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Chemistry > 26 - Compounds Containing the Carbonyl Group > Flashcards

26 - Compounds Containing the Carbonyl Group Flashcards

1
Q

What is the carbonyl group?

A

C=O

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2
Q

What is an aldehyde and it naming?

A

C=O group at the last carbon.
-al suffix (except benzaldehyde)

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3
Q

What is a ketone and its naming?

A

C=O group in between two R groups.
-one suffix

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4
Q

What is the boiling point of the carbonyl group like?

A

The carbonyl group is polar therefore there are permanent dipole-dipole forces between molecules therefore higher boiling points than alkanes but lower than alcohols where hydrogen bonding occurs.

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5
Q

What is the solubility of aldehydes and ketones like?

A

The shorter chain ones are completely soluble in water as hydrogen bonds form between them, but as the chain length increases they become less soluable.

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6
Q

What are the typical reactions of the carbonyl group?

A

Nucleophilic additions. The big difference in electronegativity makes the C=O bond extremely polar, making it susceptible to nucleophilic attack and the double bond means addition reactions are possible.

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7
Q

What will the reaction of cyanide + aldehydes/ketones produce?

A

A racemic mixture, as the :CN- ion could attack from above or below the plane C=O group. (only unsymmetrical ketones).

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8
Q

What are aldehydes oxidised to?

A

Carboxylic acids.

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9
Q

What are ketones oxidised to?

A

They aren’t oxidised easily, as the C-C bond must be broken. Stronger oxidising agents produce a shorter chain molecule + CO2 + H2O.

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10
Q

What is Fehling’s solution?

A

A copper (II) complex ion. (Blue solution)

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11
Q

What does Fehling’s solution + aldehydes/ketones produce?

A

Aliphatic aldehydes are oxidised to carboxylic acids, forming a brick red precipitate of copper oxide.
Ketones have no reaction.

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12
Q

What is Tollens’s reagent?

A

Ammoniacal silver nitrate.

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13
Q

What does Tollens’ reagent + aldehydes/ketones produce?

A

Aldehydes are oxidised to carboxylic acid and a silver mirror of metallic silver.
Ketones have no reaction.

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14
Q

How are aldehydes/ ketones reduced?

A

Using the reducing agent NaBH4 and the nucleophile :H-.
By nucleophilic addition.

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15
Q

What are aldehydes/ketones reduced to?

A

Alcohols.

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16
Q

What are carboxylic acids and their naming?

A

The -COOH group.
-oic acid suffix.

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17
Q

What is the solubility of carboxylic acids like?

A

Soluble in water due to its ability to hydrogen bond. Only soluble up to 4 carbons.

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18
Q

What is the melting point of carboxylic acids like?

A

Higher melting point than alkanes of similar Mr, as the acids form hydrogen bonds with one another in the solid state.

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19
Q

What are esters?

A

-COOR

20
Q

How are esters named?

A

The name starts with the alkyl group attached to the oxygen.
-oate suffix.

21
Q

What are the uses of esters?

A

Solvents
Plasticisers
Flavourings
Perfume.

22
Q

What is a carboxylate ion?

A

RCOO-

23
Q

Why are carboxylate ions stable?

A

The negative charge is shared over the whole of the carboxylate group, and this delocalisation makes the resulting ion stable.

24
Q

Are carboxylic acids strong or weak acids?

A

Weak, meaning they don’t fully dissociate in an aqueous solution.

25
Q

What groups do carboxylic acids form ionic salts with?

A

Metals
Alkalis
Metal oxides
Metal carbonates.

26
Q

Are carboxylic acids proton acceptors or donors?

A

Proton donors.

27
Q

How are esters formed?

A

From carboxylic acids + alcohols with a strong acid catalyst.

28
Q

What are the conditions of carboxylic acids + alcohols?

A

Reflux.
Strong H2SO4 catalyst which acts as a dehydrating agent, increasing the yield of the ester.

29
Q

What does the hydrolysis of esters produce?

A

An equilibrium mixture of ester, water, acid and alcohol, as it does not go to completion.

30
Q

What are the conditions for the hydrolysis of esters?

A

At room temperature with a strong catalyst.

31
Q

What does the hydrolysis of esters with basic conditions produce?

A

A salt rather than the acid itself.
The reaction goes to completion.

32
Q

Why are acid derivatives formed?

A

As the carboxyl group is very stable it means nucleophilic reactions don’t take place readily so they are used.

33
Q

What are acyl chlorides and naming?

A

RCOCl
Replace -oic with -oyl chloride

34
Q

Why are acyl chlorides useful?

A

The Cl group is a good leaving group, as it is electron withdrawing, making the C more positive, so it is more reactive towards nucleophiles.

35
Q

What are the reactions between acyl chlorides and acid anhydrides?

A

Addition-elimination reactions.

36
Q

What is more reactive acid anhydrides or acyl chlorides?

A

Acyl chlorides.

37
Q

What are the reagents, conditions and products of acyl chlorides + water?

A

Reagents - H2)
Conditions - room temperature
Products - Carboxylic acid + HCl

38
Q

What are the conditions and products of acyl chlorides + alcohols?

A

Conditions - reflux in anhydrous conditions.
Products - ester + HCl

39
Q

Why are esters made via acyl chlorides rather than carboxylic acids?

A

Via carboxylic acids is slower, reversible and a low yield of esters. Acyl chlorides are faster, better yield but must be kept in anhydrous conditions.

40
Q

What are the conditions and products of acyl chlorides + ammonia?

A

Conditions - low temperature, excess ammonia.
Products - amide + HCl

41
Q

What are acid anhydrides?

A

Two acyl groups bonded to the same oxygen.
O=C-O-C=O

42
Q

How are acid anhydrides named?

A

The corresponding acid -acid suffix is replaced with anhydride.

43
Q

What do acid anhydrides and water form?

A

Carboxylic acids they were formed from.

44
Q

What do acid anhydrides + alcohols produce?

A

ester + ethanoic acid

45
Q

Why are acid anhydrides used over acyl chlorides?

A

Not as reactive so a slower reaction.
Cheaper.
Safter reaction as its less exothermic
Less corrosive
Not so readily hydrolysed
Safer as the by-product is ethanoic acid, rather than corrosive fumes of HCl.

Chemistry (24 decks)

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