolysis of acid chlorides

What happens when ethanoyl chloride is opened?

A

They produce carboxylic acids

NUCLEOPHILIC substitution

When ethanoyl chloride is opened - misty fumes of HCl is seen- it reacts wth water vapour in the air

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8
Q

How soluble are aliphatic acids?

A

Fairly soluble in water eg ethanoic

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9
Q

How soluble are aromatic acids in water?

A

Sparingly soluble e.g benzoicacid

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10
Q

How to form a aromatic carboxylic acid from a. Sodium salt?

A

Treat sodium salt of benzoicacid with HCl and the benzoicacid will precipitate out of solution as ts sparingly soluble

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11
Q

How do isolate the product?

A

Filter product
Wash with cold solvent water
Recrystallise from hot water
Dry crystals in oven just below MP

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12
Q

How are aromatic carboxylic acids formed?

A

Acids are produced by the oxidisation of a side chain of an aromatic compound. Aromatic compound is heated with aqueous alkaline KMnO4 where the alkali is Na2CO3

This produces a sodium salt of the acid

Salt is then acidified with hydrochloric acid to produce the aromatic acid

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13
Q

Reagent used in the formation of aromatic carboxylic acids

And conditions

A

Aqueous alkaline potassium manganate (VII)

(Use HCl to acidify salt)

Condition: heat

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14
Q

Steps of forming aromatic carboxylic acids

A

Aromatic compound
(Alkaline aqueous KMnO4 + heat)

Sodium salt produced of the carboxylic acid

(HCl) acidified salt

Aromatic acid formed

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15
Q

Method of decarboxylation

A
  1. React carboxylic acid with aqueous sodium hydroxide which forms sodium salt
  2. Heat sodium salt with soda lime (NaOH)
  3. hydrocarbon formed with 1 less C
  4. Carbon dioxide gas isn’t evolved

Mass spec can be used to identify the hydrocarbon and hence the patent carboxylic acid

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16
Q

Reaction equation for the acid hydrolysis of an ester

A

Water + water —> (Heat/H+) carboxylic acid and alcohol

17
Q

Reaction equation for the acid hydrolysis of an ester

A

Water + water —> (Heat/H+) carboxylic acid and alcohol

18
Q

Describe the solubility of aromatic and aliphatic acids

A

Aromatic acids are sparingly soluble in water always, eg barely dissolves, aliphatic acids are fairly soluble in water always - dissolves