chapter 4 Carbon and the Molecular Diversity of Life.pptx

Campbell Biology: Reece, Urry, Cain, Wasserman, Minorsky, Jackson

1. C A MPBE L L © 2014 Pearson Education, Inc. BIOLOGY Reece • Urry • Cain • Wasserman • Minorsky • Jackson TE N T H E DI T I ON 4 Carbon and the Molecular Diversity of Life

2. Carbon: The Backbone of Life © 2014 Pearson Education, Inc. 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. Figure 4.1 © 2014 Pearson Education, Inc.

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

5. Concept 4.1: Organic chemistry is the study of carbon compounds © 2014 Pearson Education, Inc. 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. 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 © 2014 Pearson Education, Inc.

7. Organic Molecules and the Origin of Life on Earth © 2014 Pearson Education, Inc. 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. Figure 4.2 Cooled “rain” containing organic molecules Cold w ater Co n de n ser “Atmosphere” CH 4 Water vapor Electrode H 2 O “ sea ” Sample for chemical analysis © 2014 Pearson Education, Inc.

9. 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 © 2014 Pearson Education, Inc.

10. Concept 4.2: Carbon atoms can form diverse molecules by bonding to four other atoms © 2014 Pearson Education, Inc. 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. The Formation of Bonds with Carbon © 2014 Pearson Education, Inc. 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. Figure 4.3 © 2014 Pearson Education, Inc. Molecule Molecul a r Formula St r uctura l Formula Ball-and-Stick Model Spac e- F illi n g Model (a) Methane CH 4 (b) Ethane C 2 H 6 (c) Ethene ( e th y le ne ) C 2 H 4

13. 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 © 2014 Pearson Education, Inc.

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

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

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

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

18. Figure 4.5 © 2014 Pearson Education, Inc. (a) Length Ethane (b) Branching (c) Double bond position Pro p ane 1-Butene (d) Presence of rings 2 - Bu t ene Bu t ane 2 - Meth y lpro p a ne (isobutane) Cyclohexane Benzene

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

20. Figure 4.5a © 2014 Pearson Education, Inc. (a) Length Et h ane Pro p ane

21. Figure 4.5b © 2014 Pearson Education, Inc. (b) Branching Butane 2-Meth y l p ropane (isobutane)

22. Figure 4.5c © 2014 Pearson Education, Inc. (c) Double bond position 1-Bute n e 2-Bute n e

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

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

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

27. Isomers © 2014 Pearson Education, Inc. 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. Figure 4.7 © 2014 Pearson Education, Inc. (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 CO 2 H CO 2 H H CH 3 L isomer CH 3 D isomer H NH 2 NH 2 C C

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

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

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

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

33. 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 © 2014 Pearson Education, Inc.

34. Figure 4.8 © 2014 Pearson Education, Inc. Drug Effects Effective Enantio m er Ineffective Enantio m er Ibu p rofen Albuterol Reduces infla m mation and pain Relaxes bronchial (airway) muscles, improving airflow in asthma patients S -Ibu p rofen R -AIbuterol S -AIb u terol R -Ibu p rofen

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

36. Figure 4.UN09 © 2014 Pearson Education, Inc. L-dopa D -dopa

37. Concept 4.3: A few chemical groups are key to molecular function © 2014 Pearson Education, Inc. 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

38. The Chemical Groups Most Important in the Processes of Life © 2014 Pearson Education, Inc. 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

39. Figure 4.UN03 © 2014 Pearson Education, Inc. Estradiol Testosterone

40. 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 © 2014 Pearson Education, Inc.

41. 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 © 2014 Pearson Education, Inc.

42. Figure 4.9 E x a m p les E thanol Pr opanal A c e tone Acetic acid Gl y cine C y steine Glycerol phosphate Organic phosphate T hiol A mine Carboxylic acid, or organic acid Ketone A ldeh y de Compound Name Alcohol Chemic a l G r oup Hydroxyl group (—OH) Carboxyl group (—COOH) Amino group (—NH 2 ) Sulfhydryl group (—SH) 3 Phosphate group (—OPO 2− ) Methyl group (—CH 3 ) M et h y lated compound 5-Methyl cytosine C ar bon y l group ( C ＝ O) © 2014 Pearson Education, Inc.

43. Figure 4.9a Exam p les Et h a no l Propanal A cet on e Acetic acid Glycine A mi n e Carboxylic acid, or organic acid Ketone A l d e h y d e Co m poun d N ame Alcohol Chemical Group Hydroxyl group (—OH) Carboxyl group (—COOH) Amino group (—NH 2 ) C ar bon y l g r ou p ( C ＝ O ) © 2014 Pearson Education, Inc.

44. Figure 4.9aa © 2014 Pearson Education, Inc. 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—)

45. 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 ) © 2014 Pearson Education, Inc.

46. Figure 4.9ac © 2014 Pearson Education, Inc. 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

47. Figure 4.9ad © 2014 Pearson Education, Inc. 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

48. Figure 4.9b © 2014 Pearson Education, Inc. Cysteine Glycerol phosphate Organic pho s ph ate 3 Phosphate group (—OPO 2− ) Methyl group (—CH 3 ) M et h y lated compound 5-Methyl cytosine Chemical Group Sulfhydryl group (—SH) Co m poun d N ame Thiol Exam p les

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

50. Figure 4.9bb © 2014 Pearson Education, Inc. 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− )

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

52. ATP: An Important Source of Energy for Cellular Processes © 2014 Pearson Education, Inc. 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

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

54. Figure 4.UN05 © 2014 Pearson Education, Inc. Reacts with H 2 O A DP En e rgy Adenosine P P P Adenosine ATP P i P P Inorganic p h osp h ate

55. The Chemical Elements of Life: A Review © 2014 Pearson Education, Inc. 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

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

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

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

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

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

61. Figure 4.UN08 © 2014 Pearson Education, Inc. a b c d e

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