Double Bonded Functional

Groups
Carbonyl group: A carbon atom double bonded to an oxygen atom (R-
C=O)
Aldehydes
•carbonyl group is at the END of the carbon chain (thus, aldehydes do
not require a number to indicate the position of the carbonyl group)
•compound with an =O and an –H attached to a carbon on the end of a
parent chain
Ketone
•carbonyl group is in the MIDDLE of the carbon chain
•an =O attached to a carbon within the parent chain
How to Name Aldehydes
1. Take the parent alkane name, drop the e, and add “al” to the end.
2. Start numbering the chain so the aldehyde is always on the first
carbon (but “1’ is not included in the name).
3. Name any side branches.
 O
║ methanal
H–C–H (formaldehyde)

O
║
CH3 – CH2– C – H propanal

O CH3
║ │
H – C – CH2 – CH – CH3 3-methylbutanal
1 2 3 4

OH O
5 4
│3 2 1
║
CH3 – CH – CH2 – CH2– CH 4-hydroxypentanal
How to Name Ketones
1. Take the parent alkane name, drop e , and add “one” to the end.

2. Number the parent chain from the end that reaches the carbonyl group first.

3. Show position of carbonyl group in name.

4. Name any side branches.

 propan
O one
║
CH3 – C – CH3 (acetone)

O pentan-3-
║ one
CH3 – CH2 – C – CH2 – CH3
O O CH3
║ ║ │
1 2 3 4 5 6
Note: C=O group has priority
CH3 – C – CH2 – C – C – CHover
3 alkyl groups
│
CH3
5,5-dimethylhexa-2,4-dione
Properties of Aldehydes and
Ketones
•Like alcohols, low molecular masses of aldehydes and ketones are
soluble in water.
•The C=O bond in aldehydes and ketones is polar.
• This makes them more soluble in water than hydrocarbons

•They do not contain an OH group, which means they cannot form

hydrogen bonds.
• This makes their boiling points lower than alcohols

•Aldehydes and ketones can mix well with both polar and nonpolar
substances.
• Aldehydes have strong, unpleasant odour
• Large aldehydes have pleasant, flowery odours
Carboxylic Acids
•Contain the carboxyl group located at the end of a parent chain:
•The carboxyl group will always be at the end.
How to Name Carboxylic Acids:
1. Name carboxylic acids by replacing the – e with –oic acid.
2. Number the chain so that the carboxyl group is at position #1 (but 1
isn’t included in the name).
3. Name any side branches
 O
II
CH3 C OH ethanoic acid (acetic acid)

CH3

CH3 – C – CH2 – C=O 3,3-dimethyl butanoic acid

CH3 OH

O O
II II
HO – C – CH2– C – OH propanedioic acid
 Phenylmethanoic acid
Preferred name: benzoic acid

O
H2C C
OH
Phenylethanoic acid

2-hydroxybenzoic acid
Draw the following carboxylic
acids:
methanoic acid

3-chloropropanoic acid

propenoic acid
Properties of Carboxylic Acids
•The polar carboxyl groups cause carboxylic acids to have higher melting
points compared to similar hydrocarbons.
•Since they are polar, carboxylic acids can form hydrogen bonds with
water molecules
◦ Smaller acids are soluble in water
◦ Longer carbon chains in larger acids make them relatively insoluble in water.

•Carboxylic acids react with bases in neutralization reactions.

•Carboxylic acids are found in citrus fruits, rhubarb, and other foods with
a sour taste.
Esters alkyl group
•Formed from carboxylic acids and alcohols
•–OH group is replaced by –O-R
main chain

How to Name Esters:

1. Alcohol: name the alkyl group attached to the O, indicate position #
2. Carboxylic acid: name the parent chain which includes the C=O
group
•Put the 2 names together (but as separate words)
•Change the ending of the carboxylic acid from ‘-anoic acid’ to ‘-anoate’
 O
II
CH3CH2CH2C-O-CH2CH3 ethyl butanoate

O
II 1-propyl methanoate
H C-O-CH2CH2CH3
Note: main chain does not
have to be the longest chain

CH3CH2COOCH(CH3)CH2CH3

O
II
CH3CH2C-O-CHCH2CH3 2-butyl propanoate
CH3
Properties of Esters
•Esters have a carbonyl group, but no hydroxyl group.
This makes them:
•Less soluble in water than their corresponding carboxylic
acids
◦ Esters with ≤4 carbons are soluble in water while larger esters are
insoluble
•Have lower boiling points than their corresponding
alcohols and carboxylic acids
•Smaller esters are gases and liquids at room temperature,
but the larger esters are waxy solids
Fats and Oils
•Fats and oils are large ester compounds called lipids
•The long-chain carboxylic acid component is called a fatty acid
•The alcohol component is glycerol
◦ Glycerol is a 3-carbon alcohol with three hydroxyl groups that can bond
freely with three fatty acids at once
◦ Therefore, the ester that is formed is called a triglyceride
◦ Fats & oils are triglycerides

glycerol
Properties of Fats
•Lipids are insoluble in water because of the long non-polar section of
the fatty acids
•Saturated lipids (only single bonds) have higher melting points and are
therefore solids at room temperature (fats)
•Unsaturated lipids with cis geometry will have kinks in their structure
which causes lower melting points (oils)
•Unsaturated lipids with trans geometry have smaller bends and similar
melting points to the unsaturated fats but have increased stability
(longer shelf life) but can cause health problems when digested
Saponification
When triglycerides are heated with a strong base, they can be split into
glycerol and a sodium salt through a hydrolysis reaction.
This sodium salt is soap, and this is a saponification reaction:
Amines
Organic derivatives of ammonia in which one, two or three
hydrocarbon groups have replaced hydrogen

Name amines by replacing the – e of the parent alkane with –amine

including a position number if necessary to show the location of the
functional group
The nitrogen group becomes
the branch:

•name the other alkyl groups using N- to locate the groups

•complex molecules use the name –amino for the functional group as a
substituent
To Name an Amine:

1. Identify the longest chain attached to the N atom as

the parent chain.
2. Replace the – e at the end with the name –amine.
3. Indicate position #.
4. Name the other alkyl groups using N- instead of a
position #

NH2
CH3CH2CH2CHCH3 pentan-2-amine
 N-methyl butan-1-amine

CH3
CH3-N-CHCH3 N,N-dimethyl propan-2-amine
CH3

CH3
CH3CH2CHCH- N-CH3 N-methyl- 3-methyl pentan-2-amin
CH3 H
Properties:
• polar compounds that can form hydrogen bonds
• amines with low molecular masses have a fishy odour and others are
responsible for the odour of decaying (cadaverine, putrescine)
• amines act as weak bases
Properties of Amines:
The N-C and N-H bonds in amines are polar. This means that:
•amines have higher boiling points and melting points than similar-sized
hydrocarbons.
•They have ower boiling points than similar sized alcohol molecules due
to N-H being less polar than O-H.
•Smaller amines are highly soluble in water.
•Amines act as weak bases.
They often have an unpleasant odour! (For example, the smell of fish is a
mixture of amines.)
Amides:
Formed from the reaction between a carboxylic acid and an amine to
form primary, secondary, or tertiary amides
Naming Amides
1. Name amides by first identifying the part of the amide that contains
the C=O group.
◦ Name this parent carboxylic acid, assigning the carbon in the C=O group
position number 1

2. Replace the oic acid ending of the name to –amide

3. Name any other alkyl groups attached to the nitrogen atom with the
letter N- rather than a number
 O
CH3C-NH2 ethanamide

N-ethyl- N-methylpropanamide

O
(CH3)2CHCONHCH2CH2CH3
O
CH3CHC-NH-CH2CH2CH3 N-prop-1-yl-2-methylpropanamide
CH3
Note: not alphabetical – write N first, then #’s
Properties of Amides
•Contain a polar carbonyl group and 1º and 2º amides have at least one
–NH group which allows them to form strong hydrogen bonds among
themselves
•Smaller amides are soluble in water because they can form hydrogen
bonds with water