Slide 1 / 97. Slide 2 / 97. Slide 3 / 97. Organic Chemistry: Carbon and the Molecular Diversity of Life. Organic Chemistry. Biological Molecules

Transcription

1 Slide 1 / 97 Organic hemistry: arbon and the Molecular iversity of Life Organic hemistry 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. ompounds containing only carbon and hydrogen are called hydrocarbons; they are commonly used as a fuel source. iological Molecules Slide 3 / 97 arbon is the backbone of biological molecule. arbon 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 arbon arbon has four valence electrons to make covalent bonds arbon 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. 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. 2 Which property of the carbon atom allows it to bond with many different elements? Slide 6 / 97 arbon has 6 to 8 neutrons. arbon has 4 valence electrons. arbon forms ionic bonds. and only,, and

3 3 How many electron pairs does carbon share in order to complete its valence shell? Slide 7 / What type/s of bond/s does carbon have a tendency to form? Slide 8 / 97 Ionic Hydrogen ovalent and, and Hydrocarbons Slide 9 / 97 Hydrocarbons are compounds made up of carbon and hydrogen atoms liphatic hydrocarbons: compounds with carbon atoms connected in a straight chain 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

4 liphatic hydrocarbons: lkanes 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, utane, Octane lkanes Slide 11 / 97 lkanes Slide 12 / 97 The general formula n H 2n+2 n = number of carbon atoms H 4 2H 6 3H 8 Methane thane Propane Hexane Heptane Octane 4H 10 utane Nonane 5H 12 Pentane ecane

5 Straight hain lkanes Slide 13 / 97 Straight chain alkanes are alkanes that have all their carbon atoms connected in a row. These are structural formulas. H 3 -H 2 -H 3 This is a condensed formula for propane. ranched hain lkanes Slide 14 / 97 ranched chain alkanes are alkanes that have a branching connection of carbons. For example, butane has the formula 4 H 10. Shown below are the straight chain and branched forms of butane. H 3 -H 2 -H 2 -H 3 Straight chain butane ranched chain butane lkanes Slide 15 / 97 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.

6 5 What is the reason why hydrocarbons are not soluble in water? Slide 16 / 97 The majority of their bonds are polar covalent -H linkages The majority of their bonds are nonpolar covalent -H linkages They are hydrophilic They exhibit considerable molecular complexity and diversity They are lighter than water 6 Gasoline and water do not mix because gasoline is. Slide 17 / 97 less dense than water less viscous than wtaer nonpolar and water is polar volatile and water is not polar and water is nonpolar 7 Which substance would be the most soluble in gasoline? Slide 18 / 97 water sodium nitrate, NaNO 3 hydochloric acid, Hl hexane, 6 H 14 sodium chloride, Nal

7 liphatic hydrocarbons: lkenes Slide 19 / 97 lkenes have at least one double bond between two carbon atoms. General formula: n H 2n where n = # of carbon atoms The name uses the ending -ene. The simplest alkenes are: 2 H 4 thene (from 2-carbon parent, ethane) 3 H 6 Propene (from 3-carbon parent, propane) thene liphatic hydrocarbons: lkynes Slide 20 / 97 lkynes have at least one triple bond between two carbon atoms. General formula: n H 2n-2 where n = # of carbon atoms The name uses the ending -yne. The simplest alkynes are: 2 H 2 3 H 4 thyne (commonly known as acetylene) Propyne or propylene thyne Representing liphatic Hydrocarbons Slide 21 / 97 all and stick model Space filling model Structural formula Molecular formula

8 ycloalkanes Slide 22 / 97 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 romatic hydrocarbons Slide 23 / 97 They have benzene ring structure ( hexagon) and have particular aroma associated with it. H3 enzene Toluene ( methyl benzene) 8 Hydrocarbons Slide 24 / 97 are polar. are held together by ionic bonds. contain nitrogen. contain only hydrogen and carbon atoms. are held together by hydrogen bonds.

9 9 Hydrocarbons containing only single bonds between the carbon atoms are called. Slide 25 / 97 alkenes alkynes aromatics alkanes ketones 10 The general formula of an alkane is. Slide 26 / 97 2n H 2n+2 n H 2n n H 2n+2 n H 2n-2 n H n 11 Which is the formula of an alkane? Slide 27 / H H H H H 24

10 12 The molecular geometry of each carbon aton in an alkane is. Slide 28 / 97 octahedral sqaure planar trigonal planar tetrahedral trigonal pyramidal 13 Hydrocarbons containing carbon-carbon triple bonds are called. Slide 29 / 97 alkenes alkynes aromatics alkanes ketones 14 Which is the formula of an alkyne? Slide 30 / H H H H H 24

11 15 n alkene has at least one and has the general formula. Slide 31 / 97 - single bond, n H 2n+2 - double bond, n H 2n - triple bond, n H 2n - double bond, n H 2n-2 - triple bond, n H 2n-2 16 could be the formula of an alkene. Slide 32 / 97 3 H 8 3 H 6 6 H 6 17 H 36 H 8 17 Which of the following hydrocarbons has a double bond in its carbon skeleton? Slide 33 / 97 3H 8 2H 6 H 4 2H 4 2H 2

12 18 The compound below is an. Slide 34 / 97 alkyne alkene alkane aromatic compound olefin 19 The gasoline consumed by an automobile is a fossil fuel consisting mostly of Slide 35 / 97 aldehydes amino acidd alcohols hydrocarbons thiols Isomers Slide 36 / 97 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 click here for an animation on Isomers nantiomers

13 Structural Isomers Slide 37 / 97 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 Slide 38 / 97 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 H 3 groups are on the same side. trans isomer: The two H 3 groups are on opposite sides. nantiomers Slide 39 / 97 nantiomers are isomers that are mirror images of each other. nantiomers cannot be superimposed on each other. nantiomers differ in spatial arrangement around an asymmetric carbon, resulting in molecules that are mirror images, like left and right hands. The two isomers are designated the L and isomers from the Latin for left and right (levo and dextro).

14 20 Structural isomers are molecules that: Slide 40 / 97 are enantiomers. are hydrocarbons. have a ring structure. are mirror images. differ in the covalent arrangements of their atoms. 21 The two molecules shown are best described as Slide 41 / 97 optical isomers radioactive isotopes structural isomers nonradioactive isotopes geometric isomers 22 Which of the following is true of geometric isomers? Slide 42 / 97 They have variations in arrangement around a double bond. 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

15 Functional groups Slide 43 / 97 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 Slide 44 / 97 Haloalkanes, haloalkenes, and haloalkynes are characterized by the presence of a halogen atom (F, l, r or I), in place of a hydrogen atom. H 3 l, H 2 l 2, Hl 3, l 4, r 4, F 2 =F 2, F = F They are formed when one or more H atoms are replaced by halogen atom/s. lcohols Slide 45 / 97 lcohols contain the functional group -OH (hydroxyl group). For example, in H 4, one H is replaced by -OH The name ends with -ol, drop the alkane "e" add "ol", So, methane becomes methyl alcohol or methanol, H 3 OH. H 3 H 2 OH is called ethyl alcohol or ethanol. Thiols contain the functional group -SH, (sulfhydryl group)

16 Naming lcohols Slide 46 / 97 lkane formula lkane name lcohol formula lcohol name H 4 methane H 3 OH methanol 2 H 6 ethane 2 H 5 OH ethanol 3 H 8 propane 3 H 7 OH propanol 4 H 10 butane 4 H 9 OH butanol 23 Which of the following statements is true concerning a compound that contains a hydroxyl group? Slide 47 / 97 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. 24 In which of the structures are the atoms bonded ionic bonds? Slide 48 / 97,, None of the structures

17 arboxylic acids Slide 49 / 97 The functional group is -OOH Replace one H atom in the alkane by a -OOH group HOOH = Methanoic acid or formic acid H 3 OOH = thanoic acid or acetic acid or vinegar H 3 H 2 OOH = Propanoic acid rop the "e" from the parent alkane and add "oic acid" OH mines Slide 50 / 97 The functional group is - NH 2 H 3 NH 2, replace one H by an -NH 2 group H 3 NH 2 mino 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 25 Which of the structures contain(s) a carboxyl group? Slide 51 / 97 & None of the structures

18 26 What is the name of the functional group shown in the following figure? Slide 52 / 97 carbonyl ketone aldehyde carboxyl hydroxyl 27 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 53 / 97 Ketones Slide 54 / 97 The functional group is -=O or "carbonyl" group Usually sandwiched between two carbon groups H 3 H 2 H 3 = propane H 3 O H 3 propanone or acetone ( nail polish remover) rop e and add none H 3 O 2 H 5 thyl methyl ketone or butanone O H H 3

19 Ketones function the functional group can make! Slide 55 / 97 strogen- has two hydroxyl groups in it. Testosterone - one hydroxyl group is replaced by a ketone. ldehydes Slide 56 / 97 The functional group is -HO with a =O bond drop 'e' of the parent alkane and add 'nal' HHO - (1 carbon) Methanal or Formaldehyde H 3 HO- (2 carbon) thanal or cetaldehyde 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 57 / 97 The =O is between two other carbon atoms ( alkyl groups) in the molecule The =O group is at the end ( terminal carbon) of the molecule and should be connected to a H atom The =O bond should be connected to an OH group

20 28 What is the name of the functional group shown in the following figure? (R = any carbon group) R-=O R Slide 58 / 97 carbonyl ketone aldehyde carboxyl hydroxyl ster Slide 59 / 97 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. They are usually pleasant smelling compounds ( natural oils and essence) H 3 OOH + H 3 OH --> H 3 OOH 3 H 3 OOH 3 H 3 OO 2 H 5 methyl acetate ethyl acetate 2 H 5 OOH 3 methyl propanoate ther Slide 60 / 97 The functional group is an O atom sandwiched between two carbon groups H 3 -O- H 3 dimethyl ether They are highly flammable and used as solvents in organic synthesis

21 Groups with a arbon Oxygen ouble ond (arbonyl Groups) Slide 61 / 97 mides Slide 62 / 97 mides are formed by the reaction of carboxylic acids with amines. ROOH + H 2 NR' --> -H 2 O 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 / Which is the best description of a carbonyl group? 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 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. carbonyl ketone aldehyde carboxyl hydroxyl 31 Which of the following contains nitrogen in addition to carbon, oxygen, and hydrogen? Slide 65 / 97 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 32 What type of functional group is shown in the compound below? Slide 66 / 97 carbonyl ketone aldehyde carboxyl hydroxyl

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

24 36 Which one of the following is not an alcohol? Slide 70 / 97 acetone glycerol ethanol cholesterol ethylene glycol Slide 71 / 97 Macromolecules Macromolecules are large molecules composed of smaller molecules. They are complex in their structures. arbon has the unique property of joining together via covalent bonding to form large (macro) molecules. Most macromolecules are polymers, built from monomers. Macromolecules Slide 72 / 97 Three of the classes of life s organic molecules are polymers: Proteins arbohydrates Nucleic acids There are some macromolecules that are not polymers: lipids phospholipids steroids

25 Polymers Slide 73 / 97 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 arbohydrates Nucleic acids Made of these monomers mino acids Simple sugars (monosaccharides) Nucleotides Polymers Slide 74 / 97 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 mino cids and Proteins Slide 75 / 97 Proteins are formed when several amino acids combine together 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.

26 arbohydrates (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. Glucose and fructose are monosaccharides. Sucrose is a disaccharide. glucose fructose (monosaccharide) arbohydrates (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 cids Slide 78 / 97 Nucleic acids are made up of monomer units called nucleotides Sugar + ase + PO 4 3- = nucleotide

27 Nucleic cids Slide 79 / 97 Two of the building blocks of RN and N are sugars (ribose or deoxyribose) and cyclic bases (adenine, guanine, cytosine, and thymine or uracil) Slide 80 / 97 cid Sugar ases RN Ribonucleic acid ribose,, G and U N eoxyribonucleic acid deoxyribose,, G and T Function make proteins carry genetic code Nucleic cids Slide 81 / 97 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 -T, -G etc.

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

29 40 nucleotide consists of. Slide 85 / 97 glucose + fructose + amino acid glucose + fructose + phosphate group amino acid + protein + phosphate group sugar + base + amino acid sugar + base + phosphate group 41 Polymers of polysaccharides and proteins are all synthesized from monomers by which process? Slide 86 / 97 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 Other complex molecules of life Fats and Lipids Slide 87 / 97 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

30 Fats and Fatty cids Fats re constructed from two types of smaller molecules, a single glycerol and usually three fatty acids Slide 88 / 97 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 a fatty acid ehydration 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 cids 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 Phospholipids Slide 92 / 97 Have only two fatty acids Have a phosphate group instead of a third fatty acid Results in a bilayer arrangement found in cell membranes Steroids Slide 93 / 97 re 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 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. 43 Saturated fatty acids Slide 95 / 97 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. 44 The hydrogenation of vegetable oil would result in which of the following? Slide 96 / 97 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

33 Slide 97 / 97