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Organic Chemistry Topic 10.

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Presentation on theme: "Organic Chemistry Topic 10."— Presentation transcript:

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

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

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