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

24
Q

What does acyl chloride/acid anhydride + primary amine produce

A

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

25
What does acyl chloride/acid anhydride + water produce
Carboxylic acid
26
What does acid anhydride/acyl chloride + ammonia produce
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
Structure of an amide functional group
R=O | NH2
28
What are industrial advantages of ethanoic anhydride compared to ethanoyl chloride when manufacturing aspirin
Cheaper Less corrosive Less vulnerable to hydrolosis Less dangerous
29
Test for an acyl chloride
Add a carboxylic acid, white steamy fumes of HCL is given off
30
Nucleophillic addition elimination of acyl chloride/acid anhydride with nucleophile (water, alcohol, ammonia, primary amine)
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