Chapter 16 and GHW#6
Questions
Carboxylic Acids, Esters, and
Other Acid Derivatives
Bonding Characteristics of Carboxylic Acids
A carboxylic acid has functional a carboxyl group. A
carboxyl group is a carbonyl group (C=O) with a hydroxo
group (—OH) bonded to the carboxyl carbon atom.
Physical Properties of Carboxylic Acids
Both polar molecules
and hydrogen bonding
makes:
BP and MP are higher
than alcohols ,
hydrocarbons and
ether with comparable
carbon numbers
Physical Properties of carboxylic
acids derivatives
Esters, amides, acid
chlorides and acid
anhydride have lower
boiling and
melting points than
parent acid, Except
Carboxylic Acid Salts
IUPAC Nomenclature of Carboxylic Acid
and Esters
• The IUPAC system deals with functional
groups two different ways.
• Modification of the hydrocarbon name to
indicate the presence of a functional group.
• Acid – R-COOH
use -oic ending.
• Esters –R-COOR’
use -oate ending.
Common Names of Carboxylic Acids
IUPAC Nomenclature of Carboxylic Acid
and Esters
Common/IUPAC Nomenclature of Esters
1. Identify the carboxylic acids, esters, amides and acid
from the following and give their common and/or
IUPAC names. Carboxylic Acids, Esters, and Other Acid
Derivatives
a)Type:_____________ b) Type:___________________ c)Type:___________________
Name:______________ Name:__________________
Name:__________________
____
d)Type:____________ e) Type:___________________ f) Type:___________________
Name:______________ Name:__________________
Name:__________________
1. Identify the carboxylic acids, esters, amides and
acid from the following and give their common
and/or IUPAC names. Carboxylic Acids, Esters, and
Other Acid Derivatives
g)
h)
Type:___________________ Type:___________________
Name:__________________ Name:__________________
i)
Type:___________________
Name:__________________
2. Draw the condensed formula of following
carboxylic acid and their derivatives.
a) methyl
propanoate
b) ethyl
pentanoate
c) propanoyl d) N-methyl
chloride
propanamide
e) N,N-dimethyl f) 2-methyl
h) butanoic
g) 2(a)pentanamide aminopropan ethanoic
ethanamide
oic
anhydride
Polyfunctional Carboxylic Acids
• Dicarboxylic acids
Oxylic acid Oh my, such great apple pie!" (oxalic,
malonic, succinic, glutaric, adipic, pimelic)
• "Metabolic" Acids
Propionic acid, (C3 mono acids): lactic, glyceric, and
pyruvic acids
Succinic acid (C4 diacid): fumaric, oxaloacetic, and malic acids
Glutaric acid (C5 diacid): a-ketoglutaric and citric acids
3. Identify type and give name of each of the
following poly functional carboxylic acids.
a)
b)
c)
Type:___________________ Type:________________ Type:__________________
Name:__________________ Name:_______________ Name:_________________
_
d)
Type:___________________ e) Type:__________
Name:__________________
Name:________
f)
Type:______________
Name:_____________
3. Give common/IUPAC names of following
dicarboxylic acids. Use "Oh my, such great apple
pie!" (oxalic, malonic, succinic, glutaric, adipic,
pimelic).
a)
b)
c)
Common:______________ Common:_____________ Common:_____________
IUPAC:_______________ IUPAC:_______________ IUPAC:_______________
d)
Common:_____________
IUPAC:_______________
e) Common:___________
IUPAC:_____________
3. Give common/IUPAC names of following
dicarboxylic acids.
f) Name:______________
g) Name:___________
h)Common:___________
IUPAC:_______________
Saturated Fatty Acids
• Long chain even carbon atoms C >10
Unsaturated Fatty Acids
• Long chain even carbon atoms with C=C bonds
5. Give type/name of following fatty acids, and
their derivatives.
a) CH3(CH2)10CO2H
b) CH3(CH2)14CO2H
Type:________________
Name:_______________
Type:________________
Name:_______________
c) CH3(CH2)16CO2H
Type:________________
Name:_______________
5. Give type/name of following fatty acids, and
their derivatives.
d) H3(CH2)7CH=CH(CH2)7CO2H
Type:________________
Name:_______________
e)
f)
Type:________________ Type:____________________
Name:_______________ Name:___________________
Triglycerides: Triesters of glycerol
Preparation of Carboxylic Acids
Oxidation of primary alcohol to carboxylic acid
(described in reactions of alcohols)
Oxidation using Tollen’s basic Ag(NH3)2+ or
Bendict’s CuSO4/Na2CO2/Citrate
(described in reactions of aldehydes)
Oxidation of alkyl side chain of substituted aromatic
hydrocarbons (reactions of aromatic alkyl
compounds)
Hydrolysis of esters. Described in this chaper)
Hydrolysis of acid, amides and cholrides etc.. )
Chemical Reactions of Carboxylic Acids
Reaction with strong bases to form acid salts
(described below in preparation of acid salts)
Reaction with strong alcohols to form esters
(described below in preparation of esters)
Reaction with halogen compounds to form acid
chlorides(described below in preparation of acid
chloride preparations)
Reaction with ammonia and amine compounds to
form amides (described in amides chapter 18)
Reduction to alcohols with reducing agents
(LiAlH4, NaBH4 etc.)
5) Name and complete following reactions
a)
b)
c)
d)
5) Name and complete following reactions
e)
f)
7) Name and complete following reactions.
a) Condensation Polymerization
b) Aspirin synthesis
7) Name and complete following reactions.
c) Cyclic ester formation
d) Decarboxylation of b- ketoacids
7) Name and complete following reactions.
e) Base hydrolysis of esters
f) Base hydrolysis of triglycerides
Base hydrolysis of triglycerides
Saponification-Soap formation