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Chemistry > Carboxylic Acid > Flashcards

Carboxylic Acid Flashcards

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1
Q

2 physical properties of CA

A

High mp/bp
H bond between two molecules
Dimer
Double molecule size
Stronger London forces
Solubility
Don’t dimerise know water
H bond to H2O
C length 4 or lower dissolve
NRG made with new bonds > NRG between old bonds

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2
Q

CA reactivity

A

C+ open p to nuc attack
O- attacked by + species
H+ can be lost
(Acid behaviour)

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3
Q

Dipole strength trend ald/ket, alc, CA

A

Ald/ket, accept H bond, can’t form alone
Alc, form H bonds
CA, 2 Os, make more H bonds

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4
Q

CA delocalisation

A

H lost
-ve carboxylate ion forms
-ve charge shared across carboxylate group
Increase ion stability

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5
Q

Name 2 methods of CA synthesis

A

Oxidation
Hydrolysis

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6
Q

CA oxidation synthesis

A

Ald/p alc
Did H2SO4, potassium dichromate
Reflux

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7
Q

CA hydrolysis synthesis

A

Nitriles
Dil acid/aqu alkali
Reflux
CN bond breaks
C remains
N —> ammonia/ammonium
Nitrile, organic intermediate, increases chain length

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8
Q

Name 5 CA reactions

A

Reduction
Oxidation
Neutralisation
Esterification
Halogenation

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9
Q

CA reduction

A

Becomes a p alc not ald
LiAlH4, dry ether

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10
Q

CA neutralisation

A

Weak/partially dissociate in water
NaOH —> CH3COO-Na+ + H2O
NH3 —> CH3COO- + NH4+
Na2CO3 —> CH3COO-Na+ + CO2 + H2O
NaHCO3 —> CH3COO-Na+ + CO2 + H2O

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11
Q

CA Halogenation

A

OH replaced by X
FG : COCl
Phosphorus (V) chloride
Anhydrous, (react with water)
Vigorous now heating
Frac dist ethanyl chloride+ phosphorus tri chloride oxide

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12
Q

CA esterification

A

CA + alc
Reflux
Conc H2SO4 cat

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13
Q

Uses of esters

A

Solvents
Polymers
Perfume
Animal fat/veg oils

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14
Q

CA oxidation

A

Methanoic acid
Combustion

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15
Q

Acyl chloride functional group

A

C=O and C-X
Not carbonyl, but has a carbonyl group

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16
Q

Name 4 methods of acyl chloride nucleophilic eliminations and additions

A

Hydrolysis
Alcohol
Ammonia
Amine

17
Q

Hydrolysis nucleophilic eliminations and addition acyl chloride

A

Cold water
HCl misty fumes
(Mechanisms)

18
Q

Alc nucleophilic eliminations and addition acyl chloride

A

Faster
Irreversible
Better for esters
Room temp
HCl misty fumes
(Mechanism)

19
Q

Amine nucleophilic eliminations and addition acyl chloride

A

Room temp
Misty HCl fumes
(Mechanism)

20
Q

Ammonia nucleophilic eliminations and addition acyl chloride

A

HCl misty fumes —> NH4Cl
Room temp
(Mechanism)

21
Q

Esters

A

RCOOR
Alc (yl), CA (anoate)
Not high yield
Reversible
Equm est
Dilute acid cat
OH from CA, H from alc

22
Q

Name 4 physical ester properties

A

Small bp
Semi-soluble
Volatile
Pleasant smell, perfumes

23
Q

Ester bp

A

Small, similar to ald/ket with same no.Cs
Permanent dipole + LF
Don’t H bond with each other
Smaller than CA with same no.Cs

24
Q

Ester solubility

A

Short, soluble
H bond using polar C=O
Long, insoluble
HC tail between water molecules
NRG to break H2O > NRG bonds made
Energetically less profitable

25
Q

Hydrolysis of esters

A

Acid
Warm water
Reflux
Equm est
H2SO4 cat
Alkali
Aqu NaOH
Reflux
Carboxylate salt

26
Q

Saponification esters

A

Org compounds in veg/animal fats —> soap
Veg oil has many triglycerides
Glycerol + 3 CA chains
Makes soap salts and glycerol
Soap depends on fatty acid present

27
Q

Ester soaps

A

Dissociate —> Na+ + RCOO-
Ionic
Long HC
Hydrophobic, non-polar
Need emulsifier
Water + oil (cleansing agent) mix

28
Q

Addition polymers and biodegradability

A

C=C monomer
Double bond opens
Monomers bond —> C backbone
Saturated, strong non-polar alkane
Very unreactive
Not attacked by bio agents (enzymes)
Not biodegradable

29
Q

Condensation polymers

A

2 molecules —> product + small molecule
Polyesters, polyamides, polypeptides
Reverted by hydrolysis
Saves non- renewable crude oil —> plastics
Less landfill waste
Collected, sorted, transported
Expensive, labour intensive

30
Q

Polyesters

A

COO ester linkage
Diols, diCA/hydroxyCA
Bottles, clothing, duvet filling
Biodegradable, high temp/enzymes

Chemistry (24 decks)

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