Chap14 Lecture.pdf - Fundamentals of Organic and...

Fundamentals of Organic
and Biochemistry
Chapter 14:
Introduction to Carboxylic Acids, Esters,
Amines, Amides
1

2

Carbonyl Functional
Groups
3

The Carbonyl Family (R
2
C=O)
The carbonyl carbon atom is trigonal planar , with bond angles
of !"#° . O is more electronegative than C, so the carbonyl
group is polar .
The carbonyl O is %
&
rich '
&
and the carbonyl C is %
&
poor
'
(
.
4

Carboxylic Acids
(R-COOH)
5

What are Carboxylic Acids?
Carboxylic acids are organic compounds containing
a COOH (carboxyl) group.
General structure:
Example:
Carboxylic acids are abbreviated as RCOOH or !"#
$
% .
6

Where are Carboxylic Acids found?
7

Where are Carboxylic Acids found?
8

9

Common Names of Common Carboxylic Acids
formic acid acetic acid benzoic acid
10

IUPAC Nomenclature for Carboxylic Acids
• To name a carboxylic acid using the IUPAC system:
• Find the longest chain containing the COOH group .
• Change the ± - e ² ending of the parent alkane
to ² - oic acid ² .
• Number the chain to put the COOH group at C1,
but omit ± 1 ² from the name. WHY?
• Apply all other nomenclature rules.
11

Learning Check: Name the Compounds
12

Learning Check: Name the Compounds
13

Learning Check: Name the Compounds
14

Draw the Skeletal Structure for the
following:
• 3-ethyl-4,6-diiodoheptanoic acid
• 2-isobutyl-3,4,5,6-tetraflourononoic acid
• 2-methyl-3-butyl-4-hexylbenzoic acid
15

Reactions for Carboxylic
Acids
16

Reactions: Reduction of Carboxylic Acids
17

Neutralization of Carboxylic Acids
• Since Carboxylic acids are weak organic acids, they react
with strong bases such as NaOH or KOH to form a
carboxylate salt and water .
• The carboxylic acid donates the proton to the base, !"
#
,
which accepts it.
18

Neutralization of Carboxylic Acids
• To name the metal salts of carboxylate ions, put the
three pieces below together:
!"#$ %& '($ #$'") *"'+%!
+ -".$!' !"#$ %& %./"!+* *%#-%!$!' (#+!12 '($ “4”)
+ −89:4(21&&+;)
19

Neutralization of Carboxylic Acids
• Learning Check:
20