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F.Chem 6 - Organics 1,2,3 > Carboxylic Acids And Derivatives > Flashcards

Carboxylic Acids And Derivatives Flashcards

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1
Q

Name 2 ways to make Carboxylic acid

A

Oxidation of primary alcohols

Hydrolysis of nitriles

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2
Q

What can the reagent for hydrolysing nitriles either be

A

Solution of strong acid or base

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3
Q

Conditions + reaction of acid hydrolysis of Nitrile

A

HCl (aq) + Heat

CH3CH2CN = CH3CH2COOH + NH4cl

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4
Q

Conditions + reaction of alkali hydrolysis of Nitrile

A

Heat Nitrile + NaOH(aq)

CH3CH2CN = CH3CH2COO(-)Na(+) + NH3

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5
Q

Conditions of Carboxylic acids back to alcohols

A

LiAlH4 + dry Ether + heat under reflux

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6
Q

Conditions + reagents of producing acyl Chlorides from Carboxylic acids

A

PCl5 - Phosphorous Chloride

Swaps OH for Cl = produces Acyl Chloride + POCl3 + HCl

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7
Q

How do you remove POCl3 from reaction mixture

A

Distillation

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8
Q

Why do Carboxylic acids have higher Bps than alcohols despite them both being able to hydrogen bond

A

More hydrogen bonds per molecule

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9
Q

What happens to Bp if Carboxylic acid “Dimerises”

A

Doubles
London forces 2x as strong as Mr x2

Dimerising is very Common

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10
Q

Are Carboxylic acids soluble in water

A

Yes
They form hydrogen bonds

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11
Q

What type of acids are Carboxylic acids and what do they produce when they react with Carbonates (same as all acids)

A

Weak acids = only partially ionise I. Water
They react with carbonates = produce CO2
This can be used as a test for Carboxylic acids

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12
Q

What could a test for Carboxylic acids be

A

Add carbonate
If CO2 produced turns limewater cloudy

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13
Q

What forms when alcahols react with Carboxylic acids

A

Esters + water (Condensation reaction)

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14
Q

Conditions for esterification of Carboxylic acid

A

Alcohol + Carboxylic acid
Heat under reflux + H2SO4

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15
Q

What happens In the reaction between alcohol + Carboxylic acid

A

-OH from Carboxylic acid + H from alcohol removed and from water = condensation reaction

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16
Q

How do Carboxylic acid derivatives form

A

Hydroxyl -OH group replaced by different group

17
Q

General formula for ester

A

RCOOR

R= alkyl group or benzene ring

18
Q

Name this ester

A

Methyl ethanoate

“First word on single side”

19
Q

Name this ester

A

Ethyl Methanoate

20
Q

What 2 reagents can react with alcahols to produce esters and what conditions required

A

Carboxylic acids or Acyl Chlorides

Heat + H2SO4

21
Q

What do Acyl chlorides produce instead of water when reacting with Alcohols in esterification

A

HCl

22
Q

What 2 ways can esters be hydrolysed

A

Acid - HCl + H2O
Alkali - NaOH followed by HCl to convert salt to Carboxylic acid

Both heath under reflux

HCl is a catalyst + not in equation

23
Q

What do acid and alkali hydrolysis of esters produce

A

Acid = Carboxylic acids + Alcahol - Dilute HCl + Heat under reflux

Alkali = Salt of Carboxylic acid + alcahol - NaOH +followed by HCl

24
Q

How can the salt produced in hydrolysis of ester be converted into Carboxylic acid

A

Add HCl

CH3CH2COO(-)Na(+) + HCl = CH3CH2COOH + NaCl

25
Q

Why is using the base/Alkali catalyst preferable in hydrolysis of esters to produce Carboxylic acids

A

Reaction is non reversible unlike acid reaction

= due to forming negative ion that does not react with alcohol
CH3CH2COO(-)

26
Q

Acylation

A

Substitution of Acyl group for Hydrogen atom
- the H atom that is removed and replaced may be part of OH,NH2, or benzene ring

27
Q

Acyl chloride + Water what does this from

A

Carboxylic acid + HCl

HCl made by H+ removed from H20 + Cl- removed from Acyl chloride

28
Q

How do Acyl chlorides react with alcohols

A

Forms ester + HCl

29
Q

What is produced in reaction of Acyl Chloride + Ammonia NH3

A

Amide + HCl

30
Q

Reaction of Acyl Chlorides + Amines

A

Produces N-substituted Amides
+ HCl

31
Q

Summary of Acyl Chloride reactions with
1- water
2- Alcahol
3- Ammonia
4- Amine

A

1- Carboxylic acid
2- Ester
3- Amide
4- N-Substituted Amide

All replace a hydrogen on them and replace with Acyl RC=O group

All produce HCl aswell

32
Q

Summary of esters Reaction with
1- water + Acid
2- NaOH

A

1- Carboxylic acid + Alcohol
2- Carboxylic acid salt + Alcohol

33
Q

What type of polymer are polyesters

A

Condensation polymers

34
Q

What are polyesters made from

A

Diol + either Di-Carboxylic acid or Diolyl Chloride

Only difference is HCl produced instead of water with Acyl chlorides

35
Q

Difference between Addition polymers and condensation polymers

A

Addition = monomers are unsaturated compounds- Alkenes
Polymer only product formed

Condensation = monomers linked together by ester groups
- polymer not the only product formed in formation

36
Q

What happens in polyester formation

A

-H from Alcahol + -OH from Carboxylic acid removed

37
Q

Compare positives + negatives of Acid vs Alkali hydrolysis of esters

A

Acid
Directly produces Carboxylic acid with no extra steps
Acid used is a catalyst and will be regenerated
But - reaction is reversible

Alkali
Produces carboxylate/Ion (forms salt with Na) requires an extra step of adding HCl to reach Carboxylic acid

Reaction is non-reversible due to forming Negative Ion that does not react with Alcahol

F.Chem 6 - Organics 1,2,3 (9 decks)

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