Hydrocarbon Derivatives

Aldehydes, Ketones, Carboxylic

Acids, & Esters
 Carbonyl Group
• >CO

• Oxygen attached to a carbon by a double

covalent bond.

• Strong dipole
 Aldehydes
O

• General formula: RCH or RCHO
• Carbonyl group is always at the end of the
aldehyde (C on one side, H on the other).
• Find the name of the alkane with the same
# of carbons. Change the final e to -al.
• Never need #’s for aldehydes – always at
end.
 O
H

=
HCO H  HCH
H

Aldehyde comes from

Alcohol Dehydrogenated
 O
Methanal

HCH
Common name =
formaldehyde
O
H


HCCH Ethanal
H = acetaldehyde

1 metabolic product of ethanol on its route

to acetic acid.
 Acetaldehyde
• Evidence that it is carcinogenic.
• Natural component of many ripe fruits.
• Contributes to odors of rosemary, daffodil,
bitter orange, camphor, angelica, fennel,
mustard, & peppermint.
• A component of cigarette smoke.
CH3CH2CH2CHO Ends in CHO so it’s
an aldehyde.

4 Carbons so base name is butane.

Drop final -e and add –al  butanal.

 Properties of Aldehydes -
O
R R - H H
- +
C=O C=O
 + +
H H
Aldehydes are polar! Bumps up the
boiling point.

1-way Hydrogen bonding in H2O.

Bumps up solubility.
 Ketones
• Carbonyl group , >C=O, located within a C chain
instead of at the end.
• General Format:

O
=

RCR'

R and R' may or may not be the same.

 Naming Ketones
• Nearly always have a number.
• Take the corresponding alkane name.
• Drop final –e.
• Add –one.
• Number in front gives location of >C=O.
(Lowest possible #.)
 H O H

=
HCCCH propanone
H H
Common name = acetone

O
=

CH3CH2CH2CCH3 2-pentanone
 Aldehydes & Ketones
• Known for appealing tastes & smells.
• Used as flavorings in food & candy.
• Used as fragrances in perfumes.
• Vanilla & cinnamon = aldehydes
 Properties of Aldehydes & Ketones

• Aldehydes & ketones contain C=O group,

which makes the molecules polar.
• Boiling point: Higher than alkanes, lower
than alcohols.
• In pure aldehydes & ketones, hydrogen
bonding does NOT occur. No H bonded to
O.
• Can have 1-way Hydrogen bonding in
water, so they are pretty soluble in H2O.
 Carboxylic Acids
O Acidic H+

=
• General Formula = RCOH
• Contains a carbonyl group & a hydroxyl
group bonded to same C.
• The H is acidic. It ionizes in water!
• Carboxylic Acids are electrolytes!
 Ionization of Acetic Acid
CH3COOH + H2O  CH3COO- + H3O+
 Table R
O

=
• General Format: R-C-OH or R-COOH
Which of the following is an
electrolyte?
A. CH3OH alcohol
B. CH3COOH
C. CH2O aldehyde
D. C 3H 6O ketone

Correct answer is B, the carboxylic acid.

 Which of the following is a
nonelectrolyte?
A. HCl
B. CH3COOH
C. NaOH
D. CH3OH

Correct answer is D, an alcohol.

 Naming Carboxylic Acids
• Never need a number – functional group
always at end.
• Find name of corresponding hydrocarbon.
• Drop final –e.
• Add the ending –oic + the word acid.
 O

=
HCOH

1 C  methane. Methanoic acid

Sting in red ants, bees

O
H
=

HCCOH Ethanoic Acid

H or
Acetic acid
2 C  ethane
CH3CH2CH2CH2COOH

5 C’s  pentane so the name

is pentanoic acid.
 Common carboxylic acids
• Acetic acid – vinegar. Also produced in
doughs leavened with a specific yeast 
sourdough bread
• Citric acid
• Tannic acid
• Ascorbic acid
• Lactic acid
– Poly(lactic acid) – biodegradable polymers
used as sutures in internal surgery.
 Properties of Carboxylic Acids
• Contain –COOH group.

• H is bonded to O. Hydrogen bonding

occurs. Leads to increases in boiling point
over corresponding alkane.
• Also can form hydrogen bonds with water
so the smaller acids are pretty soluble.
 Esters
O

=
• General format: RCOR‘

• R and R‘ = hydrocarbon branches. Can be the

same or different.
• Esters contain a carbonyl group and a bridge O,
both in the middle of the chain.
• Esters are POLAR, but NO H bonded to O
however.
 O Esters
=
• RCOR‘ or RCOOR’

• Combination of a carboxylic acid & an

alcohol.
• The carbonyl group and “R” come from the
carboxylic acid.
• The bridging O and the R’ come from the
alcohol.
 Esters
• Responsible for many distinctive odors

• Pineapple
• Banana
• Orange
• Apple
• Wintergreen
 Naming Esters
• Name the hydrocarbon branch bonded to
the bridge O first. Branches end in –yl.
• The base name is derived from the branch
containing the carbonyl group. Count up
all the C atoms in this branch, including
the C in the carbonyl.
• Find the hydrocarbon base name. Drop
the final –e and add –oate.
 O So you name this

=
CH3CH2COCH3 branch 1st.

Carbonyl Bridge O
Group

Methyl Propanoate
 O Bridge O

=
CH3CH2CH2COCH2CH3

Name this branch 1st.

Ethyl Butanoate

Pineapple
 Bridge O
O
=
CH3COCH2CH2CH2CH2CH3

Name this branch 1st.

Pentyl Ethanoate

Banana
 O

=
CH3OCCH2CH2CH3

Bridge O
Name this branch 1st.
4 C’s on the other side = but

Methyl butanoate - apple

 O

=
CH3CH2CH2CH2CH2CH2CH2CH2-O-C-CH3

Bridge O

Name this branch 1st.

2 C’s on the other side: ethane

Octyl Ethanoate orange

 AMIDES
-Has a nitrogen atom attached to a carbonyl
- The carbonyl carbon-to-nitrogen bond is
called amide linkage.
- The amide linkage is called peptide linkage
or peptide bond in repeating units of proteins
or amino acid O
=
- basic formula is R-C-NH2
 AMIDES
-Simple amides are named as derivatives of
carboxylic acids
-the –oic acid ending of the carboxylic acid is
replaced with suffix -amide

O O

=
=

H-C-OH H-C-NH2

Methanoic acid Methanamide

 AMIDES

=
- Hexanamide
O O

=
=

CH2CH2-C-NH2 CH3CH2CH-C-NH2
CH3
propanamide

2-methylbutanamide