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1 Slide 1 / 97 Organic Chemistry: Carbon and the Molecular Diversity of Life Organic Chemistry Slide 2 / 97 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. Compounds containing only carbon and hydrogen are called hydrocarbons; they are commonly used as a fuel source. Slide 3 / 97 Biological Molecules Carbon is the backbone of biological molecule. Carbon has the ability to form long chains. This property allows the formation of large biomolecules (such as proteins, lipids, carbohydrates, and nucleic acids).

2 Slide 4 / 97 Carbon Carbon has four valence electrons to make covalent bonds Carbon atoms can form diverse molecules by bonding to four other atoms 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 Slide 5 / 97 1 Organic chemistry is a science based on the study of. A compounds that can only be made by living cells. B vital forces interacting with matter. C carbon compounds. D 2 water and its interaction with other kinds of molecules. Which property of the carbon atom allows it to bond with many different elements? A Carbon has 6 to 8 neutrons. B Carbon has 4 valence electrons. C Carbon forms ionic bonds. D A and C only A, B, and C Slide 6 / 97

3 3 How many electron pairs does carbon share in order to complete its valence shell? Slide 7 / 97 A 1 B 2 C 3 D What type/s of bond/s does carbon have a tendency to form? Slide 8 / 97 A Ionic B Hydrogen C Covalent D A and B A, B and C Slide 9 / 97 Hydrocarbons Hydrocarbons are compounds made up of carbon and hydrogen atoms Aliphatic hydrocarbons: compounds with carbon atoms connected in a straight chain Aliphatic compounds consist of three classes of compounds: Alkanes Alkenes Alkynes Aromatic hydrocarbons: compounds with carbon atoms connected in cyclic (ringed) structures that have an odor

4 Aliphatic hydrocarbons: Alkanes Slide 10 / 97 Hydrocarbon chains where all the bonds between carbons are SINGL bonds They are also known as saturated hydrocarbons. They are saturated with hydrogens. Name uses the ending -ane xamples: Methane, Propane, Butane, Octane Slide 11 / 97 Alkanes Slide 12 / 97 Alkanes The general formula CnH2n+2 n = number of carbon atoms CH4 Methane C 2H 6 thane Heptane C 3H 8 Propane Octane Hexane C4H10 Butane Nonane C5H12 Pentane Decane

5 Slide 13 / 97 Straight Chain Alkanes Straight chain alkanes are alkanes that have all their carbon atoms connected in a row. These are structural formulas. CH3-CH2-CH3 This is a condensed formula for propane. Branched Chain Alkanes Slide 14 / 97 Branched chain alkanes are alkanes that have a branching connection of carbons. For example, butane has the formula C4H10. Shown below are the straight chain and branched forms of butane. CH3-CH2-CH2-CH3 Straight chain butane Branched chain butane Alkanes Hydrocarbons are non polar, since the difference in electronegativity between C and H is below 0.5. Note that larger molecules are more polarizable and therefore have stronger London dispersion forces which increases boiling point. Slide 15 / 97

6 Slide 16 / 97 5 What is the reason why hydrocarbons are not soluble in water? A The majority of their bonds are polar covalent C-H linkages B The majority of their bonds are nonpolar covalent C-H linkages C They are hydrophilic D 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. A less dense than water B less viscous than wtaer C nonpolar and water is polar D volatile and water is not polar and water is nonpolar Slide 18 / 97 7 Which substance would be the most soluble in gasoline? A water B sodium nitrate, NaNO3 C hydochloric acid, HCl D hexane, C6H14 sodium chloride, NaCl

7 Aliphatic hydrocarbons: Alkenes Slide 19 / 97 Alkenes have at least one double bond between two carbon atoms. General formula: CnH2n where n = # of carbon atoms The name uses the ending -ene. The simplest alkenes are: C2H4 thene (from 2-carbon parent, ethane) C 3H 6 Propene (from 3-carbon parent, propane) thene Aliphatic hydrocarbons: Alkynes Slide 20 / 97 Alkynes have at least one triple bond between two carbon atoms. General formula: CnH2n-2 where n = # of carbon atoms The name uses the ending -yne. The simplest alkynes are: C2H2 thyne (commonly known as acetylene) C3H4 Propyne or propylene thyne Slide 21 / 97 Representing Aliphatic Hydrocarbons Ball and stick model Space filling model Structural formula Molecular formula

8 Slide 22 / 97 Cycloalkanes Carbon 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 Aromatic hydrocarbons Slide 23 / 97 They have benzene ring structure ( hexagon) and have particular aroma associated with it. CH3 Benzene 8 Toluene ( methyl benzene) Hydrocarbons A are polar. B are held together by ionic bonds. C contain nitrogen. D contain only hydrogen and carbon atoms. are held together by hydrogen bonds. Slide 24 / 97

9 Slide 25 / 97 9 Hydrocarbons containing only single bonds between the carbon atoms are called. A alkenes B alkynes C aromatics D alkanes ketones Slide 26 / The general formula of an alkane is. A C2nH2n+2 B CnH2n C CnH2n+2 D CnH2n-2 Cn Hn Which is the formula of an alkane? 11 A C10H10 B C10H18 C C10H20 D C10H22 C10H24 Slide 27 / 97

10 Slide 28 / 97 The molecular geometry of each carbon aton in an alkane is. 12 A octahedral B sqaure planar C trigonal planar D tetrahedral trigonal pyramidal Slide 29 / 97 Hydrocarbons containing carbon-carbon triple bonds are called. 13 A alkenes B alkynes C aromatics D alkanes ketones Which is the formula of an alkyne? 14 A C10H10 B C10H18 C C10H20 D C10H22 C10H24 Slide 30 / 97

11 15 An alkene has at least one and has the general formula. A C-C single bond, CnH2n+2 B C-C double bond, CnH2n C C-C triple bond, CnH2n D C-C double bond, CnH2n-2 C-C triple bond, CnH2n-2 Slide 31 / 97 Slide 32 / could be the formula of an alkene. A C 3H 8 B C 3H 6 C C 6H 6 D C17H36 CH8 Slide 33 / Which of the following hydrocarbons has a double bond in its carbon skeleton? A C 3H 8 B C 2H 6 C CH4 D C 2H 4 C 2H 2

12 Slide 34 / The compound below is an. A alkyne B alkene C alkane D aromatic compound olefin Slide 35 / The gasoline consumed by an automobile is a fossil fuel consisting mostly of A aldehydes B amino acidd C alcohols D hydrocarbons thiols Slide 36 / 97 Isomers Hydrocarbons exhibit a phenomenon called isomerism- existence of different molecular arrangement but same formula Isomers are compounds with the same molecular formula but different structures and properties. There are 3 different types of isomers: Structural isomers Geometric isomers nantiomers click here for an animation on Isomers

13 Slide 37 / 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. Slide 38 / 97 Geometric Isomers Geometric isomers must contain a C=C 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 CH3 groups are on the same side. trans isomer: The two CH3 groups are on opposite sides. Slide 39 / 97

14 Structural isomers are molecules that: 20 Slide 40 / 97 A are enantiomers. B are hydrocarbons. C have a ring structure. D are mirror images. differ in the covalent arrangements of their atoms. Slide 41 / 97 The two molecules shown are best described as 21 A optical isomers B radioactive isotopes C structural isomers D nonradioactive isotopes geometric isomers Slide 42 / Which of the following is true of geometric isomers? A They have variations in arrangement around a double bond. B They have an asymmetric carbon that makes them mirror images. C They have the same chemical properties. D They have different molecular formulas. Their atoms and bonds are arranged in different sequences

15 Functional groups Slide 43 / 97 A functional group is an atom or group of atoms that imparts special physical and chemical properties to the compound Based on the functional group, the compounds are classified as follows. Haloalkanes/alkenes/alkynes Alcohols Acids Amines Ketones Aldehydes sters ther Slide 44 / 97 Halo- alkanes/alkenes/alkynes Haloalkanes, haloalkenes, and haloalkynes are characterized by the presence of a halogen atom (F, Cl, Br or I), in place of a hydrogen atom. CH3Cl, CH2Cl2, CHCl3, CCl4, CBr4, F2C=CF2, FC = CF They are formed when one or more H atoms are replaced by halogen atom/s. Alcohols Alcohols contain the functional group -OH (hydroxyl group). For example, in CH4, one H is replaced by -OH The name ends with -ol, drop the alkane "e" add "ol", So, methane becomes methyl alcohol or methanol, CH3OH. CH3CH2OH is called ethyl alcohol or ethanol. Thiols contain the functional group -SH, (sulfhydryl group) Slide 45 / 97

16 Slide 46 / 97 Naming Alcohols Alkane formula Alkane name Alcohol formula Alcohol name CH4 methane CH3OH methanol C 2H 6 ethane C2H5OH ethanol C 3H 8 propane C3H7OH propanol C4H10 butane C4H9OH butanol Which of the following statements is true concerning a compound that contains a hydroxyl group? 23 Slide 47 / 97 A It lacks an asymmetric carbon, and it is probably a fat or lipid. B It should dissolve in water. C It should dissolve in a nonpolar solvent. D It won't form hydrogen bonds with water. It is hydrophobic. Slide 48 / In which of the structures are the atoms bonded ionic bonds? A A B B C C D C, D, None of the structures

17 Slide 49 / 97 Carboxylic acids The functional group is -COOH Replace one H atom in the alkane by a -COOH group HCOOH = Methanoic acid or formic acid CH3COOH = thanoic acid or acetic acid or vinegar CH3CH2COOH = Propanoic acid Drop the "e" from the parent alkane and add "oic acid" C C C OH Slide 50 / 97 Amines The functional group is - NH2 CH3NH2, replace one H by an -NH2 group CH3NH2 Amino methane or Methyl amine More than one functional groups, same or different are common in organic compounds example: amino acids. They have amine and acid groups Slide 51 / Which of the structures contain(s) a carboxyl group? A A B B C C D C& None of the structures

18 26 What is the name of the functional group shown in the following figure? C carbonyl ketone aldehyde D carboxyl A B Slide 52 / 97 hydroxyl Slide 53 / Which two functional groups are always found in amino acids? A ketone and aldehyde carbonyl and carboxyl carboxyl and amino phosphate and sulfhydryl hydroxyl and aldehyde B C D Ketones The functional group is -C=O or "carbonyl" group Usually sandwiched between two carbon groups CH3CH2CH3 = propane CH3CO CH3 propanone or acetone ( nail polish remover) Drop e and add none CH3COC2H5 thyl methyl ketone or butanone O H3C- C- CH3 Slide 54 / 97

19 Slide 55 / 97 Ketones A function the functional group can make! strogen- has two hydroxyl groups in it. Testosterone - one hydroxyl group is replaced by a ketone. Slide 56 / 97 Aldehydes The functional group is -CHO with a C=O bond drop 'e' of the parent alkane and add 'nal' HCHO - (1 carbon) CH3CHO- (2 carbon) Methanal or Formaldehyde thanal or Acetaldehyde Aldehydes, Ketones and Acids The way the carbonyl group is bonded to the main body of the molecule is different in acids, ketones and aldehydes The C=O is between two other carbon atoms ( alkyl groups) in the molecule The C=O group is at the end ( terminal carbon) of the molecule and should be connected to a H atom The C=O bond should be connected to an OH group Slide 57 / 97

20 What is the name of the functional group shown in the following figure? 28 Slide 58 / 97 (R = any carbon group) R-C=O R A B C D carbonyl ketone aldehyde carboxyl hydroxyl Slide 59 / 97 ster The functional group is -COOR 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. They are usually pleasant smelling compounds ( natural oils and essence) CH3COOH + CH3OH --> CH3COOCH3 CH3COOCH3 methyl acetate CH3COOC2H5 ethyl acetate C2H5COOCH3 methyl propanoate Slide 60 / 97 ther The functional group is an O atom sandwiched between two carbon groups CH3-O- CH3 dimethyl ether They are highly flammable and used as solvents in organic synthesis

21 Slide 61 / 97 Groups with a Carbon Oxygen Double Bond (Carbonyl Groups) Amides Slide 62 / 97 Amides are formed by the reaction of carboxylic acids with amines. RCOOH + H2NR' --> -H2O CONH 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 / Which is the best description of a carbonyl group? A an oxygen joined to a carbon by a single covalent bond B a nitrogen and two hydrogens joined to a carbon by covalent bonds C a carbon joined to two hydrogens by single covalent bonds D a sulfur and a hydrogen joined to a carbon by covalent bonds a carbon atom joined to an oxygen by a double covalent bond

22 Slide 64 / What is the name of the functional group shown below. A carbonyl B ketone C aldehyde D carboxyl hydroxyl 31 Which of the following contains nitrogen in addition to carbon, oxygen, and hydrogen? Slide 65 / 97 A an alcohol such as ethanol B a monosaccharide such as glucose C a steroid such as testosterone D an amino acid such as glycine a hydrocarbon such as benzene 32 What type of functional group is shown in the compound below? A carbonyl B ketone C aldehyde D carboxyl hydroxyl Slide 66 / 97

23 33 Which molecule contains an amine functional group? 34 Which molecule contains an aldehyde functional group? 35 Which molecule contains an alcohol functional group? Slide 67 / 97 Slide 68 / 97 Slide 69 / 97

24 Slide 70 / Which one of the following is not an alcohol? A acetone B glycerol C ethanol D cholesterol ethylene glycol Slide 71 / 97 Macromolecules Macromolecules are large molecules composed of smaller molecules. They are complex in their structures. Carbon has the unique property of joining together via covalent bonding to form large (macro) molecules. Most macromolecules are polymers, built from monomers. Slide 72 / 97 Macromolecules Three of the classes of life s organic molecules are polymers: Proteins Carbohydrates Nucleic acids There are some macromolecules that are not polymers: lipids phospholipids steroids

25 Slide 73 / 97 Polymers Although organisms share the same limited number of monomer types, each organism is unique based on the arrangement of monomers into polymers An immense variety of polymers can be built from a small set of monomers Polymer Proteins Made of these monomers Amino acids Carbohydrates Simple sugars (monosaccharides) Nucleic acids Nucleotides Slide 74 / 97 Polymers 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 Amino Acids and Proteins Proteins are formed when several amino acids combine together Acid 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 75 / 97

26 Carbohydrates (sugars) Slide 76 / 97 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. C Glucose and fructose are monosaccharides. Sucrose is a disaccharide. glucose fructose (monosaccharide) Carbohydrates (sugars) Slide 77 / 97 In solution, they form cyclic structures. These can form chains of sugars that form structural molecules such as starch and cellulose. Nucleic Acids Nucleic acids are made up of monomer units called nucleotides Sugar + Base + PO43- = nucleotide Slide 78 / 97

27 Slide 79 / 97 Nucleic Acids Two of the building blocks of RNA and DNA are sugars (ribose or deoxyribose) and cyclic bases (adenine, guanine, cytosine, and thymine or uracil) Slide 80 / 97 RNA Acid Ribonucleic acid Sugar ribose Bases Function DNA Deoxyribonucleic acid deoxyribose A, C, G and U make proteins A, C, G and T carry genetic code Nucleic Acids Nucleotides combine to form the familiar double-helix form of the nucleic acids The blue ribbon is the sugar/ phosphate backbone The bases are the rungs in the (spiral) ladder The nucleotides join together via hydrogen bonding through their bases A-T, C-G etc. Slide 81 / 97

28 37 Which of the following is not one of the four major groups of macromolecules found in living organisms? Slide 82 / 97 A glucose B carbohydrates C lipids D proteins nucleic acids Slide 83 / 97 Glucose is a type of. 38 A amino acid B protein C carbohydrate D nucleotide 39 nucleic acids Nucleic acids are made up of. A amino acids B proteins C carbohydrates D nucleotides sugars Slide 84 / 97

29 A nucleotide consists of. 40 A B C D Slide 85 / 97 glucose + fructose + amino acid glucose + fructose + phosphate group amino acid + protein + phosphate group sugar + base + amino acid sugar + base + phosphate group Polymers of polysaccharides and proteins are all synthesized from monomers by which process? 41 Slide 86 / 97 connecting monosaccharides together (condensation reactions) B the addition of water to each monomer (hydrolysis) A C the removal of water (dehydration reactions) D ionic bonding of the monomers the formation of disulfide bridges between monomers Other complex molecules of life Fats and Lipids Are a diverse group of hydrophobic molecules Are the one class of large biological molecules that do not consist of polymers Share the common trait of being hydrophobic Slide 87 / 97

30 Fats and Fatty Acids Slide 88 / 97 Fats Are constructed from two types of smaller molecules, a single glycerol and usually three fatty acids Fatty acids Carboxylic acids with a very long chain of carbon atoms. Vary in the length and number and locations of double bonds they contain CH2OH CH2OH CH2OH glycerol a fatty acid Dehydration Synthesis Slide 89 / 97 The attachment of a fatty acid to glycerol results in a removal of a water molecule. Slide 90 / 97 The diagram shows three fatty acids added to glycerol producing a fat molecule.

31 Saturated and Unsaturated Fatty Acids Slide 91 / 97 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 When hydrogenated ( add more Hydrogen) they become solid and saturated Mainly plant origin Slide 92 / 97 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 Slide 93 / 97 Steroids Are lipids characterized by a carbon skeleton consisting of three or more fused rings cholesterol

32 42 Which of the following is (are) true for the class of large biological molecules known as lipids? Slide 94 / 97 A They are insoluble in water. B They are an important constituent of cell membranes. They provide the least amount of energy in living organisms D Only A and B are correct. A, B, and C are correct. C 43 Saturated fatty acids Slide 95 / 97 A are the predominant fatty acid in corn oil. B have double bonds between carbon atoms of the fatty acids. C have a higher ratio of hydrogen to carbon than do unsaturated fatty acids. D are usually liquid at room temperature. are usually produced by plants. 44 The hydrogenation of vegetable oil would result in which of the following? A a decrease in the number of carbon-carbon double bonds in the oil (fat) molecules B an increase in the number of hydrogen atoms in the oil (fat) molecule C the oil (fat) being a solid at room temperature D A and C only A, B, and C Slide 96 / 97

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