9O- Carboxylic Acids And Derivatives Flashcards

1
Q

What’s the structure of a carboxylic acid

A

-COOH (functional group)
Consists of a C=O and an -OH group

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2
Q

How to name straight/branched chain carboxylic acids

A

Alkane name, remove e, oic acid
If there are substitute groups use the C atom in COOH as carbon 1

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3
Q

How to name straight/branched chain carboxylic acids with 2 carboxyl groups

A

Alkane name, dioic acid (2 carboxyl groups)

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4
Q

How to name carboxylic acids when -COOH is attached to a benzene

A

Benzenecarboxylic acid

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5
Q

How to name esters

A

Look at the half of the chain to the side of the C-O bond but without the C=O bond, alkyl name
Count the number of carbons on the other side, alkane name, remove e, oate

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6
Q

Why are carboxylic acids weak acids

A

The only partially ionise into H+

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7
Q

What is observed when a carboxylic acid is mixed with metal carbonates

A

Effervescence, produces CO2 gas

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8
Q

What produces esters

A

Carboxylic acid + alcohol —> ester + water

Conc H2SO4 catalyst
Heat under reflux
Low yield as reaction is reversible

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9
Q

What’s the structure of an ester

A

C=O bond
O-H is replaced by O-R

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10
Q

Uses of esters

A

Solvents
Plasticisers
Food flavouring
Perfume

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11
Q

Reaction for hydrolosis of an ester with dilute acid

A

CH3CH2COOCH2CH3 +H2O —> CH3CH2COOH + CH3CH2OH
Ethyl propanoate + water —> propanoic acid + ethanol

Alkyl—>alcohol
Salt—>acid

Heat under reflux
Dilute H2SO4

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12
Q

Reaction for hydrolosis of an ester with NaOH

A

CH3CH2COOCH2CH3 +NaOH —> CH3CH2COONa + CH3CH2OH

Ethyl propanoate + sodium hydroxide —> sodium propanoate + ethanol

Heat under reflux
NaOH
Higher yield, carboxylic acid salt is resistant to attack by weak nucleophiles such as alcohols

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13
Q

How to name an ester formed from a 2°/3° alcohol

A

If alcohol is known take stem and number, replace -ol with -yl
eg propan-2-ol —> propan-2-yl

If ester is known count longest chain up to the C-O bond but without the C=O bond, write like an alkane chain end in -yl, count carbons on other side end in -oate

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14
Q

What’s a fatty acid

A

Long chain carboxylic acid

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15
Q

What’s the iupac name of glycerol

A

Propane-1,2,3-triol

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16
Q

What happens when glycerol reacts with a fatty acid

A

Formation of a fat

17
Q

What’s a saturated fat

A

No double bonds in hydrocarbon chain

18
Q

Unsaturated fat

A

Contains a double bond in hydrocarbon chain

19
Q

Reaction to form a triester

A

CH2OH OH-C=O-R CH2-O-C=O-R
CHOH + OH-C=O-R—> CH-O-C=O-R
CH2OH OH-C=O-R CH2-O-C=O-R

3 H2O molecules are also formed

20
Q

How is glycerol (propane-1,2,3-triol) used

A

Cosmetics and food, forms hydrogen bonds easily and is soluble in water
Soap, glycerol forms esters which are hydrolysed in alkaline conditions. Polar CO2- end mixed with water, non polar end mixed with grease allowing it to be washed away

21
Q

What’s biodiesel

A

Mixture of methyl esters and long chain carboxylic acids

22
Q

How is biodiesel produced

A

Vegetable oils are reacted with methanol
KOH catalyst present

23
Q

What does acyl chloride/ acid anhydride + alcohol produce

A

Ester

24
Q

What does acyl chloride/acid anhydride + primary amine produce

A

N- sub Amide
N- alkyl name, Alkane name remove e, amide

25
Q

What does acyl chloride/acid anhydride + water produce

A

Carboxylic acid

26
Q

What does acid anhydride/acyl chloride + ammonia produce

A

Amide (if there’s an oxygen it’s an amide, if there’s no oxygen it’s an amine)

Alkane name remove e, amide

27
Q

Structure of an amide functional group

A

R=O
|
NH2

28
Q

What are industrial advantages of ethanoic anhydride compared to ethanoyl chloride when manufacturing aspirin

A

Cheaper
Less corrosive
Less vulnerable to hydrolosis
Less dangerous

29
Q

Test for an acyl chloride

A

Add a carboxylic acid, white steamy fumes of HCL is given off

30
Q

Nucleophillic addition elimination of acyl chloride/acid anhydride with nucleophile (water, alcohol, ammonia, primary amine)

A

Carbonyl bond is polar, s- on oxygen, s+ on carbon, lone pair on nucleophile goes to carbon, arrow from double bond onto oxygen

Oxygen from double bind has lone pair and is -ve, arrow from lone pair to carbon, Oxygen from nucleophile is +ve, arrow from adjacent hydrogen bond onto oxygen, arrow from Cl or RCOO bond goes onto itself

HCL is produced from acyl chlorides
RCOOH is produced from acid anhydrides