1. Unit 13: Organic Chemistry

2. Organic Chemistry
Organic chemistry is the study of carbon containing compounds
Carbon is unique because it almost always forms four bonds

3. Hydrocarbons
The simplest organic compounds, containing only hydrogen and carbon, are called hydrocarbons
Hydrocarbons that have only single bonds are called saturated hydrocarbons

4. Alkanes
An alkane is a saturated hydrocarbon with no double or triple bonds
Each bond is with another carbon atom or a hydrogen atom
Straight-chain alkanes have all the carbons bonded in one long chain
All alkanes have the formula CnH(2n + 2)
Examples: CH4, C4H10
To name straight-chain alkanes, use the prefixes in Table P and add -ane

5. Practice Problem
Draw the structural formula for each straight-chain alkane below and then name them
C2H?
C5H?
C7H?

6. Alkanes
Alkanes are ______________ molecules that will not dissolve in water
The melting point and boiling point of alkanes increase with the size of the molecule due to increasing _______________________ forces
Alkanes combust easily with oxygen and are a common component in fuels

7. Practice Problem
Match the alkane on the left with its correct boiling point on the right
CH °C
C5H °C
C10H22 36°C

8. Alkanes
Branched-chain alkanes have carbons attached to the central parent chain
Compounds that have the same molecular formula but different structural formulas are called isomers

9. How to name branched-chain alkanes
Count the carbons in the parent chain (the longest chain) and use the corresponding alkane name
Number the carbons in the parent chain starting with the one closest to the branch chain
Name each branch with a –yl ending and place it before the name of the parent chain
Use the number of the carbon to which it’s attached to indicate the branch’s position (if necessary)

10. Practice Problem
Name the molecule below

11. Practice Problem
Name the molecule below

12. Practice Problem
Name the molecule below

13. Practice Problem
Name the molecule below

14. Aim: How do we name and draw structures for alkenes and alkynes??
Do Now: Draw the structural formulas for two isomers of C4H10 Homework 13.1: Worksheet entitled, “Naming Hydrocarbons”

15. Group-Pair Share Problem
Give the structural formula, condensed structural formula, and molecular formula for 4-propyloctane

16. Group Pair Share Problem
Give the structural formula, condensed structural formula, and molecular formula for 2-methylhexane

17. Group Pair Share Problems
Draw all isomers of pentane
Draw all isomers of hexane

18. Alkenes and Alkynes
Hydrocarbons that contain double and triple bonds are called unsaturated hydrocarbons
Compounds with double bonds between carbons are called alkenes
Alkenes have the formula CnH2n
Alkynes are compounds with triple bonds between carbons
Alkynes have the formula CnH(2n – 2)

19. Label the following compounds as alkanes, alkenes, or alkynes
Practice Problem
Label the following compounds as alkanes, alkenes, or alkynes
C3H4
C8H18
C6H12

20. How to name alkenes and alkynes
Count the carbons in the parent chain and use the corresponding alkane name
Change the ending to –ene or -yne
2. Number the carbons in the parent chain starting with the one closest to the double or triple bond
3. Use the number of the carbon where the bond starts to indicate the bond’s position

21. Name the compound below:
Practice Problem
Name the compound below:

22. Name the compound below
Practice Problem
Name the compound below

23. Group-Pair Share Problem
Name the compounds below:

24. Aim: How do we name and draw structures for alkenes and alkynes?
Do Now: Copy general rules for naming hydrocarbons. Homework 13.1: Worksheet entitled, “Naming Hydrocarbons” Quiz: TOMORROW!! (On drawing hydrocarbon structures)

25. Group-Pair Share Problems
Give the structural formula, condensed structural formula, and molecular formula for 3-octene
Give the structural formula, condensed structural formula, and molecular formula for 1-butyne

26. Branched Unsaturated Hydrocarbons
With unsaturated hydrocarbons that have attached groups, the longest chain containing the double (or triple) bond is considered the parent chain.

27. Name the following:
This vertex represents a carbon bonded to two hydrogen atoms
Structural Formulas are sometimes represented by skeletal structures.
A skeletal structure usually shows the carbon framework of a molecule only as lines representing bonds
Carbon atoms are understood to be at each bond, along with enough hydrogen atoms so that each carbon makes four bonds

28. Hint: Start by filling in carbon and hydrogen atoms
Name the following:
Hint: Start by filling in carbon and hydrogen atoms

29. Aim: How are functional groups named?
Do Now:
Remove everything from your desk except for:
Pen/pencil
Reference table

30. Quiz # 10 Version A complete questions: 2, 4, 6
Version B complete questions: 3, 5, 7

31. Cycloalkanes
Alkanes that are connected in a loop are called closed- chain alkanes or cycloalkanes
They are named by using the prefix cyclo- and the name of the straight-chain alkane with the same number of carbons

32. Aromatic Hydrocarbons
Benzene is a six carbon ring with alternating single and double bonds
Compounds that contain benzene rings are called aromatic compounds
Compounds without benzene rings are called aliphatic
The hexagon represents the six carbon atoms and the circle represents the delocalized electrons

33. Draw C4H6 as a cycloalkene
Practice Problem
Draw C4H6 as a cycloalkene

34. The symbols R and R’ represent bonded atoms or groups of atoms
Functional Groups
Atoms other than hydrogen and carbon occur in organic molecules as functional groups
The symbols R and R’ represent bonded atoms or groups of atoms

35. Halocarbons
When any of the halogens (F, Cl, Br, or I) replaces a hydrogen, the compound is called an organic halide
They are named by citing the location of the halogen and the type of halogen on the chain

36. They are not polar enough to dissolve in water
Halocarbons
Because of the high EN _________________ of halogens, organic halides are slightly polar
They are not polar enough to dissolve in water
The boiling points of halocarbons are slightly higher than the corresponding alkane

37. Name the compound shown below
Practice Problem
Name the compound shown below

38. Group-Pair Share Problem
Draw the structure of 4-iodononane

39. Aim: How are functional groups named?
Do Now:
Draw the structures for:
3,3- dimethyl-1-butyne
3-ethyl-2,4,5-trimethyloctane

40. –OH is called a hydroxyl group (not to be confused with OH-!)
Alcohols
–OH is called a hydroxyl group (not to be confused with OH-!)
When a hydroxyl group is attached to an organic molecule it is called an alcohol
Alcohols are named by adding –ol to the parent chain and using a number to indicate the location

41. Alcohols with five carbons or less are completely soluble in water
Alcohols have hydrogen bonding and are much more polar than their parent alkanes
Alcohols with five carbons or less are completely soluble in water

42. Group-Pair Share Problem
Draw the structural formula for 1-butanol

43. Name the compounds below:
Practice Problem
Name the compounds below:

44. Ethers
An ether is an organic compound containing an oxygen atom bonded to two carbon atoms
Ethers are named by listing the two groups attached before the word ether
If the two groups attached are the same the ether is named by putting di- in front

45. Draw the structure of methylpropyl ether
Practice Problem
Draw the structure of methylpropyl ether

46. Name the compound below
Practice Problem
Name the compound below

47. Organic Joke
Two hydrocarbons were in the cafeteria having lunch and talking. One hydrocarbon brings up “Methyl Ethyl” the school gossip. Methyl Ethyl had a reputation for causing problems between the hydrocarbons. The two hydrocarbons finished their lunches and started to head to their next class. One hydrocarbon turns to the other and says, “Yeah that Methyl Ethyl is a bad egg, I don’t like her.” The other hydrocarbon says, “Yeah, I don’t like Methyl Ethyl Ether”

48. Many functional groups are based around a carbonyl group:
Carbonyl Compounds
The arrangement in which an oxygen atom is double bonded to a carbon atom is called a carbonyl group
Many functional groups are based around a carbonyl group:
Aldehydes
Ketones
Carboxylic Acids
Esters
Amides

49. Aldehydes
An aldehyde is an organic compound with a carbonyl group located on a terminal carbon
Aldehydes are named by adding –al to the name of the parent chain
Aldehydes are polar, but slightly less so than alcohols or amines

50. Draw the structure of propanal
Practice Problem
Draw the structure of propanal

51. Group-Pair Share Problem
Name the compound below:

52. Ketones are slightly polar
A ketone is a compound in which the carbonyl group is on a central carbon
Ketones are named by adding –one to the parent chain and using a number to indicate the position of the oxygen
Ketones are slightly polar

53. Name the compound below:
Practice Problem
Name the compound below:

54. Group Pair Share Problem
Draw the structure of 2-hexanone

55. Aim: How are functional groups named?
Do Now:
Draw the structural formulas for:
3-heptanone
3,3-diethyl-2,5-dimethylnonane
1,1,1,2- tetrabromobutane

56. Carboxylic Acids
Carboxylic acids, also called organic acids, have a carbonyl group bonded to a hydroxyl group (called a carboxyl group)
They are named with the suffix –oic acid
They are very polar, weak acids

57. Name the compound below:
Practice Problem
Name the compound below:

58. Group Pair Share Problem
Draw the structure of propanoic acid

59. Esters
A compound formed by replacing the hydrogen in a carboxyl group with a hydrocarbon is called an ester
An ester is named by naming the hydrocarbon group followed by the name of the acid but changing –oic acid to – oate

60. Name the compound below
Practice Problem
Name the compound below

61. Group Pair Share Problem
Draw the structure of methyl butanoate

62. Group Pair Share Questions
Name the following compounds:

63. Amides are named by adding –amide to the parent chain
When the hydroxyl group of a carboxylic acid is replaced with a nitrogen atom, the result is an amide
Amides are named by adding –amide to the parent chain

64. Draw the structure of methanamide
Practice Problem
Draw the structure of methanamide

65. Name the compound below
Practice Problem
Name the compound below

66. Amines Amines contain nitrogen atoms bonded to carbon atoms
They are named with the suffix –amine
Amines are slightly less polar than alcohols
They often have strong, offensive odors (like dead fish)

67. Group-Pair Share Problem
Name the compound below

68. Draw the structure of ethanamine
Practice Problem
Draw the structure of ethanamine

69. Amino acids have an amine group and a carboxylic acid
They can bond together in long chains to form proteins and are essential for all life

70. Substitution Reactions
A substitution reaction is one in which one atom or group of atoms is replaced by another atom or group of atoms
The most common organic substitution reaction is when a hydrogen is replaced by a halogen

71. Write a possible reaction between chlorine and propane
Practice Problem
Write a possible reaction between chlorine and propane

72. They are essentially the reverse of elimination reactions
Addition Reactions
Addition reactions are when a double or triple bond is broken by the addition of atoms to both sides of the bond
They are essentially the reverse of elimination reactions

73. Write the following reaction: HCl is added to 2-hexene
Practice Problem
Write the following reaction: HCl is added to 2-hexene

74. Write the following reaction: I2 is added to propyne
Practice Problem
Write the following reaction: I2 is added to propyne

75. Group Pair Share Problem
Explain why alkanes do not undergo addition reactions.

76. Esterification Reactions
In an esterification reaction, an organic acid and an alcohol combine to form an ester and water

77. Practice Problem
Write the reaction between ethanoic acid and 1-butanol and name the product

78. Write the reaction for the synthesis of methyl ethanoate
Practice Problem
Write the reaction for the synthesis of methyl ethanoate

79. The products are always CO2 and H2O
Combustion Reactions
In a combustion reaction, oxygen combines with hydrocarbons releasing energy in the form of heat and light
The products are always CO2 and H2O

80. Write the reaction for the combustion of propane
Practice Problem
Write the reaction for the combustion of propane

81. Fermentation
The process in which glucose is broken down into ethanol is known as fermentation
Yeasts and some bacteria ferment glucose to produce ethanol, carbon dioxide, and energy

82. The product of the reaction, an organic salt, is soap
Saponification
The reaction of a triglyceride, which is a triple ester, with a base is called saponification
The product of the reaction, an organic salt, is soap

83. Plastics, synthetic fibers, and rubber are all examples of polymers
Polymerization
Polymers consist of smaller molecules bonded together by a series of chemical reactions
Plastics, synthetic fibers, and rubber are all examples of polymers
The reaction in which small organic units, called monomers, are bonded together into a very large molecule is called a polymerization reaction

84. Polymerization

85. Polymerization

86. Group Pair Share Questions
Classify the following compounds as an alcohol, carboxylic acid, aldehyde, ketone, ester, or ether.

87. Group Pair Share Questions
Name or draw the following compounds:

88. Group Pair Share Questions
Draw structural formulas for the following compounds:
Butanoic acid
2,2-dichloro-1,1-difluoropropane
3,4-dimethylpentanal
2,3-butanediol