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 General Formula CnH2n+2 C3H8 C4H10 C5H12
H H H
│ │ │
H─ C─ C─ C─ H
H H H H
│ │ │ │
H─ C─ C─ C─ C─ H
H H H H H
│ │ │ │ │
H ─ C─ C─ C─ C─ C─ H
C3H8
C4H10
C5H12
General Formula
CnH2n+2

5. Alkenes At least one double C=C bond General Formula CnH2n C3H6 C4H8
H H H
│ │ │
H─ C─ C= C─ H │ H
H H H H
│ │ │ │
H─ C─ C─ C= C─ H
│ │
H H
H H H H H
│ │ │ │ │
H ─ C─ C─ C─ C= C─ H
│ │ │
H H H
C3H6
C4H8
C5H10
General Formula
CnH2n

6. Alkynes At least one triple C≡C bonds General Formula CnH2n-2 C3H4│
H─ C─ C≡ C─ H
H H
│ │
H─ C─ C─ C≡ C─ H
H H H
│ │ │
H ─ C─ C─ C─ C≡ C─ H
C3H4
C4H6
C5H8
General Formula
CnH2n-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─ C─ H
CH4
H H
│ │
H─ C─ C─ H
C2H6
H H H
│ │ │
H─ C─ C─ C─ H
C3H8
H H H H
│ │ │ │
H─ C─ C─ C─ C─ H
C4H10
H H H H H
│ │ │ │ │
H ─ C─ C─ C─ C─ C─ H
C5H12
H H H H H H
│ │ │ │ │ │
H ─ C─ C─ C─ C─ C─ C─ H
C6H14

9. Alkene Homologous Series
H H
│ │
H─ C= C─ H
C2H4
H H H
│ │ │
H─ C─ C= C─ H │ H
C3H6
H H H H
│ │ │ │
H─ C─ C─ C= C─ H
│ │
H H
C4H8
H H H H H
│ │ │ │ │
H ─ C─ C─ C─ C= C─ H
│ │ │
H H H
C5H10
H H H H H H
│ │ │ │ │ │
H ─ C─ C─ C─ C─ C= C─ H
│ │ │ │
H H H H
C6H12

10. Alkyne Homologous Series
H─ C≡ C─ H
C2H2 H │
H─ C─ C≡ C─ H
C3H4
H H
│ │
H─ C─ C─ C≡ C─ H
C4H6
H H H
│ │ │
H ─ C─ C─ C─ C≡ C─ H
C5H8
H H H H
│ │ │ │
H ─ C─ C─ C─ C─ C≡ C─ H
C6H10

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─ C─ C─ C─ C─ H
Butane
Pentane
H H H H H
│ │ │ │ │
H ─ C─ C─ C─ C─ C─ H

14. Alkenes and Alkynes Name includes location of multiple bond
Carbons numbered to give multiple bond the lowest possible number
1-butyne 2-butyne
H H
│ │
H─ C─ C─ C≡ C─ H
H H
│ │
H─ C─ C≡ C ─ C─ H

15. Chemical Formula Shows only number of each type of element C2H6
C6H12O6

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─ C─ C─ C≡ C─ 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─ C─ C= C─ H │ H

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 CH3 H H │ │ │ │ │
│ │ │ │ │
H ─ C─ C─ C─ C─ C─ H
H H H H H
3-Methyl Pentane
2-Methyl 1-Butene H │
H─ C─ H
H CH2 H
│ │ │
H─ C─ C= C─ H

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 Br H H │ │ │
│ │ │ │
H─ C─ C─ C─ C─ H
H H H H
Br H H
│ │ │
H─ C─ C= C─ H │ H
2-Chlorobutane
3-Bromopropene
CH3CH2CHClCH3
CH2BrCHCH2

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 H H │ │ │ │ │ │
│ │ │ │
HO─ C─ C─ C─ C─ H
H H H H H H
│ │ │ │ │ │
H ─ C─ C─ C─ C─ C─ C─ H
H H H OH H H
1-Butanol
3-Hexanol
CH3CH2CH2CH2OH
CH3CH2CH2CHOHCH2CH3

27. Aldehyde Carbonyl group at end of chain O ǁ ─ C ─ H 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 H H H H O │ │ │ │ ǁ
│ │ ǁ
H─ C─ C─ C─ H
│ │
H H
H H H H O
│ │ │ │ ǁ
H ─ C─ C─ C─ C─ C─ H
│ │ │ │
H H H H
Propanal
Pentanal
CH3CH2CHO
CH3CH2CH2CH2CHO

29. Ketones Carbonyl group not on end of chain O ǁ ─ C ─
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 H O H H H │ ǁ │ │ │
│ ǁ │
H─ C─ C─ C─ H
│ │
H H
H O H H H
│ ǁ │ │ │
H ─ C─ C─ C─ C─ C─ H
│ │ │ │
H H H H
Propanone
2-Pentanone
CH3COCH3
CH3COCH2CH2CH3

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 │ │ │ │ H2N─ C─ C─ C─ C─ H H H H H H H │ │ │ │ │ │
│ │ │ │
H2N─ C─ C─ C─ C─ H
H H H H H H
│ │ │ │ │ │
H ─ C─ C─ C─ C─ C─ C─ H
H H H NH2 H H
1-Butanamine
3-Hexanamine
CH3CH2CH2CH2NH2
CH3CH2CH2CHNH2CH2CH3

34. Amide Carbonyl group with an amine group attached to it O H ǁ ǀ
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─ NH2 │ │ H H H H H H O │ │ │ │ ǁ
│ │ ǁ
H─ C─ C─ C─ NH2
│ │
H H
H H H H O
│ │ │ │ ǁ
H ─ C─ C─ C─ C─ C─ NH2
│ │ │ │
H H H H
Propanamide
Pentanamide
CH3CH2CONH2
CH3CH2CH2CH2CONH2

36. Organic Acid O ǁ
─ C ─ O ─ H
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

37. Organic Acid H O │ ǁ H ─ C─ C─ OH │ H H H H O │ │ │ ǁ
│ ǁ
H ─ C─ C─ OH │ H
H H H O
│ │ │ ǁ
H ─ C─ C─ C─ C─ OH
│ │ │
H H H
Ethanoic Acid
Butanoic Acid
CH3COOH
CH3CH2CH2COOH

38. Ether Single oxygen between 2 carbon chains Name each carbon chain
H H H H H H
│ │ │ │ │ │
H ─ C─ C─ C─ C─ O─ C─ C─ H
H H H H
│ │ │ │
H─ C─ C─O ─ C─ C─ H
Butyl Ethyl Ether
Diethyl Ether
CH3CH2CH2CH2OCH2CH3
CH3CH2OCH2CH3

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

40. Ester H O H │ ǁ │ H ─ C─ O ─ C─ C─ H │ │ H H H H H O H H │ │ │ ǁ │ │
│ ǁ │
H ─ C─ O ─ C─ C─ H
│ │
H H
H H H O H H
│ │ │ ǁ │ │
H ─ C─ C─ C─ C─ O─ C─ C─ H
│ │ │ │ │
H H H H H
Methyl Ethanoate
Ethyl Butanoate
CH3COOCH3
CH3CH2CH2COOCH2CH3

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

43. Organic Reactions Saponification Fermentation Production of Soap
Production of ethanol and CO2 from sugar
C6H12O6  2C2H5OH + 2CO2

44. Combustion Complete Combustion of a Hydrocarbon Example:
CxHy + O2  CO2 + H2O
Example:
C3H8 + 5O2  3CO2 + 4H2O

45. Addition Addition of a halogen onto an alkene or alkyne Br Br │ │
│ │
H─ C≡ C─ H + Br─Br  H─ C= C─ H
Br Br Br Br
│ │ │ │
H─ C= C─ H + Cl─Cl  H─ C─ C─ H
│ │
Cl Cl

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 -(C2H4)n-
Connecting of smaller pieces into a long repeating chain
Plastics, starches, nylon
Two types:
Addition
Condensation
-(C2H4)n-

48. Addition Polymerization
Double or triple bonds break to connect pieces together n
H H H H H H H H
│ │ │ │ │ │ │ │
C═C + C═C  ─ C─C─C─ C ─
│ │ │ │ │ │ │ │
H H H H H H H H

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 + H2O
│ │ │ │ │ │ │ │
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 H2O
│ │
H H

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

53. Isomer Example C5H12 H H H H H │ │ │ │ │ H ─ C─ C─ C─ C─ C─ H
│ │ │ │ │
H ─ C─ C─ C─ C─ C─ H
H H CH3 H
│ │ │ │
H─ C─ C─ C─ C─ H
H H H H
Pentane
Methyl Butane
H CH3 H
│ │ │
H─ C─ C─ C─ H
2,2-Dimethyl Propane

54. Isomer Example C4H10O H H H H │ │ │ │ HO─ C─ C─ C─ C─ H H H H H
│ │ │ │
HO─ C─ C─ C─ C─ H
H H H H
│ │ │ │
H─ C─ C─O ─ C─ C─ H
1-Butanol
Diethyl Ether

55. Isomer Example C3H6O H H O │ │ ǁ H─ C─ C─ C─ H │ │ H H H O H │ ǁ │
│ │ ǁ
H─ C─ C─ C─ H
│ │
H H
H O H
│ ǁ │
H─ C─ C─ C─ H
│ │
H H
Propanal
Propanone

56. Isomer Example C3H6O2 H O H H H O │ ǁ │ │ │ ǁ H ─ C─ O ─ C─ C─ H
│ ǁ │
H ─ C─ O ─ C─ C─ H
│ │
H H
H H O
│ │ ǁ
H ─ C─ C─ C─ OH
│ │
H H
Propanoic Acid
Methyl Ethanoate