5/2/2012 1 Session 22 Organic Chemistry, UNAM School of Medicine 1 Carboxylic Acids & Carboxylic Acids & Carboxylic Acids & Carboxylic Acids & Carboxylic Acid Derivatives II Carboxylic Acid Derivatives II Carboxylic Acid Derivatives II Carboxylic Acid Derivatives II Dr L.H.A. Prins (Ph.D.) Dept. of Pharmacy UNAM Learning Outcomes 2 By the end of this session, the student should be able to: Understand the importance of the carboxylic acid derivatives, namely aldehydes & ketones Describe the structure of aldehydes & ketones Name aldehydes & ketones according to IUPAC system Describe the physical properties of carboxylic acids & all of its derivatives Organic Chemistry, UNAM School of Medicine Carbonyl Compounds II Carbonyl Compounds II
16
Embed
(22) session 22 carboxylic acids & carboxylic acid derivatives ii
This document is posted to help you gain knowledge. Please leave a comment to let me know what you think about it! Share it to your friends and learn new things together.
Structure of aldehydesStructure of aldehydesStructure of aldehydesStructure of aldehydes
5
� Aldehyde (R-CHO): Carbonyl C is bonded to a H on the one side
& to an alkyl/aryl group or a H on the other side
� Hybridisation structure: Refer to Session 21 (Slides 11-12)
Organic Chemistry, UNAM School of Medicine
Structure of aldehydesStructure of aldehydesStructure of aldehydesStructure of aldehydes
6
� Examples:
Organic Chemistry, UNAM School of Medicine
5/2/2012
4
Nomenclature of aldehydesNomenclature of aldehydesNomenclature of aldehydesNomenclature of aldehydes
7
� Common names:- Derived from the common names of carboxylic acids (see Table on next slide)
- “ic acid” (or “oic acid”) is substituted for “aldehyde”
- Greek letters - used to give locations of substituents (as with COOH’s & other COOH derivatives)
� Examples:
Organic Chemistry, UNAM School of Medicine
Nomenclature of aldehydesNomenclature of aldehydesNomenclature of aldehydesNomenclature of aldehydes
8
5/2/2012
5
Nomenclature of aldehydesNomenclature of aldehydesNomenclature of aldehydesNomenclature of aldehydes
9
� Systematic names (IUPAC):- Replace the terminal “e” from the name of the parent hydrocarbon with “al”
- Carbonyl C:Always at the end of the parent hydrocarbon, therefore always # 1
• Remember: “Alkanal”
• Examples:
Organic Chemistry, UNAM School of Medicine
Nomenclature of aldehydesNomenclature of aldehydesNomenclature of aldehydesNomenclature of aldehydes
10
� Systematic names (IUPAC):- Aldehyde group attached to a ring - named by adding“carbaldehyde” to the name of the cyclic compound - C to which aldehyde group is attached is carbon “1”
• Examples:
Organic Chemistry, UNAM School of Medicine
5/2/2012
6
KetonesKetonesKetonesKetones
11 Organic Chemistry, UNAM School of Medicine
Importance??Importance??Importance??Importance??
12
� Many compounds found in nature have aldehyde or ketone
functional groups
� Camphor: Ketone responsible
for characteristic sweet odour
of the camphor tree
Organic Chemistry, UNAM School of Medicine
5/2/2012
7
Structure of ketonesStructure of ketonesStructure of ketonesStructure of ketones
13
� Ketone (R-COR'): Carbonyl C is bonded to 2 carbon chains or
carbon rings
� Hybridisation structure: Refer to Session 21 (Slides 11-12)
Organic Chemistry, UNAM School of Medicine
Structure of ketonesStructure of ketonesStructure of ketonesStructure of ketones
14
� Examples:
Organic Chemistry, UNAM School of Medicine
5/2/2012
8
Nomenclature of ketonesNomenclature of ketonesNomenclature of ketonesNomenclature of ketones
15
� Common names:
- Name the two alkyl groups attached to the carbonyl group followed by the word “ketone”
- Greek letters - used to give locations of substituents (as with COOH’s & other COOH derivatives)
� Examples:
Organic Chemistry, UNAM School of Medicine
ethyl methyl ketone
Nomenclature of ketonesNomenclature of ketonesNomenclature of ketonesNomenclature of ketones
16
� Common names:- Some ketones have historical common names- Some of these names are allowed by IUPAC- Dimethyl ketone is always called “acetone”- Alkyl phenyl ketones: Named as acyl group followed by suffix “phenone”
� Examples:
Organic Chemistry, UNAM School of Medicine
5/2/2012
9
Nomenclature of ketonesNomenclature of ketonesNomenclature of ketonesNomenclature of ketones
17
� Systematic names (IUPAC):- Replace the terminal “e” from the name of the parent hydrocarbon with “one”
- Number chain to give carbonyl carbon smallest possible #
• Remember: “Alkanone”
• Examples:
Organic Chemistry, UNAM School of Medicine
Nomenclature of ketonesNomenclature of ketonesNomenclature of ketonesNomenclature of ketones
18
� Systematic names (IUPAC):
- Cyclic ketones: Carbonyl C is assumed to be at position # 1
• Examples:
Organic Chemistry, UNAM School of Medicine
5/2/2012
10
Nomenclature of ketonesNomenclature of ketonesNomenclature of ketonesNomenclature of ketones
19
� Systematic names (IUPAC):
- Ketone as a substituent: If the ketone has a 2nd FG of higher
naming priority, the ketone oxygen is indicated by the prefix
“oxo”
• Examples:
Organic Chemistry, UNAM School of Medicine
Physical properties of COOH Physical properties of COOH Physical properties of COOH Physical properties of COOH