26.4 Carboxylic Acid Derivatives Flashcards by Sreya Wadud

What are carboxylic acid derivatives?

molecules which can be HYDROLYSED

to form CARBOXYLIC ACIDS

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What are 4 examples of carboxylic acid derivatives?

ESTERS

ACYL CHLORIDES

AMIDES

ACID ANHYDRIDES

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What group do all carboxylic acid derivatives contain?

acyl group

RCO (OH from carboxylic acid is removed + replaced)

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What is the functional group of esters?

-COOR

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What is the functional group of acyl chlorides?

-COCl

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What is esterification?

Reaction of CARBOXYLIC ACID + ALCOHOL ⟶ ESTER + WATER

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Under what 2 conditions can esters be hydrolysed in?

ACIDIC hydrolysis

ALKALINE hydrolysis

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What does acidic hydrolysis of an ester form?

CARBOXYLIC ACID + ALCOHOL

(reverse of esterification)

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What does alkaline hydrolysis of an ester form?

CARBOXYLATE + ALCOHOL

(reflux with aqueous OH-)

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

reflux

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

carboxylic acid derivatives

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How do you form a carboxylic acid from a carboxylate?

Add H+ ions

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How do you prepare an ester in the lab?

alcohol + carboxylic acid (1:1)
- Concentrated H2SO4 catalyst
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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What is alkaline hydrolysis also known as?

saponification

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Which hydrolysis is irreversible?

saponification / alkaline hydrolysis

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What are the reactions of acyl chlorides?

+ ALCOHOL ⟶ ESTER

+ PHENOL ⟶ ESTER

+ WATER ⟶ CARBOXYLIC ACID

+ AMMONIA/AMINE ⟶ AMIDE

How are acyl chlorides prepared?

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

What products made when WATER added to acyl chloride?

carboxylic acid + HCl GAS

What products made when ALCOHOL added to acyl chloride?

ester + HCl

What products made when PHENOL added to acyl chloride?

ester + HCl

What are the conditions for esterification?

Concentrated sulfuric acid

What are the conditions for acid hydrolysis?

reflux + dilute acid catalyst

Which bond is broken in an ester during hydrolysis?

C–O

What are the conditions for alkaline hydrolysis?

aqueous OH-

reflux

Carboxylic acid + Alcohol ⟶

ester (esterification) + water (conc H₂SO₄ catalyst)

What is the order of reactivity from lowest to highest? Acid anhydride, Carboxylic acid, Acyl chloride

LOWEST ⟶ HIGHEST: 1. carboxylic acid 2. acid anhydride 3. acyl chloride

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

Their reactions are TOO VIGOROUS

During what reaction is HCl gas released?

Acyl chloride + Water

Which group of organic compounds follows this structure of naming? \_\_yl \_\_anoate

ester

Which group of organic compounds follows this structure of naming? \_\_anoyl chloride

acyl chloride

Which group of organic compounds follows this structure of naming? \_\_anoic anhydride

acid anhydride

What is the meaning of anhydride?

removal of water

What is the systematic name for this molecule?

ethyl 3-bromopropanoate

Draw the organic products for the following reaction:

How would you synthesise methyl propanoate starting from propanal?

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.