Introduction to Organic Compounds Carbohydrates Figure 3.0_1 Chapter 3: Big Ideas Lipids Proteins Nucleic Acids 1

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The Chemical Building Blocks of Life Four major classes of molecules are essential to life: Carbohydrates Proteins Lipids Nucleic acids Each of these molecules is made up of varying combinations of carbon, hydrogen, oxygen, nitrogen, phosphorus, and sulfur

The Chemical Building Blocks of Life Small organic molecules can covalently bond to other organic molecules to form macromolecules Macromolecules are made up of building blocks called polymers, which contain small, repeating organic molecules known as monomers

Figure 5.12 Polymers Are Long Chains Made from Repeating Units Known as Monomers A handful of monomers can be assembled into a great variety of polymers. The formula is: number of available monomersn, where n is the chain length (total number of monomers in each polymer). In this example, we have 56, which is 15,625.

Structural formula Ball-and-stick model Space-filling model Figure 3.1A Structural formula Ball-and-stick model Space-filling model Figure 3.1A Three representations of methane (CH4) The four single bonds of carbon point to the corners of a tetrahedron. p. 34 7

TABLE 5.1 The Versatility of Carbon Atoms

Length. Carbon skeletons vary in length. Figure 3.1B_1 Length. Carbon skeletons vary in length. Ethane Propane Figure 3.1B_1 Four ways that carbon skeletons can vary (part 1) p. 34 10

Skeletons may be unbranched or branched. Figure 3.1B_2 Branching. Skeletons may be unbranched or branched. Figure 3.1B_2 Four ways that carbon skeletons can vary (part 2) Butane Isobutane p. 34 11

Skeletons may have double bonds. Figure 3.1B_3 Double bonds. Skeletons may have double bonds. 1-Butene 2-Butene Figure 3.1B_3 Four ways that carbon skeletons can vary (part 3) p. 34 12

Rings. Skeletons may be arranged in rings. Figure 3.1B_4 Rings. Skeletons may be arranged in rings. Figure 3.1B_4 Four ways that carbon skeletons can vary (part 4) Cyclohexane Benzene p. 34 13

The properties of organic polymers depend on the clusters of atoms covalently bonded together, called functional groups

The functional groups are hydroxyl group—consists of a hydrogen bonded to an oxygen, carbonyl group—a carbon linked by a double bond to an oxygen atom, carboxyl group—consists of a carbon double-bonded to both an oxygen and a hydroxyl group, amino group—composed of a nitrogen bonded to two hydrogen atoms and the carbon skeleton, and phosphate group—consists of a phosphorus atom bonded to four oxygen atoms. Student Misconceptions and Concerns General biology students might not have previously taken a chemistry course. The concept of molecular building blocks that cannot be seen can be abstract and difficult to comprehend for such students. Concrete examples from our diets and good images will increase comprehension. Teaching Tips A drill with interchangeable drill bits is a nice analogy to carbon skeletons with different functional groups. The analogy relates the role of different functions to different structures. © 2012 Pearson Education, Inc. 15

Table 3.2_1 Table 3.2_1 Important chemical groups of organic compounds (part 1) p. 35 16

Table 3.2_2 Table 3.2_2 Important chemical groups of organic compounds (part 2) p. 35 17

Testosterone Estradiol p. 35 Figure 3.2 Figure 3.2 Differences in the chemical groups of sex hormones p. 35 18

Polymers are broken apart by hydrolysis, the addition of water. Monomers are linked together to form polymers through dehydration reactions, which remove water. Polymers are broken apart by hydrolysis, the addition of water. All biological reactions of this sort are mediated by enzymes, which speed up chemical reactions in cells. Student Misconceptions and Concerns General biology students might not have previously taken a chemistry course. The concept of molecular building blocks that cannot be seen can be abstract and difficult to comprehend for such students. Concrete examples from our diets and good images will increase comprehension. Teaching Tips 1. Train cars linking together to form a train is a nice analogy to linking monomers to form polymers. Consider adding that as the train cars are joined, a puff of steam appears—a reference to water production and a dehydration reaction when linking molecular monomers. 2. The authors note that the great diversity of polymers mainly results from the arrangement of polymers, the different sequences made possible by combinations or permutations of the same monomers. Consider illustrating this by simply asking students how many different ways can we arrange the letters A, B, and C, using each letter, and only once, to form 3-lettered words. The answer is 6 permutations: ABC, ACB, BAC, BCA, CBA, CAB (the factorial of 3). And if letters can be repeated, the answer is 27 (= 33): AAA, BBB, CCC, ABB, ACC, etc. © 2012 Pearson Education, Inc. 19

Unlinked monomer Short polymer p. 36 Figure 3.3A_s1 Figure 3.3A_s1 Dehydration reaction building a polymer chain (step 1) p. 36 20

Dehydration reaction forms a new bond Figure 3.3A_s2 Unlinked monomer Short polymer Dehydration reaction forms a new bond Figure 3.3A_s2 Dehydration reaction building a polymer chain (step 2) Longer polymer p. 36 21

Figure 3.3B_s1 Figure 3.3B_s1 Hydrolysis breaking down a polymer (step 1) p. 36 22

Hydrolysis breaks a bond Figure 3.3B_s2 Hydrolysis breaks a bond Figure 3.3B_s2 Hydrolysis breaking down a polymer (step 2) http://www.youtube.com/watch?v=UyDnnD3fMaU http://www.youtube.com/watch?v=b7TdWLNhMtM p. 36 23

Short polymer Monomer Longer polymer Dehydration Hydrolysis Figure 3.UN01 Dehydration Hydrolysis Short polymer Monomer Longer polymer Figure 3.UN01 Reviewing the Concepts, 3.3 24

Carbohydrates Sugars are a source of stored energy and are called carbohydrates Glucose is a type of simple sugar called a monosaccharide Glucose is found in almost every cell and is involved in every chemical reaction that produces energy in living organisms

Carbohydrates Table sugar is an example of a disaccharide, which is formed when two monosaccharides, glucose and fructose, are covalently bonded Disaccharides are broken down via hydrolytic reactions, which use water to break the covalent bonds between monomers Polysaccharides are large polymers built by linking many monosaccharides together

Figure 5.13 Monosaccharides Can Bond Together to Form Disaccharides Glucose and fructose are sugar monomers that, when linked by a covalent bond, form the disaccharide sucrose, or table sugar.

Glucose (an aldose) Fructose (a ketose) Figure 3.4B Figure 3.4B Structures of glucose and fructose Glucose (an aldose) Fructose (a ketose) 28

Abbreviated structure Figure 3.4C 6 5 4 1 3 2 Figure 3.4C Three representations of the ring form of glucose Structural formula Abbreviated structure Simplified structure 29

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Glucose Glucose p. 38 Figure 3.5_s1 Figure 3.5_s1 Disaccharide formation by a dehydration reaction (step 1) p. 38 33

Glucose Glucose Maltose Figure 3.5_s2 Glucose Glucose Figure 3.5_s2 Disaccharide formation by a dehydration reaction (step 2) p. 38 Maltose 34

Figure 5.14 Monosaccharides Can Bond Together to Form Polysaccharides Cellulose, starch, and glycogen are all polymers built from glucose subunits.