General, Organic, and
Biological Chemistry
Fourth Edition
Karen Timberlake
Chapter 15
Carbohydrates
15.1
Carbohydrates
2013 Pearson Education, Inc.
Lectures
Carbohydrates
Carbohydrates
include table sugar, lactose,
and cellulose.
are made of carbon,
hydrogen, and oxygen.
make up about 65% of our
diet.
2013 Pearson Education, Inc. Chapter 15, Section 1 2
Carbohydrates
Glucose is a carbohydrate
produced by photosynthesis in plants from CO2,
H2O, and energy from the sun.
oxidized in living cells (respiration) to produce
CO2, H2O, and energy.
2013 Pearson Education, Inc. Chapter 15, Section 1 3
Carbon Cycle
During photosynthesis,
energy from the sun
combines CO2 and H2O
to form glucose,
C6H12O6, and O2.
During respiration in the
body, carbohydrates are
oxidized to CO2 and
H2O, while energy is
produced.
2013 Pearson Education, Inc. Chapter 15, Section 1 4
Types of Carbohydrates
The types of carbohydrates are
monosaccharides, the simplest carbohydrates.
disaccharides, which consist of two monosaccharides.
polysaccharides, which contain many monosaccharides.
2013 Pearson Education, Inc. Chapter 15, Section 1 5
Monosaccharides
Monosaccharides consist of
3 to 6 carbon atoms (typically).
a carbonyl group (aldehyde or ketone).
several hydroxyl groups.
There are two types of monosaccharide structures.
Aldoses, in which the carbonyl group on the first
carbon is an aldehyde.
Ketoses, which contain a ketone carbonyl group on
the second carbon.
2013 Pearson Education, Inc. Chapter 15, Section 1 6
Monosaccharides
2013 Pearson Education, Inc. Chapter 15, Section 1 7
Naming Monosaccharides
The names of monosaccharides end in -ose.
They may be named according to the number of
carbons in the monosaccharide.
triose (3 C atoms)
tetrose (4 C atoms)
pentose (5 C atoms)
hexose (6 C atoms)
2013 Pearson Education, Inc. Chapter 15, Section 1 8
Aldoses
Aldoses are monosaccharides
with an aldehyde group.
with many hydroxyl (OH)
groups.
Examples:
aldotriose (3 C atoms)
aldotetrose (4 C atoms)
aldopentose (5 C atoms)
aldohexose (6 C atoms)
2013 Pearson Education, Inc. Chapter 15, Section 1 9
Ketoses
Ketoses are monosaccharides
with a ketone group.
with many hydroxyl (OH)
groups.
Examples:
ketotriose (3 C atoms)
ketotetrose (4 C atoms)
ketopentose (5 C atoms)
ketohexose (6 C atoms)
2013 Pearson Education, Inc. Chapter 15, Section 1 10
Examples of Monosaccharides
2013 Pearson Education, Inc. Chapter 15, Section 1 11
Learning Check
Identify each as aldo- or keto- and as tetrose, pentose,
or hexose.
A. O B. CH2OH
C H C O
H C OH HO C H
H C OH H C OH
H C OH
CH2OH
H C OH
CH2OH
2013 Pearson Education, Inc. Chapter 15, Section 1 12
Solution
Identify each as aldo- or keto- and as tetrose, pentose
or hexose.
A. O B. CH2OH
C H C O
H C OH HO C H
H C OH H C OH
H C OH
CH2OH
H C OH
CH2OH
aldohexose ketopentose
2013 Pearson Education, Inc. Chapter 15, Section 1 13
General, Organic, and
Biological Chemistry
Fourth Edition
Karen Timberlake
Chapter 15
Carbohydrates
15.2
Fischer Projections
of Monosaccharides
2013 Pearson Education, Inc.
Lectures
2013 Pearson Education, Inc. Chapter 15, Section 1 14
Fischer Projections
A Fischer projection
is used to represent carbohydrates.
places the most oxidized group at the top.
shows chiral carbons at the intersection of vertical and
horizontal lines.
2013 Pearson Education, Inc. Chapter 15, Section 1 15
D and L Notations
In a Fischer projection, the OH group on the
chiral carbon farthest from the carbonyl group
determines if it is an L or D isomer.
left is assigned the letter L for the L-isomer.
right is assigned the letter D for the D-isomer.
2013 Pearson Education, Inc. Chapter 15, Section 1 16
Learning Check
Identify each as the D or L isomer.
A. B. C. CH2OH
O
C H O O
HO H C H HO H
HO H H OH H OH
HO H HO H H OH
CH2OH CH2OH CH2OH
__-Ribose __-Threose __-Fructose
2013 Pearson Education, Inc. Chapter 15, Section 1 17
Solution
Identify each as the D or L isomer.
A. B. C. CH2OH
O
C H O O
HO H C H HO H
HO H H OH H OH
HO H HO H H OH
CH2OH CH2OH CH2OH
__-Ribose
L __-Threose
L __-Fructose
D
2013 Pearson Education, Inc. Chapter 15, Section 1 18
Important Monosaccharides
The hexoses glucose, galactose, and fructose are
the most important monosaccharides.
The D stereoisomers are commonly found in
nature and used in the cells of the body.
2013 Pearson Education, Inc. Chapter 15, Section 1 19
D-Glucose, C6H12O6
D-Glucose, also known as dextrose or
blood sugar is
an aldohexose found in fruits, corn
syrup, and honey.
found in polymers of starch, cellulose,
and glycogen.
Excess glucose is converted to fat and stored.
2013 Pearson Education, Inc. Chapter 15, Section 1 20
Blood Glucose Level
In the human body,
glucose has a normal blood level of 7090 mg/dL.
a glucose tolerance test measures blood glucose for
several hours after ingestion.
2013 Pearson Education, Inc. Chapter 15, Section 1 21
D-Galactose
D-Galactose
is an aldohexose with the
formula C6H12O6.
is obtained from lactose, a
disaccharide.
has a similar structure to
glucose except for the OH
on C4.
is important in cell
membranes of the brain and
nervous system.
2013 Pearson Education, Inc. Chapter 15, Section 1 22
D-Fructose
D-Fructose
is a ketohexose with
the formula C6H12O6.
is the sweetest
carbohydrate.
is found in fruit
juices and honey.
is converted to
glucose in the body.
2013 Pearson Education, Inc. Chapter 15, Section 1 23
Learning Check
Draw the Fischer projection of D-fructose.
2013 Pearson Education, Inc. Chapter 15, Section 1 24
Solution
Draw the Fischer projection of D-fructose.
2013 Pearson Education, Inc. Chapter 15, Section 1 25
General, Organic, and
Biological Chemistry
Fourth Edition
Karen Timberlake
Chapter 15
Carbohydrates
15.3
Haworth Structures
of Monosaccharides
2013 Pearson Education, Inc.
Lectures
2013 Pearson Education, Inc. Chapter 15, Section 1 26
Haworth Structures
Haworth structures
are the prevalent form of monosaccharides with 5 or
6 carbon atoms.
form when the hydroxyl group on carbon 5 (C5)
reacts with either the aldehyde or ketone group.
2013 Pearson Education, Inc. Chapter 15, Section 1 27
Haworth Structures
Haworth structures
are cyclic hemiacetals.
form when the CO group and
the OH are part of the same
molecule.
of hexoses form when the OH
on C5 reacts with a CO group.
of a D-isomer place the CH2OH
of C6 above the ring.
2013 Pearson Education, Inc. Chapter 15, Section 1 28
Guide to Drawing Haworth
Structures
2013 Pearson Education, Inc. Chapter 15, Section 1 29
Drawing the Haworth Structures
for Glucose
Step 1 Turn the Fischer projection for D-Glucose
clockwise by 90.
2013 Pearson Education, Inc. Chapter 15, Section 1 30
Drawing the Haworth Structures
for Glucose
Step 2 Fold the horizontal carbon chain into a
hexagon and bond the O on carbon 5 to
the carbonyl group to form the hemiacetal.
2013 Pearson Education, Inc. Chapter 15, Section 1 31
Drawing the Haworth Structures
for Glucose
Step 3 Complete the Haworth structure by
drawing the OH group on carbon 1
below the ring to give the anomer, or
above the ring to give the anomer.
2013 Pearson Education, Inc. Chapter 15, Section 1 32
Mutarotation of -D-Glucose and
-D-Glucose
The process of rings opening and closing is called
mutarotation. Both anomers are converted to the open
chain and back to a cyclic hemiacetal.
2013 Pearson Education, Inc. Chapter 15, Section 1 33
Haworth Structures of Fructose
Fructose
is a ketohexose.
forms Haworth structures when the OH on C5
bonds to the CO on C2.
2013 Pearson Education, Inc. Chapter 15, Section 1 34
Learning Check
Draw the Haworth structure of -D-galactose.
2013 Pearson Education, Inc. Chapter 15, Section 1 35
Solution
Step 1 Turn the open-chain Fischer projection
clockwise by 90.
2013 Pearson Education, Inc. Chapter 15, Section 1 36
Solution
Step 2 Fold the horizontal carbon chain into a
hexagon and bond the O on carbon 5 to the
carbonyl group to form the hemiacetal.
2013 Pearson Education, Inc. Chapter 15, Section 1 37
Solution
Step 3 Complete the Haworth structure by drawing
the OH group on carbon 1 below the ring
to give the anomer, or above the ring to
give the anomer.
2013 Pearson Education, Inc. Chapter 15, Section 1 38
General, Organic, and
Biological Chemistry
Fourth Edition
Karen Timberlake
Chapter 15
Carbohydrates
15.4
Chemical Properties of
Monosaccharides
2013 Pearson Education, Inc.
Lectures
2013 Pearson Education, Inc. Chapter 15, Section 1 39
Oxidation of Monosaccharides
Reducing sugars
are monosaccharides with an aldehyde group that
can be oxidized to a carboxylic acid.
undergo reaction with Benedicts reagent (Cu2+) to
give the corresponding carboxylic acid.
are sugars that reduce other substances.
include the monosaccharides glucose, galactose,
and fructose.
are named by replacing the -ose ending with -onic
acid when they form the corresponding carboxylic
acid.
2013 Pearson Education, Inc. Chapter 15, Section 1 40
Oxidation of D-Glucose, a
Reducing Sugar
Glucose is oxidized
to a carboxylic acid.
Benedicts
reagent
2013 Pearson Education, Inc. Chapter 15, Section 1 41
Oxidation of Fructose
Fructose, a ketohexose, is also a reducing sugar.
In a basic solution such as Benedict's, the
carbonyl group moves from carbon 2 to carbon 1,
so it can be oxidized as glucose.
2013 Pearson Education, Inc. Chapter 15, Section 1 42
Reduction of Monosaccharides
Monosaccharides can be reduced
turning the carbonyl group into an
alcohol group.
producing sugar alcohols called
alditols.
and the products named by
replacing the -ose ending with
-itol.
D-Glucose reduces to D-Glucitol,
also called D-Gorbitol.
2013 Pearson Education, Inc. Chapter 15, Section 1 43
Reduction of Monosaccharides
Sugar alcohols such as
sorbitol, and mannitol
are used as sweeteners
in many sugar-free
products such as diet
drinks and sugarless
gum.
2013 Pearson Education, Inc. Chapter 15, Section 1 44
Urine Test for Diabetes
A symptom of diabetes
mellitus is a high level of
glucose in the urine.
If the blood level exceeds
about 160 mg of glucose/dL
of blood, the kidneys cannot
reabsorb it all, and glucose
spills over into the urine.
The color of a test strip
determines the glucose
level in urine.
2013 Pearson Education, Inc. Chapter 15, Section 1 45
Learning Check
Write the products of the oxidation and reduction of
D-Mannose.
O
C H
HO H
HO H
H OH
H OH
CH2OH
D-Mannose
2013 Pearson Education, Inc. Chapter 15, Section 1 46
Solution
Write the products of the oxidation and reduction of
D-Mannose.
O O
CH2OH C H C OH
HO H HO H HO H
Reduction Oxidation
HO H HO H HO H
H OH H OH H OH
H OH H OH H OH
CH2OH CH2OH CH2OH
D-Mannitol D-Mannose D-Mannonic
acid
2013 Pearson Education, Inc. Chapter 15, Section 1 47
General, Organic, and
Biological Chemistry
Fourth Edition
Karen Timberlake
Chapter 15
Carbohydrates
15.5
Disaccharides
2013 Pearson Education, Inc.
Lectures
2013 Pearson Education, Inc. Chapter 15, Section 1 48
Important Disaccharides
A disaccharide consists of two monosaccharides
linked together.
When two monosaccharides combine in a
dehydration reaction, the product is an acetal and
water.
2013 Pearson Education, Inc. Chapter 15, Section 1 49
Maltose
Maltose is
a disaccharide also known as malt sugar.
composed of two D-glucose molecules.
obtained from the hydrolysis of starch.
linked by an -1,4-glycosidic bond between the
OH on C1 of the first glucose and OH on C4 of
the second glucose.
used in cereals, candies, and brewing.
found in both the - and - forms.
2013 Pearson Education, Inc. Chapter 15, Section 1 50
Formation of Maltose
2013 Pearson Education, Inc. Chapter 15, Section 1 51
Lactose
Lactose
is a disaccharide of -D-galactose and - or -D-
glucose.
contains a -1,4-glycosidic bond.
is found in milk and milk products.
is found in both the - and -forms.
2013 Pearson Education, Inc. Chapter 15, Section 1 52
Lactose
2013 Pearson Education, Inc. Chapter 15, Section 1 53
Sucrose
Sucrose, or table sugar,
is obtained from sugar cane and sugar beets.
consists of -D-glucose and -D-fructose.
has an ,-1,2-glycosidic bond.
is hydrolyzed in the body by the enzyme sucrase to
form glucose and fructose.
2013 Pearson Education, Inc. Chapter 15, Section 1 54
Sucrose
2013 Pearson Education, Inc. Chapter 15, Section 1 55
Learning Check
Draw the Haworth structures and give the names of the
two monosaccharides that form when sucrose is
hydrolyzed.
2013 Pearson Education, Inc. Chapter 15, Section 1 56
Solution
2013 Pearson Education, Inc. Chapter 15, Section 1 57
Sweeteners
Sugars and artificial
sweeteners
differ in sweetness.
are compared to
sucrose (table sugar),
which is assigned a
value of 100.
2013 Pearson Education, Inc. Chapter 15, Section 1 58
Sucralose
Sucralose is made from
sucrose by replacing
some of the hydroxyl
groups with chlorine
atoms.
2013 Pearson Education, Inc. Chapter 15, Section 1 59
Learning Check
Identify the monosaccharides in each of the following.
1. lactose
A. -D-glucose B. -D-fructose C. -D-galactose
2. maltose
A. -D-glucose B. -D-fructose C. -D-galactose
3. sucrose
A. -D-glucose B. -D-fructose C. -D-galactose
2013 Pearson Education, Inc. Chapter 15, Section 1 60
Solution
Identify the monosaccharides in each of the following.
1. lactose
A. -D-glucose C. -D-galactose
2. maltose
A. -D-glucose
3. sucrose
A. -D-glucose B. -D-fructose
2013 Pearson Education, Inc. Chapter 15, Section 1 61
General, Organic, and
Biological Chemistry
Fourth Edition
Karen Timberlake
Chapter 15
Carbohydrates
15.6
Polysaccharides
2013 Pearson Education, Inc.
Lectures
2013 Pearson Education, Inc. Chapter 15, Section 1 62
Polysaccharides
Polysaccharides
are polymers of many monosaccharides linked
together.
differ in the type of links between monosaccharides,
and the monosaccharides in the polymer.
differ by the amount of branching in the polymer.
2013 Pearson Education, Inc. Chapter 15, Section 1 63
Important Polysaccharides
Important polysaccharides include
starches made of -D-glucose molecules, amylose,
and amylopectin.
glycogen (animal starch in muscle), which is made of
-D-glucose.
cellulose (plants and wood), which is made of -D-
glucose.
2013 Pearson Education, Inc. Chapter 15, Section 1 64
Structures of Amylose and
Amylopectin
2013 Pearson Education, Inc. Chapter 15, Section 1 65
Amylose
Amylose is
a polymer of -D-glucose molecules.
linked by -1,4 glycosidic bonds.
a continuous (unbranched) chain.
2013 Pearson Education, Inc. Chapter 15, Section 1 66
Amylopectin
Amylopectin
is a branched chain polymer of -D-glucose molecules.
has -1,4-glycosidic bonds between the glucose units.
has -1,6 bonds to branches.
2013 Pearson Education, Inc. Chapter 15, Section 1 67
Glycogen
Animal starch or glycogen is
stored in the liver and muscles of animals.
hydrolyzed in our cells to maintain glucose and
energy levels between meals.
similar to amylopectin, but is more highly branched.
2013 Pearson Education, Inc. Chapter 15, Section 1 68
Cellulose
Cellulose
is a major structural unit of wood and plants.
is a polysaccharide composed of unbranched glucose
units in unbranched chains.
has -1,4-glycosidic bonds.
cannot be digested by humans because humans lack
the enzyme to break -1,4-glycosidic bonds.
2013 Pearson Education, Inc. Chapter 15, Section 1 69
Cellulose
The polysaccharide cellulose is composed of glucose
units connected by -1,4-glycosidic bonds.
2013 Pearson Education, Inc. Chapter 15, Section 1 70
Learning Check
Identify the polysaccharides and types of glycosidic
bonds in each of the following.
A. B.
2013 Pearson Education, Inc. Chapter 15, Section 1 71
Solution
Identify the polysaccharides and types of glycosidic
bonds in each of the following.
A. Cellulose -1,4-glycosidic bonds
B. Amylose -1,4-glycosidic bonds
Amylopectin -1,4- and
-1,6-glycosidic bonds
2013 Pearson Education, Inc. Chapter 15, Section 1 72
