1. CAMPBELL BIOLOGY Reece Urry Cain Wasserman Minorsky Jackson © 2014 Pearson Education, Inc. TENTH EDITION CAMPBELL BIOLOGY Reece Urry Cain Wasserman Minorsky Jackson TENTH EDITION 4 Carbon and the Molecular Diversity of Life Lecture Presentation by Nicole Tunbridge and Kathleen Fitzpatrick

2. © 2014 Pearson Education, Inc. Carbon: The Backbone of Life  Living organisms consist mostly of carbon-based compounds  Carbon is unparalleled in its ability to form large, complex, and varied molecules  Proteins, DNA, carbohydrates, and other molecules that distinguish living matter are all composed of carbon compounds

3. © 2014 Pearson Education, Inc. Figure 4.1

4. © 2014 Pearson Education, Inc. Figure 4.1a Carbon can bond to four other atoms or groups of atoms, making a large variety of molecules possible.

5. © 2014 Pearson Education, Inc. Concept 4.1: Organic chemistry is the study of carbon compounds  Organic chemistry is the study of compounds that contain carbon  Organic compounds range from simple molecules to colossal ones  Most organic compounds contain hydrogen atoms in addition to carbon atoms

6. © 2014 Pearson Education, Inc.  Vitalism was the belief in a life force outside the jurisdiction of physical and chemical laws  It was thought that organic compounds could only be produced in living organisms  Vitalism was disproved when chemists were able to synthesize organic compounds

7. © 2014 Pearson Education, Inc. Organic Molecules and the Origin of Life on Earth  Stanley Miller’s classic experiment demonstrated the abiotic synthesis of organic compounds  Experiments support the idea that abiotic synthesis of organic compounds, perhaps near volcanoes, could have been a stage in the origin of life

8. © 2014 Pearson Education, Inc. Figure 4.2 Water vapor Cooled “rain” containing organic molecules Sample for chemical analysis Cold water Condenser Electrode “Atmosphere” CH 4 NH 3 H2H2 H 2 O “sea ”

9. © 2014 Pearson Education, Inc.  Pioneers of organic chemistry helped shift the mainstream of biological thought from vitalism to mechanism  Mechanism is the view that physical and chemical laws govern all natural phenomena

10. © 2014 Pearson Education, Inc. Concept 4.2: Carbon atoms can form diverse molecules by bonding to four other atoms  Electron configuration is the key to an atom’s characteristics  Electron configuration determines the kinds and number of bonds an atom will form with other atoms

11. © 2014 Pearson Education, Inc. The Formation of Bonds with Carbon  With four valence electrons, carbon can form four covalent bonds with a variety of atoms  This ability makes large, complex molecules possible  In molecules with multiple carbons, each carbon bonded to four other atoms has a tetrahedral shape  However, when two carbon atoms are joined by a double bond, the atoms joined to the carbons are in the same plane as the carbons

12. © 2014 Pearson Education, Inc. Figure 4.3 Molecule (a) Methane (b) Ethane (c) Ethene (ethylene) Molecular Formula Structural Formula Ball-and-Stick Model Space-Filling Model CH 4 C2H6C2H6 C2H4C2H4

13. © 2014 Pearson Education, Inc.  The electron configuration of carbon gives it covalent compatibility with many different elements  The valences of carbon and its most frequent partners (hydrogen, oxygen, and nitrogen) are the building code for the architecture of living molecules

14. © 2014 Pearson Education, Inc. Figure 4.4 Hydrogen (valence = 1) Oxygen (valence = 2) Nitrogen (valence = 3) Carbon (valence = 4)

15. © 2014 Pearson Education, Inc.  Carbon atoms can partner with atoms other than hydrogen; for example:  Carbon dioxide: CO 2  Urea: CO(NH 2 ) 2

16. © 2014 Pearson Education, Inc. Figure 4.UN02 Urea

17. © 2014 Pearson Education, Inc. Molecular Diversity Arising from Variation in Carbon Skeletons  Carbon chains form the skeletons of most organic molecules  Carbon chains vary in length and shape

18. © 2014 Pearson Education, Inc. Figure 4.5 (a) Length (b) Branching(d) Presence of rings (c) Double bond position EthanePropane1-Butene2-Butene Butane2-Methylpropane (isobutane) Cyclohexane Benzene

19. © 2014 Pearson Education, Inc. Animation: Carbon Skeletons

20. © 2014 Pearson Education, Inc. Figure 4.5a (a) Length EthanePropane

21. © 2014 Pearson Education, Inc. Figure 4.5b (b) Branching Butane2-Methylpropane (isobutane)

22. © 2014 Pearson Education, Inc. Figure 4.5c (c) Double bond position 1-Butene2-Butene

23. © 2014 Pearson Education, Inc. Figure 4.5d (d) Presence of rings Cyclohexane Benzene

24. © 2014 Pearson Education, Inc. Hydrocarbons  Hydrocarbons are organic molecules consisting of only carbon and hydrogen  Many organic molecules, such as fats, have hydrocarbon components  Hydrocarbons can undergo reactions that release a large amount of energy

25. © 2014 Pearson Education, Inc. Figure 4.6 Nucleus Fat droplets (b) A fat molecule(a) Part of a human adipose cell 10 μ m

26. © 2014 Pearson Education, Inc. Figure 4.6a Nucleus Fat droplets (a) Part of a human adipose cell 10 μ m

27. © 2014 Pearson Education, Inc. 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

28. © 2014 Pearson Education, Inc. Figure 4.7 (a) Structural isomers (b) Cis-trans isomers Pentane cis isomer: The two Xs are on the same side. 2-methyl butane trans isomer: The two Xs are on opposite sides. (c) Enantiomers L isomerD isomer CO 2 H H CH 3 H NH 2 C C

29. © 2014 Pearson Education, Inc. Animation: Isomers

30. © 2014 Pearson Education, Inc. Figure 4.7a (a) Structural isomers Pentane 2-methyl butane

31. © 2014 Pearson Education, Inc. Figure 4.7b (b) Cis-trans isomers cis isomer: The two Xs are on the same side. trans isomer: The two Xs are on opposite sides.

32. © 2014 Pearson Education, Inc. Figure 4.7c (c) Enantiomers L isomer D isomer CO 2 H H CH 3 H NH 2 CO 2 H NH 2 CH 3 C C

33. © 2014 Pearson Education, Inc.  Enantiomers are important in the pharmaceutical industry  Two enantiomers of a drug may have different effects  Usually only one isomer is biologically active  Differing effects of enantiomers demonstrate that organisms are sensitive to even subtle variations in molecules

34. © 2014 Pearson Education, Inc. Figure 4.8 DrugEffects Effective Enantiomer Ineffective Enantiomer Ibuprofen Albuterol Reduces inflammation and pain Relaxes bronchial (airway) muscles, improving airflow in asthma patients S-Ibuprofen R-AIbuterol S-AIbuterol R-Ibuprofen

35. © 2014 Pearson Education, Inc. Animation: L-Dopa

36. © 2014 Pearson Education, Inc. Concept 4.3: A few chemical groups are key to molecular function  Distinctive properties of organic molecules depend on the carbon skeleton and on the chemical groups attached to it  A number of characteristic groups can replace the hydrogens attached to skeletons of organic molecules

37. © 2014 Pearson Education, Inc. The Chemical Groups Most Important in the Processes of Life  Estradiol and testosterone are both steroids with a common carbon skeleton, in the form of four fused rings  These sex hormones differ only in the chemical groups attached to the rings of the carbon skeleton

38. © 2014 Pearson Education, Inc. Figure 4.UN03 EstradiolTestosterone

39. © 2014 Pearson Education, Inc.  Functional groups are the components of organic molecules that are most commonly involved in chemical reactions  The number and arrangement of functional groups give each molecule its unique properties

40. © 2014 Pearson Education, Inc.  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

41. © 2014 Pearson Education, Inc. Figure 4.9 Chemical GroupCompound Name Examples Ethanol Propanal Acetone Acetic acid Glycine Cysteine Glycerol phosphate Organic phosphate Thiol Amine Carboxylic acid, or organic acid Ketone Aldehyde AlcoholHydroxyl group (—OH) Carboxyl group (—COOH) Amino group (—NH 2 ) Sulfhydryl group (—SH) Phosphate group (—OPO 3 2− ) Methyl group (—CH 3 ) Methylated compound 5-Methyl cytosine Carbonyl group ( C ＝ O) — —

42. © 2014 Pearson Education, Inc. Figure 4.9a Chemical Group Compound Name Examples Ethanol Propanal Acetone Acetic acid Glycine Amine Carboxylic acid, or organic acid Ketone Aldehyde Alcohol Hydroxyl group (—OH) Carboxyl group (—COOH) Amino group (—NH 2 ) Carbonyl group ( C ＝ O) — —

43. © 2014 Pearson Education, Inc. Figure 4.9aa Ethanol, the alcohol present in alcoholic beverages Polar due to electronegative oxygen. Forms hydrogen bonds with water. Compound name: Alcohol Hydroxyl group (—OH) (may be written HO—)

44. © 2014 Pearson Education, Inc. Figure 4.9ab Propanal, an aldehyde Acetone, the simplest ketone Sugars with ketone groups are called ketoses; those with aldehydes are called aldoses. Compound name: Ketone or aldehyde Carbonyl group ( C ＝ O) — —

45. © 2014 Pearson Education, Inc. Figure 4.9ac Acetic acid, which gives vinegar its sour taste Acts as an acid. Compound name: Carboxylic acid, or organic acid Carboxyl group (—COOH) Ionized form of —COOH (carboxylate ion), found in cells

46. © 2014 Pearson Education, Inc. Figure 4.9ad Glycine, an amino acid (note its carboxyl group) Acts as a base. Compound name: Amine Amino group (—NH 2 ) Ionized form of —NH 2, found in cells

47. © 2014 Pearson Education, Inc. Figure 4.9b Cysteine Glycerol phosphate Organic phosphate Thiol Sulfhydryl group (—SH) Phosphate group (—OPO 3 2− ) Methyl group (—CH 3 ) Methylated compound 5-Methyl cytosine Chemical Group Compound Name Examples

48. © 2014 Pearson Education, Inc. Figure 4.9ba Cysteine, a sulfur- containing amino acid Two —SH groups can react, forming a “cross-link” that helps stabilize protein structure. Compound name: Thiol Sulfhydryl group (—SH) (may be written HS—)

49. © 2014 Pearson Education, Inc. Figure 4.9bb Glycerol phosphate, which takes part in many important chemical reactions in cells Contributes negative charge. When attached, confers on a molecule the ability to react with water, releasing energy. Compound name: Organic phosphate Phosphate group (—OPO 3 2− )

50. © 2014 Pearson Education, Inc. Figure 4.9bc Methyl group (—CH 3 ) Affects the expression of genes. Affects the shape and function of sex hormones. Compound name: Methylated compound 5-Methyl cytosine, a component of DNA that has been modified by addition of a methyl group

51. © 2014 Pearson Education, Inc. ATP: An Important Source of Energy for Cellular Processes  An important organic phosphate is adenosine triphosphate (ATP)  ATP consists of an organic molecule called adenosine attached to a string of three phosphate groups  ATP stores the potential to react with water, a reaction that releases energy to be used by the cell

52. © 2014 Pearson Education, Inc. Figure 4.UN04 Adenosine

53. © 2014 Pearson Education, Inc. Figure 4.UN05 Reacts with H 2 O Inorganic phosphate ADP Energy Adenosine ATP PPPPPP i

54. © 2014 Pearson Education, Inc. The Chemical Elements of Life: A Review  The versatility of carbon makes possible the great diversity of organic molecules  Variation at the molecular level lies at the foundation of all biological diversity

55. © 2014 Pearson Education, Inc. Figure 4.UN01a

56. © 2014 Pearson Education, Inc. Figure 4.UN01b Some of Stanley Miller’s notes from his 1958 hydrogen sulfide (H 2 S) experiment

57. © 2014 Pearson Education, Inc. Figure 4.UN01c Some of Stanley Miller’s original vials from his 1958 hydrogen sulfide (H 2 S) experiment

58. © 2014 Pearson Education, Inc. Figure 4.UN06

59. © 2014 Pearson Education, Inc. Figure 4.UN07

60. © 2014 Pearson Education, Inc. Figure 4.UN08 abc de

61. © 2014 Pearson Education, Inc. Figure 4.UN09 L-dopaD-dopa

62. © 2014 Pearson Education, Inc. Figure 4.UN10