Unit 12 Organic Chemistry

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1 Unit 12 Organic Chemistry

2 Day 138 5/5/14 QOD: What is Organic Chemistry? Do Now: True or false? 1. Electrochemical cells generate electricity. 2. Electrons flow from left to right in a battery. 3. Redox reactions happen in both batteries and electrolytic cells

3 Organic Chemistry The study of carbon, hydrogen, oxygen and nitrogen containing compounds

4 TE YDROCARBONS Characteristics contain only carbon and hydrogen non-polar molecules low boiling point - decompose easily insoluble in water (most) slow reactivity non-electrolytes (poor ionization)

5 NOMENCLATURE in Ref. Tables The number of carbon atoms is determined by the root part of the name meth eth prop but pent hex hept oct 1 carbon 2 carbon 3 carbon 4 carbon 5 carbon 6 carbon 7 carbon 8 carbon

6 The Alkanes Characteristics saturated hydrocarbons (single bonds only) homologous series (follow same pattern) fewer # of carbons - lower boiling points follow same general formula - C n 2n+2 end in -ane

7 The Alkanes - Saturated hydrocarbons Methane C C 4 Ethane C C C 2 6 Propane C C C C 3 8

8 Day 139 5/6/14 QOD: What are isomers? Do Now: What prefix is used if there are three carbons in a carbohydrate?

9 Naming 1- find longest chain of C atoms and name it 2- name attached group 3- indicate the address of the attached group with number

10 Isomers - molecule has the SAME chemical formula, but DIFFERENT structural formula Butane is the first hydrocarbon to exhibit isomerism. n- Butane C C C C C methyl propane (isobutane) C C C C C 4 10

11 n-pentane C C C C C C methylbutane (isopentane) C C C C C C ,2-dimethylpropane (neopentane) C C C C C 5 12 C

12 Exit question What elements will you find in a hydrocarbon molecule? Draw a methane and an ethane molecule.

13 Day 141 5/8/14 QOD: ow do we define and name alkenes? Do Now: Draw the structural formula for pentane and write the condensed formula. ow many isomers can you come up with for pentane? Try as many as you can.

14 n-hexane C C C C C C C 6 14 n-heptane C C C C C C C C 7 16 n-octane C C C C C C C C C 8 18

15 The Alkenes - Unsaturated hydrocarbons Characteristics unsaturated hydrocarbons ( have at least 1 double bond) homologous series (follow same pattern) fewer # of carbons - lower boiling points follow same general formula - C n 2n end in -ene

16 The Alkenes Ethene C 2 4 Propene C 3 6

17 Isomers compounds with the same chemical formula but differing shapes (structural formulae) 1-Butene 2-Butene

18 The Alkynes - Unsaturated hydrocarbons Characteristics unsaturated hydrocarbons (have at least 1 triple bond) homologous series (follow same pattern) fewer # of carbons - lower boiling points follow same general formula - C n 2n-2 end in -yne

19 Alkynes C n 2n-2 Ethyne Propyne 1-Butyne 2-Butyne

20 Exit Question Draw and name the following hydrocarbon: C 3 CCC(C 3 )C 3 What type of hydrocarbon is it? Is it saturated or unsaturated? Why?

21 Exit question Draw and name the following hydrocarbon: C 3 C 2 C(C 3 )C 3

22 Exit question Write the combustion reaction of ethane.

23 Day 142 5/9/14 QOD: ow do alkanes react? Do Now: Draw 3,4 dimethyl 2- heptene.

24 Reactions of the Alkanes 1. Combustion Alkane + Oxygen Ex. C 4(g) + 2 O 2(g) Carbon dioxide + Water CO 2 (g) O (g) 2. alogen Substitution One hydrogen from a saturated hydrocarbon is replaced by a halogen atom forming a halogen substituted hydrocarbon. Ex. C Cl 2 C 2 5 Cl + Cl Two products are always produced.

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28 Reactions of the Alkenes 1. Combustion Alkene + Oxygen Carbon dioxide + Water 2. Addition A. ydrogen (hydrogenation) - breaks double bond, adds two hydrogen atoms Alkene + ydrogen Alkane C C 3 8 B. alogen (halogenation) - breaks double bond, adds two halogen atom Alkene + alogen alogen substituted hydrocarbon C Cl 2 C 3 6 Cl 2

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31 Activity With your partner, build an alkane, an alkene and an alkyne from your sheet.

32 Day 143 5/12/14 QOD: What are the functional groups? Do Now: Draw the structural formula for C 3 C(C 3 )CCC 3 and name it. What group of hydrocarbons does this molecule belong? Is it saturated or unsaturated? Why?

33 Reactions of the Alkynes 1. Combustion Alkyne + Oxygen Carbon dioxide + Water 2. Addition A. ydrogen (hydrogenation) - breaks triple bond, adds four hydrogen atoms Alkyne + 2 ydrogen Alkane C C 2 6 B. alogen (halogenation) - breaks triple bond, adds four halogen atoms Alkyne + 2 alogen alogen substituted hydrocarbon C Cl 2 C 2 2 Cl 4

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37 The Functional Groups The Alcohols - Characteristics Functional Group : -O hydroxyl group General Formula : R-O (R stands for a radical - methyl, ethyl propyl, etc.) Soluble in water (less than 5 C atoms) Non-electrolyte: 0% ionization Name ends in - ol

38 Monohydroxy Alcohols Methanol C O C 3 O Ethanol C C O C 2 5 O Produced by Fermentation Glucose zymase Carbon dioxide + Ethanol C 6 12 O 6 CO 2 + C 2 5 O

39 1-propanol C C C O C 3 7 O The above is a primary alcohol 2-propanol (isopropyl alcohol) C C C C 3 7 O O The above is a secondary alcohol. The -O is attached to a C atom which is attached to two others. 1-butanol C C C C O C 4 9 O

40 2-butanol C C C C C 4 9 O O 2-methyl-2-propanol (tertiary butanol) C C C C C 4 9 O O Tertiary alcohol - the -O is attached to a C atom which is attached to three others.

41 Alcohols - Diols Diols these alcohols have 2 O groups Example 1,2 Propanediol Triols these alcohols have 3 O groups Example - Glycerol

42 Ether Generally two hydrocarbons are joined together through a common bond to an oxygen -O- Example ethyl methyl ether

43 Aldehyde A hydrocarbon with a CO group Example - ethanal

44 Ketones Generally two hydrocarbons are joined by a mutual bond to a C=O group Example 2-butanone

45 Organic Acids Generally hydrocarbons with a COO group are organic, or carboxylic acids (the acidic is the one in the COO group) Example pentanoic acid

46 Ester Generally 2 hydrocarbons that are joined by a mutual bond to a COO group These compounds often have characteristic tastes and odors (grapefruit, spearmint, banana, etc) Example methyl ethanoate (the -oate ending is on the group where the C is bonded to 2 O s

47 Amine Generally 3 hydrocarbons (or ydrogens) are joined by mutual bonds to a Nitrogen This is one end of an amino acid (that is where they get their name Example ethyl methylamine

48 Amide Generally 2 ydrocarbons (or hydrogens) are joined by a mutual attraction to an amide group Example Ethyl methanamide

49 Exit question Write the the hydrogenation reaction of ethene.

50 Activity With your partner, draw the isomers on the worksheet. Then get a molecular kit and follow directions on the third page. Before returning the kits, please organize the atoms nicely and make sure that nothing is missing from your kit.

51 Day 144 5/13/14 QOD: What types of alcohols are there? Do Now: Trial quiz 1. Write the halogenation reaction of 1 - Butene with Fluorine (F 2 ). 2. Draw the structural formula for C3C(C3)C2C3 and name it. 3. Bonus: Which types of hydrocarbons are unsaturated?

52 Monohydroxy Alcohols Methanol C O C 3 O Ethanol C C O C 2 5 O Produced by Fermentation Glucose zymase Carbon dioxide + Ethanol C 6 12 O 6 CO 2 + C 2 5 O

53 1-propanol C C C O C 3 7 O The above is a primary alcohol 2-propanol (isopropyl alcohol) C C C C 3 7 O O The above is a secondary alcohol. The -O is attached to a C atom which is attached to two others. 1-butanol C C C C O C 4 9 O

54 2-butanol C C C C C 4 9 O O 2-methyl-2-propanol (tertiary butanol) C C C C C 4 9 O O Tertiary alcohol - the -O is attached to a C atom which is attached to three others.

55 Alcohols - Diols Diols these alcohols have 2 O groups Example 1,2 Propanediol Triols these alcohols have 3 O groups Example - Glycerol

56 The Benzene Series (Aromatic hydrocarbons) The benzene series consists of molecules which are cyclic in nature. The general formula is C n 2n-6. Benzene C C C C C C C 6 6

57 Although it appears that the structure has alternating double and single bonds, the bonding involves six identical bonds. A resonance structure is used to show structural formula of benzene. C C C C C C C C C C C C An abbreviated structural formula can be used in place of the above: OR

58 Toluene or Methylbenzene C 7 8 C C C C 3 C C C An abbreviated structural formula can be used in place of the above: C 3 C 3

59 Day 145 5/14/14 QOD: ow do we determine isomers? Do Now: Trial quiz 1. Write the halogen substitution of exane with chlorine. 2. Draw the structural formula for C 3 C 2 OC 2 C 2 C 3 and name it. 3. Bonus: Why are alkanes saturated hydrocarbons?

60 Fermentation Fermentation is a reaction in which living things (bacteria, yeast, humans) convert a sugar into alcohol and carbon dioxide Glucose zymase Carbon dioxide + Ethanol C 6 12 O 6 CO 2 + C 2 5 O

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62 Esterification the reaction of an organic acid and an alcohol yields an ester and water +

63 Saponification Saponification hydrolysis of fat (complex esters) by bases to make soap and glycerol

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67 Polymerization Making large molecules or polymers from small molecules or monomers Dehydration Polymerization monomers are joined together by O groups with the removal of water Addition Polymerization double or single bonds are broken to link monomers together

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69 Exit question Which general formula represents the compound C 3 C 2 CC? (1) C n n (3) C n 2n 2 (2) C n 2n (4) C n 2n+2

70 Day 141 5/14/13 QOD: ow do we determine isomers? Do Now: Per 4 1. Write the halogenation reaction of 1 - Pentene with Chlorine (Cl 2 ). 2. Draw the structural formula for C3C(C3)C3 and name it. 3. Bonus: Which type of hydrocarbons are saturated?

71 Day 142 5/15/13 QOD: What are functional groups? Do Now: Per 2 1. Write the halogen addition of Butyne with Fluorine (F 2 ). 2. Draw the structural formula for C 3 CCC 2 C 3 and name it. 3. Draw 3 methyl pentane

72 Day 142 5/15/13 QOD: What are functional groups? Do Now: Per 4 1. Write the hydrogenation of Propyne. 2. Draw the structural formula for C 3 CCC 2 C 2 C 3 and name it. 3. Draw 2 methyl hexane

73 Day 142 5/15/13 QOD: What are functional groups? Do Now: Per 7 1. Write the halogenation of Pentyne with Iodine (I 2 ). 2. Draw the structural formula for C 3 C 2 CCC 2 C 3 and name it. 3. Draw 2 methyl butane

74 Day 143 5/16/13 QOD: What are functional groups? Do Now: Write the halogenation reaction of 1 - exyne with Iodine.

75 Day 155 5/17/13 OD: What additional organic reactions are there? Do Now: Pick one of the following molecules. Draw the structural formula and name the molecule. C 3 C 2 C(O)C 2 C 3 C 3 C 2 OC 3

76 Fermentation Fermentation is a reaction in which living things (bacteria, yeast, humans) convert a sugar into alcohol and carbon dioxide Glucose zymase Carbon dioxide + Ethanol C 6 12 O 6 CO 2 + C 2 5 O

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78 Esterification the reaction of an organic acid and an alcohol yields an ester and water +

79 Saponification Saponification hydrolysis of fat (complex esters) by bases to make soap and glycerol

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83 Polymerization Making large molecules or polymers from small molecules or monomers Dehydration Polymerization monomers are joined together by O groups with the removal of water Addition Polymerization double or single bonds are broken to link monomers together

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85 Day 147 5/16/14 QOD: What do I need to know about organic chemistry? Do Now: What type of organic reaction is this? Name the product. + C C O C C C C C C C C C O

86 Green Book Group Activity In the Green Book, find these pages and complete the assignments: Level 1: pg 100 Set 2 Questions 6-10 Level 2: pg 104 Set 1 Questions 1 16 ydrocarbons Level 3: pg 116 Set 1 Questions 1 14 Functional groups

87 Exit question 1. What are the products of a fermentation reaction? 2. What do we need to add to form an ester? 3. What is soap made out of?

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