1. Introduction to organic chemistry

2. Organic compounds “ Organic ” originally referred to any chemicals that came from Organisms Organic chemistry is the study of the compounds of carbon Organic chemistry is the study of the compounds of carbon Carbon atoms are unique because they form strong covalent bonds with each other Carbon atoms are unique because they form strong covalent bonds with each other Composition of organic compounds: C,H,N,O,halogens (Cl,Br) Composition of organic compounds: C,H,N,O,halogens (Cl,Br)

3. A. Carbon Bonding When carbon has 4 atoms bound to it these atoms have a tetrahedral shape. When carbon has 4 atoms bound to it these atoms have a tetrahedral shape.

4. An organic molecule (hydrocarbon) is formed when carbon bonds to hydrogen. The simplest hydrocarbon consists of 4 hydrogen atoms bonded to a carbon atom (called methane) In addition to binding to hydrogen, carbon can also bind to other carbon atoms, as illustrated below: Hydrocarbons Hydrogen + Carbon

5. In fact the uniqueness of carbon comes from the fact that it can bind to itself. Carbon atoms can form long chains: branched chains: rings

6. in fact, there appears to be almost no limit to the number of different structures that carbon can form. To add to the complexity of organic chemistry, neighboring carbon atoms can form double and triple bonds in addition to single carbon-carbon bonds A carbon-carbon single bond A carbon-carbon double bond A carbon-carbon triple bond

7. Saturated hydrocarbons Have the maximum number of hydrogen atoms attached to each carbon atom.Have the maximum number of hydrogen atoms attached to each carbon atom. Are alkanes and cycloalkanes with single C-C bonds.Are alkanes and cycloalkanes with single C-C bonds. CH 3 — CH 2 — CH 3 Saturated Hydrocarbons

8. Unsaturated hydrocarbons Have fewer hydrogen atoms attached to the carbon chain than alkanes.Have fewer hydrogen atoms attached to the carbon chain than alkanes. Are alkenes with double bonds.Are alkenes with double bonds. Are alkynes with triple bonds.Are alkynes with triple bonds. Unsaturated Hydrocarbons

10. Formulas Molecular formulas just tell you what kinds of atoms are in the molecule, but they don ’ t tell you how they are attached Molecular formulas just tell you what kinds of atoms are in the molecule, but they don ’ t tell you how they are attached structural formulas show you the attachment pattern in the molecule structural formulas show you the attachment pattern in the molecule In expanded structural formulas, all the individual bonds are drawn. In expanded structural formulas, all the individual bonds are drawn. In condensed structural formulas, each carbon is written with the H atoms connected to it. In condensed structural formulas, each carbon is written with the H atoms connected to it. models not only show you the attachment pattern, but give you an idea about the shape of the molecule models not only show you the attachment pattern, but give you an idea about the shape of the molecule

11. Line-Angle Formulas Each angle, and beginning and end represent a C atom Each angle, and beginning and end represent a C atom H omitted on C H omitted on C –included on functional groups –double line is double bond, triple line is triple bond Multiple bonds indicated Multiple bonds indicated

12. Formulas

13. Formulas

14. C1 – C5: Are Gases at Room Temperature C15: Are Solids at Room Temperature C6 - C15: Are Liquids at Room Temperature

15. Types of Carbon Atoms Primary carbon (1 o ) Primary carbon (1 o ) –a carbon bonded to one other carbon one other carbon Secondary carbon (2 o ) Secondary carbon (2 o ) –a carbon bonded to two other carbons two other carbons Tertiary carbon (3 o ) Tertiary carbon (3 o ) –a carbon bonded to three other carbons three other carbons

16. Functional Groups other organic compounds are hydrocarbons in which functional groups have been substituted for hydrogens other organic compounds are hydrocarbons in which functional groups have been substituted for hydrogens a functional group is a group of atoms that show a characteristic influence on the properties of the molecule a functional group is a group of atoms that show a characteristic influence on the properties of the molecule –generally, the reactions that a compound will perform are determined by what functional groups it has –since the kind of hydrocarbon chain is irrelevant to the reactions, it may be indicated by the general symbol R CH 3 —OH R groupfunctional group

17. An alcohol contains the hydroxyl (-OH) functional group. In an ether, an oxygen atom is bonded to two carbon atoms. – C – O – C –. In amines, the functional group is a nitrogen atom. | — N — Carboxylic acids contain the carboxyl group, which is a carbonyl group attached to a hydroxyl group. O ║ — C — OH An ester contains the carboxyl group between carbon atoms. An aldehyde contains a carbonyl group (C=O), which is a carbon atom with a double bond to an oxygen atom. In a ketone, the carbon of the carbonyl group is attached to two other carbon atoms.

19. Alkanes paraffins paraffins aliphatic aliphatic general formula C n H 2n+2 for chains general formula C n H 2n+2 for chains Straight-Chain Alkanes Combined with the -ane ending is a prefix for the number of carbons very unreactive very unreactive come in chains or/and rings come in chains or/and rings –CH 3 groups at ends of chains, CH 2 groups in the middle –chains may be straight or branched saturated saturated branched or unbranched branched or unbranched

20. Naming Alkanes The name for an alkane is based on Greek root with the suffix – ane. The name for an alkane is based on Greek root with the suffix – ane.

21. Alkanes – saturated hydrocarbons (C n H 2n+2 ) methane ethane hexane 3-methylpenthane ! Alkanes are not planar !

23. Alkyl Groups An alkyl group An alkyl group is composed of one or more carbon atoms attached to a carbon chain is composed of one or more carbon atoms attached to a carbon chain Is derived from the corresponding alkane by removing one hydrogen Is derived from the corresponding alkane by removing one hydrogen Is named by replacing the – ane ending of the corresponding alkane with – yl Is named by replacing the – ane ending of the corresponding alkane with – yl Derived from methane is methyl and from ethane is ethyl Derived from methane is methyl and from ethane is ethyl

24. Alkyl Groups

25. Naming Each name consists of 3 parts Each name consists of 3 parts ü prefix  indicates position, number, and type of branches  indicates position, number, and type of each functional group ü parent  indicates the length of the longest carbon chain or ring ü suffix  indicates the type of hydrocarbon –ane, ene, yne  certain functional groups Prefix- Parent- Suffix Prefix- Parent- Suffix where are the substituents How many carbons What family?

26. Summary: IUPAC (International Union of Pure and Applied Chemistry) Rules for Alkane Nomenclature 1. Find and name the longest continuous carbon chain. This is called the parent chain. (Examples: methane, propane, etc.) 1. Find and name the longest continuous carbon chain. This is called the parent chain. (Examples: methane, propane, etc.) 2. Number the chain consecutively, starting at the end nearest an attached group (substituent). 2. Number the chain consecutively, starting at the end nearest an attached group (substituent). 3. Identify and name groups attached to this chain. (Examples: methyl-, bromo-, etc.) 3. Identify and name groups attached to this chain. (Examples: methyl-, bromo-, etc.) 4. Designate 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. (Example: 3-chloropentane) 4. Designate 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. (Example: 3-chloropentane) 5. Assemble 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. (Example: 2,3-dichloropropane) 5. Assemble 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. (Example: 2,3-dichloropropane)

27. Example – Name the alkane 1) find the longest continuous C chain and use it to determine the base name since the longest chain has 5 C the base name is pentane

28. Prefixes for # of Carbons 1Meth6Hex 2Eth7Hept 3Prop8Oct 4But9Non 5Pent10Dec

29. Endings Alkanes (all C-C single bonded parent chain) end in – ane Alkanes (all C-C single bonded parent chain) end in – ane –Methane CH 4 –Ethane C 2 H 6 –Propane C 3 H 8 Attached carbon groups (substituents) end in – yl Attached carbon groups (substituents) end in – yl –Methyl CH 3 - –Ethyl CH 3 CH 2 - –Propyl CH 3 CH 2 CH 2 – –Propyl CH 3 CH 2 CH 2 – 3-ethylpentane

30. Step 2. Number the parent chain. Number the parent chain so that the attached groups are on the lowest numbers Number the parent chain so that the attached groups are on the lowest numbers 1 2 3 4 5 Methyl is on carbon #2 of the parent chain 5 4 3 2 1 Methyl is on carbon #4 of the parent chain GREEN is the right way for this one! 1 2 3 7 8 4 5 6 8 7 6 2 1 5 4 3 Groups on 2, 3, and 5 Groups on 4, 6, and 7 1 2 3 4 5 6 7 Groups on 2 and 5 7 6 5 4 3 2 1 Groups on 3 and 6

31. Step 3. Name the attached groups. Carbon (alkyl) groups Carbon (alkyl) groups –Methyl CH 3 - –Ethyl CH 3 CH 2 - –Propyl CH 3 CH 2 CH 2 – Halogens Halogens –Fluoro (F-) –Chloro (Cl-) –Bromo (Br-) –Iodo (I-)

32. Step 4. Designate where the group is attached to the parent chain. Use the numbers of the parent chain from step 2 to designate the location of the attached groups to the parent chain. Use the numbers of the parent chain from step 2 to designate the location of the attached groups to the parent chain. 1 2 3 4 5 2-methyl

33. Step 5. Alphabetize the groups, combine like groups, and assemble. The prefixes di, tri, tetra etc., used to designate several groups of the same kind The prefixes di, tri, tetra etc., used to designate several groups of the same kind Prefixes are not considered when alphabetizing (Example: dimethyl = m for alphabetizing) Prefixes are not considered when alphabetizing (Example: dimethyl = m for alphabetizing) Parent chain goes LAST Parent chain goes LAST 1,1,1-trichloro-1- fluoromethane 1,1-dichloro-1,1- difluoromethane

34. Practice – Name the Following 3-ethyl-2-methylpentane

35. Practice – Name the Following CH 3 CH 3 CH 2 CH CH 2 CH CH 3 CH CH 3 CH 3 CH CH 3 CH 3 CH 3 2,3-dimethylpentane 2,3-dimethylpentane 5-ethyl-3,4-dimethyloctane 5-ethyl-3,4-dimethyloctane

36. Alkenes also known as olefins also known as olefins aliphatic, unsaturated aliphatic, unsaturated –C=C double bonds formula for one double bond = C n H 2n formula for one double bond = C n H 2n –subtract 2 H from alkane for each double bond trigonal shape around C trigonal shape around C –flat much more reactive than alkanes much more reactive than alkanes polyunsaturated = many double bonds polyunsaturated = many double bonds

38. Alkynes also known as acetylenes also known as acetylenes aliphatic, unsaturated aliphatic, unsaturated C º C triple bond C º C triple bond formula for one triple bond = C n H 2n-2 formula for one triple bond = C n H 2n-2 –subtract 4 H from alkane for each triple bond linear shape linear shape more reactive than alkenes more reactive than alkenes

40. Naming Alkenes and Alkynes change suffix on main name from -ane to -ene for base name of alkene, or to -yne for the base name of the alkyne change suffix on main name from -ane to -ene for base name of alkene, or to -yne for the base name of the alkyne number chain from end closest to multiple bond number chain from end closest to multiple bond number in front of main name indicates first carbon of multiple bond number in front of main name indicates first carbon of multiple bond

41. Name the Alkene 1) find the longest, continuous C chain that contains the double bond and use it to determine the base name since the longest chain with the double bond has 6 C the base name is hexene

42. Name the Alkene 2) identify the substituent branches there are 2 substituents one is a 1 C chain, called methyl the other one is a 2 C chain, called ethyl

43. Name the Alkene 3) number the chain from the end closest to the double bond then assign numbers to each substituent based on the number of the main chain C it’s attached to 1234 56 4 3

44. Name the Alkene 4) write the name in the following order 1)substituent number of first alphabetical substituent – substituent name of first alphabetical substituent – use prefixes to indicate multiple identical substituents use prefixes to indicate multiple identical substituents 2)repeat for other substituents 3)number of first C in double bond – name of main chain 3–ethyl–4–methyl–2–hexene 1234 56 4 3

45. Practice – Name the Following

46. 3,4-dimethyl-3-hexene 12 34 56

47. Name the Alkyne 1) find the longest, continuous C chain that contains the triple bond and use it to determine the base name since the longest chain with the triple bond has 7 C the base name is heptyne

48. Name the Alkyne 2) identify the substituent branches there are 2 substituents one is a 1 C chain, called methyl the other one is called isopropyl

49. Name the Alkyne 3) number the chain from the end closest to the triple bond then assign numbers to each substituent based on the number of the main chain C it’s attached to 4 6 1234567

50. Name the Alkyne 4) write the name in the following order 1)substituent number of first alphabetical substituent – substituent name of first alphabetical substituent – use prefixes to indicate multiple identical substituents use prefixes to indicate multiple identical substituents 2)repeat for other substituents 3)number of first C in double bond – name of main chain 4–isopropyl–6–methyl–2–heptyne 4 6 1234567

51. Practice – Name the Following

52. 3,3-dimethyl-1-pentyne 123 45

53. IUPAC Rules for Naming Hydrocarbons 1. Choose the correct ending: -ane, -ene, or -yne 2. Determine the longest carbon chain. Where a double or triple bond is present, choose the longest chain that includes this bond. If there is a cyclic structure present, the longest chain starts and stops within the cyclic structure. 3. Assign numbers to each C of the parent chain. For alkenes and alkynes the first carbon of the multiple bond should have the smallest number. For alkanes the first branch (or first point of difference) should have the lowest #. Carbons in a multiple bond must be numbered consecutively. 4. Attach a prefix that corresponds to the number of carbons in the parent chain. Add cyclo- to the prefix if it is a cyclic structure.

54. 5. Determine the correct name for each branch (“alkyl” groups include methyl, ethyl, propyl, etc.) 6. Attach the name of the branches alphabetically, along with their carbon position, to the front of the parent chain name. Separate numbers from letters with hyphens (e.g. 4-ethyl-2- methyldecane) 7. When two or more branches are identical, use prefixes (di-, tri-, etc.) (e.g. 2,4-dimethylhexane). Numbers are separated with commas. Prefixes are ignored when determining alphabetical order. (e.g. 2,3,5-trimethyl-4-propylheptane) 8. When identical groups are on the same carbon, repeat the number of this carbon in the name. (e.g. 2,2-dimethylhexane) IUPAC Rules for Naming Hydrocarbons

55. ene Naming Side Chains Example: use the rules on this handout to name the following structure Rule 1: choose the correct ending

56. ene Rule 2: determine the longest carbon chain Naming Side Chains

57. Rule 3: Assign numbers to each carbon ene Naming Side Chains

58. Rule 3: Assign numbers to each carbon ene Naming Side Chains

59. 1-hexene ene Rule 4: attach prefix (according to # of Cs) Naming Side Chains

60. Rule 5: Determine name for side chains 1-hexene ethyl methyl Naming Side Chains

61. 1-hexene2-ethyl-4-methyl-4-methyl-1-hexene ethyl methyl Rule 6: attach name of branches alphabetically Naming Side Chains

62. Rule 7,8: group similar branches 1-hexene2-ethyl-4-methyl-4-methyl-1-hexene ethyl methyl Naming Side Chains

63. Rule 7,8: group similar branches 2-ethyl-4,4-dimethyl-1-hexene 2-ethyl-4,4-dimethyl-1-hexene ethyl methyl Naming Side Chains 0

64. 2-butene propene 1-butyne 2,4-dimethyl-2-pentene

65. b) same c) 5-ethyl-4-methyl-2-heptyne a) 3,3-dimethyl-1-pentene CHCHCH 2 CH 2 CH 3 CC CH 3 CH 3 CH 3 For more lessons, visit www.chalkbored.com www.chalkbored.com