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Organic Chemistry Chapter 22-23. Organic Chemistry Study of carbon-based compounds Carbon has 4 valence electrons Carbon always forms 4 covalent bonds.

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Presentation on theme: "Organic Chemistry Chapter 22-23. Organic Chemistry Study of carbon-based compounds Carbon has 4 valence electrons Carbon always forms 4 covalent bonds."— Presentation transcript:

1 Organic Chemistry Chapter 22-23

2 Organic Chemistry Study of carbon-based compounds Carbon has 4 valence electrons Carbon always forms 4 covalent bonds Carbon compounds form chains and/or rings

3 Hydrocarbons Molecule or compound composed of carbon and hydrogen only Three Main Types Alkanes, Alkenes, Alkynes

4 Alkanes All single C C bonds H H H H H H C C C C C H H H H H H H H H H H C C C C H H H H H H H H H C C C H H H H C 5 H 12 C 4 H 10 C3H8C3H8 General FormulaC n H 2n+2

5 Alkenes At least one double C=C bond H H H H H H C C C C= C H H H H H H H H H C C C= C H H H H H H H C C= C H H C 5 H 10 C4H8C4H8 C3H6C3H6 General FormulaC n H 2n

6 Alkynes At least one triple C C bonds H H H H C C C C C H H H H H H H C C C C H H H H H C C C H H C5H8C5H8 C4H6C4H6 C3H4C3H4 General FormulaC n H 2n-2

7 Homologous Series Group of compounds with similar structure and function Table Q Members increase by one carbon and two hydrogens

8 Alkane Homologous Series H H H H H H C C C C C H H H H H H C 5 H 12 H H H H H C C C C H H H H H C 4 H 10 H H H H C C C H H H H C3H8C3H8 H H H C C H H H C2H6C2H6 H H C H H CH 4 H H H H H H H C C C C C C H H H H H H H C 6 H 14

9 Alkene Homologous Series H H H H H H C C C C= C H H H H C 5 H 10 H H H H H C C C= C H H H C4H8C4H8 H H H H C C= C H H C3H6C3H6 H H H C= C H C2H4C2H4 H H H H H H H C C C C C= C H H H H H C 6 H 12

10 Alkyne Homologous Series H H H H C C C C C H H H H C5H8C5H8 H H H C C C C H H H C4H6C4H6 H H C C C H H C3H4C3H4 H C C H C2H2C2H2 H H H H H C C C C C C H H H H H C 6 H 10

11 Saturated vs. Unsaturated Saturated Hydrocarbons Contain only single Carbon to Carbon bonds (Alkanes) Unsaturated Hydrocarbons Contains at least one multiple (double, triple) Carbon to Carbon bond Alkenes and Alkynes

12 Naming Simple Hydrocarbons Name is based on two parts Number of carbons in longest continuous chain (Table P) Type of bonds between carbons Single –ane Double –ene Triple –yne

13 Examples Butane Pentane H H H H H C C C C H H H H H H H H H H H C C C C C H H H H H H

14 Alkenes and Alkynes Name includes location of multiple bond Carbons numbered to give multiple bond the lowest possible number 1-butyne2-butyne H H H C C C C H H H H C C C C H H H

15 Chemical Formula Shows only number of each type of element C 2 H 6 C 6 H 12 O 6

16 Structural Formula Shows how each atom is bonded to each other H H H H H H C C C C C H H H H H H H H H C C C C H H H

17 Condensed Structural Formula Shows who is bonded to who, without the actual bonds H H H H C C= C H H H H H H C C C H H H H

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19 Branched Hydrocarbons Alkyl Group Hydrocarbon branch Branch name ends with -yl Location of branch is indicated by number Number carbons to give lowest possible number Multiple bond still takes priority in numbering

20 Examples 3-Methyl Pentane 2-Methyl 1-Butene H H CH 3 H H H C C C C C H H H H H H H H C H H CH 2 H H C C= C H H

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22 Functional Groups Specific arrangement of atoms that give compounds a unique property Table R Examples Hydroxyl Group, -OH O Carbonyl Group, C ǁ

23 Halides Halogen attached to a carbon Prefix indicates which halogen Table R # for which carbon halogen is attached Multiple bonds still take priority in numbering

24 Halides H H Cl H H C C C C H H H H H 2-Chlorobutane Br H H H C C= C H H 3-Bromopropene CH 3 CH 2 CHClCH 3 CH 2 BrCHCH 2

25 Alcohol Hydroxyl group (-OH) attached to a carbon # for which alcohol group is attached Name ends in –ol Multiple bonds still take priority in numbering

26 Alcohol H H H H HO C C C C H H H H H 1-Butanol 3-Hexanol H H H H H H H C C C C C C H H H H OH H H CH 3 CH 2 CH 2 CH 2 OHCH 3 CH 2 CH 2 CHOHCH 2 CH 3

27 Aldehyde Carbonyl group at end of chain Name ends with –al Condensed structural formula ends with -CHO O ǁ C H

28 Aldehyde H H O ǁ H C C C H H H Propanal CH 3 CH 2 CHO H H H H O ǁ H C C C C C H H H H H Pentanal CH 3 CH 2 CH 2 CH 2 CHO

29 Ketones Carbonyl group not on end of chain Number indicates which carbon the oxygen is attached to Name ends with –one Condensed structural formula has -CO- in it O ǁ C

30 Ketones H O H ǁ H C C C H H H Propanone CH 3 COCH 3 H O H H H ǁ H C C C C C H H H H H 2-Pentanone CH 3 COCH 2 CH 2 CH 3

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32 Amine Nitrogen attached to a carbon Number indicates which carbon the nitrogen is attached to Name ends in –amine Multiple bonds still take priority in numbering

33 Amine H H H H H 2 N C C C C H H H H H 1-Butanamine 3-Hexanamine H H H H H H H C C C C C C H H H H NH 2 H H CH 3 CH 2 CH 2 CH 2 NH 2 CH 3 CH 2 CH 2 CHNH 2 CH 2 CH 3

34 Amide Carbonyl group with an amine group attached to it Must be on an end Name ends in -amide O H ǁ ǀ C N H

35 Amide H H O ǁ H C C C NH 2 H H Propanamide CH 3 CH 2 CONH 2 H H H H O ǁ H C C C C C NH 2 H H H H Pentanamide CH 3 CH 2 CH 2 CH 2 CONH 2

36 Organic Acid Carbonyl group with a hydroxyl group attached to it Must be on an end Name ends in –oic acid Condensed structural formula ends with -COOH Hydroxyl H is the acidic H O ǁ C O H

37 Organic Acid H O ǁ H C C OH H Ethanoic Acid CH 3 COOH H H H O ǁ H C C C C OH H H H Butanoic Acid CH 3 CH 2 CH 2 COOH

38 Ether Single oxygen between 2 carbon chains Name each carbon chain Butyl Ethyl Ether H H H H H H H C C C C O C C H H H H H H H H H H H H C C O C C H H H H H Diethyl Ether CH 3 CH 2 OCH 2 CH 3 CH 3 CH 2 CH 2 CH 2 OCH 2 CH 3

39 Ester Carbonyl group with single oxygen between carbon chains Name in two parts 1 st Branch off oxygen first as alkyl group 2 nd Chain containing Carbonyl group Ending in –oate O ǁ C O

40 Ester H O H ǁ H C O C C H H H Methyl Ethanoate CH 3 COOCH 3 Ethyl Butanoate H H H O H H ǁ H C C C C O C C H H H H H H CH 3 CH 2 CH 2 COOCH 2 CH 3

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42 Organic Reactions Saponification Fermentation Combustion Addition Substitution Polymerization (2 types) Esterification

43 Organic Reactions Saponification Production of Soap Fermentation Production of ethanol and CO 2 from sugar C 6 H 12 O 6 2C 2 H 5 OH + 2CO 2

44 Combustion Complete Combustion of a Hydrocarbon C x H y + O 2 CO 2 + H 2 O Example: C 3 H 8 + 5O 2 3CO 2 + 4H 2 O

45 Addition Addition of a halogen onto an alkene or alkyne Br Br Br Br H C= C H + Cl Cl H C C H Cl Cl Br Br H C C H + Br Br H C= C H

46 Substitution Substitution of one halogen in place of a hydrogen on an alkane H H H H H C C H + Cl Cl H C C H + H Cl H H H Cl H H Br H H C C H + Br Br H C C H + H Br H Cl H Cl

47 Polymerization Connecting of smaller pieces into a long repeating chain Plastics, starches, nylon Two types: Addition Condensation -(C 2 H 4 ) n -

48 Addition Polymerization Double or triple bonds break to connect pieces together H H H H H H H H C C + C C C C C C H H H H H H H H n

49 Condensation Polymerization Removal of water is used to link pieces together H H H H H H H H H O C C O H + H O C C O H H O C C O C C O H + H 2 O H H H H H H H H

50 Esterification Production of an Ester from an alcohol and acid Alcohol + Acid Ester + Water H O H O ǁ ǁ H C O H + H O C H H C O C H + H 2 O H H

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52 Isomers Two or more compounds with the same chemical formulas, but different structural formulas and properties Different Names

53 Isomer Example H H H H H H C C C C C H H H H H H H H CH 3 H H C C C C H H H H H Pentane Methyl Butane C 5 H 12 H CH 3 H H C C C H H CH 3 H 2,2-Dimethyl Propane

54 Isomer Example H H H H HO C C C C H H H H H 1-Butanol H H H H H C C O C C H H H H H Diethyl Ether C 4 H 10 O

55 Isomer Example H H O ǁ H C C C H H H Propanal H O H ǁ H C C C H H H Propanone C3H6OC3H6O

56 Isomer Example H H O ǁ H C C C OH H H Propanoic Acid H O H ǁ H C O C C H H H Methyl Ethanoate C3H6O2C3H6O2


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