Slide 1 / 123. Slide 2 / 123. Slide 3 / 123. Organic Chemistry. Organic Chemistry. New Jersey Center for Teaching and Learning

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1 New Jersey enter for Teaching and Learning Slide 1 / 123 Progressive Science Initiative This material is made freely available at and is intended for the non-commercial use of students and teachers. These materials may not be used for any commercial purpose without the written permission of the owners. NJTL maintains its website for the convenience of teachers who wish to make their work available to other teachers, participate in a virtual professional learning community, and/or provide access to course materials to parents, students and others. lick to go to website: Organic hemistry Slide 2 / 123 arbon and the Molecular iversity of Life Organic hemistry Organic chemistry is the chemistry of carbon compounds. arbon is the backbone of biological molecule arbon has the ability to form long chains. Without this property, large biomolecules such as proteins, lipids, carbohydrates, and nucleic acids could not form. Slide 3 / 123 Stearate 17H 36O 2

2 Organic hemistry Slide 4 / 123 Organic compounds range from simple molecules to colossal ones Most organic compounds contain hydrogen atoms in addition to carbon atoms Slide 5 / 123 Organic hemistry arbon has four valence electrons to make covalent bonds arbon atoms can form diverse molecules by bonding to four other atoms lectron configuration is the key to an atom s characteristics lectron configuration determines the kinds and number of bonds an atom will form with other atoms Slide 6 / Organic chemistry is a science based on the study of functional groups. vital forces interacting with matter. carbon compounds. water and its interaction with other kinds of molecules. inorganic compounds.

3 2 Which property of the carbon atom gives it compatibility with a greater number of different elements than any other type of atom? Slide 7 / 123 arbon has 6 to 8 neutrons. arbon has a valence of 4. arbon forms ionic bonds. and only,, and 3 How many electron pairs does carbon share in order to complete its valence shell? 1 Slide 8 / What type/s of bond/s does carbon have a tendency to form? Slide 9 / 123 Ionic Hydrogen ovalent and, and

4 5 Organic chemistry is currently defined as Slide 10 / 123 the study of compounds that can be made only by living cells. the study of carbon compounds. the study of vital forces. the study of natural (as opposed to synthetic) compounds. the study of hydrocarbons. Hydrocarbons Slide 11 / 123 Hydrocarbons are compounds made up of carbon and hydrogen atoms. There are two major categories: liphatic and romatic 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 to form cyclic structure and with an aroma (smell or odor) liphatic hydrocarbon: lkanes Slide 12 / 123 Hydrocarbon chains made up of all SINGL carbon bonds They are also known as saturated hydrocarbons They are saturated with hydrogens Name uses the ending -ane xamples: Methane, Propane, utane, Octane

5 liphatic hydrocarbon: lkanes Slide 13 / 123 The general formula nh 2n+2 n = number of carbon atoms Formula Name Formula Name H 4 Methane Hexane 2H 6 thane Heptane 3H 8 Propane Octane 4H 10 utane Nonane 5H 12 Pentane ecane (The students can fill this) liphatic hydrocarbon: lkanes Slide 14 / 123 liphatic hydrocarbon: lkanes Slide 15 / 123 Hydrocarbons are non polar. ll -H bonds are nonpolar. s the number of electrons in the molecule increases ( larger molecules), it would be easily polarizable and hence the L forces increases. This increases the bpt. of the higher alkanes.

6 liphatic hydrocarbon: lkanes Slide 16 / 123 Straight chain alkanes: n alkane that has all its carbons connected in a row. H 3-H 2-H 3 ranched chain alkanes: n alkane that has a branching connection of carbons. H 3 H 3 -H-H 2 -H 3 lkanes: thane Slide 17 / 123 Structural formula ondensed formula H H H 3 - H 3 H H H H ranched chain lkanes Slide 18 / 123 Pentane Isopentane H 3 - H 2 - H 2 - H 2 - H 3 H 3 - H(H 3) - H 2 - H 3 Neopentane (H 3) 4 ranched chain

7 6 What is the reason why hydrocarbons are not soluble in water? Slide 19 / 123 The majority of their bonds are polar covalent carbon to hydrogen linkages The majority of their bonds are nonpolar covalent carbon to hydrogen linkages They are hydrophilic They exhibit considerable molecular complexity and diversity They are lighter than water lkenes Slide 20 / 123 lkenes have at least one 1 double bond between two carbon atoms. General formula: nh 2n The name uses the ending -ene The first member would be 2H 4 - thene (from 2 carbon parent, ethane) 3H 6 - Propene thene lkynes Slide 21 / 123 lkyne general formula: nh 2n-2 They must have at least one triple bond The name uses the ending -yne 2H 2 thyne or commonly known as acetylene 3H 4 Propyne or propylene thyne

8 liphatic hydrocarbons Slide 22 / 123 all and stick model Space filling model Structural formula Molecular formula ycloalkanes Slide 23 / 123 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 tetrahedra angle. Smaller rings are quite strained romatic hydrocarbons Slide 24 / 123 They have benzene ring structure (hexagon) and a particular aroma. H 3 enzene Toluene (methyl benzene)

9 7 Hydrocarbons Slide 25 / 123 are polar. are held together by ionic bonds. contain nitrogen. contain only hydrogen and carbon atoms. are held together by hydrogen bonds. 8 Which of the following hydrocarbons has a double bond in its carbon skeleton? Slide 26 / H 8 2 H 6 H 4 2 H 4 2 H 2 9 The gasoline consumed by an automobile is a fossil fuel consisting mostly of Slide 27 / 123 aldehydes amino acidd alcohols hydrocarbons thiols

10 10 Hydrocarbons containing only single bonds between the carbon atoms are called. Slide 28 / 123 alkenes alkynes aromatics alkanes ketones 11 Which is the formula of an alkane? Slide 29 / H H H H H Hydrocarbons containing carbon-carbon triple bonds are called. Slide 30 / 123 alkenes alkynes aromatics alkanes ketones

11 Which is the formula of an alkyne? 13 Slide 31 / H H 18 10H H H The molecular geometry of each carbon atom in an alkane is. Slide 32 / 123 octahedral square planar trigonal planar tetrahedral trigonal pyramidal 15 The general formula of an alkane is. Slide 33 / 123 2nH 2n+2 nh 2n nh 2n+2 nh 2n-2 nh n

12 16 n alkene has at least one and has the general formula. Slide 34 / single bond, nh 2n+2 - double bond, nh 2n - triple bond, nh 2n - double bond, nh 2n-2 - triple bond, nh 2n-2 17 The compound below is an. Slide 35 / 123 alkyne alkene alkane aromatic compound olefin 18 Gasoline and water do not mix because gasoline is. Slide 36 / 123 less dense than water less viscous than wtaer nonpolar and water is polar volatile and water is not polar and water is nonpolar

13 19 Which substance would be the most soluble in gasoline? Slide 37 / 123 water NaNO 3 Hl hexane Nal 20 could be the formula of an alkene. Slide 38 / 123 3H 8 3H 6 6H 6 17H 36 H 8 Isomers Slide 39 / 123 Hydrocarbons exhibit a phenomenon called isomerismexistence of different molecular arrangement but same formula. Isomers are compounds with the same molecular formula but different structures and properties: Structural isomers have different covalent arrangements of their atoms Geometric isomers have the same covalent arrangements but differ in spatial arrangements nantiomers are isomers that are mirror images of each other

14 Isomers Slide 40 / 123 Structural Isomers Isomers Slide 41 / 123 trans isomer: The two H 3 are on opposite sides. cis isomer: The two H 3 are on the same side. Geometric Isomers Isomers Slide 42 / 123 nantiomers are isomers that are nonsuperimposable mirror images nantiomers (optical isomers) 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). nantiomers cannot be superimposed on each other.

15 ond ngle at ach tom Slide 43 / 123 lkane lkene lkyne 21 Structural isomers are molecules that Slide 44 / 123 are enantiomers. are hydrocarbons. have a ring structure. are mirror images. differ in the covalent arrangements of their atoms. 22 The two molecules shown here are best described as H 3 - H 2 -O-H optical isomers radioactive isotopes H 3-O-H 3 structural isomers nonradioactive isotopes geometric isomers Slide 45 / 123

16 23 Which of the following is true of geometric isomers? 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 Slide 46 / The two molecules shown below are best described as Slide 47 / 123 optical isomers. radioactive isotopes. structural isomers. nonradioactive isotopes. geometric isomers. Naming Organic ompounds 1. Find and name the longest continuous carbon chain. This is called the parent chain. (xamples: methane, propane, etc.) Slide 48 / Number the chain consecutively, starting at the end nearest an attached group (substituent). 3. Identify and name groups attached to this chain. (xamples: methyl-, bromo-, etc.) 4. esignate the location of each substituent group with the number of the carbon parent chain on which the group is attached. Place a dash between numbers and letters. (xample: 3-chloropentane) 5. ssemble the name, listing groups in alphabetical order. The prefixes di, tri, tetra etc., used to designate several groups of the same kind, are not considered when alphabetizing. Place a comma between multiple numbers. (xample: 2,3-dichloropropane)

17 Naming Organic ompounds Slide 49 / 123 Where is the longest continuous chain of carbons? Naming Organic ompounds Slide 50 / 123 Number the parent chain so that the attached groups are on the lowest numbers. Naming Organic ompounds Slide 51 / 123 Names of attached groups/substituents arbon (alkyl) groups Methyl H3 - thyl H3H2- Propyl H3H2H2 Halogens Fluoro (F-) hloro (l-) romo (r-) Iodo (I-)

18 Naming Organic ompounds Slide 52 / 123 1,1,1-trichloro-1-fluoromethane 1,1-dichloro-1,1-difluoromethane Naming Organic ompounds Slide 53 / 123 Name the compounds below raw the structures H 3 H 3 H H 2 H 2 H 3 H 3 H H H 2 H 3 H 3 H 3 3-ethylhexane 2,2-dimethylbutane 2,3-dimethylbutane Naming Organic ompounds Slide 54 / 123 IN TI, halogens get the lower number before alkyl groups H 3 l H 3 H H 2 H H 3 4-chloro-2-methylpentane or 2-chloro-4-methylpentane? IN TI between SIMILR GROUPS, the group lower LPHTILLY gets the lower number H3 H3 l r 4-bromo-2-chloropentane or 2-bromo-4-chloropentane?

19 Naming Organic ompounds Slide 55 / 123 IUP nomenclature rules for alkenes and alkynes are similar to alkanes. Step 1. Name the parent compound. Find the longest chain containing the double or triple bond, and name the parent compound by adding the suffix ene or yne to the name of the main chain. Naming Organic ompounds Slide 56 / 123 Naming Organic ompounds Slide 57 / 123 H 2=HH 2H 3 1-butene but-1-ene H 3H=HH 3 2-butene but-2-ene H 3 H 3 2-butyne but-2-yne

20 Naming Organic ompounds Write the IUP name for each of the following unsaturated compounds: Slide 58 / 123. H 3H H 3 H 3. H 3=HH 3 H 3. Naming Organic ompounds Slide 59 / 123 ouble bond is fixed is/trans Isomers are possible H 3 H 3 H 3 H = H H = H cis trans H 3 Naming Organic ompounds Slide 60 / 123 Many aromatic compounds are common in nature and in medicine. HO OOH OOH3 aspirin vanillin OH3 OH H3 H3 H3 -H-H2 H OOH ibuprofen

21 Naming Organic ompounds Slide 61 / 123 romatic compounds are named with benzene as the parent chain. One side group is named in front of the name benzene. No number is needed for mono-substituted benzene since all the ring positions are identical. l H3 chlorobenzene methylbenzene/toluene Naming Organic ompounds Slide 62 / 123 When two groups are attached to benzene, the ring is numbered to give the lower numbers to the side groups. The prefixes ortho (1,2), meta (1,3-) and para (1,4-) are also used H3 l l H3 l 1,2 dmethylbenzene Orthodimethylbenzene 1,3 dichlorobenzene metadichlorobenzene H3 1-chloro- 4-methyl benzene parachloromethylbenzene Naming Organic ompounds Slide 63 / 123 Write the structural formulas for each of the following:. 1,3-dichlorobenzene. Ortho-chlorotoluene

22 Functional Groups Slide 64 / 123 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/thiols cids mines Ketones ldehydes sters ther Halo- alkanes/alkenes/alkynes Slide 65 / 123 Presence of a Halogen atom (F, l, r or I) H 3l, H 2l 2, Hl 3, l 4, F 2=F 2, F = F They are formed when one or more H atoms are replaced by halogen atom/s l l H3H2H2H H3 H3H2H2 H2 lcohols and Thiols Slide 66 / 123 The functional group is a hydroxyl group, -OH If O is replaced by a S atom, it is called a thiol -SH Thiol is the same as sulfhydride OH - - hydroxyl group SH - - sulfhydryl group In H 4, if one H is replaced by -OH The name ends with -ol, drop the alkane "e" add "ol"

23 lcohols and Thiols Slide 67 / 123 H H OH Methane becomes methyl alcohol or Methanol H H H H OH thane becomes ethyl alcohol or ethanol H H 25 compound contains hydroxyl groups as its predominant functional group. Which of the following statements is true concerning this compound? Slide 68 / 123 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. 26 Which of the structures contain(s) a hydroxyl group? Slide 69 / 123 & None of the structures

24 27 In which of the structures are the atoms bonded ionic bonds? Slide 70 / 123,, None of the structures cids or arboxylic cids Slide 71 / 123 The functional group is -OOH Replace one H atom in the alkane by a -OOH group HOOH = Methanoic acid or formic acid H 3OOH = thanoic acid or acetic acid or vinegar H 3H 2OOH = Propanoic acid rop the " e" from the parent alkane and add " oic acid" OOH OOH ethane di-carboxylic acid or oxalic acid mines Slide 72 / 123 The functional group is - NH 2 H 3NH 2 Replace one H by an -NH 2 group H 3NH 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 28 What is the name of the functional group shown in the following figure? Slide 73 / 123 carbonyl ketone aldehyde carboxyl hydroxyl 29 Which two functional groups are always found in amino acids? Slide 74 / 123 ketone and aldehyde carbonyl and carboxyl carboxyl and amino phosphate and sulfhydryl hydroxyl and aldehyde Ketones The functional group is -=O or "carbonyl" group and is usually sandwiched between two carbon groups. Slide 75 / 123 H 3H 2H 3 = propane H 3O H 3 propanone or acetone ( nail polish remover) rop e and add none O H 3- - H 3 H 3O 2H 5 thyl methyl ketone or butanone

26 Ketones Slide 76 / 123 strogen- has two hydroxyl groups in it. Testosterone - one hydroxyl group is replaced by a ketone.the property and function of the molecules changes. ldehydes Slide 77 / 123 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 3HO - (2 carbon) thanal or cetaldehyde ldehydes, Ketones and cids Slide 78 / 123 The way the carbonyl group is bonded to the main body of the molecule is different in acids, ketones and aldehydes The =O is between two other carbon atoms ( alkyl groups) in the molecule

27 ldehydes, Ketones and cids Slide 79 / 123 The way the carbonyl group is bonded to the main body of the molecule is different in acids, ketones and aldehydes The =O group is at the end ( terminal carbon) of the molecule and should be connected to a H atom ldehydes, Ketones and cids Slide 80 / 123 The way the carbonyl group is bonded to the main body of the molecule is different in acids, ketones and aldehydes The =O bond should be connected to an OH group 30 What is the name of the functional group shown in the following figure? R-=O R carbonyl ketone aldehyde carboxyl hydroxyl (R = any carbon group) Slide 81 / 123

28 31 raw the structure of propanoic acid Slide 82 / 123 ster Slide 83 / 123 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 3OOH + H 3OH --> H 3OOH 3 H 3OOH 3 - methyl acetate H 3OO 2H 5 - ethyl acetate 2H 5OOH 3 - methyl propanoate ther Slide 84 / 123 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

29 Groups with a arbon Oxygen ouble ond (arbonyl Groups) Slide 85 / 123 mides Slide 86 / 123 mides are formed by the reaction of carboxylic acids with amines. ROOH + H 2NR' --> -H 2O 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. 32 Which is the best description of a carbonyl group? Slide 87 / 123 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

30 33 What is the name of the functional group shown below. Slide 88 / 123 carbonyl ketone aldehyde carboxyl hydroxyl 34 Which of the following contains nitrogen in addition to carbon, oxygen, and hydrogen? Slide 89 / 123 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 35 What type of functional group is shown in the compound below? Slide 90 / 123 carbonyl ketone aldehyde carboxyl hydroxyl

31 36 Which molecule contains an amine functional group? Slide 91 / Which molecule contains an aldehyde functional group? Slide 92 / Which molecule contains an alcohol functional group? Slide 93 / 123

32 39 Which one of the following is not an alcohol? Slide 94 / 123 acetone glycerol ethanol cholesterol ethylene glycol Macromolecules Slide 95 / 123 Marcromolecules are large molecules composed of smaller molecules. They have complex 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 96 / 123 In living things, three major classes of organic molecules are polymers Proteins arbohydrates Nucleic acids

33 Polymers Slide 97 / 123 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 Is a long molecule consisting of many similar building blocks called monomers The Synthesis and reakdown of Polymers Monomers form larger molecules by condensation reactions called dehydration reactions Slide 98 / 123 short polymer Monomer longer polymer Polymers The Synthesis and reakdown of Polymers Slide 99 / 123 short polymer Monomer longer polymer

34 mino cids and Proteins Slide 100 / 123 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. Peptide hain 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. Sugars are otherwise known as saccharides. Slide 101 / 123 Glucose and fructose are monosaccharides. Sucrose is a disaccharide. Glucose (Monosaccharide) Fructose arbohydrates/sugars Slide 102 / 123 In solution, carbohydrates form cyclic structures. They can form chains of sugars that form structural molecules such as starch and cellulose. Not all sugars are sweet.

35 Nucleic cids Slide 103 / 123 Nucleic acids are made up of monomer units called nucleotides. Sugar + ase + PO 4 3- = nucleotide nucleotide is made up of 3 components: a 5-carbon sugar (ribose or deoxyribose) + a nitrogenous base + a phosphate group, PO 4 3- 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) Slide 104 / 123 Sugars ases Nucleic cids Slide 105 / 123 RN Ribonucleic acid ontains the sugar ribose Uses bases,, G and U N eoxyribonucleic acid ontains the sugar deoxyribose Uses bases,, G and T Function is to make proteins Function is to carry genetic code

36 Nucleic cids Slide 106 / 123 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. 40 Which of the following is not one of the four major groups of macromolecules found in living organisms? Slide 107 / 123 glucose carbohydrates lipids nucleic acids proteins Slide 108 / Glucose is a type of. amino acid protein carbohydrate nucleotide nucleic acids

37 Nucleic acids are made up of. 42 Slide 109 / 123 amino acids proteins carbohydrates nucleotides sugars 43 nucleotide consists of. Slide 110 / 123 glucose + fructose + amino acid glucose + fructose + phosphate group amino acid + protein + phosphate group sugar + base + amino acid sugar + base + phosphate group 44 Polymers of polysaccharides and proteins are all synthesized from monomers by which process? Slide 111 / 123 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

38 Other omplex Molecules of Life Slide 112 / 123 Fats and Lipids are another major category of molecules found in living things. They are a diverse group of hydrophobic molecules and, unlike the other macromolecules, are not made up of polymers. Fats and Lipids Slide 113 / 123 Fats and lipids are constructed from two types of smaller molecules, a single glycerol and usually three fatty acids. arboxylic acids have a very long chain of carbon atoms and v ary in the length and number and locations of double bonds they contain. H2OH H2OH H2OH Glycerol fatty acid Fats and Lipids Slide 114 / 123 ttachment of fatty acids to glycerol

39 Fats and Lipids Slide 115 / fatty acids added to glycerol producing a fat molecule Fats and Lipids Slide 116 / 123 Saturated fatty acids: have the maximum number of hydrogen atoms possible have no double bonds in their carbon chain animal origin Fats and Lipids Slide 117 / 123 Unsaturated fatty acids have one or more double bonds when hydrogenated (more hydrogens are added) they become solid and saturated mainly plant origin

40 Fats and Lipids Slide 118 / 123 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 Fats and Lipids Slide 119 / 123 Steroids are lipids characterized by a carbon skeleton consisting of three or more fused rings. holesterol 45 Which of the following is (are) true for the class of large biological molecules known as lipids? Slide 120 / 123 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.

41 46 Saturated fatty acids Slide 121 / 123 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. 47 The hydrogenation of vegetable oil would result in which of the following? Slide 122 / 123 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 Slide 123 / 123