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A level Chemistry OCR A > 26.4 Carboxylic Acid Derivatives > Flashcards

26.4 Carboxylic Acid Derivatives Flashcards

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1
Q

What are carboxylic acid derivatives?

A

molecules which can be HYDROLYSED

to form CARBOXYLIC ACIDS

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2
Q

What are 4 examples of carboxylic acid derivatives?

A

ESTERS

ACYL CHLORIDES

AMIDES

ACID ANHYDRIDES

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3
Q

What group do all carboxylic acid derivatives contain?

A

acyl group

RCO (OH from carboxylic acid is removed + replaced)

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4
Q

What is the functional group of esters?

A

-COOR

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5
Q

What is the functional group of acyl chlorides?

A

-COCl

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6
Q

What is esterification?

A

Reaction of CARBOXYLIC ACID + ALCOHOL ⟶ ESTER + WATER

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7
Q

Under what 2 conditions can esters be hydrolysed in?

A

ACIDIC hydrolysis

ALKALINE hydrolysis

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8
Q

What does acidic hydrolysis of an ester form?

A

CARBOXYLIC ACID + ALCOHOL

(reverse of esterification)

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9
Q

What does alkaline hydrolysis of an ester form?

A

CARBOXYLATE + ALCOHOL

(reflux with aqueous OH-)

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10
Q

During general hydrolysis of an ester, what condition is used to make sure the reaction is complete?

A

reflux

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11
Q

What do you call molecules which can be HYDROLYSED to form carboxylic acids?

A

carboxylic acid derivatives

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12
Q

How do you form a carboxylic acid from a carboxylate?

A

Add H+ ions

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13
Q

How do you prepare an ester in the lab?

A
  1. alcohol + carboxylic acid (1:1)
    • Concentrated H2SO4 catalyst
  3. Place in water bath @ 80°C
    - ester has formed, but unreacted carboxylic acid remains.
    • aqueous sodium carbonate which reacts with excess carboxylic acid to remove, forming salt + water + carbon dioxide.
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14
Q

What is alkaline hydrolysis also known as?

A

saponification

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15
Q

Which hydrolysis is irreversible?

A

saponification / alkaline hydrolysis

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16
Q

What are the reactions of acyl chlorides?

A

+ ALCOHOL ⟶ ESTER

+ PHENOL ⟶ ESTER

+ WATER ⟶ CARBOXYLIC ACID

+ AMMONIA/AMINE ⟶ AMIDE

17
Q

How are acyl chlorides prepared?

A

Carboxylic acid + SOCl2 ⟶ ACYL CHLORIDE + SO2(g) + HCl(g)

18
Q

What products made when WATER added to acyl chloride?

A

carboxylic acid + HCl GAS

19
Q

What products made when ALCOHOL added to acyl chloride?

A

ester + HCl

20
Q

What products made when PHENOL added to acyl chloride?

A

ester + HCl

21
Q

What are the conditions for esterification?

A

Concentrated sulfuric acid

22
Q

What are the conditions for acid hydrolysis?

A

reflux + dilute acid catalyst

23
Q

Which bond is broken in an ester during hydrolysis?

A

C–O

24
Q

What are the conditions for alkaline hydrolysis?

A

aqueous OH-

reflux

25
Q

Carboxylic acid + Alcohol ⟶

A

ester (esterification) + water

(conc H2SO4 catalyst)

26
Q

What is the order of reactivity from lowest to highest?

Acid anhydride, Carboxylic acid, Acyl chloride

A

LOWEST ⟶ HIGHEST:

  1. carboxylic acid
  2. acid anhydride
  3. acyl chloride
27
Q

Why are the reactions of acyl chlorides not used in labs?

A

Their reactions are TOO VIGOROUS

28
Q

During what reaction is HCl gas released?

A

Acyl chloride + Water

29
Q

Which group of organic compounds follows this structure of naming?

__yl __anoate

A

ester

30
Q

Which group of organic compounds follows this structure of naming?

__anoyl chloride

A

acyl chloride

31
Q

Which group of organic compounds follows this structure of naming?

__anoic anhydride

A

acid anhydride

32
Q

What is the meaning of anhydride?

A

removal of water

33
Q

What is the systematic name for this molecule?

A

ethyl 3-bromopropanoate

34
Q

Draw the organic products for the following reaction:

A
35
Q

Draw the organic products for the following reaction:

A
36
Q

How would you synthesise methyl propanoate starting from propanal?

A
  1. oxidise propanal under reflux using acidified potassium dichromate ions to form propanoic acid.
  2. add methanol to form impure methyl propanoate. conditions for esterification are acid catalyst + reflux.
  3. Purify the ester:
  4. Filter under reduced pressure.
  5. Recrystallise.
  6. Measure melting point.

A level Chemistry OCR A (44 decks)

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