1. Organic Chemistry
Topic 10

2. Uniqueness of carbon Up to 4 bonds with other atoms
Single, double and triple bonds
Stable covalent bonds C-C or C-H
Can form chains and rings
Octet cannot expand so not as reactive

3. Describe the features of an homologous series
Organic means carbon based compounds
Alkanes C, H all single bonds
CnH2n+2
Alcohols have OH group bonded to C
CnH2n+1OH

4. Features of an homologous series
Same functional group
Same general formula
Successive members add CH2
Gradation of physical properties
Similar chemical properties
Question 1 and 2

5. Longer chains are stickier and have higher boiling points (bp)
Question 3

6. Formulas ethane Empirical CH3 Molecular C2H6
Structural full and condensed

7. animation

8. Try ethanoic acid

9. Try glucose empirical formula CH2O Mr = 180

10. conventions
R or R‘ used for hydrocarbon part
ROH
Benzene ring

11. 4 single bonds is tetrahedral 109.5o not 90o, tetrahedral
3 bonds no lone pairs form 120o, triangular planer
Sterochemical formula wedge = forward of a page, dotted line = behind

12. nomenclature Learn names of 1-6 carbons Rule #1 Name the longest chain
Page 370 in your book
Rule #1 Name the longest chain
Build pentane and show how it rotates around a single bond

13. `

14. #2 Use the functional group ending as the suffix of the name page 371 in the book
-ane, -ene, -anol,-anone, -anoic acid

15. Name the side chain
Methyl, ethyl, propyl
Build 2-methyl butane
This is an isomer of pentane
Use the lowest # possible to number the carbon it is on
What is 4-methyl pentane?

16. Use prefixes di-, tri-,tetra- to represent more than one side chain in alphabetical order
1,2 dichloropropane

17. 1-chloro-2-methylpropane (notice alphabetical order)

18. Propan-2-ol

19. But-1-ene

20. If a functional group can only be in one place leave off the number
Like propene

21. Butanoic acid

22. Propanone

23. Name the following a) CH3CH2CH2COOH
b) CHCl2CH2CH3
c) CH3CH2COCH3

24. Draw the structural formulas of the following molecules a) hexanoic acid
b) butanal

25. Do questions 4-6
Handout on nomenclature
Do questions 1-4 pages 374-5

26. Aromatic groups
Para dichloro benzene

28. Structural isomers
Same molecular formula, different arrangement of atoms
Different structural formula
Butane and 2-methylpropane

29. Draw and name all the isomers of pentane
Start with the straight chain and progressively pull off the ends

30. Draw and name all the isomers of C6H14

31. Structural isomers in alkenes
Draw and name the isomers of C4H8

32. Draw and name the straight chain isomers of C6H12

33. Classes of compounds Primary, secondary, tertiary
To how many carbons is the carbon attached to the functional group attached
Ethanol
Propan-2-ol
2-methylpropan-2-ol

34. Trends in physical properties
Volatility (how easily evaporated)
Smaller less sticky
Branched less sticky
Animation 1
Functional polar groups more sticky less volatile
alkane>halogenoalkane >aldehyde >ketone >alcohol >acid

35. Solubility in water More polar more soluble
Alcohol, aldehyde, ketone and acid are all soluble

36. Which compound has the lowest boiling point? CH3CH2CH(CH3)CH3
(CH3)4C CH3CH2CH2CH2CH3
CH3CH2OCH2CH3
Do questions 8 and 9
Do questions 5-8 page 382 for HW

37. 10:2 Alkanes CnH2n+2 Saturated Hydrocarbons
Strong bonds – low reactivity
However, they burn easily forming CO2 and H2O
If not enough O2 they form CO or C (soot)

38. Show the equation for burning octane

39. Halogenation of alkanes page 384 in your book
UV light and Cl2 yields 2 Cl. Radicals
Called homolytic fission

40. Propagation or chain reaction
Show termination step
Do this all with molecular models

41. Do question set 1 for homework
Ready for a quiz???

42. 10:3 Alkenes Unsaturated hydrocarbons
= bond has a weak pi( )bond along with the sigma (σ)

43. Addition reactions Ni catalyst and H2
Used in margarine to make saturated fats with higher melting points

44. Reaction with halogens
Propene with Br2 (test for a = bond)

45. Hydrogen halides Produce halogenoalkanes Propene with HCl
HI weaker bonds more reactive than HBr then HCl

46. Reaction with water Called hydration Alkene to alcohol
Use conc. H2SO4 as a catalyst and steam
Ethene to ethanol (industrial use to get alcohol)

47. polymerization
Polyethylene
Monomer is
Polymer is

48. Polyvinylchloride (PVC)

49. Teflon (polytetrafluoroethene) what is the starting material?
Do questions 10-12

50. 10:4 alcohols CnH2n+1OH Nomenclature handout alcohols
-OH (hydroxyl group) functional group
Shorter chains soluble in water

51. combustion Like alkanes Equation for burning of ethanol
Longer chains give off more energy

52. oxidation
Alcohols with orange K2Cr2O7 reduce it to green Cr2O3 (breathalyzer test)
Primary alcohols oxidize to aldehyde then to acids
Ethanol with K2CrO7
Distill to get ethanal (apple smell)

53. Reflux to get acid
Lab activity distillation and refluxing

54. Secondary alcohols make ketones
Propan-2-ol (reflux)

55. Tertiary alcohols do not readily oxidize
Do questions 13-14
Do question set 2 for homework

56. 10:5 Halogenoalkanes CnH2n+1X X = halogen
Used as intermediaries in other reactions
Polar Cδ+ - Clδ- C e- deficient
Nucleophiles e- rich lone pairs attack the e- deficient area
SN substitution nucleophile reactions

57. Examples of nucleophiles H2O OH- NH3 CN-
SN2 (bimolecular) primary halogenoalkanes

58. SN1 tertiary halogenoalkanes
Unimolecular
Secondary halogenoalkanes can undergo either

59. Go to page 395 and draw the 2 mechanisms showing curly arrows
Animation
Do questions 15-17

60. 10:6 Reaction pathways
see page 406 in the textbook fill in the reagents and conditions needed
Convert 1-chlorobutane into butanoic acid

61. Do proponal from 1-bromopropane

62. 1,2,3 trichlorpropane from propene

63. Esters
Formed when organic acids react with alcohols
Fragrances and flavors
RCOOR‘

64. Draw methyl methanoate from methanol and ethanoic acid

65. Ester from methanoic acid and propanol
Name and draw the structure
Nomenclature handout esters
Do question 7
Ester lab

66. Do questions 18-20
Do questions 1-4,6-9,11 pages 416 and 417 in your textbook
Do the SL questions (1-11) in your study guide on page 74
Homework question set 3
Quiz 10:3-6