1. Welcome to the OC Organic Chem OB: Mastering the alkanes, the alkenes, and the alkynes. Take out table P + Q now. At the end of today you should be able to name and draw, and recognize any alkane, alkene, or alkyne, 1 → 10 carbons long.

2. All chemistry we have been doing is technically “inorganic” chem. The compounds are all found in nature. For a while, at the beginning, some molecules were considered “organic”, which meant that only living things (plants and animals) could produce them. Urea was the first organic molecule that scientists synthesized, and they’ve been busy since. The organic molecules we will study are more complex than the simpler molecular and ionic compounds so far, but we get a bunch of tables to help us name them. Some compounds, like acetic acid and ethanoic acid, are the SAME THING, but they have different naming styles. So what? Not to be scared of. Organic chemistry is the real class in college that students cry in all of the time. It’s there exactly that their hopes and dreams for med school end. Not because it’s too hard, but because it’s too much to study and retain. We will make it easy and it only lasts 2 weeks. You shouldn’t cry over this.

3. Carbon. 1. The first atom of organic chem. Then comes hydrogen, H Followed by some others, like oxygen, O The halogens: F, Cl, Br, and I And the other cool atoms: N and S Count to 4, that’s most important. 2. Single, double and triple bonds. Then count to 1, 2, 3, also important. But 4 is most important. 3. No metals, not ever in organic. Table P, Q, and R. Take out P and Q now please. OUR FRIEND

4. Prefix Number of carbon atoms meth-1 eth-2 prop-3 but-4 pent-5 hex-6 hept-7 oct-8 non-9 dec-10 4. You must use this table to learn to count carbon atoms in Latin. Memorize this, and remember it’s right there as table P, and look at it a lot. All organic molecules use the number of carbons in their chemical names. This is really important.

5. 5. Carbon makes 4 bonds because it has a 2-4 electron configuration, and it needs the octet for bonding stability. All carbon atoms make 4 bonds. They can be: 4 single bonds, 2 single bonds + 1 double bond 2 double bonds 1 single + 1 triple bond 4 Bonds no matter what. Look at your hand, learn how many fingers FOUR is. Don’t forget how many 4 is, not ever. Hydrogen has 1 electron and can only bond as a single bond. Look at your hand, how many fingers is 1? Don’t forget that either.

6. 6. If you have 1 hydrogen atom, and enough hydrogen atoms, how many hydrogen atoms does it take to completely bond one carbon atom? 7. What’s the formula for this SIMPLEST of all organic molecules?

7. 6. If you have 1 hydrogen atom, and enough hydrogen atoms, how many hydrogen atoms does it take to completely bond one carbon atom? 4H + 1 C 7. What’s the formula for this SIMPLEST of all organic molecules? CH 4 H H C H H A ONE CARBON molecule is called METHANE

8. 8. When 2 carbon atoms bond together (single bonds only now) how many atoms of Hydrogen can also bond together with them? 9. What is the name of a 2 carbon simple (single bond) hydrocarbon molecule? Look at table P and Q

9. 8. When 2 carbon atoms bond together (single bonds only now) how many atoms of Hydrogen can also bond together with them? C–C leaves room for 6 H atoms 9. What is the name of a 2 carbon simple (single bond) hydrocarbon molecule? ethane

10. Name all of the SINGLE BONDED CARBON hydrocarbons 1 to 10 carbons in length, draw the structural diagrams for each. # C NameStructural Diagram 10 1 11 2 12 3 14 4

11. # CNameStructural Diagram 15 5 16 6 17 7

12. # CNameStructural Diagram 18 8 19 9 20 10

13. Vocab Alert: 21. Organic chem: chemical compounds that at one time were thought to be made only by living organisms like plants or animals. This is not true, nor was it. 22. Carbon: the central atom in organic chem, it makes 4 bonds because of it’s electron configuration of 2-4. It can make single or double or triple bonds to itself. 23. Hydrogen: the second atom of organic chem. It only makes single bonds, and is in abundance in organic molecules. 24. Oxygen: makes 2 bonds, double or two singles, and is in the midst of all the really cool organic molecules. Where it is changes chemical names and properties. 25. Nitrogen: makes 3 bonds, and has a simpler role in high school chem, but is very much the coolest atoms in amino acids and proteins 26. Halogens: make single bonds only. In our class makes decorations on compounds 27. Hydrocarbons: base molecles of organic chem, made up only of H + C (hence the name)

14. 28. ALKANES: hydrocarbons with only single C-C bonding. Only contain carbon and hydrogen atoms. Chains of 1 to 10 labeled with prefixes in table P. All end in –ane. 29. AKLENES: hydrocarbons with only one double C=C bond. Only contain carbon and hydrogen atoms. Chains of 1 to 10 labeled with prefixes in table P. All end in –ene. In college molecules can have multiple double bonding, but we have a single double bond to keep it simple. 30. ALKYENES: hydrocarbons with only one triple C ≡ C bond. Only contain carbon and hydrogen atoms. Chains of 1 to 10 labeled with prefixes in table P. All end in –yne. In college molecules can have multiple triple bonding, but we have a single triple bond to keep it simple.

15. Look at Table Q. 31. What is the general formula for these ALKANES? 32. Alkane means that the hydrocarbon has NO double bonded carbon atoms, and no triple bonded carbon atoms. ONLY SINGLE BONDS (or none for methane). 33. Hydrocarbons are the simplest organic molecules. 34. What are the only two atoms that are in hydrocarbons? 35. If it had an oxgyen atom attached, or a chlorine atom attached, would it still be a hydrocarbon? 36.Will we learn about other kinds of molecules? 37.Homologous series means: _________________________

16. 38. The 2 nd type of hydrocarbon chains are called alkenes. 39. Their general formula is They have less hydrogens than the alkanes because they contain 1 double bond. 40. In our class they will contain JUST 1 double bond, but in the real world, more than one double bond is possible. 41, 42, and 43. We will draw the first three in a row now… Try that “methene” but don’t get frustrated, it’s not possible. You need at least 2 carbons to have a double bond between 2 carbon atoms! Now go for ethene and propene…

17. 42. Ethene Hydrogen atoms at an angle is cool, or you can stick with the 90° angles, it’s just a drawing. 43. Propene Straight lines, or bent, the chain is 3 carbons in a row and that’s all that matters. Double bond left or right, it’s the same thing, molecules float!

18. 44. Try to draw butene now.

19. With 4 carbons things start to get a touch more complicated. You can you put that double bond in 2 different places (between carbon 1 + 2, or between carbon 2 + 3) Where is that double bond? It’s attached to which carbon atoms? It’s crooked, but still a line. Where is that double bond? How do we tell these apart?

20. 45. The carbon atoms need to be named 1, 2, 3, and 4. The “rule” is that the carbon atom closest to the double bond is #1. So, the first molecule has carbon #1 on the left. The double bond is between carbon #1 and #2, so we’ll call it 1-butene. 46. This one at right has the double bond between the 2 nd and 3 rd carbon. Note that from EITHER SIDE that is true. You could call the left carbon #1, or the far right hand carbon #1, but the double bond still attaches carbon #2 to carbon #3 This one is 2-butene.

21. Draw these next 47 1-pentene 48 2-pentene 49 3-hexene

22. Draw these next 503-heptene 513-octene 524-nonene 531-decene

23. Draw the following (you MAY omit the “H” atoms, but not the bonds 1-pentene 2-pentene 3-hexene 3-heptene

24. Draw the following (you MAY omit the “H” atoms, but not the bonds 3-octene -c-c-c = c-c-c-c-c- 4-nonene -c-c-c-c = c-c-c-c-c- 1-decene

25. 54. The third group of hydrocarbons are the ALKYNES Small change in name, this one has a triple bond. In our class the ALKYNES will ONLY have one triple bond. 55. Naming and drawing will be just like the alkynes, the bond placement must be stated (unless it’s the same from both ends). 56. There is no “methyne” either, you need at least 2 carbons to triple bond together. 57. Draw ethyne, and propyne now…

26. 57. Ethyne and one triple bonded carbon pair, and as many hydrogen atoms that fit, JUST 2. 58. This is NOT 1-propyne, because if the triple bond were on the right side, you’d just count carbons from that side (the end closest to the fancy part, here it’s a triple bond, is carbon #1. Just PROPYNE

27. 59. Let’s draw 1-butyne and 2 butyne next (put your triple bond in the right place!)

28. That’s 1-butyne above, counting from the right side. Right, left, who cares? Just keep track of the “first” carbon, it does not matter right or left. Below is 2 butyne The triple bond is between carbon #2 and #3, counting from EITHER direction.

29. Let’s draw some more… 60. 1-decyne 61. 1-pentyne 62. 2-pentyne 63. 3-hexyne

30. Let’s draw some more… 1-decyne 1-pentyne 2-pentyne 3-hexyne

31. Review: Use Table P to count to 10 in Latin prefixes Use Table Q for hydrocarbons. There are 3 kinds of hydrocarbons (3 homologous series) they contain ONLY Carbon + Hydrogen atoms Alkanes all C-C bonds are single, these are “saturated” hydrocarbons - they hold the MOST hydrogen atoms Alkenes Must contain only one C=C double bond in our class, The double bond must be enumerated unless too small to matter these are unsaturated hydrocarbons Alkynes Must contain only one CΞC triple bond in our class, The triple bond must be enumerated unless too small to matter these are also unsaturated hydrocarbons

32. Organic Chem Class #3 OB: adding halogens into all three kinds of hydrocarbons. Take out Table R 64. Why do Pirates Love Organic Chem? They really like table ARRRRGGHHHHH!

33. Now let’s look at the top of Table R The first “FUNCTIONAL GROUP” are the halogens. 65. Functional groups are added to hydrocarbons to make them fancier, to make them more difficult, to make them smell better or worse, to give them a wide variety of properties. That’s the organic chem part. The first, and the simplest functional groups we’ll add in are the halogens. 66. As you remember, group 17 contains the halogens: F, Cl, Br, and I When they are added to hydrocarbons we need to BOND them to the chains. 67. Each halogen has 7 valence electrons. They all need to share ONE electron with something else (a carbon atom) to make a single bond. They all make only single bonds. Only single bonds. Only.

34. If we start with a simple ethane molecule we can substitute in a halogen for a hydrogen with a substitution reaction. We’re learning 2 new things at once. 68. Ethane is a saturated hydrocarbon molecule (alkanes have as many H atoms as possible). 69. We can’t ADD a halogen atom into ethane, but we can substitute in an atom for an H atom. This is a substitution reaction 70. Ethane + Fluorine yields… + F 2 F + HF Fluoro-ethane + hydrogen monofluoride

35. Draw and name these molecules now. Br Cl F F F 71. 72. 73. 74.

36. Let’s name these molecules now. Br Cl F F F Bromo-ethane Chloro-ethane 1,2 di-fluoro-ethane 1,1 di-fluoro-ethane 71. 72. 73. 74.

37. The rules to naming these halo-carbons is easy. We’ll write them once, practice them lots, then you will just remember them because they are easy… 75. Rules to naming halocarbons: 1. Figure out the base chain name, that’s going to be the “LAST NAME” of the molecule. 2. Double and Triple bonds “trump” fancy functional groups. They will decide the carbon atom counting. 3. If no double or triple bonds, figure out which side we’ll count the carbons from, the fancy atoms (or groups) will decide which is the “short end to count from”. 4. The halogens are named in ALPHABETICAL order first, numbers second. Cl Br F F 76. Draw and name this molecule

38. There is a 4 carbon butane base chain that these halogens are attached to… Bromine comes first, since B is before Cl or F. Br is on the 2 nd carbon. Cl is second, it’s on the first carbon. Both of the F atoms are on the carbon atoms # 3 + 4 76. This would be 2-bromo, 1-chloro, 3,4-difluro-butane Cl Br F F

39. Cl Cl Cl F Br F 77. Name this molecule… First, how many carbons in a row, and are they single bonds only? This is a nonane base chain. Which is carbon #1, then work out the first names

40. Cl Cl Cl F Br F Carbon #1 is the right side one, since the functional group closest to one end is closer to the right side carbon. Names go alphabetical, and numbered, so… 77. 2-bromo, 5,6,7-tri-chloro, 1, 4-difluro-nonane

41. I F Cl I 78. Name this funky thing. Base chain first always…

42. I F Cl I Name the base chain first 1-octyne The base chain sets the carbon count. The chlorine comes first, so… 78. 6-chloro, 7-fluoro, 8,8-di-iodo, 1-octyne

43. + Cl 2 Let’s substitute in a Cl, over + over + over 4x Cl + HCl Methane + chlorine → chloromethane + HCl Cl + Cl 2 chloromethane + HCl ? #79

44. Cl + Cl 2 Cl + HCl Cl Chloromethane + chlorine makes dichloromethane + HCl 79. Cl + Cl 2 Cl ? #80

45. 80. Do the next 2 substitution reactions, draw molecules, name the products Cl + Cl 2 Cl Cl + HCl Cl trichloromethane + HCl Cl Cl + Cl 2 Cl ? #81

46. Cl Cl + Cl 2 Cl Trichloromethane + chlorine tetrachloromethane + HCl 81.

47. 82 + 83. Name us

48. Trichloro, fluoro- methane Tribromo, fluoro- methane

49. Organic Class #3b You’ll get up, look at the models I made, draw the structural diagrams, and name them, if you get them all correct I will give you…

50. Not really, you have to learn to work for yourself, not for pay. It’s not about cash, it’s about your mind. Hard work now pays off later.

51. 84, 85, 86, 87. Draw structural diagrams for these molecules (omit your H’s if you want to) propane, pentane, 2-butene, and then 3-hexyne

52. 84, 85, 86, 87. propane pentane 2-butene 3-hexyne

53. 88 + 89. Draw these: 3-bromo, 4,5-dichloro, 1-heptene 5,5,5-trifluoro, 1-pentyne

54. 88. 3-bromo, 4,5-dichloro, 1-heptene 89. 5,5,5-trifluoro, 1-pentyne -C=C-C-C-C-C-C- Br Cl Cl -CΞC-C-C-C- F F F

55. CCCC H H Cl F H H H F H H H H 90. Name Me C Which is carbon #1???

56. CCCC H H Cl F H H H F H H H H 90. Name Me C First carbon on left (F) attached, so 3-chloro, 1,4-difluoro-pentane

57. Get up, bring paper and your reference tables to guide you through these molecules…

58. Organic Classes # 4 The next 4 functional groups of Table R Alcohols, ethers, aldehydes, & ketones

59. On table R we’ll notice that there is something called an “R” group. 91. “R” can stand for any hydrocarbon, of any length. It could even stand in for just an “H” atom. It’s generic. 92. For halocarbons, the general formula is R ― X Where R stands for any hydrocarbon, say a methane, or an ethane, or a propane. X stands for any halogen. 93. Chloro-hydrocarbon could be R ― Cl

60. Today we will look into the alcohols, the ethers, the aldehydes + the ketones (not key tones) By the time we finish today you should be able to recognize what type of molecule you are looking at by its structural diagram, or condensed structural formula. You will be able to draw one from its name or formula as well. This will keep you busy. Alcohols 94. According to table R, alcohols have an “–OH” group which is NOT a hydroxide. When the anion hydroxide is ionically bonded to a metal, that is an Arrhenius base. This is different. 95. When the –OH group is bonded covalently to a hydrocarbon, it’s called an alcohol.

61. 94. The general formula for alcohols is R ― OH 95. Where R is any hydrocarbon that the ―OH group can bond onto.

62. Draw and name each alcohol molecule 96. one carbon 97. two carbons 98. three carbons H H HOHmethanol The –OH really means –O–H But we abbreviate it and just “know” that the oxygen and hydrogen make a single covalent bond. It’s prettier that way. C

63. Draw and name each alcohol molecule 96. 97. 98A. 98B. H H HOHmethanol H HOHethanol H H H HOH 1-propanol 2-propanol H OH H H H H HH C CC CCCCC C

64. 99. Draw & name each 5 carbon alcohol molecule possible

65. 99. Draw and name each 5 carbon alcohol molecule that you can… H H H H H H H H H H H OH H H OH H H H OH H H 1-pentanol 2-pentanol 3-pentanol Name the base chain (count carbon atoms) Enumerate where the alcohol group is located. Alcohol names always end with an -anol suffix CCCCC CCCCC CCCCC

66. This is a list of ALL the alcohols in our class, none are missing. # names of the carbons alcohols 1 methanol 2 ethanol 3 1-propanol, 2-propanol 4 1-butanol, 2-butanol 5 1-pentanol, 2-pentanol, 3-pentanol 6 1-hexanol, 2-hexanol, 3-hexanol 7 1-heptanol, 2-heptanol, 3-heptanol, 4-heptanol 8 1-octanol, 2-octanol, 3-octanol, 4-octanol 9 1-nonanol, 2-nonanol, 3-nonanol, 4-nonanol, 5-nonanol 10 1-decanol, 2-decanol, 3-decanol, 4-decanol, 5-decanol

67. Ethers 101. Ethers have a general formula of ___________ We need to introduce one more new thing now. Methane is CH 4 Ethane is CH 3 CH 3 Propane is CH 3 CH 2 CH 3 There is NO WAY to attach a methane to an oxygen, or an ethane, or propane, etc. But if we remove a hydrogen, we can attach what’s left of methane, or ethane, or propane. 100. Ethers are easy because they have a single atom of oxygen in the middle, and two different “R” groups, left + right.

68. Ethers are R―O―R’ which means that on either side of the ether there is a hydrocarbon chain, one to ten carbons long. But not the “whole” methane, or ethane, propane, butane, pentane, hexane, etc. 102. Methane minus 1 hydrogen is called methyl 103. Ethane minus 1 hydrogen atom is called ethyl 104. Propane minus 1 hydrogen atom is called propyl 105. Butane minus 1 hydrogen atom is called butyl. 106. Then comes pentyl, hexyl, heptyl, octyl, nonyl, + decyl.

69. 107. Name this: CH 3 ―O―CH 3 108. Name this one: CH 3 CH 2 ―O―CH 3 O C C H H H O C C H H H H H C

70. CH 3 ―O―CH 3 is methyl methyl ether but we say dimethyl ether CH 3 CH 2 ―O―CH 3 is ethyl methyl ether 109. Even though it doesn’t really matter because it’s just left and right, we alphabetize the alkyl groups. We will only add alkane chains to ethers, no double or triple bonds. KISS.

71. Draw these ethers. 110. Butyl ethyl ether 111. Methyl pentyl ether 112. Heptyl hexyl ether

72. Draw these ethers. (wow!) Butyl ethyl ether CH 3 CH 2 CH 2 CH 2 OCH 2 CH 3 Methyl pentyl ether CH 3 OCH 2 CH 2 CH 2 CH 2 CH 3 Heptyl hexyl ether CH 3 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 OCH 2 CH 2 CH 2 CH 2 CH 2 CH 3

73. Draw these ethers… Butyl ethyl ether Pentyl methyl ether Heptyl hexyl ether O H H H H H O H H O H H H H H HH H H H CCCCCC CCC CC C CCCCCCCCCCCCC

74. Ethers always have at least 1 carbon on each side – the smallest ether is dimethyl ether. They are named alphabetically. They always have the last name ether. There is a mistake in your reference table, it shows “methyl ethyl” ether when really what’s showing is ethyl methyl ether. Really that’s the same only named backwards.

75. 114. Aldehydes and Ketones we will examine together, since they are nearly the same thing, but they are located in different places. 115. They both have a C=O bond, just in different places. 116. Aldehydes always have the C=O at the end of a hydrocarbon chain, 117. Ketones always have the C=O in the middle of a chain. 118. Draw and name the 3 carbon aldehyde 119. Draw and name the 3 carbon ketone now

76. 118. 3 carbon aldehyde propanal 119. 3 carbon ketone propanone H H O H HHC C C H O H H HHC CC CH 3 CH 2 CHO CH 3 COCH 3

77. 120. Draw METHANAL (no such thing as methanone) 121. Draw ETHANAL (no such thing as ethanone) 122. Draw BUTANAL 123. Draw 2-Pentanone Need at least 3 carbons to “be in the middle” of a chain of carbons. Ketones “start” at 3 or propanone.

78. 120. METHANAL 121. ETHANAL 122. BUTANAL 123. 2-Pentanone HH O C HH O C H H H H H O H H H H H H H H O H H H H H It’s the placement of that double bonded oxygen that makes these 2 molecules different. C C CC C CC CC C