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Chapter 17 An Introduction to Organic Chemistry, Biochemistry, and Synthetic Polymers
An Introduction to Chemistry by Mark Bishop
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Chapter Map
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Organic Chemistry
• Organic chemistry is the chemistry of carbon-based compounds.
• There are two reasons why there are millions of organic chemicals. – Carbon atoms can form strong bonds to
other carbon atoms and still form bonds to atoms of other elements.
– There are many different ways to arrange the same atoms in carbon-based compounds.
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Ways to Describe Organic Compounds
• Lewis structures
• Condensed Formulas CH3CH(CH3)CH3
• Line Drawings
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Alkanes
2,2,4-trimethylpentane, CH3C(CH3)2CH2CH(CH3)CH3
Hydrocarbons (compounds composed of carbon and hydrogen) in which all of the carbon-carbon bonds are single bonds
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Pre-ignition Knock and Octane Rating
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Steps to Octane Rating
• Measure efficiency and degree of vibration for a test engine running on various percentages of heptane (a straight-chain hydrocarbon) and 2,2,4-trimethylpentane (a branched-chain hydrocarbon).
• Run the same test engine with the gasoline to be tested, and measure its efficiency and degree of vibration.
• Assign an octane rating to the gasoline based on comparison of the efficiency and degree of vibration of the test engine with the gasoline and the various percentages of 2,2,4-trimethylpentane (octane or isooctane) and heptane. For example, if the gasoline runs the test engine as efficiently as 91% 2,2,4-trimethylpentane (octane or isooctane) and 9% heptane, it gets an octane rating of 91.
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Alkenes
2-methylpropene (isobutene), CH2C(CH3)CH3
Hydrocarbons that have one or more carbon-carbon double bonds
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Alkynes
Ethyne (acetylene), HCCH
Hydrocarbons that have one or more carbon-carbon triple bonds
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Benzene
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Arenes (or Aromatics) - Compounds that contain the benzene ring
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Alcohols
Glycerol, HOCH2CH(OH)CH2OH
Compounds with one or more -OH groups attached to a hydrocarbon group
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Carboxylic Acids
Stearic acid, CH3(CH2)16CO2H
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Ethers
Diethyl ether, CH3CH2OCH2CH3
Two hydrocarbon groups surrounding an oxygen atom
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Aldehyde
2-methylbutanal, CH3CH(CH3)CH2CHO
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Ketones
2-propanone (acetone), CH3COCH3
The R’s must be hydrocarbon groups. They cannot be hydrogen atoms.
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Esters
Ethyl butanoate, CH3CH2CH2CO2CH2CH3
The R’ must be a hydrocarbon group. It cannot be a hydrogen atom.
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Amine
Trimethylamine, (CH3)3N
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Amides
Ethanamide (acetamide), CH3CONH2
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Difunctional Compounds - GABA
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Types of Biomolecules
• Carbohydrates – Monosaccharides (glucose and fructose) – Disaccharides (maltose, lactose, and
sucrose) – Polysaccharides (starch and cellulose)
• Amino Acids and Proteins • Triglycerides • Steroids
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Monosaccharides
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Glucose
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Galactose
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Fructose
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Maltose
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Sucrose
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Lactose
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Amylose
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Amylopectin or Glycogen
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Cellulose
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Amino Acids
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Alanine
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Formation of Ala-Ser-Gly-Cys
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Protein – Bovine Pancreatic Trypsin Inhibitor (BPTI)
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Primary and Secondary Protein Structures
• Primary Structure = the sequence of amino acids in the protein
• The arrangement of atoms that are close to each other in the polypeptide chain is called the secondary structure of protein. – Three types
• -helix • -sheet • irregular
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-helix – Secondary Structure
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-Sheet Secondary Structure
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Tertiary Protein Structure
• The very specific overall shape of the protein called its tertiary structure.
• The protein chain is held in its tertiary structure by interactions between the side chains of its amino acids. – Disulfide bonds – Hydrogen bonds – Salt bridges
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Disulfide Bonds in Proteins
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Hydrogen Bonding in Proteins
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Salt Bridge in Proteins
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The Ribbon Structure of the Protein BPTI
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Disruption of Salt Bridge
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Triglycerides (Fats and Oils)
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Saturated Triglyceride - Tristearin
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Tristearin – Line Drawing
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Unsaturated Triglyceride
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Cis and Trans
• When there is a double bond between two carbons and when like groups are on different carbons and the same side of the double bond the arrangement is called cis.
• When the like groups are on opposite sides of the double bond the arrangement is called trans.
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Hydrogenation
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Hydrogenation - Example
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Trans Fats
• Hydrogenation is reversible. • When the double bond is reformed, it is more
likely to form the more stable trans form than the less stable cis form.
• Therefore, partial hydrogenated vegetable oils contain trans fats, which are considered to be damaging to your health.
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Olestra – a Fat Substitute
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Steroid Skeleton
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Cholesterol
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Testosterone Formation
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Estradiol
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Hydrolysis
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Digestion Products
Substance in Food Products of Digestion
disaccharides monosaccharides
polysaccharides glucose
protein amino acids
Triglycerides (fats and oils)
glycerol and fatty acids
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Disruption of Salt Bridge
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Amide Hydrolysis
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Enzymes
• Enzymes are naturally occurring catalysts. Catalysts speed chemical changes without being permanently altered themselves.
• The chemicals that they act on are called substrates.
• Very specific due to – Shape – “Lock and Key” – Positions of binding groups, which attract
substrates to the active site, the portion of the enzyme where the reaction occurs.
– Positions of the catalytic groups that speed the reaction.
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Enzymes Speed Chemical Reactions
• Provide a different path to products that has more stable intermediates and therefore requires less energy.
• Give the correct orientation every time.
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Nylon Formation
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Nylon-66
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Polyester Formation
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Polyethylene Formation
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Poly(vinyl chloride) or PVC
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Addition Polymers
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Thermoplastics’ Uses
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Thermosets’ Uses
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Recycling Codes