ch 22 organic reactions and biochemistry n.
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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:. End of soap molecule w/ a charge (Na ion) is polar and soluble in water

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saponification
Saponification
  • Process of making soap
  • Soap is the metallic salt of a fatty acid
  • Reaction: fat + base -> soap + glycerol
how soap works
How soap works:
  • 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
soap molecule
Soap molecule

Hydrophyllic end (polar) Hydrophobic end

-likes water -non-polar

-likes dirt/oil

hard water
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
Quality of Soap
  • Depends:
    • on the oils and fats you use
    • On the amount of stirring
    • The temperature
hardness
Hardness
  • Related to the degree of saturation
  • Saturated fats= harder soaps
  • Unsaturated fats= softer soaps
  • Liquid soaps = soap w/ lots of water
detergent
Detergent
  • Formed from coal and petroleum
  • Ability not diminished in hard water
  • Have a benzene-sulfonic acid anion instead of carboxylic acid

SO3

breadmaking history
BreadmakingHistory
  • 6000-5000 BC
    • Start of bread making/brewing in Egypt
  • 5000-4000 BC
    • Bread ovens found in Babylon
  • 500-200 BC
    • Commercial breadmakers in Greece/Rome
  • 100 AD
    • Rome flour quality standardization
  • Sandwich – John Montague (Earl of Sandwich)
bread making components of bread
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

Bran shell Germ

slide13
Protein

-keeps gas bubbles in bread

    • like spring, kneading organizes it
    • Overkneading breaks chains
slide14
Gas
    • Yeast

-sugar + yeast  ferment

(form CO2 (trapped))

(form alcohol-evaporate-brown edges)

-yeast die at 130 º F

slide15
Chemical Agents
    • Baking soda and acid

NaHCO3 + vinegar, cream of tarter, buttermilk 

CO2 + water + salt

    • Baking powder

-has baking soda and acid salt (calcium phosphate and NaAl(SO4)2 ) all in one

-produces CO2, when mixed with water

slide16
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

definition
Definition
  • Gigantic molecules
  • Mer= unit
  • Monomer = 1 unit
  • Polymer = many units hooked together, covalently
polymerization
Polymerization
  • Joining together of molecules that contain double or triple bonds
cross linking
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
Addition Polymerization
  • Monomer adds to monomer
  • Get chains 1000’s carbons long
  • Ex. Teflon, PVC, polyethylene
condensation polymerization
Condensation Polymerization
  • Reaction in which you get water and the polymer as products
  • Types: nylon, polyester, cellophane, rayon
types of polymers
Types of Polymers
  • 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
slide27
Thermosetting
    • 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)
slide29
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

slide32
HDPEHigh Density Polyethylene-have long chains w/ few side chains (less than 1 per 100 carbons)

Product examples:pails; milk jugs, containers for liquiddetergent and fruit juice

slide33
VPolyvinyl Chloride (PVC)Product examples:pipes; bottles for shampooand mineral waterMonomer: vinyl chloride CH2=CHCl
slide34
LDPELow Density Polyethylene-have lots of side chains (take up a lot of space)

Product examples:shopping bags; housewares, bread bags

slide36
PSPolystyreneProduct examples:foam products likedrinking cup and food tray, plastic forks

Monomer: styrene C=CH2

slide37
OTHEROther type of less commonly used plasticsProduct examples:bottles for ketchup and syrup

Ex. Polyester, polytetrafluroethylene (teflon)

history of polymers
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)

slide39
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)

slide40
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
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
slide42
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 nylon-killed self (depressed)
slide43
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
oxidation reaction
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.)
slide48
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
balance
Balance:

___ CH3CH2CH2OH + __ O2

__CO2 + ___H2O

substitution reaction
Substitution Reaction
  • 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
Alkanes

H Br

H-C-H + Br2 H-C-H + HBr

H H

-notice only one Br attaches to hydrocarbon

others
Others:

Making an amine:

R-X + NH3 R-NH2 + HX

CH3-Cl + NH3  CH3 – NH2 + HCl

addition reactions
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)
examples halogen addition alkene
Examples: Halogen Addition (alkene)

H H H H

C=C +Br2  H -C - C – H

H H Br Br

(notice: both Br’s attach)

halogen addition alkyne
Halogen Addition (alkyne)

H H

H-C = C – H + 2 Br2 Br-C-C-Br

Br Br

hydration addition
Hydration Addition
  • Add water, form alcohol, sulfuric acid (catalyst)

H H H H

C=C +H2OH2SO4> H -C - C – H

H H H OH

hydrogenation addition
Hydrogenation Addition
  • Used to make unsaturated oils more solid, less liquidy- to make margarine

H H H H

C=C +H2Pt> H -C - C – H

H H H H

(note: double bonds in benzene ring too stable- addition rxn fails)

elimination reaction
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)
example dehydration elimination
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)

biochemistry1
Biochemistry
  • Study of substances and the chemical reactions involved in life processes
a proteins
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)
slide64
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
test for protein
Test for Protein
  • Biuret’s test
  • NaOH and CuSO4 is added to protein, gives pink or blue/violet color change
high protein foods
High Protein Foods
  • Meat, nuts, eggs, legumes, fish
b carbohydrates
B. Carbohydrates
  • Made of aldehydes, ketones, and numerous hydroxyl (-OH) groups
  • Have simple sugars and polymers of sugars
1 sugar
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)
test for sugar
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
2 polymers of sugar
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
slide71
Cellulose
    • 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
C. Lipids
  • Not soluble in water, like other biochem. Molecules
  • Includes fats, oils, waxes,steroids
  • Made from the triple esters of glycerol
slide73
Fats
    • 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)
slide74
Steroids
    • 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
  • How steroids workSteroids 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
Anabolic Steroid Side effects
  • 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
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
slide78
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)
e enzymes
E. Enzymes
  • 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
slide81
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
F. Vitamins
  • 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
Fat soluble vitamins
  • Soluble in non-polar solvents
  • Overdose – stores in liver & becomes toxic (hair loss, nausea, jaundice, death)
examples of fat soluble vitamins
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
slide85
E = antioxidant to protect blood cells
    • Source – grains
    • Deficient – anemia
  • K = blood clotting
    • Source- intestinal flora, leafy veggies, liver
    • Deficient – easy bruising, easy bleeding
water soluble vitamins
Water soluble vitamins
  • Soluble in polar water
  • Overdose – dissolves in fluids, excrete in urine
example of water soluble vitamins
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
slide88
B1( thiamine) – aids rxns in brain
    • Source- grains
    • Deficient- beri beri (nervous disorder)
  • B2 (riboflavin) – converts food into energy, healthy skin and eyes
    • Source – cereal, green leafy, lean meat
    • Deficient – eye problems
slide89
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
slide90
B6 (pyridoxine)- converts food-> energy
  • B12 (cobalamin) red blood cells, nervous system
  • Folic Acid – cell production, prevention of birth defects (dna, rna)
    • Source- raw leafy veggies
  • Biolin