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Organic 2 > Carboxylic Acids > Flashcards

Carboxylic Acids Flashcards

1
Q

Nomenclature - ending

A

-anoic acid

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2
Q

Nomenclature - what do you count from

A

The C on COOH

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3
Q

What is the functional group

A

COOH

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4
Q

Neutral or charged

A

Neutral

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5
Q

Describe how boiling points change with increased size and branching

A

INCREASE AS SIZE INCREASES
- No change in hydrogen bonding
- increase in LDF give higher boiling points

HIGHER IF CHAIN IS STRAIGHT, NOT BRANCHED
- Branched chains have less surface area contact between molecules
- Fewer LDF

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6
Q

Describe how solubility changes with increase length

A

INCREASED LENGTH MEANS LOWER SOLUBILITY
- Due to longer hydrocarbon ‘tails’ getting between water molecules and carboxylic acid.
- Breaks the hydrogen bonds needed for solubility
- Stronger hydrogen bonds are replaces by weaker LDF

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7
Q

What are carboxylic acids soluble in and what can smaller carboxylic acids dissolve in

A

Dissolve in organic solvents and water
Small ones dissolve in cold water

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8
Q

Test for carboxylic acids
What is used?
What is positive?

A

Sodium bicarbonate
Fizzing occurs

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9
Q

Name the ways in which a carboxylic acid can be produced

A

Oxidation
Hydrolysis of nitriles —> Acid or Alkaline
Acyl chlorides and water
Ester hydrolysis - acidic

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10
Q

Equation for oxidation to produce carboxylic acids

A

ROH + [O] —> RCHO ~ ALDEHYDE
RCHO + [O] —> RCOOH ~ CARBOXYLIC ACID

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11
Q

How many times does a primary alcohol need to be oxidised to form a carboxylic acid

A

Twice
First to aldehyde and then carboxylic acid

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12
Q

Conditions for oxidation

A

Potassium dichromate(VI) and dilute sulfuric acid
Heated under reflux

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13
Q

What shows oxidation has occurred

A

A colour change from orange —> green

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14
Q

What happens to bonds during hydrolysis of nitriles to produce COOH
What is the nitrile functional group

A

Functional group: CN

The CN bond breaks.
The carbon atom remains part of the organic product.
The nitrogen atom becomes either ammonia or the ammonium ion.

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15
Q

Acid hydrolysis of nitriles to produce carboxylic acid equation

A

RCN + H+ + H2O —> RCOOH + NH4+

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16
Q

Alkaline hydrolysis of nitriles to produce carboxylic acids

1st and 2nd step required
Conditions for the second step

A

RCN + OH- + H2O —> RCOO- + NH3
1st step creates a carbonate ion and ammonia

Dilute acid is now added to the ion.
RCOO- + H+ —> RCOOH
Second step forms carboxylic acid

17
Q

Acyl chloride and cold water to produce carboxylic acids equation
How does the product appear?

A

RCOCl + H2O —> RCOOH + HCl
White misty fumes of HCl gas are produced.

18
Q

Mechanism for Acyl chlorides and water forming COOH

A

Check on oneNote

19
Q

Equation for ester hydrolysis - acidic
What is different about this reaction

A

R1COOR2 + H2O <—> R1COOH + R2OH
It is reversible

20
Q

Conditions for ester hydrolysis to form COOH

A

Done under reflux in dilute HCl or H2SO4 (catalyst)

21
Q

Name the reactions Carboxylic acids can do

A

Reduction
Halogenation
Salt formation
Esterification

22
Q

Reduction of COOH equation

A

RCOOH + 4[H] —> ROH + H2O
Carboxylic acid + hydrogen —> alcohol + water

23
Q

Reduction of COOH conditions

A

LiAlH reagent is used in dry ether

24
Q

Can carboxylic acids be reduced to aldehydes

A

NO
Only alcohols

25
Q

Equation for the halogenation of carboxylic acids

List products

A

RCOOH + PCl5 —> RCOCl + POCl3 + HCl

Forms acyl chloride and phosphorus trichloride oxide.
Misty fumes visible due to HCl product

26
Q

Conditions for the halogenation of COOH

A

PCl5 is used as a reagent
Must be anhydrous conditions as both the reagent and acyl chloride react with water.

27
Q

How can POCl3 and the acyl chloride be separated

A

Fractional distillation

28
Q

Salt formation from COOH equation

A

RCOOH + NaOH —> RCOO- Na+ + H2O

29
Q

Conditions or reagent used

A

Aqueous alkali and complete neutralisation produces COOH

E.g. NaOH

30
Q

Esterification of COOH equation
What is important about this equation

A

R1COOH + R2OH <—> R1COOR2 + H2O
It is reversible
The opposite produces carboxylic acids!

31
Q

What is required for the esterification of carboxylic acids

A

An acid catalyst

32
Q

Salts of carboxylic acids functional group

A

COO-

33
Q

Nomenclature - ending for salts of carboxylic acids
What is placed in front

A

-oate
The metals name

34
Q

What must be remembered about the displayed structure for the COO and Na bond
Why is this the case

A

It is shown as COO- Na+ with no bond drawn.
It is ionic bonding not covalent

Organic 2 (10 decks)

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