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Chapter 9 Aldehydes and Ketones
Chapter 9 Aldehydes and Ketones
Chapter 9 Aldehydes and Ketones
AND
KETONES
Benzaldehyde is found in the kernels of bitter
almonds
Cinnamaldehyde is found in Ceylonese and Cinnamon oils
KEY QUESTIONS:
• What are the Aldehydes and Ketones?
• How do we name Aldehydes and Ketones?
KETONES
• In IUPAC name, change the suffix –e of the
parent alkane to –one, indicating the
presence of carbonyl group.
ALDEHYDES and KETONES with –OH and –NH2
• -OH substituent is indicated by hydroxy
• -NH2 substituent is indicated by amino-
Both numbered and alphabetized along with
any other substituent that might be present.
Common Names
We derive the common name for an
aldehyde from the common name of
carboxylic acid. The word “acid” is dropped
and the suffix “-ic” or “-oic” is changed to
“–aldehyde”.
Ketones [O]
------------------> No
Reaction
Tollens’ Reagent – A reagent with a mild
oxidizing agent use to distinguish between
Aldehydes and Ketones
Characteristic Reactions
1. OXIDATION
Tollens’ Reagent – contains silver nitrate
and ammonia in water, readily reacts with
aldehyde, which acts as reducing agents,
reduces the complex silver ion to silver ion.
Ketones reduced
to 2o OH
1. NaBH4
2. H3O+
H2
Ni
Characteristic Reactions
3. ADDITION OF ALCOHOLS
Addition of a molecule of alcohol to the
carbonyl group of an aldehyde or ketone
forms a hemiacetal (a half-acetal). The
functional group of a hemiacetal is a carbon
bonded to one -OH group and one -OR
group.
Characteristic Reactions
3. ADDITION OF ALCOHOLS
In forming a hemiacetal, the H of the
alcohol adds to the carbonyl oxygen and the
OR group of the alcohol adds to the
carbonyl carbon.
Characteristic Reactions
3. ADDITION OF ALCOHOLS
Hemiacetals are generally unstable and can
react further with alcohols to form acetals
plus water. This reaction is acid-catalyzed.
The functional group of an acetal is a
carbon bonded to two -OR groups.
Characteristic Reactions
3. ADDITION OF ALCOHOLS
All steps in hemiacetal and acetal formation
are reversible. As with any other
equilibrium, we can make this one go in
either direction by using Le Chatelier’s
principle. If we want to drive it to the right
(formation of the acetal), we either use a
large excess of alcohol or remove water
from the equilibrium mixture. If we want to
drive it to the left (hydrolysis of the
acetal to the original aldehyde or ketone and
alcohol), we use a large excess of water.
Characteristic Reactions
3. ADDITION OF ALCOHOLS
Characteristic Reactions
3. ADDITION OF ALCOHOLS
Draw the hemiacetal and then the acetal
formed in each reaction. In each case,
assume an excess of the alcohol