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B. Alcohols
 R—OH
Functional Group = hydroxyl group = OH
Alcohol names all end in –ol.
Numbers tell which C atom the OH is attached to.
Ex: 1-propanol
parent:
propane
H H H
molecular: C3H7OH
H C C C OH
empirical: C3H8O
structural: CH3CH2CH2OH
H H H
 Because it has 1 OH, it is a monohydroxy alcohol
The OH group makes alcohols polar.
OH +
Alcohols dissolve in water because H2O is polar:
H
-O
+
H
Compare:
OH group:
electrolyte:
water soluble…
because….
Alcohols
covalently attached
no
yes
OH is polar
Ex. 1,2-ethanediol is a
dihydroxy alcohol
(two OH groups)
Ex. 1,2,3-propanetriol
is a trihydroxy alcohol
(three OH groups)
H
H C
Bases
an ion in solution
yes
yes
OH- is ion
H
C H
O O
H H
H
H C
H H
C C H
O O O
H H H
(aka
ethylene
glycol)
(aka
glycerol)
ethylene glycol
H
H C
H
C H
O O
H H
Ethylene glycol is widely used as an automotive
antifreeze and a precursor to polymers. In its pure
form, it is an odorless, colorless, syrupy, sweettasting liquid. Ethylene glycol is toxic, and ingestion
can result in death.
Glycerin (glycerol):
--> clear, sweet tasting, oily liquid
--> used to keep dried fruits and pastry fillings moist,
in toothpaste, hand creams, eye and ear drops,
suppositories (for laxatives, eg), and as an
antifreeze
aka nitroglycerin
Also:
(dynamite)
H2SO4
for drying
glycerin + nitric acid -->
glycerol trinitrate
Ex. ethanol (ethyl alcohol) = drug, solvent, fuel
parent:
ethane
H H
molecular:
C2H5OH
H C C OH
empirical:
C2H6O
condensed:
CH3CH2OH
H H
Ex. Alcohols can also be classified as:
1/ primary:
OH attached to an end C as in ethanol
2/ secondary: OH is attached to a C
that is directly attached to two other
C atoms. At right: 2-butanol 
3/ tertiary: OH is attached to a C
that is directly attached to three
H
other C atoms
At right: 2-methyl, 2-propanol 
H
H
H
H
H
C
C
C
C H
H
H
H
O
H
H
H C H
H
H
C C C H
H O H
H
Ex. For each example below, give the name. Circle if a mono-,
di-, or trihydroxy and if a primary, secondary or tertiary alcohol.
1/
H
H C OH
H
methanol
name: _________________
type: mono- ditriclass: prim. sec. tert.
K OH K OH
3/
OH K OH K
K OH K OH
OH K OH K
KOH
name: ________________
type: mono- ditriclass: prim. sec. tert.
H
2/
H C H
H H
H H
H C C C C C
H O H H H
H
4/
H
H
3-methyl, 2-pentanol
name: _________________
type: mono- ditriclass: prim. sec. tert.
H
H
H
H
H
H
C
C
C
C
C
C H
H
H
O
H
O O H
H H
2,3,4-hexanetriol
name: ________________
type: mono- ditriclass: prim. sec. tert.
C. Ethers - two C chains joined by an oxygen O “bridge”
Formula: R—O—R‘
Name: (name R without -ane) + oxy + name of R‘
Ex. methoxymethane
H
H C O
H
H
C H
H
Ex. methoxyethane
H
H H
H C O C C H
H
aka: dimethyl ether
molecular: C2H6O
condensed: CH3OCH3
H H
aka: methyl ethyl ether
molecular: C3H8O
condensed: CH3OCH2CH3
Ethers are common in organic chemistry and pervasive in
biochemistry, as they are common linkages in
carbohydrates and lignin.
D. Aldehydes: When a carbonyl group (—C=O) replaces
the CH2 at the end of a hydrocarbon
O
Formula
Ex.
R—C—H Name: replace –e with –al
methane:
methanal:
H
O
H C H
H C H
aka: formaldehyde
molecular: CH2O
structural: HCOH
H
Ex. ethane:
H H
H C C H
H H
ethanal:
H
O
H C C H
H
aka: acetaldehyde
molecular: C2H4O
structural: CH3COH
O
or:
CH3C H
Carbonyl group:
C=O
Formaldehyde was the first polyatomic organic
molecule detected in the interstellar medium[6]
and since its initial detection has been observed
in many regions of the galaxy.
Carbonyl group:
C=O
Acetaldehyde occurs naturally in coffee, bread, and
ripe fruit, and is produced by plants as part of their
normal metabolism. It is also produced by oxidation of
ethanol and is popularly believed to be a cause of
hangovers.[2]
E. Ketones: When a carbonyl group (—C=O) replaces a C
in the interior of a hydrocarbon:
O
Formula: R—C—R'
Name: replace –e with –one
Ex. propane:
propanone:
aka: acetone
H H H
H O H
molecular: C3H6O
H C C C H
H C C C H
condensed: CH3COCH3
O
H H H
H
H
or:
CH3CCH3
Ex. Isomers: 2-pentanone
and
3-pentanone:
H O H H H
H H O H H
H C C C C C H
H C C C C C H
H H H H H
H H H H H
condensed: CH3CHOCH2CH2CH3
CH3CH2CHOCH2CH3
The word ketone comes from the word: acetone
Ketones are produced on massive scales in
industry as solvents, polymer precursors, and
pharmaceuticals.
F. Organic Acids are formed by adding the carboxyl group
–COOH to a hydrocarbon chain. They are weak acids and
weak electrolytes, and are known as carboxylic acids
Functional group = --COOH =
O
—C—OH
Name: replace –e with –oic acid
Ex. ethanoic acid (aka acetic acid in vinegar):
ethanoic
ethane:
acid:
H H
H C C H
H H
H
H
O
C
C —OH
H
molecular: HC2H3O2
condensed: CH3COOH
O
or:
CH3C—OH
Ex. A fatty acid is a carboxylic acid –COOH with a
long unbranched hydrocarbon chain “tail.”
the “fatty” tail
the acid
Saturated fatty acids:
-single C-C bonds
-pack closely
-solids at room temp
-animal “fats”
Unsaturated fatty acids:
-double C=C bonds
bend up the tail
-liquids at room temp
-vegetable “oils”
Fats and oils are triglycerides. They are
formed when the alcohol glycerol combines with
3 fatty acids by condensing out water.
benzoic acid
--COOH
Used in toothpastes, mouthwashes,
cosmetics and deodorants for its antimicrobial
properties
ascorbic acid – Vitamin C
--COOH
G. Esters have the functional group:
General formula:
They are the result of an esterification reaction:
organic + alcohol
 water
+
ester
acid
Ex.
H2SO4
Sulfuric acid (H2SO4) is used as a catalyst and as a
dehydrating agent to remove the water, which is why
this is sometimes called condensation reaction.
alcohol + acid…es terrifying!
+
Notice: In the general formula:
this part comes
from the acid
this part is from
the alcohol
Naming: The alkyl name of the alcohol is added to
the acid group modified to end in –oate or -ate
Esters have strong, fragrant aromas and are the
cause of the odors and flavors of pineapple, banana,
wintergreen and oranges.
Ex. The smell of pineapples is due to ethyl butyrate
ethanol + butanoic acid  water
(alcohol)
+ ethyl butyrate
(ester)
ethanol + butanoic acid  water
+ ethyl butyrate
(alcohol)
(ester)
From the acid:
From the alcohol:
acid:
alcohol:
octanol + acetic acid  water
+ octyl acetate
(alcohol)
(ester)
From the acid:
From the alcohol:
acid:
alcohol: