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Chapter 4 Carbon and the molecular diversity of life

Understand the importance of carbon in life and how it forms diverse molecules. Explore the properties of carbon-based compounds found in proteins, DNA, and carbohydrates. Learn about vitalism versus mechanism and the versatility of carbon in bonding.

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Chapter 4 Carbon and the molecular diversity of life

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  1. Chapter 4 Carbon and the molecular diversity of life • OBJECTIVE: • Understand the properties of carbon that make it so important to life • Although cells are 70–95% water, the rest consists mostly of carbon-based compounds • Carbon: unparalleled in ability to form large complex/diverse molecules • Proteins, DNA, carbohydrates, and other molecules that distinguish living matter are all composed of carbon compounds

  2. Vitalism vs Mechanism • Vitalism: Belief in life force • Synthesis of complex compounds impossible • Disproved in 1953 by Miller • Mechanism: all natural phenomena governed by physical and chemical laws.

  3. Fig. 4-2 EXPERIMENT “Atmosphere” CH4 Water vapor Electrode H2 NH3 Condenser Cooled water containing organic molecules Cold water H2O “sea” Sample for chemical analysis

  4. CARBON • Has 4 valence electrons • Can form 4 covalent bonds • Versatility in bonding • Single • Double • Triple • Can form molecules of almost infinite variability

  5. Name andComment Structural Formula Space-Filling Model Molecular Formula Ball-and- Stick Model Figure 4.3 (a) Methane CH4 (b) Ethane C2H6 (c) Ethene (ethylene) C2H4

  6. CARBON • What determines the chemical properties of an element? Hydrogen (valence = 1) Oxygen (valence = 2) Nitrogen (valence = 3) Carbon (valence = 4)

  7. Figure 4.5 (c) Double bond position (a) Length Ethane Propane 2-Butene 1-Butene (b) Branching (d) Presence of rings Benzene 2-Methylpropane (isobutane) Butane Cyclohexane

  8. ISOMERS • Isomers: compounds with the same molecular formula but different structures and properties: • Structural isomers: • different covalent arrangements of their atoms • Geometric isomers: • same covalent arrangements, differ in spatial arrangements • Enantiomers: • isomers that are mirror images of each other

  9. Isomers • Isomers are compounds with the same molecular formula but different structures and properties • Structural isomers have different covalent arrangements of their atoms • Cis-trans isomers have the same covalent bonds but differ in spatial arrangements • Enantiomers are isomers that are mirror images of each other

  10. Fig. 4-7 Pentane 2-methyl butane (a) Structural isomers cis isomer: The two Xs are on the same side. trans isomer: The two Xs are on opposite sides. (b) Geometric isomers L isomer D isomer (c) Enantiomers

  11. Fig. 4-8 Effective Enantiomer Ineffective Enantiomer Drug Condition Pain; inflammation Ibuprofen S-Ibuprofen R-Ibuprofen Albuterol Asthma R-Albuterol S-Albuterol

  12. Functional Groups • Functional Groups: Attached to carbons skeleton and have diverse properties that dictate the behavior of organic molecules. • The seven functional groups that are most important in the chemistry of life: • Hydroxyl group • Carbonyl group • Carboxyl group • Amino group • Sulfhydryl group • Phosphate group • Methyl group

  13. Fig. 4-9 Estradiol Testosterone

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