Carbon has four valence electrons to make covalent bonds Carbon is the backbone of biological molecule.

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1 Slide 1 / 97 Slide 2 / 97 Organic hemistry Organic hemistry: arbon and the Molecular iversity of Life Organic chemistry is the study of carbon compounds Organic compounds range from simple molecules to colossal ones. Most organic compounds contain hydrogen atoms in addition to carbon atoms. ompounds containing only carbon and hydrogen are called hydrocarbons; they are commonly used as a fuel source. Slide 3 / 97 Slide 4 / 97 iological Molecules arbon arbon has four valence electrons to make covalent bonds arbon is the backbone of biological molecule. arbon atoms can form diverse molecules by bonding to four other atoms arbon has the ability to form long chains. Recall that electron configuration is the key to an atom s characteristics because it determines the kinds of bonds and number of bonds an atom will form with other atoms This property allows the formation of large biomolecules (such as proteins, lipids, carbohydrates, and nucleic acids). Slide 5 / 97 1 Organic chemistry is a science based on the study of. compounds that can only be made by living cells. vital forces interacting with matter. carbon compounds. water and its interaction with other kinds of molecules. Slide 6 / 97 2 Which property of the carbon atom allows it to bond with many different elements? arbon has 6 to 8 neutrons. arbon has 4 valence electrons. arbon forms ionic bonds. and only,, and

2 Slide 7 / 97 3 How many electron pairs does carbon share in order to complete its valence shell? Slide 8 / 97 4 What type/s of bond/s does carbon have a tendency to form? Ionic Hydrogen ovalent and, and Slide 9 / 97 Hydrocarbons Hydrocarbons are compounds made up of carbon and hydrogen atoms liphatic hydrocarbons: compounds with carbon atoms connected in a straight chain Slide 10 / 97 liphatic hydrocarbons: lkanes Hydrocarbon chains where all the bonds between carbons are SINGL bonds They are also known as saturated hydrocarbons. They are saturated with hydrogens. liphatic compounds consist of three classes of compounds: lkanes lkenes lkynes romatic hydrocarbons: compounds with carbon atoms connected in cyclic (ringed) structures that have an odor Name uses the ending -ane xamples: Methane, Propane, utane, Octane Slide 11 / 97 Slide 12 / 97 lkanes lkanes The general formula nh2n+2 n = number of carbon atoms H4 Methane 2H 6 thane Heptane 3H 8 Propane Octane Hexane 4H10 utane Nonane 5H12 Pentane ecane

3 Slide 13 / 97 Slide 14 / 97 ranched hain lkanes Straight hain lkanes Straight chain alkanes are alkanes that have all their carbon atoms connected in a row. ranched chain alkanes are alkanes that have a branching connection of carbons. For example, butane has the formula H Shown below are the straight chain and branched forms of butane. These are structural formulas. H3-H2-H3 This is a condensed formula for propane. H3-H2-H2-H3 Straight chain butane Slide 15 / 97 lkanes ranched chain butane Slide 16 / 97 5 What is the reason why hydrocarbons are not soluble in water? The majority of their bonds are polar covalent -H linkages The majority of their bonds are nonpolar covalent -H linkages They are hydrophilic Hydrocarbons are non polar, since the difference in electronegativity between and H is below 0.5. Note that larger molecules are more polarizable and therefore have stronger London dispersion forces which increases boiling point. They exhibit considerable molecular complexity and diversity They are lighter than water Slide 17 / 97 6 Gasoline and water do not mix because gasoline is. Slide 18 / 97 7 Which substance would be the most soluble in gasoline? less dense than water water less viscous than wtaer sodium nitrate, NaNO3 nonpolar and water is polar hydochloric acid, Hl volatile and water is not hexane, 6H14 polar and water is nonpolar sodium chloride, Nal

4 Slide 19 / 97 Slide 20 / 97 liphatic hydrocarbons: lkynes liphatic hydrocarbons: lkenes lkenes have at least one double bond between two carbon atoms. General formula: nh2n where n = # of carbon atoms lkynes have at least one triple bond between two carbon atoms. The name uses the ending -ene. The name uses the ending -yne. The simplest alkynes are: The simplest alkenes are: 2H4 thene (from 2-carbon parent, ethane) 3H 6 Propene (from 3-carbon parent, propane) thene General formula: nh2n-2 where n = # of carbon atoms 2H2 thyne (commonly known as acetylene) 3H4 Propyne or propylene Slide 21 / 97 Slide 22 / 97 ycloalkanes Representing liphatic Hydrocarbons all and stick model Space filling model Structural formula thyne Molecular formula arbon can also form ringed structures. Five- and six-membered rings are most stable. They can take on conformations in which their bond angles are very close to the tetrahedral angle. Smaller rings are quite strained Slide 23 / 97 Slide 24 / 97 romatic hydrocarbons They have benzene ring structure ( hexagon) and have particular aroma associated with it. H3 8 Hydrocarbons are polar. are held together by ionic bonds. contain nitrogen. contain only hydrogen and carbon atoms. enzene Toluene ( methyl benzene) are held together by hydrogen bonds.

5 Slide 25 / 97 9 Hydrocarbons containing only single bonds between the carbon atoms are called. Slide 26 / 97 alkenes alkynes aromatics alkanes ketones The general formula of an alkane is. 10 2nH2n+2 nh2n nh2n+2 nh2n-2 n Hn Slide 27 / 97 Which is the formula of an alkane? 11 10H10 10H18 10H20 10H22 10H24 Slide 28 / 97 The molecular geometry of each carbon aton in an alkane is. 12 octahedral sqaure planar trigonal planar tetrahedral trigonal pyramidal Slide 29 / Hydrocarbons containing carbon-carbon triple bonds are called. alkenes alkynes aromatics alkanes ketones Slide 30 / 97 Which is the formula of an alkyne? 14 10H10 10H18 10H20 10H22 10H24

6 Slide 31 / n alkene has at least one and has the general formula. Slide 32 / could be the formula of an alkene. 3H 8 - double bond, nh2n 3H 6 - triple bond, nh2n 6H 6 - double bond, nh2n-2 - triple bond, nh2n-2 17H36 H8 - single bond, nh2n+2 Slide 33 / Which of the following hydrocarbons has a double bond in its carbon skeleton? 3H 8 18 The compound below is an. alkyne alkene 2H 6 alkane H4 aromatic compound 2H 4 Slide 34 / 97 2H 2 olefin Slide 35 / Slide 36 / 97 Isomers The gasoline consumed by an automobile is a fossil fuel consisting mostly of Hydrocarbons exhibit a phenomenon called isomerism- existence of different molecular arrangement but same formula aldehydes amino acidd alcohols Isomers are compounds with the same molecular formula but different structures and properties. hydrocarbons There are 3 different types of isomers: thiols Structural isomers Geometric isomers nantiomers click here for an animation on Isomers

7 Slide 37 / 97 Slide 38 / 97 Structural Isomers Structural isomers have different covalent arrangements of their atoms. These three compounds all have the same molecular formula, but differ in which atoms are bonded together. Geometric Isomers Geometric isomers must contain a = double bond. Geometric isomers have the same covalent arrangements but differ in spatial arrangements. Geometric isomers are referred to as either cis or trans. cis isomer The two H3 groups are on the same side. Slide 39 / 97 trans isomer: The two H3 groups are on opposite sides. Slide 40 / Structural isomers are molecules that: are enantiomers. are hydrocarbons. have a ring structure. are mirror images. Slide 41 / The two molecules shown are best described as differ in the covalent arrangements of their atoms. Slide 42 / Which of the following is true of geometric isomers? optical isomers They have variations in arrangement around a double bond. radioactive isotopes They have an asymmetric carbon that makes them mirror images. They have the same chemical properties. They have different molecular formulas. Their atoms and bonds are arranged in different sequences structural isomers nonradioactive isotopes geometric isomers

8 Slide 43 / 97 Slide 44 / 97 Functional groups functional group is an atom or group of atoms that imparts special physical and chemical properties to the compound ased on the functional group, the compounds are classified as follows. Haloalkanes/alkenes/alkynes lcohols cids mines Ketones ldehydes sters ther Halo- alkanes/alkenes/alkynes Haloalkanes, haloalkenes, and haloalkynes are characterized by the presence of a halogen atom (F, l, r or I), in place of a hydrogen atom. H3l, H2l2, Hl3, l4, r4, F2=F2, F = F They are formed when one or more H atoms are replaced by halogen atom/s. Slide 45 / 97 Slide 46 / 97 lcohols lcohols contain the functional group -OH (hydroxyl group). For example, in H4, one H is replaced by -OH Naming lcohols lkane formula lkane name lcohol formula lcohol name H4 methane H3OH methanol 2H 6 ethane 2H5OH ethanol 3H 8 propane 3H7OH propanol 4H10 butane 4H9OH butanol The name ends with -ol, drop the alkane "e" add "ol", So, methane becomes methyl alcohol or methanol, H3OH. H3H2OH is called ethyl alcohol or ethanol. Thiols contain the functional group -SH, (sulfhydryl group) Slide 47 / Which of the following statements is true concerning a compound that contains a hydroxyl group? It lacks an asymmetric carbon, and it is probably a fat or lipid. It should dissolve in water. It should dissolve in a nonpolar solvent. It won't form hydrogen bonds with water. It is hydrophobic. Slide 48 / In which of the structures are the atoms bonded ionic bonds?,, None of the structures

9 Slide 49 / 97 Slide 50 / 97 arboxylic acids mines The functional group is -OOH The functional group is - NH2 Replace one H atom in the alkane by a -OOH group H3NH2, HOOH = Methanoic acid or formic acid H3OOH = thanoic acid or acetic acid or vinegar H3NH2 mino methane or Methyl amine H3H2OOH = Propanoic acid rop the "e" from the parent alkane and add "oic acid" replace one H by an -NH2 group More than one functional groups, same or different are common in organic compounds example: amino acids. They have amine and acid groups OH Slide 51 / Which of the structures contain(s) a carboxyl group? Slide 52 / What is the name of the functional group shown in the following figure? carbonyl ketone aldehyde carboxyl & hydroxyl None of the structures Slide 53 / Which two functional groups are always found in amino acids? ketone and aldehyde carbonyl and carboxyl carboxyl and amino phosphate and sulfhydryl hydroxyl and aldehyde Slide 54 / 97 Ketones The functional group is -=O or "carbonyl" group Usually sandwiched between two carbon groups H3H2H3 = propane H3O H3 propanone or acetone ( nail polish remover) rop e and add none H3O2H5 thyl methyl ketone or butanone O H3- - H3

10 Slide 55 / 97 Slide 56 / 97 Ketones ldehydes function the functional group can make! The functional group is -HO with a =O bond strogen- has two hydroxyl groups in it. drop 'e' of the parent alkane and add 'nal' HHO - (1 carbon) H3HO- (2 carbon) Methanal or Formaldehyde thanal or cetaldehyde Testosterone - one hydroxyl group is replaced by a ketone. Slide 57 / 97 ldehydes, Ketones and cids The way the carbonyl group is bonded to the main body of the molecule is different in acids, ketones and aldehydes Slide 58 / 97 What is the name of the functional group shown in the following figure? 28 (R = any carbon group) R-=O The =O is between two other carbon atoms ( alkyl groups) in the molecule R The =O group is at the end ( terminal carbon) of the molecule and should be connected to a H atom carbonyl ketone aldehyde carboxyl hydroxyl The =O bond should be connected to an OH group Slide 59 / 97 Slide 60 / 97 ster ther The functional group is -OOR where R could be another alkyl group. sters are formed by the combination of an acid and an alcohol by eliminating one molecule of water. The functional group is an O atom sandwiched between two carbon groups H3-O- H3 dimethyl ether They are usually pleasant smelling compounds ( natural oils and essence) H3OOH + H3OH --> H3OOH3 H3OOH3 methyl acetate H3OO2H5 ethyl acetate 2H5OOH3 methyl propanoate They are highly flammable and used as solvents in organic synthesis

11 Slide 61 / 97 Groups with a arbon Oxygen ouble ond (arbonyl Groups) Slide 62 / 97 mides mides are formed by the reaction of carboxylic acids with amines. ROOH + H2NR' --> -H2O ONH linkage is known as the amide linkage ( peptide) in proteins This linkage is formed when several amino acids join with their acid and amino groups together. Slide 63 / Slide 64 / 97 Which is the best description of a carbonyl group? 30 What is the name of the functional group shown below. carbonyl ketone aldehyde carboxyl an oxygen joined to a carbon by a single covalent bond a nitrogen and two hydrogens joined to a carbon by covalent bonds a carbon joined to two hydrogens by single covalent bonds hydroxyl a sulfur and a hydrogen joined to a carbon by covalent bonds a carbon atom joined to an oxygen by a double covalent bond Slide 65 / Which of the following contains nitrogen in addition to carbon, oxygen, and hydrogen? Slide 66 / What type of functional group is shown in the compound below? carbonyl ketone an alcohol such as ethanol a monosaccharide such as glucose a steroid such as testosterone an amino acid such as glycine a hydrocarbon such as benzene aldehyde carboxyl hydroxyl

12 Slide 67 / Which molecule contains an amine functional group? Slide 68 / 97 Which molecule contains an aldehyde functional group? 34 Slide 69 / Which molecule contains an alcohol functional group? Slide 70 / Which one of the following is not an alcohol? acetone glycerol ethanol cholesterol Slide 71 / 97 Macromolecules Macromolecules are large molecules composed of smaller molecules. They are complex in their structures. ethylene glycol Slide 72 / 97 Macromolecules Three of the classes of life s organic molecules are polymers: Proteins arbohydrates Nucleic acids arbon has the unique property of joining together via covalent bonding to form large (macro) molecules. Most macromolecules are polymers, built from monomers. There are some macromolecules that are not polymers: lipids phospholipids steroids

13 Slide 73 / 97 Slide 74 / 97 Polymers Polymers lthough organisms share the same limited number of monomer types, each organism is unique based on the arrangement of monomers into polymers n immense variety of polymers can be built from a small set of monomers Polymer Proteins Made of these monomers mino acids arbohydrates Simple sugars (monosaccharides) Nucleic acids Nucleotides Is a long molecule consisting of many similar building blocks called monomers Monomers form larger molecules by condensation reactions called dehydration reactions short polymer Monomer longer polymer Slide 75 / 97 Slide 76 / 97 mino cids and Proteins arbohydrates (sugars) Simple sugars are poly-hydroxy aldehydes or ketones. Table sugar, (sucrose) is made up of glucose and fructose. They all have several hydroxyl groups in their structure that makes them soluble in water. Proteins are formed when several amino acids combine together Glucose and fructose are monosaccharides. cid and amine end of the molecules join together to form long peptide chain Peptide chain with 50 or more amino acids can form an individual protein. Slide 77 / 97 arbohydrates (sugars) Sucrose is a disaccharide. glucose fructose (monosaccharide) Slide 78 / 97 Nucleic cids In solution, they form cyclic structures. These can form chains of sugars that form structural molecules such as starch and cellulose. Nucleic acids are made up of monomer units called nucleotides Sugar + ase + PO43- = nucleotide

14 Slide 79 / 97 Slide 80 / 97 Nucleic cids Two of the building blocks of RN and N are sugars (ribose or deoxyribose) and cyclic bases (adenine, guanine, cytosine, and thymine or uracil) RN cid Ribonucleic acid Sugar ribose ases make proteins Slide 81 / Which of the following is not one of the four major groups of macromolecules found in living organisms? carbohydrates lipids The bases are the rungs in the (spiral) ladder proteins The nucleotides join together via hydrogen bonding through their bases -T, -G etc. nucleic acids Slide 83 / 97 Slide 84 / amino acid protein carbohydrate nucleotide nucleic acids carry genetic code glucose The blue ribbon is the sugar/ phosphate backbone Glucose is a type of.,, G and T Slide 82 / 97 Nucleotides combine to form the familiar double-helix form of the nucleic acids 38 eoxyribonucleic acid deoxyribose,, G and U Function Nucleic cids N Nucleic acids are made up of. amino acids proteins carbohydrates nucleotides sugars

15 Slide 85 / 97 nucleotide consists of. 40 glucose + fructose + amino acid glucose + fructose + phosphate group Slide 86 / 97 Polymers of polysaccharides and proteins are all synthesized from monomers by which process? 41 amino acid + protein + phosphate group sugar + base + amino acid sugar + base + phosphate group connecting monosaccharides together (condensation reactions) the addition of water to each monomer (hydrolysis) the removal of water (dehydration reactions) ionic bonding of the monomers the formation of disulfide bridges between monomers Slide 87 / 97 Slide 88 / 97 Other complex molecules of life Fats and Lipids re a diverse group of hydrophobic molecules re the one class of large biological molecules that do not consist of polymers Share the common trait of being hydrophobic Fats and Fatty cids Fats re constructed from two types of smaller molecules, a single glycerol and usually three fatty acids Fatty acids arboxylic acids with a very long chain of carbon atoms. Vary in the length and number and locations of double bonds they contain H2OH H2OH H2OH glycerol Slide 89 / 97 a fatty acid Slide 90 / 97 ehydration Synthesis The attachment of a fatty acid to glycerol results in a removal of a water molecule. The diagram shows three fatty acids added to glycerol producing a fat molecule.

16 Slide 91 / 97 Slide 92 / 97 Saturated and Unsaturated Fatty cids Saturated fatty acids Have the maximum number of hydrogen atoms possible Have no double bonds in their carbon chain Mainly animal origin Unsaturated fatty acids Have one or more double bonds Phospholipids Have only two fatty acids Have a phosphate group instead of a third fatty acid Results in a bilayer arrangement found in cell membranes When hydrogenated ( add more Hydrogen) they become solid and saturated Mainly plant origin Slide 93 / 97 Steroids Slide 94 / re lipids characterized by a carbon skeleton consisting of three or more fused rings Which of the following is (are) true for the class of large biological molecules known as lipids? They are insoluble in water. They are an important constituent of cell membranes. They provide the least amount of energy in living organisms Only and are correct.,, and are correct. cholesterol Slide 95 / Saturated fatty acids are the predominant fatty acid in corn oil. have double bonds between carbon atoms of the fatty acids. have a higher ratio of hydrogen to carbon than do unsaturated fatty acids. are usually liquid at room temperature. are usually produced by plants. Slide 96 / The hydrogenation of vegetable oil would result in which of the following? a decrease in the number of carbon-carbon double bonds in the oil (fat) molecules an increase in the number of hydrogen atoms in the oil (fat) molecule the oil (fat) being a solid at room temperature and only,, and

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