Hydrocarbon Derivatives

Aldehydes, Ketones, Carboxylic

Acids, & Esters
 Carbonyl Group
• >CO

• Oxygen attached to a carbon by a double

covalent bond.

• Strong dipole
 Aldehydes
Al
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.
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
one
• 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 2-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. C3H6O 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.
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