Transcript Ch. 21- Organic Reactions and Biochemistry

Ch. 22- Organic
Reactions and
Biochemistry
Saponification
Process of making soap
 Soap is the metallic salt of a fatty acid
 Reaction: fat + base -> soap + glycerol

Reaction
How soap works:
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End of soap molecule w/ a charge (Na ion) is
polar and soluble in water
Other end (CH3- (CH2)etc) is non-polar and
soluble in oil and fat
Water= polar, dirt/oil = non polar
When using soap, dirt/oil attach to non-polar end
of the soap and the polar end of the soap
attaches to the water, forms a micelle
Micelle (soap bubble)
Soap
Water
Dirt
Soap molecule
Hydrophyllic end (polar)
-likes water
Hydrophobic end
-non-polar
-likes dirt/oil
Hard water
Hard water has ions in it (Mg, Ca, Fe)
 Will form an insoluble precipitate with soap
and water
 Makes soap ineffective =soap scum

Quality of Soap

Depends:
 on the oils and fats you use
On the amount of stirring
The temperature
Hardness
Related to the degree of saturation
 Saturated fats= harder soaps
 Unsaturated fats= softer soaps
 Liquid soaps = soap w/ lots of water

Detergent
Formed from coal and petroleum
 Ability not diminished in hard water
 Have a benzene-sulfonic acid anion
instead of carboxylic acid
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SO3
Breadmaking
History

6000-5000 BC
 Start
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of bread making/brewing in Egypt
5000-4000 BC
 Bread
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ovens found in Babylon
500-200 BC
 Commercial
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100 AD
 Rome
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breadmakers in Greece/Rome
flour quality standardization
Sandwich – John Montague (Earl of Sandwich)
Bread Making: Components of
Bread
Flour- from the wheat berry, is a complex
carbohydrate, made of starch and protein,
amylase enzyme breaks it down
Wheat Berry
Endosperm
(protein/starch)
white flour
1.
Bran shell
Germ
2.
Protein
-keeps gas bubbles in bread
like spring, kneading organizes it
Overkneading breaks chains
3.
Gas
A.
Yeast
-sugar + yeast  ferment
(form CO2 (trapped))
(form alcohol-evaporate-brown edges)
-yeast die at 130 º F
B.
Chemical Agents
1.
Baking soda and acid
NaHCO3 + vinegar, cream of tarter, buttermilk 
CO2 + water + salt
2.
Baking powder
-has baking soda and acid salt (calcium phosphate
and NaAl(SO4)2 ) all in one
-produces CO2, when mixed with water
C. Steam
-pita, cream puffs, eclairs
- take dough w/out yeast, put in very hot oven,
seals outside, moisture inside forms gas
pocket, leaves pocket of air when removed
Polymers
Silly Putty Video
Definition
Gigantic molecules
 Mer= unit
 Monomer = 1 unit
 Polymer = many units hooked together,
covalently

Polymerization

Joining together of molecules that contain
double or triple bonds
Cross-linking

Bridges formed between chains, gives
polymer new properties
-C-C-C-C-C-C-C-C-C-C-C-C-
-C-C-C-C-C-C-C-C-C-C-C-C-
Addition Polymerization
Monomer adds to monomer
 Get chains 1000’s carbons long
 Ex. Teflon, PVC, polyethylene

+

Condensation Polymerization
Reaction in which you get water and the
polymer as products
 Types: nylon, polyester, cellophane, rayon
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Types of Polymers
1.
Thermoplastic

-can be melted and re-melted
 -soften when heated, can be reshaped and
hardens when cooled (long chains lock into
place)
 Recyclable
 -ex. PVC, nylon, lucite, polystyrene
Polystyrene
Thermosetting
2.
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Permanently hardened
Not reversible (once set-they are set)
Intense heating causing charring (black)
Molded into final shape
Shape by filing or machining
Ex. Bakelite (pot handles, electrical
insulation, jewelry)
Bakelite
3.
Elastomers
-polymers with high degree of elasticity
-have folded polymer chains, like spring
-energy is needed to stretch out
-Ex. Rubber- made by vulcanization (rubber w/
sulfur) , by Charles Goodyear (1837), tires
PETE
Polyethylene Terephthalate
Product examples:
bottles for soft drink, soy sauce,
and cooking oil
HDPE
High Density Polyethylene
-have long chains w/ few side chains (less
than 1 per 100 carbons)
Product examples:
pails; milk jugs, containers for liquid
detergent and fruit juice
V
Polyvinyl Chloride (PVC)
Product examples:
pipes; bottles for shampoo
and mineral water
Monomer: vinyl chloride CH2=CHCl
LDPE
Low Density Polyethylene
-have lots of side chains (take up a lot of space)
Product examples:
shopping bags; housewares, bread bags
PP
Polypropylene
Product examples:
household storage containers, yogurt,
butter tubs
PS
Polystyrene
Product examples:
foam products like
drinking cup and food tray, plastic forks
Monomer: styrene
C=CH2
OTHER
Other type of less
commonly used plastics
Product examples:
bottles for ketchup and syrup
Ex. Polyester, polytetrafluroethylene (teflon)
History of Polymers
1811 – Gay Lussac found cellulose (cotton)
and starch have similar chemical structure
1840- Goodyear vulcanized rubber (tires
now have 20 different polymers)
1887 – Rayon invented (Chardonnet made
from wood cellulose and nitric acid)
Early 1900’s – found proteins were polymers
1907 – Bakelite invented (Leo Baekeland-1st
synthetic polymer of practical importance)
1935- Nylon invented
-invention made it clear that
macromolecules could be made in an
infinite variety of structures by organic
chemistry (found an ever-expanding
number of uses for these molecules)
History of Nylon
DuPont Co. founded to make gunpowder,
diversified after WW1, went into silk
manufacturing, hired chemist from Harvard
to replicate silk process
 Wallace Carothers (working w/ Elmer
Kraemer (UW-Madison) worked
unsuccessfully for 2 years

DuPont convinced him not to go back to
Harvard
 Discovered adipic acid, mixed it with
hexamethylenediamine- in a step-growth
condensation reaction
 Didn’t realize that he had made nylonkilled self (depressed)
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Another worker stretched the compound,
found it orients the molecules so they
increase in strength and elasticity
 1939- premiered at Worlds Fair
 1940- nylon stocking
 1946- came back on market after WWII
 Other forms: velcro, neoprene
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Nylon Reaction
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Nylon movie
Other Organic
Reactions
Oxidation Reaction
Adding oxygen to organic compounds
produces CO2 + water + energy
 More saturated a hydrocarbon, more
energy
 Oxidation = the reaction takes place
through a series of steps (at any step in
the sequence unwanted by-products could
be formed –like carbon soot or CO.)

Important reaction for: energy production
in living systems, combustion of
hydrocarbons for heating
 Balancing: balance carbons first, then
hydrogens, then oxygens. If it doesn’t
balance: start over, double the
hydrocarbon
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Balance:
___ CH3CH2CH2OH + __ O2 
__CO2 + ___H2O
_2_ CH3CH2CH2OH + _9_ O2 
_6_CO2 + _8__H2O
Substitution Reaction
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Reaction in which a hydrogen atom of a
hydrocarbon is replaced by a functional group
(like oxygen or halogen)
Proceed slower than inorganic
Are not easily controlled- produce a lot of
unwanted byproducts which have to be
separated out
Hint: all single bonds, 2 reactants, 2 products
Alkanes
H
Br
H-C-H + Br2  H-C-H
H
H
+ HBr
-notice only one Br attaches to hydrocarbon
Others:
Making an amine:
R-X + NH3  R-NH2
CH3-Cl
+ HX
+ NH3  CH3 – NH2 + HCl
Addition Reactions
Starting with a double or triple bond,
addition reactions break that bond forming
single bonds
 Forms unwanted by products
 Hint: 2 reactants (double/triple bond), 1
product (single bond)
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Examples: Halogen Addition
(alkene)
H
H
+Br2 
C=C
H
H
(notice: both Br’s attach)
H H
H -C - C – H
Br Br
Halogen Addition (alkyne)
HH
H-C = C – H + 2 Br2  Br-C-C-Br
Br Br
Hydration Addition
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Add water, form alcohol, sulfuric acid
(catalyst)
H
H
C=C
H
+H2O
H
H2SO4>
H H
H -C - C – H
H OH
Hydrogenation Addition
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H
Used to make unsaturated oils more solid,
less liquidy- to make margarine
H
H H
C=C
+H2 Pt>
H -C - C – H
H
H
H H
(note: double bonds in benzene ring too
stable- addition rxn fails)
Elimination Reaction
Forms a double bond from a single
bonded molecule by removing atoms
 Hint: 1 reactant (single bond), 2 products
(with one being a double bond)
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Example: Dehydration
elimination

Removing water from alcohols
H H OH H2SO4>
H H
H
H- C - C –C- H
H2O +H- C – C = C
H H H
H
H
(note: make sure you take off the –OH and
-H off of neighboring carbons)
Biochemistry
Biochemistry

Study of substances and the chemical
reactions involved in life processes
A. Proteins
Polymers containing long chains of amino
acids
 ½ of non-water mass is protein
 Makes up muscles & body structure
 Some used as biological catalysts
(enzymes)
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Proteins differ from each other in the
sequence of amino acids and the
coiling/twisting of the molecule
 Amino acids-contain an amine and
carboxylic acid group
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Test for Protein
Biuret’s test
 NaOH and CuSO4 is added to protein,
gives pink or blue/violet color change
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High Protein Foods

Meat, nuts, eggs, legumes, fish
B. Carbohydrates
Made of aldehydes, ketones, and
numerous hydroxyl (-OH) groups
 Have simple sugars and polymers of
sugars

1. Sugar
Common: glucose, sucrose
 Monosaccharide = one sugar (glucose)
 Disaccharide = two sugars (sucrose)
 Gives you short burst of energy through
the oxidation of sugar (forming CO2 and
H2O)
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Test for Sugar
Benedict’s Test
 Contains Copper (II) oxide (blue), when
placed w/ sugar it reduces it to copper (I)
oxide which gives it a green, red or orange
color depending on the amount & type of
sugar
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2. Polymers of Sugar
a. Starches
-
-
polysaccharides, long chains of sugars
Medium energy needs
Enzymes break them down into simple sugars
Test for Starch- Iodine or Lugol’s (turns
blue/black)
Found in seeds, roots of plants
Made of alpha glucose ( ά-glucose)
We can digest
Cellulose
b.
-
Polymer of ß- glucose (beta-glucose)
Can’t digest
Made of fibrous structures of plants (oat
husk, celery stalk)
Gives us roughage, dietary fiber
Gives plants structural strength
C. Lipids
Not soluble in water, like other biochem.
Molecules
 Includes fats, oils, waxes,steroids
 Made from the triple esters of glycerol
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Fats
1.
-
-
-
used in cell walls
formed by glycerol & fatty acids
Get unsaturated and saturated fats
Gives you stored energy (long term)
1-2% of total calorie intake
Test – Sudan IV- floating red droplets or
brown bag (see through)
Steroids
2.
-
Type of lipid w/ tetracylic ring nucleus
Cholesterol- important steroid (found in bile
and cell membrane of brain & spinal cord)
Steroid hormones – estrogen, testosterone)
How Steroids Work

How steroids work
Steroids work by imitating the properties of naturally
occurring hormones. Muscle tissue is peppered with
receptor sites specific to growth. The correct hormonal
'key' can only access these sites or 'locks'. Steroids can
activate these receptor sites because their chemical
composition is so similar to the hormone testosterone.
Once the receptor sites have been stimulated, a domino
effect of metabolic reactions takes place as the body is
instructed by the drug to increase muscle tissue
production.
Anabolic Steroid Side effects
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Damage to the gonads (testicles or ovaries)
Liver diseases
Malfunctions of the kidneys or heart
'Roid rage', which is characterised by uncontrollable outbursts of psychotic
aggression
Paranoia
Mood swings, including deep depression
Severe acne
High blood cholesterol levels
High blood pressure
Injuries to tendons that can't keep up with the increased muscle strength
Delusional feelings of being superhuman or invincible
Fluid retention
Trembling and muscle tremors
Stunted bone growth in adolescents.
D. Nucleic Acid
Found in small quantities
 Biological polymer found in nuclei of cell
 Indispensable component of every living
thing
 Determines genetic inheritance,
reproduction and growth of cells

Monomer units = nucleotide (made of
nitrogen base, sugar, and a phosphate
group)
 Sugars- ribose, deoxyribose
 DNA – deoxyribonucleic acid ( stores &
transfers genetic information)
 RNA – ribonucleic acid (transmission of
DNA info, used to make enzymes)
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E. Enzymes
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Biological catalyst made of protein molecules
Increase the rate of chemical rxns.
Over 2000 enzymes have been discovered
Each enzyme has a distinctively shaped
active site, only molecules w/ complementary
shapes can attach to the enzyme
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Active site- pocket or crevase found in peptide
chain, has a distinctive shape (substrate fits into
it like a puzzle/induced fit)
Important for biochem. Rxns
Responsible for energy, repair & growth
Enzyme remains unchanged
Doesn’t change normal equilibrium position of
rxn. (same amount of product formed w/ or w/out
the enzyme)
F. Vitamins
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Group of non-protein organic molecules
Used to aid enzymatic rxns
For growth, digestion, processing of proteins,
carboyhydrates & fats
Promotes essential biochemical rxns lack of
vitamins causes specific diseases
Not an energy source
Must come from food
Classified by solubility
Fat soluble vitamins
Soluble in non-polar solvents
 Overdose – stores in liver & becomes toxic
(hair loss, nausea, jaundice, death)

Examples of Fat soluble vitamins

A = antioxidant, vision
 Source
= animal, dark green leafy veggies
 Deficient –night blind, dry skin

D = helps absorb Calcium
 Source
= milk, liver
 Deficient - rickets

E = antioxidant to protect blood cells
– grains
 Deficient – anemia
 Source

K = blood clotting
 Source-
intestinal flora, leafy veggies, liver
 Deficient – easy bruising, easy bleeding
Water soluble vitamins
Soluble in polar water
 Overdose – dissolves in fluids, excrete in
urine

Example of Water Soluble vitamins
Vitamin C and 8 different vitamin B’s
 Vitamin C

 Formation
of connective tissue, immune
system, wound healing
 Source – orange colored foods (not cheetos)
 Deficient - scurvy

B1( thiamine) – aids rxns in brain
 Source-
grains
 Deficient- beri beri (nervous disorder)

B2 (riboflavin) – converts food into energy,
healthy skin and eyes
– cereal, green leafy, lean meat
 Deficient – eye problems
 Source

B3 (niacin) – metabolism
 Source-
lean meat
 Deficient- irritability, skin eruptions

B5 (pantothenic acid) – break down fatty
acids and carbohydrate
 Source
–mushrooms, cauliflower, sunflower
seeds
 Deficient- fatigue, tingly limbs
B6 (pyridoxine)- converts food-> energy
 B12 (cobalamin) red blood cells, nervous
system
 Folic Acid – cell production, prevention of
birth defects (dna, rna)

 Source-

Biolin
raw leafy veggies

Also need 15 minerals to help cell function
and provide structure
The
end
Oxidation
Hydrocarbon +
2 reactants->
oxygen -> carbon 2 products
dioxide and water
Substitution
Alkane + halogen
substituted
alkane +
hydrogen halide
Alkene + halogen
or water  alkyl
halide or alcohol
Alcohol  alkene
+ water
Monomer +
monomer 
polymer
Addition
Elimination
Addition Polymerization
2 reactants
2 products
2 reactants 
1 product
1 reactant 
2 products