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Chemistry > Chapter 26 - Carbonyls and Carboxylic compounds > Flashcards

Chapter 26 - Carbonyls and Carboxylic compounds Flashcards

1
Q

Define carbonyl compound

A

A compound containing the C=O functional group

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2
Q

Give 2 examples of a carbonyl compound

A

Aldehydes

Ketones

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3
Q

What is the suffix for an aldehyde?

A

-Al

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4
Q

What is the suffix for a ketone?

A

-One

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5
Q

Where is the C=O located in an aldehyde?

A

At the end of the chain

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6
Q

Where is the C=O located in a ketone

A

In the middle of a chain

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7
Q

What are carbonyls said to be in they contain a benzene ring?

A

Aromatic

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8
Q

What are carbonyls said to be if they do not contain a benzene ring?

A

Aliphatic

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9
Q

What is the simplest aromatic aldehyde called?

A

benzaldehyde

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10
Q

What is the simplest aromatic ketone called

A

Phenylethanone

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11
Q

What happens when a primary alcohol is oxidised under distillation?

A

It becomes an aldehyde

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12
Q

What happens when a primary alcohol is oxidised under reflux?

A

It becomes a carboxylic acid

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13
Q

What happens when a secondary alcohol is oxidised under reflux?

A

It becomes a ketone

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14
Q

What happens when a tertiary alcohol is oxidised under distillation or reflux?

A

Nothing as they are resistant to oxidation

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15
Q

What are alcohols reacted with to oxidise?

A

Acidified dichromate

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16
Q

Define reflux

A

The continual boiling and condensing of a reaction mixture to ensure that a reaction takes place without the contents of the flask boiling dry

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17
Q

What can an aldehyde be reduced to?

A

a primary alcohol

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18
Q

What can a ketone be reduced to?

A

a secondary alcohol

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19
Q

What is the reducing agent used for reduction of carbonyl compounds?

A

NaBH4

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20
Q

What are the conditions for the reduction of carbonyl compounds?

A

Warm and a H20 solvent

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21
Q

How can NaBH4 be represented in an equation showing the reduction of an alcohol?

A

[H]

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22
Q

How many [H] are required to reduce an aldehyde or a ketone to an alcohol?

A

2[H]

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23
Q

What is the mechanism used to reduce a carbonyl to an alcohol?

A

Nucleophilic addition

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24
Q

Why is it nucleophilic?

A

Because NaBH4 reacts with a carbonyl to produce an alcohol it releases a H- ion in solution, which is a nucleophile as it is attracted to positively charged areas

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25
Define nucleophile
an atom or group of atoms which is attracted to an electron deficient centre, where it donates a pair of e- to form a new covalent bond
26
Define addition
a reaction in which a reactant is added to an unsaturated molecule to make a saturated molecule
27
What mechanisms are required to make a hydroxynitrile from a carbonyl?
nucleophilic addition
28
What reagent is used to make a hydroxynitrile?
HCN
29
What ions does the reagent used to make a hydroxynitrile have?
CN-
30
Which atom in a carbonyl will CN- be attracted to? Why?
C, because it is partially positive
31
Which bond breaks when CN- is attracted to C? What happens after that?
C=O breaks, C-O forms and C-CN forms and O-H forms
32
Explain the process of reduction of an alcohol by NaBH4?
The C=O bond in the carbonyl is polar, with the C being partially positive and the O being partially negative. The hydride ion from NaBH4 is attracted to the C as it is a nucleophile, and forms a covalent bond with it using the lone pair. One of the bonds in the C=O breaks and the pair of electrons goes to the O atom, so the O atom becomes negatively charged The O atom uses the lone pair to form a bond with the H of a H20 (from the water solvent) and the OH bond in the water molecule breaks, forming an alcohol and an OH- ion.
33
What can be used to detect the presence of a carbonyl group in an organic compound?
2,4 - dinitrophenylhydrazine
34
What colour change is there when using 2,4 - dinitrophenylhydrazine?
Colourless to orange/yellow precipitate
35
What doesnt 2,4- dinitrophenylhydrazine detect the presence of?
Carboxylic acids or esters
36
What is the name of the precipitate formed when 2,4-dinitrophenylhydrazine reacts with a carbonyl?
2,4 - dinitrophenylhydrazone derivative
37
What can the 2,4 - dinitrophenylhydrazone derivative be used to identify?
Whether the carbonyl is a ketone/ aldehyde
38
How can the 2,4 - dinitrophenylhydrazone derivative be used to identify whether the carbonyl is a ketone or aldehyde?
1. the 2,4 DNP derivative is purified by recyrstallisation 2. the melting point is determined 3. this is compared to a database to identify whether it is an aldehyde/ ketone
39
What reagent can be used to identify only an aldehyde?
Tollen's reagent
40
What is the positive presence of an aldehyde using Tollen's presence?
colour change from colourless --> formation of a silver mirror
41
What is Tollen's reagent made of?
Ammoniacal silver nitrate
42
What is the method for using Tollen's reagent?
1. add 2cm3 of sample to a test tube 2. add 2cm3 of tollens reagent to the test tube 3. Heat in water bath
43
What is the functional group of a carboxylic acid?
COOH
44
What happens to solubility when chain length decreases? Why?
It increases, because the solubility is due to hydrogen bonding, and the hydrocarbon section of the carboxylic acid is non-polar, and therefore will not bond to water molecules, so the shorter the hydrocarbon section the more likely the acid is to dissolve
45
What is solubility of carboxylic acids?
The tendency of a carboxylic acids to dissolve in water
46
Are carboxylic acids weak or strong acids? why?
Weak because only a small proportion of acid molecules will dissociate and the position of equilibrium lies well to the left and therefore produces more acid molecules than hydrogen protons
47
What type of salt is formed from a carboxylic acid?
A Carboxylate salt
48
What is the difference between a carboxylate salt and a carboxylic acid?
Carboxylate salts have had the H atom on the OH replaced by a negatively charged atom
49
What is the name of a methanoic acid salt?
methanolate
50
What is the name of an ethanoic acid salt?
ethanoate
51
What is the name of an propanoic acid salt?
propanoate
52
Carboxylic acid + metal -->
Salt + hydrogen
53
Carboxylic acid + carbonate -->
salt + carbon dioxide + water
54
Acid + base -->
Salt + water
55
What is the functional group of an ester?
COOC
56
Alcohol + carboxylic acid -->
Ester + water
57
Alcohol + acid anhydrides -->
ester + carboxylic acid
58
Ester + alkaline -->
Alcohol + carboxylate salt
59
What is esterification?
the formation of an ester from alcohol and a carboxylic acid
60
What is an acid anhydride?
A molecule formed from 2 acid molecules, which have lost a molecule of water
61
What conditions are required for esterification?
Conc H2SO4, reflux, heat
62
What conditions are required for hydrolysis of an ester using alkaline conditions?
NaOH or KOH, heat and reflux
63
What conditions are required for hydrolysis of an ester under standard conditions?
Dilute H2SO4, reflux, heat
64
Write a general equation for the hydrolysis of an ester under standard conditions
ester + water --> carboxylic acid + alcohol
65
Write a general equation for the hydrolysis of an ester under alkaline conditions
ester + alkaline --> alcohol + carboxylate salt
66
Write a general equation for the formation of an ester under standard conditions
carboxylic acid + alcohol --> ester + water
67
Write a general equation for the formation of an ester using an acid anhydride
Alcohol + acid anhydride --> ester + carboxylic acid
68
What is the functional group of an acyl chloride ?
COCl
69
Write an equation for the preparation of an acyl chloride
Carboxylic acid + SOCl2 --> acyl chloride + SO2 + HCl
70
Acyl chloride + alcohol -->
Ester + HCl
71
Acyl chloride + 2NH3 -->
primary amide + NH4CL
72
Write an equation of the formation of a primary amide
Acyl chloride + 2NH3 --> primary amide + NH4Cl
73
Write an equation of the formation of a secondary amide
Acyl chloride + primary amide ---> secondary amide + NH4Cl
74
Acyl chloride + primary amide --->
secondary amide + NH4Cl
75
Acyl chloride + phenol -->
phenyl ester + HCl
76
Write the equation for the formation of a phenyl ester
Acyl chloride + phenol --> phenyl ester + HCl
77
Acyl chloride + water -->
Carboxylic acid + HCl
78
What is the functional group of a primary amide?
CONH2
79
What does a primary amide react similarly to?
A carboxylic ester
80
What is the functional group of a secondary amide?
CONHCH3

Chemistry (21 decks)

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