Download Important Representative Esters and Related Compounds and more Study notes Chemistry in PDF only on Docsity!
CHEM 34 Important Representative Esters
A. Low molecular weight (many have sweet or fruity smells)
H C
O
O CH 3
Methyl Formate. (IUPAC: methyl methanoate) – A fumigant for tobacco.
CH 3 C
O
O CH 2 CH 3
Ethyl Acetate. A major industrial solvent.
CH 3 CH 2 C
O
O CH 2 CH 3
Ethyl Propionate. (IUPAC: ethyl propanoate) – Artificial peach flavor.
CH 3 CH 2 C
O
O CH 2 CH 2 CH 2 CH 2 CH 3
n-Pentyl Propionate. Apricot essence.
CH 3 C
O
O CH 2 CH 2 CH
CH 3
CH 3
3-Methylbutyl Acetate. “Banana oil.”
CH 3 (CH 2 ) 2 C
O
O CH 2 CH 3
Ethyl Butyrate. Used in the manufacture of artificial rum. Its solution in alcohol is known as “pineapple oil.”
CH 3 (CH 2 ) 5 C
O
O CH 2 CH 3
Ethyl Heptanoate. Also called ethyl oenanthate, cognac oil, oil of grapes, “artificial cognac essence.”
O
O
CH 2
Alpha-Methylene Butyrolactone. This is a lactone or a cyclic ester (the alcohol and acid portions are in the same molecule). Oil of dogtooth violets.
C
O
O CH 3 Methyl Benzoate.^ Used in perfumery as “Peau d’Espagne.”
C
O
O CH 2 CH 3
Ethyl Benzoate. Also used in perfumery, odor similar to the methyl ester, above. Called “Essence de Niobe.”
C
O
O CH 3
NH 2
Methyl 2-Aminobenzoate, Methyl Anthranilate. Artificial neroli oil. Principal constituent of ylang-ylang oil.
H 2 N C
O
O CH 2 CH 3
Ethyl 4-Aminobenzoate, Benzocaine. Used as a surface (topical) anesthetic.
OH
C
O
O CH 3
Methyl Salicylate. Oil of wintergreen. Flavoring agent for candies and used in perfumery. Also used as a linament (note relationship to salicylic acid and aspirin).
O
C
C
O
CH 3
O
OH
2-Acetylsalicylic Acid, Aspirin. Most widely used painkiller.
B. Polymeric
Monomer Name Vinyl Polymer
CH 3 C
O
O CH CH 2
Vinyl Acetate Polyvinyl Acetate (adhesives)
CH 2 CH C
O
O CH 3
Methyl Acrylate Acrylic plastics (paints)
CH 2 C
CH 3
C
O
O CH 3 Methyl Methacrylate Polymethyl Methacrylate (Lucite or
Plexiglass)
Also Condensation Polymers
HO CH 2 CH 2 OH + HO C
O
C
O
OH
_
H 2 O
O CH 2 CH 2 O C
O
C
O
O CH 2 CH 2 O C
O
C
O
n This is Dacron
HO CH 2 C
O
OH
_
H 2 O
O CH 2 C
O
O CH 2 C
O
O CH 2 C
O
n
This is Dexon – a polymer used as the thread of surgical stitches – which are absorbed and biodegraded by the patient’s body
C. Lipid Type
Animal Fat. Triesters of glycerol with long chain saturated acids Triglycerides. Soaps made by boiling with aqueous NaOH (saponification – hydrolysis)
Vegetable Oil. Triesters of glycerol (Triglycerides) with long chain acids containing several C=C bonds. Remember softness of a fat is a function of number of double bonds. Remember preparation of margarine by hydrogenation.
R C
O
O CH 2 CH
OH
CH 2 OH
A monoglyceride. Some of these are commercial products; e.g. with R as C 17 H 35 (stearate) or C 15 H 31 (palmitate), used as moistening agents in cake mixes.
Waxes. For example Beeswax, Carnuba Wax, Spermaceti Wax, (from head of sperm whale – used to make candles) – These are esters of long straight chain fatty acids (C 10 -C 30 ) with long straight chain alcohols (C 20 -C 40 ). Both the acid and the alcohol components contain an even number of carbons.
