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Organic Chemistry

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Build pentane and show how it rotates around a single bond ... What is 4-methyl pentane? ... Draw and name all the isomers of pentane ... – PowerPoint PPT presentation

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Title: Organic Chemistry


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
  • CnH2n2
  • Alcohols have OH group bonded to C
  • CnH2n1OH

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
  • 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

27
(No Transcript)
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
  • alkanegthalogenoalkane gtaldehyde gtketone
    gtalcohol gtacid

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
102 Alkanes
  • CnH2n2
  • 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
103 Alkenes
  • Unsaturated hydrocarbons
  • bond has a weak pi( )bond along with the sigma
    (s)

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
104 alcohols
  • CnH2n1OH
  • 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
105 Halogenoalkanes
  • CnH2n1X X halogen
  • Used as intermediaries in other reactions
  • Polar Cd - Cld- 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
106 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 103-6
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