Organic Chemistry
Functional groups
Functional Group Chemistry
Alcohols contain the hydroxyl functional group and have the
general formula R-OH.
Sterols, ethylene glycol
24.4
Biological production of ethanol
C6H12O6 (aq)
enzyme
2CH3CH2OH (aq) + 2CO2 (g)
Commercial production of ethanol
CH2 CH2 (g) + H2O (g)
H2SO4
CH3CH2OH (g)
DRINKABLE vs. DENATURED
Alcohol
Functional Group Chemistry
Ethers have the general formula R-O-R’.
Condensation Reaction
CH3OH + HOCH3
H2SO4
catalyst
CH3OCH3 + H2O
24.4
Functional Group Chemistry
O
Aldehydes and ketones contain the carbonyl ( C
functional group.
O
)
• aldehydes have the general formula R C H
O
• ketones have the general formula R C R’
O
O
O
H C H
H C CH3
H3C C CH3
formaldehyde
acetaldehyde
acetone
24.4
Functional Group Chemistry
Carboxylic acids contain the carboxyl ( -COOH ) functional
group.
VINEGAR, ASPIRIN , ANTS, CITRUS FRUITS, PROTEINS, PRESERVATIVES
24.4
Functional Group Chemistry
Esters have the general formula R’COOR, where R is a
hydrocarbon group.
O
CH3COOH + HOCH2CH3
CH3 C O CH2CH3 + H2O
ethyl acetate
Banana: isopentyl acetate
Pineapple: ethyl butanoate
Apple: methyl butanoate
Pear: propyl ethanoate
Orange: Octyl ethanoate
Raspberry: 2-Methylpropyl ethanoate
Oil of Wintergreen: methyl salycilate
24.4
HOW TO MIMIC NATURE:
Making synthetic flavoring
•
•
A good cherry is supposed to be tough to
formulate. Here
is an example of a *minimum* synthetic cherry
flavoring:
ethyl methyl p-tolyl glycidate
16.0 %
iso-amyl acetate
12.0 %
iso-butyl acetate
12.0 %
p-methyl benzyl acetate
11.0 %
benzaldehyde
8.0 %
vanillin
7.0 %
benzyl alkcohol
5.5 %
piperonal
5.0 %
ethyl caprate
4.0 %
cinnamic aldehyde dimethyl acetal
3.0
%
p-tolyl aldehyde
3.0 %
cinnamyl anthranilate
3.0 %
ethyl caproate
2.0 %
geranyl butyrate
2.0 %
terpenyl butyrate
0.5 %
Functional Group Chemistry
Amines are organic bases with the general formula R3N.
CH3NH2 + H2O
RNH3+ + OH-
Urea
Phenylpropanolamine
(Meth)amphetamine
Caffeine
24.4
Blue jeans
• Indigo: an ancient dye, herbal remedy,
poison
• Indigofera
• Tyrian purple – 6,6’-dibromoindigo
The sweet life
sucralose
aspartame
saccharin
Drugs
aspirin
cocaine
POLYMERS
• Poly: Many Meros: Parts
• Made up of repeating monomers
• Copolymer is a polymer made up of two or more
monomers
(
CH
CH2
CH2
CH
CH
CH2 )n
• Common biopolymers: Proteins, DNA, RNA, starch,
cellulose
• PET: Polyethylene
terephthalate
– Plastic bottles
• Polytetrafluoroethylene
– Teflon™
•
•
•
•
Polypropylene
Polystyrene
Polyvinyl chloride
Nylon (synthetic
polyamide, similar to
bonds in proteins)
http://www.nationalgeographic.com/education/plastics/index.html
The stuff of life
• DNA
The stuff of life
• Proteins