Major Skills in Chapter 15 – Aldehydes & Ketones

• Context: What is a carbonyl?

– Skill: Identifying carbonyls in molecules
• Context: What is an aldehyde?
– Skill: Giving and understanding systematic (IUPAC) names for aldehydes
– Skill: Understanding common names for (a few) aldehydes
• Context: What is an ketone?
– Skill: Giving and understanding systematic (IUPAC) names for ketones
– Skill: Understanding common names for ketones
• Review: Isomerism for aldehydes and ketones
• Context: Common aldehydes and ketones
• Review: Relating polarity and hydrogen bonding to intermolecular forces, solubility, and boiling point
• Reactions that form aldehydes and ketones
– Skill: Identifying reactions that will form aldehydes and ketones
• Review: Oxidation of alcohols
• Reactions that occur with alcohols
– Review: Oxidations
– Review: Reductions (Hydrogenations)
– Review: Addition reactions
– Skill: Identifying hemiacetal and acetal products
– Skill: Identifying hemiacetals and acetals
– Skill: Identifying hydrolysis products of hemiacetals and acetals
• Context: Sulfur in carbonyls (thionyls and sulfoxides)
 Carbonyls (15.1)

O O
d-
O
-

+
+ C
d

O O O O O

H R OH OR NH2
15.3 Aldehydes and ketones
are related to alcohols
m ild o x . any ox. OH
OH O
O

any ox. any ox.

No Reaction (NR)
OH
O
15.5 IUPAC Nomenclature for Ketones
Prefix–Locant–Side–Locant–ParentSuffix
Adjectives Noun

1. Find the highest priority group (Ketone)

(Ketone)
2. Find the longest continuous chain of carbons containing this group
3. Name the main chain according to length prefix (parent) and
functional group suffix. (“one” replaces “e” (anone enone or ynone))
4. Assign numbers (locant) so that the highest priority group has the
lowest number. (ketone)
5. Identify all side groups. (alcohol = “hydroxy”)
6. Assign name and number and list alphabetically before the main
chain name.
7. Apply special descriptors (prefix)
15.5 What if the ketone is in a ring?

O O

cyclohexanone 3-methylcyclohexanone
15.5 What if there are multiple ketones?

O
butadione
dibutanone
15.5 What if there are double bonds
and ketones?

O
O

butenone 3-methylbutenone
(but-3-en-2-one)
Ketone Nomenclature Practice (15.5)

O
O

3-heptanone 3-methyl-2-pentanone

O
O

OH
3-ethyl-2-hexanone 7-hydroxy-4-octanone
 Ketone Common Names (15.5)
• Most common names follow the rule alkyl chain common names + ketone

O O O

ethyl methyl ketone ethyl isopropyl ketone

cyclohexyl ethyl ketone

O
O
O

acetone
acetophenone
benzophenone
Ketone Common Practice (15.5)

O
O

butyl ethyl ketone sec-butyl methyl ketone

O
O

acetone

isopropyl phenyl ketone

15.4 IUPAC Nomenclature of Aldehydes
Prefix–Locant–Side–Locant–ParentSuffix
Adjectives Noun

1. Find the highest priority group (Aldehyde)

(Aldehyde)
2. Find the longest continuous chain of carbons containing this group
3. Name the main chain according to length prefix (parent) and
functional group suffix. (“al” replaces “e” (enal or ynal))
4. Assign numbers (locant) so that the highest priority group has the
lowest number. (aldehyde = always “1”)
5. Identify all side groups. (alcohol = “hydroxy”)
6. Assign name and number and list alphabetically before the main
chain name.
7. Apply special descriptors (prefix)
 Running Tally on Priority

Alkanes < Alkenes / Alkynes < Alcohols < Ketones

< Aldehydes < Aromatic

Aldehyde Nomenclature Practice (15.4)

O
O
H
H
pentanal 2-methylbutanal

O
O
H
H
OH
2-ethylpentanal 4-hydroxypentanal
Aldehyde Common Nomenclature

O
O
H
H H
formaldehyde

benzaldehyde
Common Aldehydes and Ketones (15.7)
O

O HO O
O
H
vanillin
O

benzaldehyde butadione

O O

cinnamaldehyde

2-heptanone carvone
 Steroids (15.7)

s te r o id

OH

O
O
OH
OH

O
O
O

te s to s te ro n e p r o je s t e r o n e c o r tis o n e