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Organic Chemistry Chapter 03. Organic Chemistry 2Outline Organic vs Inorganic Functional Groups and Isomers Macromolecules Carbohydrates Carbohydrates.

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Presentation on theme: "Organic Chemistry Chapter 03. Organic Chemistry 2Outline Organic vs Inorganic Functional Groups and Isomers Macromolecules Carbohydrates Carbohydrates."— Presentation transcript:

1 Organic Chemistry Chapter 03

2 Organic Chemistry 2Outline Organic vs Inorganic Functional Groups and Isomers Macromolecules Carbohydrates Carbohydrates Lipids Lipids Proteins Proteins Nucleic Acids Nucleic Acids

3 Organic Chemistry 3 Organic Molecules Inorganic – Chemistry of elements other than carbon Organic – Carbon-based chemistry Usually associated living systems Often associated with nonliving matter Often quite large, with many atoms Always with few atoms Always covalent bonding Usually ionic bonding Always contain carbon and hydrogen Usually with + & - ions OrganicInorganic

4 4 Carbohydrates as structural materials

5 Organic Chemistry 5 Carbon Atom Carbon atoms: Contain a total of 6 electrons Contain a total of 6 electrons Only four electrons in the outer shell Only four electrons in the outer shell Very diverse as one atom can bond with up to four other atoms Very diverse as one atom can bond with up to four other atoms Often bonds with other carbon atoms to make hydrocarbons Can produce long carbon chains like octane Can produce long carbon chains like octane Can produce ring forms like cyclohexane Can produce ring forms like cyclohexane

6 6 Octane & Cyclohexane

7 Organic Chemistry 7 Functional Groups and Isomers Functional groups: Specific combinations of bonded atoms Specific combinations of bonded atoms Attached as a group to other molecules Attached as a group to other molecules ­Always react in the same manner, regardless of where attached ­Determine activity and polarity of large organic molecules Many functional groups, but only a few are of major biological importance

8 Organic Chemistry 8 Polar; some sugars Example: Acetone Polar, forms H-bonds; some sugars and amino acids Example: Ethanol ROH R H C O RR C O R C O R H N H RSH Biologically Important Functional Groups Thiols Phosphate Amines Amino Carboxylic Acids Carboxyl Ketones Aldehydes Carbonyl AlcoholsHydroxyl CompoundStructureGroup Sulfhydryl RR C O OH Organic Phosphates Significance Polar; some sugars Example: Formaldehyde Polar, acidic; fats and amino acids Example: Acetic acid Polar, basic; amino acids Example: Tryptophan Disulfide Bonds; some amino acids Example: Ethanethiol Polar, acidic; some amino acids Example: Adenosine triphosphate Polar, forms H-bonds; some sugars and amino acids; Example: Ethanol Polar; some sugars Example: Formaldehyde Polar; some sugars Example: Acetone Polar, acidic; fats and amino acids Example: Acetic acid Polar, acidic; some amino acids Example: Adenosine triphosphate Disulfide Bonds; some amino acids Example: Ethanethiol Polar, basic; amino acids Example: Tryptophan

9 Organic Chemistry 9Isomers Isomers - organic molecules that have: Identical molecular formulas, but Identical molecular formulas, but Differing internal arrangement of atoms Differing internal arrangement of atoms

10 Organic Chemistry 10Macromolecules Some molecules called macromolecules because of their large size Usually consist of many repeating units Resulting molecule is a polymer (many parts) Resulting molecule is a polymer (many parts) Repeating units are called monomers Repeating units are called monomers Some examples: NucleotideDNA, RNA Nucleic Acids Amino acidPolypeptide Proteins MonosaccharidePolysaccharide Carbohydrates Glycerol & fatty acidsFat Lipids Subunit(s)ExampleCategory

11 11 Common Foods

12 Organic Chemistry 12 Dehydration and Hydrolysis Dehydration - Removal of water molecule Used to connect monomers together to make polymers Used to connect monomers together to make polymers Polymerization of glucose monomers to make starch Polymerization of glucose monomers to make starch Hydrolysis - Addition of water molecule Used to disassemble polymers into monomer parts Used to disassemble polymers into monomer parts Digestion of starch into glucose monomers Digestion of starch into glucose monomers Specific enzymes required for each reaction Accelerate reaction Accelerate reaction Are not used in the reaction Are not used in the reaction

13 13 Synthesis and Degradation of Polymers

14 Organic Chemistry 14 Four Classes of Organics: 1 - Carbohydrates Monosaccharides: Single sugar molecule Single sugar molecule Glucose, ribose, deoxyribose Glucose, ribose, deoxyribose Disaccharides: Contain two monosaccharides joined during dehydration reaction Contain two monosaccharides joined during dehydration reaction Sucrose Sucrose Polysaccharides: Polymers of monosaccharides Starch, cellulose, chitin Starch, cellulose, chitin

15 15 Popular Models for Representing Glucose Molecules

16 16 Synthesis and Degradation of Maltose, a Disaccharide

17 Organic Chemistry 17 Carbohydrates Examples: Monosaccharides Single sugar molecules Quite soluble and sweet to taste Examples Glucose (blood), fructose (fruit) and galactose Glucose (blood), fructose (fruit) and galactose ­Hexoses - Six carbon atoms ­Isomers of C 6 H 12 O 6 Ribose and deoxyribose (in nucleotides) Ribose and deoxyribose (in nucleotides) ­Pentoses – Five carbon atoms ­C 5 H 10 O 5 & C 5 H 10 O 4

18 Organic Chemistry 18 Carbohydrates Examples: Disaccharides Contain two monosaccharides joined by dehydration reaction Soluble and sweet to taste Examples Sucrose Sucrose ­Table sugar, maple sugar ­One glucose and one fructose joined by dehydration Maltose Maltose ­Malt sugar ­Two glucoses joined by dehydration

19 Organic Chemistry 19 Carbohydrates Examples: Polysaccharides (1) Polymers of monosaccharides Low solubility; not sweet to taste Examples Starch Starch ­Polymer of glucose ­Used for short-term energy storage Plant starch Plant starch Often branched chain Amylose, corn starch Animal starch Animal starchUnbranched Glycogen in liver and muscles

20 Organic Chemistry 20 Carbohydrates Examples: Polysaccharides (2) More polysaccharide examples Cellulose Cellulose ­Long, coiled polymer of glucose ­Glucoses connected differently than in starch ­Structural element for plants ­Main component of wood and many natural fibers ­Indigestible by most animals Chitin Chitin ­Polymer of glucose ­Each glucose with an amino group ­Very resistant to wear and digestion ­Arthropod exoskeletons, cell walls of fungi

21 21 Starch Structure and Function

22 22 Glycogen Structure and Function

23 23 Cellulose Structure and Function

24 Organic Chemistry 24 Four Classes of Organics: 2 - Lipids Insoluble in water Long chains of repeating CH 2 units Long chains of repeating CH 2 units Renders molecule nonpolar Renders molecule nonpolar Types of Lipids Medicines Component of plasma membrane; hormones Steroids No-stick pan spray Component of plasma membrane Phospholipids Cooking oils Long-term energy storage in plants and their seeds Oils Butter, lard Long-term energy storage & thermal insulation in animals Fats Human Uses Organismal Uses Type Candles, polishes Wear resistance; retain water Waxes

25 25 Blubber

26 26 Types of Lipids: Triglycerides

27 Organic Chemistry 27 Types of Lipids: Triglycerides (1) Triglycerides (Fats) Long-term energy storage Long-term energy storage Backbone of one glycerol molecule Backbone of one glycerol molecule ­Three-carbon alcohol ­Each has an OH - group Three fatty acids attached to each glycerol molecule Three fatty acids attached to each glycerol molecule ­Long hydrocarbon chain Saturated - no double bonds between carbons Saturated - no double bonds between carbons Unsaturated - 1 double bonds between carbons Unsaturated - 1 double bonds between carbons ­Carboxylic acid at one end ­Carboxylic acid connects to –OH on glycerol in dehydration reaction

28 28 Dehydration Synthesis of Triglyceride from Glycerol and Three Fatty Acids

29 Organic Chemistry 29 Types of Lipids: Phospholipids (2) Phospholipids Derived from triglycerides Glycerol backbone Glycerol backbone Two fatty acids attached instead of three Two fatty acids attached instead of three Third fatty acid replaced by phosphate group Third fatty acid replaced by phosphate group ­The fatty acids are nonpolar and hydrophobic ­The phosphate group is polar and hydrophilic Molecules self arrange when placed in water Polar phosphate heads next to water Polar phosphate heads next to water Nonpolar fatty acid tails overlap and exclude water Nonpolar fatty acid tails overlap and exclude water Spontaneously form double layer & a sphere Spontaneously form double layer & a sphere

30 30 Phospholipids Form Membranes

31 Organic Chemistry 31 Types of Lipids: Steroids & Waxes (3) Steroids Cholesterol, testosterone, estrogen Cholesterol, testosterone, estrogen Skeletons of four fused carbon rings Skeletons of four fused carbon ringsWaxes Long-chain fatty acid bonded to a long-chain alcohol Long-chain fatty acid bonded to a long-chain alcohol ­High melting point ­Waterproof ­Resistant to degradation

32 32 Steroid Diversity

33 33 Waxes

34 Organic Chemistry 34 Four Classes of Organics: 3 -Proteins Functions Support – Collagen Support – Collagen Enzymes – Almost all enzymes are proteins Enzymes – Almost all enzymes are proteins Transport – Hemoglobin; membrane proteins Transport – Hemoglobin; membrane proteins Defense – Antibodies Defense – Antibodies Hormones – Many hormones; insulin Hormones – Many hormones; insulin Motion – Muscle proteins, microtubules Motion – Muscle proteins, microtubules

35 Organic Chemistry 35 Protein Subunits: The Amino Acids Proteins are polymers of amino acids Each amino acid has a central carbon atom (the alpha carbon) to which are attached a hydrogen atom, a hydrogen atom, an amino group –NH 2, an amino group –NH 2, A carboxylic acid group –COOH, A carboxylic acid group –COOH, and one of 20 different types of –R (remainder) groups and one of 20 different types of –R (remainder) groups There are 20 different amino acids that make up proteins All of them have basically the same structure except for what occurs at the placeholder R

36 36 Structural Formulas for the 20 Amino Acids

37 Organic Chemistry 37 Proteins: The Polypeptide Backbone Amino acids joined together end-to-end COOH of one AA covalently bonds to the NH 2 of the next AA COOH of one AA covalently bonds to the NH 2 of the next AA Special name for this bond - Peptide Bond Special name for this bond - Peptide Bond ­Two AAs bonded together – Dipeptide ­Three AAs bonded together – Tripeptide ­Many AAs bonded together – Polypeptide Characteristics of a protein determined by composition and sequence of AAs Characteristics of a protein determined by composition and sequence of AAs Virtually unlimited number of proteins Virtually unlimited number of proteins

38 38 Synthesis and Degradation of a Peptide

39 Organic Chemistry 39 Protein Molecules: Levels of Structure Primary: Literally, the sequence of amino acids Literally, the sequence of amino acids A string of beads (up to 20 different colors) A string of beads (up to 20 different colors) Secondary: The way the amino acid chain coils or folds The way the amino acid chain coils or folds Describing the way a knot is tied Describing the way a knot is tied Tertiary: Overall three-dimensional shape of a polypeptide Overall three-dimensional shape of a polypeptide Describing what a knot looks like from the outside Describing what a knot looks like from the outside Quaternary: Consists of more than one polypeptide Consists of more than one polypeptide Like several completed knots glued together Like several completed knots glued together

40 40 Levels of Protein Organization

41 41 Examples of Fibrous Proteins

42 Organic Chemistry 42 Protein-folding Diseases Assembly of AAs into protein extremely complex Process overseen by chaperone molecules Inhibit incorrect interactions between R groups as polypeptide grows Inhibit incorrect interactions between R groups as polypeptide grows Defects in these chaperones can corrupt the tertiary structure of proteins Defects in these chaperones can corrupt the tertiary structure of proteins Mad cow disease could be due to mis-folded proteins Mad cow disease could be due to mis-folded proteins

43 Organic Chemistry 43 Four Classes of Organics: 4 -Nucleic Acids Polymers of nucleotides Very specific cell functions DNA (deoxyribonucleic acid) DNA (deoxyribonucleic acid) ­Double-stranded helical spiral (twisted ladder) ­Serves as genetic information center ­In chromosomes RNA (ribonucleic acid) RNA (ribonucleic acid) ­Part single-stranded, part double-stranded ­Serves primarily in assembly of proteins ­In nucleus and cytoplasm of cell

44 Organic Chemistry 44 The Nucleotides of Nucleic Acids Three components: ­A phosphate group, ­A pentose sugar (ribose or deoxyribose), and ­A nitrogenous base (4 kinds in DNA, 3 kinds in RNA, 3 common to both Nucleotide subunits connected end-to-end to make nucleic acid Nucleotide subunits connected end-to-end to make nucleic acid Sugar of one connected to the phosphate of the next Sugar of one connected to the phosphate of the next Sugar-phosphate backbone Sugar-phosphate backbone

45 45 Nucleotides

46 46 DNA Structure

47 47 RNA Structure

48 Organic Chemistry 48NoYes Helix Interprets genetic info; protein synthesis Heredity; cellular control center Function Cell nucleus and cytoplasm Chromosomes of cell nucleus Where Comparison of DNA & RNA Table 3.4 Mostly single stranded Double-stranded; Pairing across strands Strands Cytosine, guanine; adenine, uracil Cytosine, guanine; adenine, thymine Bases RiboseDeoxyribose Sugar RNADNAFeature

49 Organic Chemistry 49 Other Nucleic Acids ATP (adenosine triphosphate) is composed of adenine, ribose, and three phosphates In cells, one phosphate bond is hydrolyzed – Yields: The molecule ADP (adenosine diphosphate) The molecule ADP (adenosine diphosphate) An inorganic phosphate molecule p i An inorganic phosphate molecule p i Energy Energy Other energy sources used to put ADP and p i back together again

50 50 ATP

51 Organic Chemistry 51Review Organic vs Inorganic Functional Groups and Isomers Macromolecules Carbohydrates Carbohydrates Lipids Lipids Proteins Proteins Nucleic Acids Nucleic Acids

52 Organic Chemistry Ending Slide Chapter 03


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