1. VII. Organic

2. What does organic chemistry have to do with my life?
J Deutsch 2003

3. J Deutsch 2003

4. J Deutsch 2003

5. deals with carbon molecules attached to hydrogen and other elements.
Organic Chemistry
deals with carbon molecules attached to hydrogen and other elements.

6. Properties of Organic Compounds
Low melting points and boiling points. Longer chains have higher melting and boiling points
Nonpolar (vdw forces)
React Slowly
Poor conductors of heat & electricity except for organic acids
J Deutsch 2003

7. It can form up to 4 covalent bonds with other carbon atoms and make single double or triple bonds with itself.

8. A structural formula show the way the atoms are arranged.
Methane Ethane
H H H
H C H H C C H
Each line represents a covalent bond - a shared pair of electrons.
J Deutsch 2003

9. A structural formulas show the way the atoms are arranged.
propene
H H
H C C C H
H H
ethyne
H C C H
The double bonds makes this hydrocarbon an alkene
The triple bonds makes this hydrocarbon an alkyne
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10. Chemical or Molecular Formulas
Tell the kind & number of atoms in a molecule.

11. Compounds containing only carbon & hydrogen
Hydrocarbons
Compounds containing only carbon & hydrogen

12. Saturated hydrocarbon
Hydrocarbon containing only single carbon-carbon bonds

13. Unsaturated hydrocarbon
Hydrocarbon containing at least 1 double or triple carbon-carbon bond

14. Homologous Series
A group of related compounds in which each member differs from the one before it by the same additional unit. Properties vary in a predictable way.

15. Table Q gives the general formula and examples (name and structure) of the homologous series of hydrocarbons.
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16. Table P gives the prefix used to name the first 10 hydrocarbons in an homologous series.
J Deutsch 2003

17. Alkanes saturated hydrocarbons. All single bonds
general formula CnH2n+2.
end in “ane”

18. Regents Question: 01/03 #25
In saturated hydrocarbons, carbon atoms are bonded to each other by
(1) single covalent bonds, only
(2) double covalent bonds, only
(3) alternating single and double covalent bonds
(4) alternating double and triple covalent bonds þ
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19. Alkenes Contain one double bond CnH2n Unsaturated Hydrocarbon
End in “ene”
# in front may give location of double bond.

20. Alkynes Unsaturated hydrocarbon Contain one triple bond CnH2n-2
End in “yne”
# in front gives location of triple bond.

21. In a multiple covalent bond, more than one pair of electrons are shared between two atoms.
Alkenes have one double bond
H H
C C
Alkynes have one triple bond
H C C H
Ethene C2H4
Ethyne C2H2
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22. Chains of carbons can form rings
Use a prefix cyclo when a ring is formed
To make a ring, two Hydrogen atoms are removed
Cyclopentane is a 5 carbon ring with all single bonds.
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23. The prefix of the name tells you how many carbons in the chain
The prefix of the name tells you how many carbons in the chain.The suffix tells you the type of hydrocarbon.
Number of Carbons
Prefix
Example
Alkane
CnH2n+2
Alkene
CnH2n
Alkyne CnH2n-2 1
Meth
Methane
CH4 2
Eth
Ethane
C2H6
Ethene
C2H4
Ethyne
C2H2 3
Prop
Propane
C3H8
Propene
C3H6
Propyne
C3H4 4
But
Butane
C4H10
Butene
C4H8
Butyne
C4H6 5
Pent
Pentane
C5H12
Pentene
C5H10
Pentyne
C5H8
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24. Regents Question: 06/03 #24
Which element has atoms that can form single, double, and triple covalent bonds with other atoms of the same element?
hydrogen
(2) oxygen
(3) fluorine
(4) carbon þ
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25. Alkanes are saturated hydrocarbons.
Regents Question: 06/03 #21
Which hydrocarbon is saturated?
(1) propene
(2) ethyne
(3) butene
(4) heptane þ
Alkanes are saturated hydrocarbons.
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26. Carbon always has 4 bonds.
Hydrogen always has 1 bond
Oxygen always has 2 bonds
Nitrogen always has 3 bonds
C or C or C
H O or O N
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27. The 4 single bonds of a carbon atom are directed to …
the corners of a regular tetrahedron.

28. Regents Question: 01/03 #13
The empirical formula of a compound is CH2 Which molecular formula is correctly paired with a structural formula for this compound? þ
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29. Carbon always has four bonds.
Regents Question: 08/02 #42
Which structural formula is incorrect?
Carbon always has four bonds. þ
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30. Naming hydrocarbons with alkyl groups:
Find the longest continuous chain of carbons. This is the backbone. Find the name of the backbone.
Find the name of the alkyl group (or groups) attached to the backbone.
Name the alkyl group and then the name of the backbone.
Use a number to indicate which carbon the alkyl group is attached to if necessary.
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31. Chains of carbons can be branched
A carbon group connected to a chain is called an alkyl group.
To name the alkyl group, use the prefix for the number of carbons and add yl.
-CH3 H
H C
Methyl
-C2H5
H H
H C C
Ethyl
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32. Find the name of this hydrocarbon.
H C H
H H H H H
H C C C C C C H
H H H H H H
Find the alkyl group
Find the longest chain 1 6 2 5 3 4 4 3 5 2 6 1 3-
methyl
hexane
Counting from each direction find the carbon where the alkyl group is attached (the lower number)
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33. The longest chain does not have to be drawn straight.
H C H
H H H H
H C C C C C H
H H H H H H
H C H
H H H H
H C C C C C H
H H H H H
3-methylhexane
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34. Isomers of organic compounds have the same molecular formula but different structures and properties. (3.1ii)
Pentane C5H12
Methylbutane C5H12
H H H H
H C C C C H
H H H
H C H H
H H H H H
H C C C C C H
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35. # of possible isomers  as # of C atoms 

36. Examples of isomers: 1-butanol (C4H9OH) diethyl ether (C2H5OC2H5)
4 Carbon, 10 Hydrogen, 1 Oxygen
propanal (C2H5CHO) propanone (CH3COCH3)
3 Carbon, 6 Hydrogen, 1 Oxygen
Isomers have the same chemical formulas but different structural formulas.
J Deutsch 2003

37. Regents Question: 08/02 #55 Given the structural formula for butane:
Draw the structural formula for an isomer of butane.
H H H
H C C C H
H H
H C H H
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38. Regents Question: 06/03 #25 þ Which compound is an isomer of pentane?
(1) butane
(2) propane
(3) methyl butane
(4) methyl propane þ
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39. Regents Question: 01/03 #18 þ Which compound has an isomer?
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40. Regents Question: 06/02 #19 þ Which formula is an isomer of butane?
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41. Organic acids, alcohols, esters, aldehydes, ketones, ethers, halides, amines, amides, and amino acids are categories of organic molecules that differ in their structures. Functional groups impart distinctive physical and chemical properties to organic compounds.
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42. Naming Halocarbons (-X)
Halocarbons (or halides) have a halogen (F, Cl, Br, I) in place of a hydrogen
Name the halogen first (fluoro, chloro, bromo, iodo) then name the alkane
If there are more than 2 carbons in the chain, use a number to indicate which carbon the –X group is attached to. (Number from the direction that gives the smallest number)
1-chloropropane
2-bromobutane
H H Cl
H C C C H
H H H
H Br H H
H C C C C H
H H H H
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43. Reference Table R lists all the functional groups.
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44. Reference Table R Cont’d.
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45. Naming Alcohols (-OH) Alcohols have the hydroxyl group -OH
Name the alkane drop the “e” and “ol”
If there are more than 2 carbons in the chain, use a number to indicate which carbon the –OH group is attached to. (Number from the direction that gives the smallest number)
1-propanol
2-propanol
H H OH
H C C C H
H H H
H OH H
H C C C H
H H H
J Deutsch 2003

46. Regents Question: 08/02 #20 þ Which compound is an alcohol? propanal
(2) ethyne
(3) butane
(4) methanol þ
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47. Naming Ethers (-O-) Ethers have an Oxygen in the chain of carbons
Name the alkyl groups on either side of the O that is in the chain
If both alkyl groups are the same it is named once with the prefix DI in front of it.
H H H
H C C O C H
Methyl ethyl ether
H H
H C O C H
Dimethyl ether
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48. Naming Aldehydes (-CHO)
Aldehydes have a double bonded Oxygen on the last carbon in the chain.
Name the alkane, drop the e and add __al
propanal
methanal
H H O
H C C C H
H H O
H C H
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49. Regents Question: 01/03 #49
Which type of organic compound is represented
by the structural formula shown below?
(1) aldehyde
(2) alcohol
(3) ether
(4) ester þ
J Deutsch 2003

50. Naming Ketones (-CO-)
Ketones have a double bonded Oxygen on a carbon in the middle of the chain. (Not the last carbon)
Name the alkane, drop the e and add __one
If there are more than 4 carbons in the chain, use a number to indicate the location of the =O
butanone
3-pentanone
H H O H
H C C C C H
H H H
H H O H H
H C C C C C H
H H H H
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51. Naming Organic Acids (-COOH)
Acids have a double bonded Oxygen and an –OH on the last carbon in the chain.
Name the acid, drop the e and add __oic acid
This is OH and not HO…the Carbon is bonded to the O
Propanoic acid
Pentanoic acid
H H O
H C C C OH
H H
O H H H H
HO C C C C C H
H H H H
J Deutsch 2003

52. Regents Question: 06/03 #44
Given the formulas of four organic compounds:
Which pair below contains an alcohol and an acid?
(1) a and b (3) b and d
(2) a and c (4) c and d þ
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53. Naming Esters (-COOC-)
Esters have a double bonded Oxygen and an –O– bonded to another carbon.
Name the alkyl group that came from the alcohol. Name the acid but drop __ic acid and replace it with ate.
Propanoic acid + pentanol Pentyl propanoate + water
Propanoic acid
1-Pentanol
H H O
H C C C OH
H H
H H H H H
HO C C C C C H
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54. Naming Amines (-NH2)
Amines have a nitrogen bonded to the carbon chain. The nitrogen may have two, one or no hydrogen atoms bonded to it.
Name the alkane, drop the e and add __amine
If there are more than two carbon atoms, use a number to indicate which carbon the N is attached to.
ethanamine
2-Pentanamine
H H
H C C NH2
H NH2 H H H
H C C C C C H
H H H H H
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55. Name the folowing: Ethanoic acid 1-Propanamine Ethanal 2-butene
H H H H
H C C C N H
H H H
H O
H C C OH H
Ethanoic acid
1-Propanamine
H O
H C C H H
H H H H
H C C C C H
H H
Ethanal
2-butene
H H O H H H
H C C C C C C H
H H H H H
H OH H H H
H C C C C C H
H H H H H
3-hexanone
2-pentanol
J Deutsch 2003

56. Regents Question: 06/02 #17
Which compound is classified as a hydrocarbon?
Ethane
(2) Ethanol
(3) chloroethane
(4) ethanoic acid þ
J Deutsch 2003

57. Regents Question: 06/02 #48 þ Which pair of compounds are alcohols?
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58. Types of organic reactions include: addition, substitution, polymerization, esterification, fermentation, saponification, and combustion. (3.2c)
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59. Organic Reactions-Addition
H2, Cl2, Br2, HCl, HBr is added to an unsaturated hydrocarbon. Both atoms are added to where the double (or triple) bond was located.
Key to look for – Unsaturated hydrocarbon reactant and one product.
H H
C C
H H
C C
Cl Cl
H C C H
H H
+ Cl2
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60. Organic Reactions-Addition Cont’d
Addition of hydrogen H2 Can be used to saturate and unsaturated hydrocarbon. It uses a catalyst such as platinum (Pt)
H H
C C
H H
C C
H H
H C C H
+ H2 Pt
J Deutsch 2003

61. Regents Question: 01/03 #26
Which formula correctly represents the product
of an addition reaction between ethene and chlorine?
CH2Cl2
(2) CH3Cl
(3) C2H4Cl2
(4) C2H3Cl þ
J Deutsch 2003

62. Organic Reactions-Substitution
A halogen is reacted with a saturated hydrocarbon. One of the halogen atoms substitutes one of the hydrogen atoms.
Key to look for – Saturated hydrocarbon reactant and two product.
H H
H C C H
H Cl
H C C H
H H
+ Cl2 UV
+ HCl
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63. Organic Reactions-Polymerization
Polymerization – joining many small molecules together to form a large molecule
A single unit is called a monomer
Many monomers are bonded together to form a polymer
Polymers can be natural or artificial
Natural Polymers
Artificial Polymers
Protein
Polyester
Rubber
Nylon
Cellulose
Styrofoam
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64. Regents Question: 06/02 #49
The process of joining many small molecules
into larger molecules is called
(1) neutralization
(2) polymerization
(3) Saponification
(4) substitution þ
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65. Regents Question: 06/03 #45
Which type of reaction is represented by the equation below?
Note: n and n are very large numbers equal to about 2000.
(1) Esterification (3) saponification
(2) fermentation (4) polymerization þ
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66. Organic Reactions-Fermentation
Fermentation – yeast and bacteria can make ethanol and carbon dioxide by breaking down sugar using an enzyme.
The alcohol can be used to make beer and wine,
The carbon dioxide can be used to make bread rise or make the bubbles in beer and champagne.
Enzyme
C6H12O C2H5OH + 2CO2
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67. Organic Reactions-Saponification
Saponification is a reaction in which a lipid (fat or oil) is used to make soap.
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68. Organic Reactions-Esterification
Esterification – making an ester by combining an alcohol with an organic acid
H H
H C C OH
O H
HO C C H H +
H H
H C C O
O H
C C H H
H2O +
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69. Making an ester by removing water from an acid and an alcohol
Propanoic acid
1-Pentanol
H H O
H C C C O
H H
H H H H H
C C C C C H
H HO
Pentyl propanoate
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70. Name the ester: Methyl ethanoate H O H H C C O C H H H Ethanoate
Acid
Alcohol
Determine which side was the alcohol and which side was the acid by drawing a line through the oxygen in the chain. The side with the double bonded O was the acid.
Alcohol will make you yl if you ate the acid.
J Deutsch 2003

71. Regents Question: 08/02 #56 Given the ester: ethyl butanoate
a. Draw the structural formula for this ester.
b. Determine the gram formula mass of this ester.
C 6 x 12 = 72
O 2 x 16 = 32
H 12 x 1 = 12
116 g
H H H O
H C C C C O
H H H
H H
C C H
Even if you got the structure wrong but you got the correct mass for the structure you drew, you got one point.
J Deutsch 2003

72. Amides (-CON) are made by reacting an organic acid with ammonia or with an amine.
From amine (CH3NH2)
H O
H C C N H
H H
H O H
H C C N C H
H H H
From ammonia (NH3)
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73. Propanoic acid + 1-pentanamine Pentyl propanamide + water
Naming Amides (-CON-)
Amides have a double bonded Oxygen and a Nitrogen.
Name the alkyl group that came from the amine. Name the acid but drop __oic acid and replace it with amide.
Propanoic acid + 1-pentanamine Pentyl propanamide + water
Propanoic acid
1-Pentanamine
H H O
H C C C OH
H H
H H H H H
H2N C C C C C H
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74. Making an amide by removing water from an acid and an amine
Propanoic acid
1-Pentanamine
H H O
H C C C
H H
H H H H H
N C C C C C H
H H H H H H
OH H
Pentyl propanamide
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75. Amino acids have both an amine group and an acid group.
An amino acid is a compound that has an amine group on one side and an acid group on the other.
O R H
HO C C N
H H
R is the only part that changes in different amino acids.
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76. Proteins are polymers of amino
Remove water
O R
HO C C N
H H
O R
C C N H
H H
O R
HO C C N H
H H
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77. Organic Reactions-Combustion
Burning
Combining with oxygen to produce carbon dioxide and water
Burning Methane CH4 + 2O CO2 + 2H2O
Burning Octane C8H18 +25O CO2 + 18H2O
Burning Ehtanol C2H5OH + 3O CO2 + 3H2O
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78. Regents Question: 08/02 #21 þ In which reaction is soap a product?
(1) addition
(2) substitution
(3) Saponification
(4) polymerization þ
J Deutsch 2003