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Organic Chemistry Topic 10 Topic 10. Uniqueness of carbon Up to 4 bonds with other atoms Up to 4 bonds with other atoms Single, double and triple bonds.

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Presentation on theme: "Organic Chemistry Topic 10 Topic 10. Uniqueness of carbon Up to 4 bonds with other atoms Up to 4 bonds with other atoms Single, double and triple bonds."— Presentation transcript:

1 Organic Chemistry Topic 10 Topic 10

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

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

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

8 Try ethanoic acid Try ethanoic acid

9 Try glucose empirical formula CH 2 O M r = 180 Try glucose empirical formula CH 2 O M r = 180

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

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

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

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

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

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

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

18 Propan-2-ol Propan-2-ol

19 But-1-ene But-1-ene

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

21 Butanoic acid Butanoic acid

22 Propanone Propanone

23 Name the following a) CH 3 CH 2 CH 2 COOH Name the following a) CH 3 CH 2 CH 2 COOH b) CHCl 2 CH 2 CH 3 b) CHCl 2 CH 2 CH 3 c) CH 3 CH 2 COCH 3 c) CH 3 CH 2 COCH 3

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 Aromatic groups Para dichloro benzene Para dichloro benzene

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28 Structural isomers Same molecular formula, different arrangement of atoms Same molecular formula, different arrangement of atoms Different structural formula Different structural formula Butane and 2-methylpropane 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 C 6 H 14 Draw and name all the isomers of C 6 H 14

31 Structural isomers in alkenes Draw and name the isomers of C 4 H 8 Draw and name the isomers of C 4 H 8

32 Draw and name the straight chain isomers of C 6 H 12 Draw and name the straight chain isomers of C 6 H 12

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

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

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

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

37 10:2 Alkanes C n H 2n+2 C n H 2n+2 Saturated Saturated Hydrocarbons Hydrocarbons Strong bonds – low reactivity Strong bonds – low reactivity However, they burn easily forming CO 2 and H 2 O However, they burn easily forming CO 2 and H 2 O If not enough O 2 they form CO or C (soot) If not enough O 2 they form CO or C (soot)

38 Show the equation for burning octane Show the equation for burning octane

39 Halogenation of alkanes page 384 in your book Halogenation of alkanes page 384 in your book UV light and Cl 2 yields 2 Cl. Radicals UV light and Cl 2 yields 2 Cl. Radicals Called homolytic fission 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 Unsaturated hydrocarbons = bond has a weak pi( )bond along with the sigma (σ) = bond has a weak pi( )bond along with the sigma (σ)

43 Addition reactions Ni catalyst and H 2 Ni catalyst and H 2 Used in margarine to make saturated fats with higher melting points Used in margarine to make saturated fats with higher melting points

44 Reaction with halogens Reaction with halogens Propene with Br 2 (test for a = bond) Propene with Br 2 (test for a = bond)

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

46 Reaction with water Called hydration Called hydration Alkene to alcohol Alkene to alcohol Use conc. H 2 SO 4 as a catalyst and steam Use conc. H 2 SO 4 as a catalyst and steam Ethene to ethanol (industrial use to get alcohol) Ethene to ethanol (industrial use to get alcohol)

47 polymerization Polyethylene Polyethylene Monomer is Monomer is Polymer is Polymer is

48 Polyvinylchloride (PVC) Polyvinylchloride (PVC)

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

50 10:4 alcohols C n H 2n+1 OH C n H 2n+1 OH Nomenclature handout alcohols Nomenclature handout alcohols -OH (hydroxyl group) functional group -OH (hydroxyl group) functional group Shorter chains soluble in water Shorter chains soluble in water

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

52 oxidation Alcohols with orange K 2 Cr 2 O 7 reduce it to green Cr 2 O 3 (breathalyzer test) Alcohols with orange K 2 Cr 2 O 7 reduce it to green Cr 2 O 3 (breathalyzer test) Primary alcohols oxidize to aldehyde then to acids Primary alcohols oxidize to aldehyde then to acids Ethanol with K 2 CrO 7 Ethanol with K 2 CrO 7 Distill to get ethanal (apple smell) Distill to get ethanal (apple smell)

53 Reflux to get acid Reflux to get acid Lab activity distillation and refluxing Lab activity distillation and refluxing

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

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

56 10:5 Halogenoalkanes C n H 2n+1 X X = halogen C n H 2n+1 X X = halogen Used as intermediaries in other reactions Used as intermediaries in other reactions Polar C δ+ - Cl δ- C e- deficient Polar C δ+ - Cl δ- C e- deficient Nucleophiles e- rich lone pairs attack the e- deficient area Nucleophiles e- rich lone pairs attack the e- deficient area S N substitution nucleophile reactions S N substitution nucleophile reactions

57 Examples of nucleophiles H 2 O OH - NH 3 CN - Examples of nucleophiles H 2 O OH - NH 3 CN - SN2 (bimolecular) primary halogenoalkanes SN2 (bimolecular) primary halogenoalkanes

58 S N 1 tertiary halogenoalkanes S N 1 tertiary halogenoalkanes Unimolecular Unimolecular Secondary halogenoalkanes can undergo either Secondary halogenoalkanes can undergo either

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

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

61 Do proponal from 1-bromopropane Do proponal from 1-bromopropane

62 1,2,3 trichlorpropane from propene 1,2,3 trichlorpropane from propene

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

64 Draw methyl methanoate from methanol and ethanoic acid Draw methyl methanoate from methanol and ethanoic acid

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

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


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