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Organic Chemistry Introduction to organic chemistry Principles of carbon chemistry Principle of polymers Hydrocarbons Organic chemistry and biochemistry Take Home Message
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Organic Chemistry Introduction to organic chemistry Principles of carbon chemistry Principle of polymers Hydrocarbons Organic chemistry and biochemistry Take Home Message
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Elements of the Solar System: Importance of Carbon 25 of 92 natural elements are known to be essential to life on Earth Four of the above make up 96%! –Carbon (C), Oxygen (O), Hydrogen (H) and Nitrogen (N) Compare to solar abundance and discuss relative to evolution of biochemistry in origin of life
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Elements of the Periodic Table
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Frequency of Carbon Carbon as a building block –C is the 4 th most common element in the solar system –Probably the same frequency elsewhere in the Universe Conclusion: C is common throughout the Universe and is likely to behave similarly (C and its tendency to form covalent bonds) in most environments
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Chemistry Subdivisions Organic Chemistry –Chemistry of compounds in which C is the principal element (biotic/living and abiotic/non- living) Inorganic Chemistry –Chemistry of all other elements Significance of C in chemistry
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Organic Chemistry Introduction to organic chemistry Principles of carbon chemistry Principle of polymers Hydrocarbons Organic chemistry and biochemistry Take Home Message
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Principles of Carbon Chemistry: C’s Atom C is unparalleled in its ability to form molecules that are large, complex and diverse in structure Key is the C atom (protons, electrons, and quantum mechanics) –C has ____ electrons –Little tendency to gain or loose electrons (i.e., no ionic bonding) –Greater likelihood for electrons to be shared in covalent bonds –Possible covalent bonds per atom from __ to ___ –Most common elements with which C bonds O, H, N and C (compare with prominence in living systems)
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Principles of Carbon Chemistry: Linkages among Carbon Atoms Linkages among C atoms form macromolecules (define) –Chains of C (methane and ethane) –Branches of C –Rings of C (e.g., benzene)
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Principles of Carbon Chemistry: Functional Groups Distinctive features of C macromolecules is a function of two aspects of the molecules –Carbon skeleton (chains, branches, rings) Chains, branches or rings Number of C atoms (2, 3, 4, etc.) –Groups of atoms attached to carbon skeleton Called functional groups (some example) –Hydroxyl (OH) –Amino (NH 2 ) –Phosphate (P) –Total of five different functional groups
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Organic Chemistry Introduction to organic chemistry Principles of carbon chemistry Principle of polymers Hydrocarbons Organic chemistry and biochemistry Take Home message
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Principle of Polymers: Introduction Principle of hierarchy theory and emergent properties Small molecules joined together to form large molecules up to 1,000’s of C atoms Macromolecules Infinite array of possible combinations, each with its own unique chemistry
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Principle of Polymers In living systems, polymers of C results in four major classes of compounds that are of extreme importance –Carbohydrates –Proteins –Nucleic acids –Lipids Linkages between C atoms via covalent bonds Calculating potential diversity of C polymers –Analogy to alphabet (26 letters) and infinite ways to “create words” –If 45 basic different C alphabet pieces, infinite ways to create polymers of C
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Organic Chemistry Introduction to organic chemistry Principles of carbon chemistry Principle of polymers Hydrocarbons Organic chemistry and biochemistry
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Hydrocarbons Carbon compounds with only two elements: –C and H C-C bonding via covalent bonds (nonpolar) Number of bonds –1, 2, 3, or 4 Most simple compound is methane H H C H H
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Hydrocarbons: C to C Bonding C to C bond can be single bond (C-C) H H –Ethane H C-C H H H C to C bond can be double bond (C = C) H –EtheneC = C H C to C bond can be triple bond (C = C) –Ethyne H C = C H
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Hydrocarbons: Groups Alkanes –Single covalent bond between C atoms Methane (C1H4) Ethane (C2H6) Propane (C3H8) Butane (C4H10) Pentane (C5H12) Octane (C__H18) Decane (C__H22) Pattern: C n H 2n+2 ) Alkynes (triple bond C = C) Alkenes (double bond or C = C) Aromatics (rings or cyclic C atoms) –Example (C 6 H 6 )
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Hydrocarbons: Saturated and Unsaturated Hydrocarbons Saturated hydrocarbons: maximum number of H atoms bonded to C H H –Ethane or H C - C H H H Unsaturated hydrocarbons: anything else H H –Ethylene or C = C H H
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Organic Chemistry Introduction to organic chemistry Principles of carbon chemistry Principle of polymers Hydrocarbons Organic chemistry and biochemistry Take Home Message
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Organic Chemistry and Biochemistry Keys: –Structure of basic unit –Polymer structure –Functional group (e.g., OH, P or NH 2 ) Types of C polymers for biotic systems –Carbohydrates –Lipids –Proteins –Nucleic acids
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Organic Chemistry and Biochemistry: Monomers Carbohydrates –Glucose or C 6 H 12 O 6 –Functional unit: hydroxyl or OH- Proteins –Amino acid –Functional unit: amine or NH 2 Nucleic Acids –Nucleotide or –Functional units: organic N base, carbohydrate, and phosphate Lipids –Fatty acids C 16-18 –Functional unit: glycerol (3 OH- groups)
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Organic Chemistry Introduction to organic chemistry Principles of carbon chemistry Principle of polymers Hydrocarbons Organic chemistry and biochemistry Take Home Message
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While the molecule of water is simple but exquisite and unique in its chemical behavior, the C atom is unusual and unique in its chemical behavior but for different reasons –Covalent bonding –Valence electrons Unusual behavior of C results in extreme array of simple to very complex molecules as a function of –Polymers –Functional groups Life as we know it is hard to imagine without C behaving as a polymer with covalent bonds to create carbohydrates, proteins, nucleic acids and lipids (C polymers) Principle of hierarchy theory and emergent properties
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Exam Coverage Text –Chapter 9 (Atomic Structure; entire chapter) –Chapter 10 (Elements & Periodic Table; entire chapter) –Chapter 11 (Compounds and Chemical Change; entire chapter excluding pages noted in lecture and posted on the www) –Chapter 12 (Chemical Formulas; ONLY: pp 278-279; p 292 - Units of Measurement) –Chapter 13 (Water & Solutions; exclude pp 306-310 (electrolytes, boiling point, and freezing point) Lecture Notes –Atoms and Elements; Valence Electrons and Bonding; Water; and Organic Chemistry Labs –Physics: Electricity and Light –NO OTHER LABS FOR THIS EXAM
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Help or Desperation Sessions Tuesday @ 5:00 PM in Honors Lounge Wednesday @ 6:30 Pm in Honors Lounge No lecture, questions only
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