Download Organic Chemistry Notes

CARBON COMPOUNDS ORGANIC CHEMISTRY
Got Lactase?
• Many people in the world suffer from lactose
intolerance
–
Lacking an enzyme (lactase) that digests
lactose, a sugar found in milk
–
“ase” = enzyme
–
“ose” = sugar
Copyright © 2005 Pearson Education, Inc. Publishing as Benjamin Cummings
• Lactose intolerance illustrates the importance of
biological molecules
–
To the functioning of living cells and to human
health
–
The atoms carbon (C), hydrogen (H), oxygen
(O), nitrogen (N), and phosphorous make up
molecules that support life
Copyright © 2005 Pearson Education, Inc. Publishing as Benjamin Cummings
4 Categories of Organic Molecules
Lipids
Carbohydrates
Fats/Oils/Steroids/Wax
Glucose/Fructose
Starch/Cellulose
Molecules of
Life
Proteins
Biochemicals
Enzymes/Structure/
Movement/Protection
(CHONP)
Copyright © 2005 Pearson Education, Inc. Publishing as Benjamin Cummings
Nucleic Acids
(DNA/RNA)
HYDROCARBONS
• All compounds are either organic, containing carbon
bonded to hydrogen and oxygen or inorganic. The
chemistry of carbon is the chemistry of life.
Structural
formula
Ball-and-stick
model
H
H
C
Space-filling
model
H
H
H
Methane
C
H
H
H
The 4 single bonds of carbon point to the corners of a tetrahedron.
Copyright © 2005 Pearson Education, Inc. Publishing as Benjamin Cummings
I.
Carbon bonding:
•
Has 4 electrons in outer energy level
•
Atoms are most stable with 8 electrons in outer
shell
•
Carbon forms bonds with other atoms, including
carbon
6P
6N
Copyright © 2005 Pearson Education, Inc. Publishing as Benjamin Cummings
I. Carbon bonding:
Single Bond
Represents 2 electrons
Double Bond
Represents 4 electrons
Triple Bond
Represents 6 electrons
Copyright © 2005 Pearson Education, Inc. Publishing as Benjamin Cummings
Cells make a huge number of large molecules from a
small set of small molecules
• The four main classes of biological molecules
–
Are carbohydrates, lipids, proteins, and nucleic
acids
• Many of the molecules are gigantic
–
And are called macromolecules
Copyright © 2005 Pearson Education, Inc. Publishing as Benjamin Cummings
• Cells make most of their large molecules
–
By joining smaller organic molecules into
chains called polymers
• Cells link monomers to form polymers
–
By dehydration synthesis
H
OH
OH
OH
Short polymer
Unlinked monomer
Dehydration
Dehydratio
reaction
n reaction
H2O
OH
O
H
H
H
Longer polymer
Copyright © 2005 Pearson Education, Inc. Publishing as Benjamin Cummings
H
H
• Polymers are broken down to monomers
–
By the reverse process, hydrolysis
Animation:
Hydrolysis of sucrose
H2O
H
OH
Hydrolysis
H
OH
OH
Copyright © 2005 Pearson Education, Inc. Publishing as Benjamin Cummings
H
VI. Molecules of Life
A. Carbohydrates- main source of energy for cells
Monosaccharides are the simplest carbohydrates
• The carbohydrate monomers are monosaccharides
• A monosaccharide has a formula that is a multiple
of CH2O ( the ratio 1:2:1)
Copyright © 2005 Pearson Education, Inc. Publishing as Benjamin Cummings
–
Monosaccharides can be shown as straight
chains or as rings
C
H
C
OH
C
O
C
H
H
C
OH
HO
C
H
H
C
OH
H
C
OH
H
C
OH
H
C
OH
H
C
OH
H
C
OH
H
Copyright © 2005 Pearson Education, Inc. Publishing as Benjamin Cummings
H
O
H
Glucose
HO
H
Fructose
• Monosaccharides can join to form disaccharides
–
Such as sucrose (table sugar) and maltose
(brewing sugar)
–
Polysaccharides are long chains of sugar units
• Polysaccharides are polymers of monosaccharides
–
CH2OH
CH2OH
O
O
H
HO
H
H
H
OH
Linked together by dehydration reactions
H
H
OH
HO
OH
H
H
H
OH
Glucose
OH
H
OH
Glucose
H2O
CH2OH
H
HO
CH2OH
O
H
OH
H
H
OH
H
H
O
O
H
OH
H
H
OH
H
OH
Maltose
Copyright © 2005 Pearson Education, Inc. Publishing as Benjamin Cummings
• Starch and glycogen are polysaccharides
–
That store sugar for later use
• Cellulose is a polysaccharide found in plant cell walls
– provides structure
O
Cellulose fibrils in
a plant cell wall
O
O
O
O
O
O
O
O
O
O
O
O
O
CELLULOSE
OO
OO
O OH
OO
O OH
OO
O
OO
Copyright © 2005 Pearson Education, Inc. Publishing as Benjamin Cummings
O
GLYCOGEN
O O
Figure 3.7
O
O O
O
Cellulose
molecules
O
O
O
Glycogen
granules in
muscle
tissue
Glucose
monomer
STARCH
Starch granules in
potato tuber cells
OO
OO
O O
O
O O
O
B. LIPIDS
Fats are lipids that are mostly energy-storage
molecules
• Lipids are diverse compounds
–
That consist mainly of carbon and hydrogen
atoms linked by nonpolar covalent bonds
–
Hydrophobic –water fearing
Insulation- thermal & electrical
Copyright © 2005 Pearson Education, Inc. Publishing as Benjamin Cummings
• Fats, also called triglycerides
–
Are lipids whose main function is energy storage
–
Consist of glycerol linked to three fatty acids
–
Saturated – no double bonds (solid room temp.)
–
Unsaturated - has double bonds (liquid room
temp.)
H2O
Fatty acid
Copyright © 2005 Pearson Education, Inc. Publishing as Benjamin Cummings
CH2
CH3
CH2
CH3
CH3
CH2
CH2
CH2
CH2
CH2
CH2
CH2
CH2
CH2
CH2
CH2
CH2
CH2
CH2
CH2
CH2
CH2
CH
CH2
CH2
CH
CH2
CH2
CH2
CH2
CH2
CH2
CH2
CH2
CH2
CH2
CH2
CH2
CH2
CH2
CH2
CH2
CH2
CH2
O
O C
O C
C
O
O
O
C
C
H
H
H
C
H
H
Unsaturated Fat
CH2
HO
C O
CH2
CH2
CH2
CH2
CH2
CH2
CH2
CH2
CH2
CH2
CH2
CH2
CH2
CH2
CH3
C H
OH
H C
C
OH OH
H
H
H
Glycerol
Phospholipids, waxes, and steroids are lipids with a
variety of functions
• Phospholipids are a major component of cell
membranes (phospholipid bilayer)
• Waxes form waterproof coatings (cuticle on leaf)
• Steroids are often hormones (anabolic steroids synthetic)
Copyright © 2005 Pearson Education, Inc. Publishing as Benjamin Cummings
What are trans fats and why are they such a big deal?
• Twinkie Video
Copyright © 2005 Pearson Education, Inc. Publishing as Benjamin Cummings
C. PROTEINS
Proteins are essential to the structures and
activities of life
• A protein
– Is a polymer constructed from amino acid
monomers
– Transport substances and fight disease
(antibodies)
– As enzymes they regulate chemical
reactions
Copyright © 2005 Pearson Education, Inc. Publishing as Benjamin Cummings
Proteins are made from amino acids linked by
peptide bonds
• Proteins are based on different arrangements
of a common set of 20 amino acid monomers
H
• Each amino acid contains
O
H
N
– A carboxyl group
C
H
– An amino group
Amino
group
C
OH
R
Carboxyl
(acid)
group
– And an “R” group which makes it unique
Copyright © 2005 Pearson Education, Inc. Publishing as Benjamin Cummings
• Cells link amino acids together
–
By dehydration synthesis
• The bonds between amino acid monomers
–
Are called peptide bonds
Carboxyl
group
Peptide
bond
Amino
group
H
H
H
O
N
H
C
C
H
+
OH
O
N
C
Dehydration
reaction
H
C
H
N
OH
R
R
Amino acid
Amino acid
Copyright © 2005 Pearson Education, Inc. Publishing as Benjamin Cummings
H2O
H
H
O
C
C
R
H
N
C
H
R
Dipeptide
O
C
OH
A protein’s specific shape determines its function
• A protein consists of one or more polypeptide
chains
–
Folded into a unique shape that determines
the protein’s function levels of structure
Groove
Copyright © 2005 Pearson Education, Inc. Publishing as Benjamin Cummings
Groove
D. NUCLEIC ACIDS
• Examples of nucleic acids include deoxyribonucleic acid
(DNA) and ribonucleic (RNA)
–
Serve as the code for building proteins and thus
control the life of a cell
• The monomers of nucleic acids are nucleotides
–
Nucleotides are composed of a 5-carbon sugar,
phosphate group, and nitrogenous base
H
H
N
N
N
H
OH
O
P
N
O
CH2
O

O
Phosphate
group
H
H
H
H
OH
H
Sugar
Copyright © 2005 Pearson Education, Inc. Publishing as Benjamin Cummings
H
N
Nitrogenous
base (A)
• DNA and RNA
–
Stretches of a DNA molecule called genes
make specific proteins
–
DNA programs the amino acid sequences of
proteins. DNA is double-stranded forming a
helix
–
RNA is a single-stranded polynucleotide
Copyright © 2005 Pearson Education, Inc. Publishing as Benjamin Cummings
• 10/17
1. What gives carbon the ability to form
chains that are almost unlimited in
length?
2. What atoms make up carbohydrates?
Copyright © 2005 Pearson Education, Inc. Publishing as Benjamin Cummings
• EXIT SLIP 10/17
1. What is the monomer of a
carbohydrate (sugar)?
2. What organic molecule would be
used for energy (quick energy)?
3. Name one specific example of a
carbohydrate (not a food, but a
chemical name)?
Copyright © 2005 Pearson Education, Inc. Publishing as Benjamin Cummings
• EXIT SLIP 10/23
1. What are the monomers of
carbohydrates?
2. What are the monomers of lipids (hint
there are two)?
3. What are the monomers of proteins?
4. Name at least two functions of
proteins.
Copyright © 2005 Pearson Education, Inc. Publishing as Benjamin Cummings
•
VOCABULARY – organic molecules
1. Organic Molecule
2. Macromolecule
3. Monomer
4. Polymer
5. Carbohydrate
6. Monosaccharide
7. Lipids
8. Protein
9. Enzyme
10. Nucleic Acid
11. Deoxyribonucleic acid (DNA)
Copyright © 2005 Pearson Education, Inc. Publishing as Benjamin Cummings