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Organic chemistry a2 > Carboxylic acids and derivatives > Flashcards

Carboxylic acids and derivatives Flashcards

a2 chem

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1
Q

What functional group to carboxylic acids have?

A

They have a carboxyl group (COOH) functional group.

(‘oic acid’)
carboxyl group found at the end of the molecule

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2
Q

What type of acids are carboxylic acids?

A

Weak so they dissociate partially to form H+ ion and carboxylate ion.

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3
Q

What is the reaction between carboxylic acids and carbonates?

A

Carboxylic acids react with carbonates to form a salt, carbon dioxide gas and water.

eg)
ethnic acid + na2co3–> 2ch3coona +h20+co2

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4
Q

How are esters formed from carboxylic acids?

A

By reacting alcohols with carboxylic acids and a sulfuric acid catalyst to make esters (COO group) and water

By reacting acid anhydrides with an alcohol to make esters (COO group) and carboxylic acid.

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5
Q

How do you name an ester?

A

Name the right side first as the alkyl group.
eg) ethyl

name the left side formed from carboxylic acid ending it with ‘oate’

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6
Q

What are uses of esters?

A

-perfumes and food flavouring (due to their sweet smell)

  • used in solvents (they are polar so can dissolve other polar compounds)
  • Plasticisers
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7
Q

Describe ester hydrolysis?

A

esters can be hydrolysed (split using water)
this process can be sped up using an acid ( acid hydrolysis)
and a base (base hydrolysis)

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8
Q

Describe ester- acid hydrolysis?

A

A dilute acid is used to split an ester into a carboxylic acid and an alcohol

CONDITIONS:
sulfuric/hydrochloric acid

under reflux

PRODUCTS:
carboxylic acid and alcohol

(oh joins onto carboxylic acid)

(h joins onto alcohol)

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9
Q

Describe ester-base hydrolysis?

A

A dilute base is used to split an ester into a carboxylate ion and an alcohol

CONDITIONS:

base= sodium hydroxide

under reflux

PRODUCTS:
carboxylate ion

alcohol

(o-) goes on carboxyl side

(h) attaches to make alcohol.

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10
Q

How are fats and oils made ( type of ester)

A

By reacting glycerol (alcohol) and fatty acids (carboxylic acid) —> produces an ester which makes fats and oils.

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11
Q

Describe how fats and oils are made is formed..

A

the alcohol loses a hydrogen

The carboxylic group loses OH.

they they join producing an ester (COO)- 3 sites of coo esters

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12
Q

Describe why vegetable oils (type of ester) are liquids at room temperature?

A

They have unsaturated hydrocarbon chains that are not straight which means the chains can’t pack together closely and hence have lower van der waals forces. They have lower melting points and are liquids at room temperature.

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13
Q

Describe why fat esters are solids at room temperature?

A

They have saturated hydrocarbon chains that are straight and more uniform than oils which means the chains can pack together closely and hence have much higher van der waals forces. They have higher melting points and are solids at room temperature.

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14
Q

How can soaps be made from animal fats/ vegetable oil ?

A

They can be hydrolysed by heating them with sodium hydroxide.

(amount of sodium hydroxide depends on number of links of fats)

The hydrogen from sodium hydroxide forms the glycerol.

The remaining NaO forms a sodium salt

eg) coo-na+

PRODUCTS:
glycerol

soap ( sodium salt)

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15
Q

How can biodiesel be made from vegetable oils?

A

CONDITIONS:
react oil with methanol and potassium hydroxide as a catalyst.

REACTION:
hydrogen from methanol makes glycerol

remaining methanol adds onto end forming ester at the front of c =o bond and r group

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16
Q

What does biodiesel consist of?

A

A mixture of fatty acids made from methyl esters and can be made from rapeseed oil.

17
Q

How do you name acyl chlorides? (cocl)

A

1) find longest carbon chain

2) add ‘oil chloride’ on the end

18
Q

What do reactions with acyl chlorides entail?

A

They rect with water, ammonia, alcohol and primary amines.

In each reaction the CL is substitute for either oxygen or nitrogen.

19
Q

Describe reaction of acyl chlorides with water..

A

acyl chlorides + water = carboxylic acid and hydrogen chloride gas produced.

20
Q

Describe reaction of acyl chlorides with ammonia..

A

acyl chlorides + ammonia= amides + hydrogen chloride gas produced.

amides=c=o nh2

needs to be done in fume cupboard

21
Q

Describe reaction of acyl chlorides with alcohol..

A

acyl chlorides+ alcohol = esters and hydrogen chloride gas produced.

22
Q

Describe reaction of acyl chlorides with primary amines..

A

acyl chlorides + primary amines = N-substituted amides + HCL

instead of nh2 one hydrogen is substituted depending on r group.

23
Q

What are acid anhydrides?

A

Acid anhydrides is a molecule made from 2 carboxylic acids that are the same.

24
Q

How do you name an acid anhydride?

A

Find carbon change name as usually for ‘oic’ instead of ending with acid replace it with ‘anhydride’

25
Q

What’s the difference between acid anhydrides and acyl chlorides?

A

Acid anhydrides are less vigorous compared to acyl chlorides.

ACID ANHYDRIDES PRODUCE CARBOXYLIC ACIDS

ACYL CHLORIDES PRODUCE HCL (gas)

26
Q

Describe reaction of acid anhydride with water..

A

acid anhydride + water = 2x carboxylic acid

one carboxylic acid gains an oh the other a hydrogen

27
Q

Describe reaction of acid anhydride with ammonia..

A

acid anhydride + ammonia = amide and carboxylic acid

28
Q

Describe reaction of acid anhydride with alcohol..

A

acid anhydride + alcohol= ester + carboxylic acid

29
Q

Describe reaction of acid anhydride with primary amines.

A

acid anhydride + primary amines= n- substituted amine and carboxylic acid

30
Q

What are carboxylic acids derivatives?

A

Esters

Acyl chlorides

Acid Anhydrides

Amides

31
Q

What mechanisms are involved with acid chlorides?

A

Nucleophillic - addition elimination reaction.

32
Q

How is aspirin made and why ?

A

By reacting ethanoic anhydride/ ethanoyl chloride and salicylic acid.

Ethnic anhydride is used because it is safer and less corrosive than ethanoyl chloride and HCL is not produced.

It is also cheaper to use and is safer as it doesn’t react vigorously with water.

Organic chemistry a2 (9 decks)

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