1. Organic Chemistry
Chem 2014

2. Organic Chemistry Organic Chemistry: - the chemistry of carbon
and carbon-based compounds
- (C – C or C – H or C – R)
- (can be a few to hundreds of carbons covalently bonded to one another)
Characteristics of Organic Compounds:
*Usually have strong odors and low boiling points
* Most do not conduct electricity
* Most will ignite and burn
* Slower rates of reactions

3. Organic Chemistry in everyday life:
Smells & tastes: fruits, chocolate, fish, mint
Medications: Aspirin, Tylenol, Decongestants, Sedatives
Addictive substances: Caffeine, Nicotine, Alcohol, Narcotics
Hormones/Neurotransmitters: Adrenaline, Epinephrine
Food/Nutrients: Carbohydrates, Protein, Fat, Vitamins
Genetics: DNA, RNA
Consumer products: Plastics, Nylon, Rayon, Polyester

4. Animals, plants, and other forms of life consist of organic compounds.
Nucleic acids, proteins, fats, carbohydrates, enzymes, vitamins, and hormones are all organic compounds
Besides carbon, the most common elements in organic compounds are hydrogen, oxygen, nitrogen, sulfur, and the halogens.
All of the preceding elements are non-metals, therefore organic compounds have covalent bonding.

5. Numbers and Types of Bonds for Common Elements in Organic Compounds Application of the octet rule indicates that these elements should bond as shown below:
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Section 14.1

6. Review: Octet Rule
Rule of Eight – elements want either 8 or 0 electrons in its outermost level (except for H and He which want 2 or 0)
Each energy level can only hold a certain number of electrons.
1st level 2 electrons
2nd level 8 electrons
3rd level 8 electrons
4th level electrons

7. Periodic Table and Valence electrons
Group Number
Number of Valence Electrons 1 2 13 3 14 4 15 5 16 6 17 7 18 8
*Helium only has 2 valence electrons

8. Let’s Practice Bohr Diagrams
Energy Levels Diagram HW wkst

9. Lewis Structure Placing valence electrons around element symbol
to decipher bonding patterns

10. Lets practice Lewis dot structures

11. Practice Lewis Dot Structures
1. Oxygen (e = _________)
2. Potassium (e = _______)
3. Bromine (e = ________)
4. Germanium (e= ______)
5. Aluminum (e = ______)
6. Phosphorus (e = ______)

12. Big Idea in Organic Chemistry
Structure controls Function
Each functional group has predictable reactivity
= atom or group of atoms that gives characteristic
chemical properties to a class of organic compounds

13. Drawing Organic Structures
Shortcuts make structures easier & faster to draw
Butane: C4H10
Lewis Structure
Structural formula
Carbon Atoms
Line Structure Carbon Skeleton
Only shows bonds
C atoms assumed at each end and intersection of bonds
H atoms not shown
Assume 4 bonds to each C
Fulfill C’s 4 bonds by adding H’s
Condensed Structures
molecular formula
CH3CH2CH2CH3
CH3(CH2)2CH3

14. Types of Organic Compounds
Classified according to functional group
Alkane
Alkene
Alkyne
Halocarbon
Alcohol
Ether
Ketone
Aldehyde
Carboxylic acid
Amine
Amino acid
Amide
Hydrocarbons (H & C only)
What about esters? What are halolkane?
Ester

15. Characteristics and Examples Hydrocarbons
Alkane
Alkene
Alkyne
Contain
C – C
single bond
C = C
double bond
C ≡ C
triple bond
Formula
n is # of carbons
CnH2n+2
CnH2n
CnH2n-2
Naming
Prefix (# of C’s)-ane
# (count from smallest direction of =) – Prefix (# C’s) - ene
# (count from smallest direction of ≡) – Prefix (# C’s) - yne
Examples
See following
Slides for
examples
Linear/
skeletal structure
\/ \

16. Organic Prefixes Meth- 1 carbon Hept- 7 carbon Eth- 2 carbon
Oct- 8 carbon
Prop- 3 carbon
Non- 9 carbon
But- 4 carbon
Dec- 10 carbon
Pent- 5 carbon
Hex- 6 carbon

17. Lewis/ Structural Formula Condensed Structural Formula
Examples
Name
Molecular Formula
Lewis/ Structural Formula
Condensed Structural Formula
Linear
propane
C3H8
CH3CH2CH3 \/
ethane
C2H6
CH3CH3 \
2-pentene
C5H10
CH3CHCHCH2CH3
2-butene
C4H8
CH3CHCHCH3

18. Condensed Structural Formula
Name
Molecular Formula
Structural Formula
Condensed Structural Formula
3-heptyne
C7H12
CH3CH2CCCH2CH2CH3
1-propyne
C3H5
CHCCH3

19. Alkanes – Energy Related Products
Methane = primary component of natural gas
Propane & Butane = primary component of bottled gas
Gasoline = pentane to decane
Kerosene = alkanes with n = 10 to 16
Alkanes with n > 16  diesel fuel, fuel oil, petroleum jelly, paraffin wax, lubricating oil, and asphalt
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Section 14.3

20. Organic Compound Nomenclature
Due to the large number, variety, and complexity of organic compounds, a consistent method of nomenclature has been developed.
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Section 14.3

21. IUPAC System of Nomenclature For Alkanes
Compound is named as a derivative of the longest continuous chain of C atoms.
Positions & names of the substituents added
If necessary, substituents named alphabetically
More than one of same type substituent – di, tri, tetra
The C atoms on the main chain are numbered by counting from the end of the chain nearest the substituents.
Each substituent must have a number.
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Section 14.3

22. Hydrocarbons wkst

23. Names of Linear Alkanes and Alkyl Substituents
C atoms
Alkane
Alkyl substituents 1 2 3 4 5 6 7 8 9 10
CH4
CH3CH3
CH3CH2CH3
CH3CH2CH2CH3
Methane
Ethane
Propane
Butane
Pentane
Hexane
Heptane
Octane
Nonane
Decane
-CH3
-CH2CH3
-CH2CH2CH3
Methyl
Ethyl
Propyl
etc.
Root: number of C atoms
Suffix: functional group
(-ane for alkanes)
(-yl for alkyl groups)

24. An Example to Consider The longest continuous chain of C atoms is five
Therefore this compound is a pentane derivative with an attached methyl group
Start numbering from end nearest the substituent
The methyl group is in the #2 position
The compound’s name is 2-methylpentane.
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Section 14.3

25. Drawing a Structure from a Name An Example
Draw the structural formula for ,3-dimethylhexane.
Note that the end name is hexane .
Draw a continuous chain of six carbon (C) atoms, with four bonds around each.
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Section 14.3

26. Drawing a Structure from a Name An Example (cont.)
Number the C atoms from right to left.
Attach a methyl group (CH3--) to carbon number 2 and number 3.
Add necessary H atoms.
2,3-dimethylhexane
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Section 14.3

27. Drawing a Structure from a Name Confidence Exercise
Draw the structural formula for ,2,4-trimethylpentane.
Note that the end name is pentane .
Draw a continuous chain of five carbon (C) atoms, with four bonds around each.
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Section 14.3

28. Drawing a Structure from a Name Confidence Exercise (cont.)
Number the C atoms from right to left.
Attach two methyl groups (CH3--) to carbon number 2 and one to number 4.
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Section 14.3

29. Drawing a Structure from a Name Confidence Exercise (cont.)
Add necessary H atoms.
2,2,4-trimethylpentane
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Section 14.3

30. H C C H
Methane
CH4
Butane
C4H10 H C ? C H ? R R
Methyl
-CH3
Butyl
-C4H9
Where R = any other C atom or arrangement of C atoms

31. Example of R group C H 2 - methylbutane Expanded Structure
Line Structure
2 - methylbutane

32. First Ten Hydrocarbons: Properties
Number of
Carbon Atoms
Molecular
Formula
Melting
Point, oC
Boiling
Point, oC
# of
Isomers
Name
Methane
Ethane
Propane
Butane
Pentane
Hexane
Heptane
Octane
Nonane
Decane 1 2 3 4 5 6 7 8 9 10
CH4
C2H6
C3H8
C4H10
C5H12
C6H14
C7H16
C8H18
C9H20
C10H22
-182.5
-183.2
-187.7
-138.3
-129.7
95.3
90.6
56.8
53.6
29.7
-161.5
-88.6
-42.1
-0.5
36.1
68.7
98.4
125.7
150.8
174.0 1 2 3 5 9 18 35 75

33. Properties of Alkanes Nonpolar → only London Dispersion Forces IMF
Larger molecular weight → Stronger London dispersion forces
Compound
Methane
Ethane
Propane
Butane
Pentane
Formula
CH4
C2H6
C3H8
C4H10
C5H12 MW 16 30 44 58 72
Boiling point (°C)
-164
-88.6
-42.1
-0.5
+36.0
Linear Alkanes:
1 - 4 C atoms: gas at room temp
C atoms: liquid at room temp
>15 C atoms: solid at room temp

34. Naming Branched Alkanes (IUPAC)
Octane
4-ethyl 6 2 8
4-ethyl-3,5-dimethyloctane 5 4 7 3 1
3-methyl and 5-methyl
= 3,5-dimethyl
Root name: name of longest continuous C chain (parent chain)
2 equally long? Choose the one with more branches
Number C atoms in chain, starting at end with first branch
Identify substituents, give each a number (C it is connected to)
Two or more identical substituents: use prefixes (di-, tri-, tetra-, etc.)
List substituents alphabetically before root name
Do not alphabetize prefixes
Punctuation: commas separate numbers from each other
hyphens separate numbers from names
no space between last substituent & root name

35. Alkenes are very Reactive and are termed “unsaturated hydrocarbons”
Alkenes will characteristically react with hydrogen to form the corresponding alkane.
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Section 14.3

36. Alkynes are Unsaturated Hydrocarbons
Due to the triple carbon bond, each alkyne molecule can react with two molecules of hydrogen.
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Section 14.3

37. Chapter 26 Hydrocarbon Derivatives

38. Hydrocarbon Derivatives
Derivatives = molecules that contain C and H, as as hydrocarbons, but also contain other elements
derivatives depend on their functional groups which are atoms or group of atoms that give the derivative its characteristic chemical behavior

39. Derivatives Alkane Alkene Alkyne Halocarbon Alcohol Ether Ketone
Aldehyde
Carboxylic acid
Amine
Amino acid
Amide
Esters

40. Halocarbon Definition
One or more of hydrogen atoms replaced with a member of halogen family
General Formula
R – X
R symbolizes the hydrocarbon portion
X symbolizes the halogen atom
X can be F, Cl, Br, or I
Naming
(IUPAC)
1. Name hydrocarbon portion
2. Add prefix to indicate halogen, add -o
3. # of halogen placement
Properties
Primarily non polar
Low boiling points
Insoluble in water
Soluble in hydrocarbon solvent
Structure
Examples
CFC’s –chlorofluorocarbons Methanol
(aerosol cans, refrigerate gases) Pesticides
Dry cleaning chemicals

41. Alcohols
Definition
One or more of hydrogen atoms replaced with a member of hydroxyl group (-OH)
General Formula
R – OH
R symbolizes the hydrocarbon portion
OH – hydroxyl group
Naming
(IUPAC)
Suffix –ol added to hydrocarbon root
Properties
*Similar to water (OH)
*Up to 4 C are soluble in water
*Higher boiling points
*Can be –diol (2 –OH) or –triol (3 -OH)
Structure
Examples
Butanol
Methanol
Ethanol – grain alcohol

42. Ethers Definition Oxygen atom that is bonded to two carbon atoms
General Formula
R – O – R’
R and R’ → hydrocarbon chains
-O- → functional group
Naming
(IUPAC)
1. Suffix –oxy added to smaller chain bonded to central oxygen atom, remainder is named as before
2. Or use similar name: add suffix –yl to each hydrocarbon and add ether
Properties
Oxygen creates slightly polar region
Some smaller molecules are soluble in water
No H bonds so lower boiling points than alcohol but higher than hydrocarbons
Structure
Examples
Ethers

43. Worksheet Review

44. Definition
-oxygen atom bonded to single carbon atom by a double bond
-called a carbonyl group (C=O)
Aldeyde has carbonyl group attached to end of hydrocarbon chain
General Formula
R – CHO
Naming
(IUPAC)
Add suffix –al to the root name
Properties
More polar than hydrocarbons
Higher melting and boiling points than hydrocarbons
Lower melting and boiling points than alcohol
Structure
Examples
-Methanol (HCOH) = formaldehyde – used to make polymers and used to be used for biological preservation – found to be carcinogenic
-Used as flavorings in food and candy and as fragrances in inhalants and perfumes
-Vanilla flavor in ice cream and cinnamon in hot chocolate
Aldehydes

45. Definition
Ketone has a carbonyl group on the interior of a hydrocarbon
General Formula
R-COR’
Naming
(IUPAC)
Add suffix –one to the root name
Name must include which C it is attached to b/c always on interior C when a Ketone
Properties
More polar than hydrocarbons
Higher melting and boiling points than hydrocarbons
Lower melting and boiling points than alcohol
Structure
Examples
-Propanone (CH3COCH3) = acetone - volatile liquid and vapor is flammable
-Cortisone= hormonal response to fight or flight, treatment of severe allergic reactions; too much bad b/c breaks down connective tissue, increases production of stomach acid and decreasing protective mucus membranes resulting in gastric ulcer
Ketones

46. Worksheet Review

47. Carboxylic Acids Definition
Characterized by presence of a carboxyl group
General Formula
R – COOH
Naming
(IUPAC)
Prefix + -anoic acid
Properties
-carboxyl end is very polar making it soluble in water
-higher boiling points than hydrocarbons
Structure
Examples
(see also book pg 852)
-Fatty acids
Formic acids (simplest form HCOOH) – from ants
Acetic acid – (CH3COOH) – responsible for sour taste of vinegar
-lactic acid – responsible for sour cow’s milk
Carboxylic Acids

48. Definition
Similar to carboxylic acid, but has hydrocarbon group in place of H atom of carboxy group
General Formula
R-COOR’
Naming
(IUPAC)
-named for the alcohol and acid from which they are produced
-alcohol name (suffix changed to –yl) + acid name (suffix changed to –oate)
Example : ethanol + propanoic acid = ethyl propanoate OR
-alcohol name (-yl) + acid (-ate) = propyl alcohol + formic acid = propyl formate
Properties
-polar but do not form H bonds with each other
-boiling points are lower than BP of similar alcohols or acids
-distinctive odors based on alcohol and acid reaction (typically fruity odors)
Structure
Examples
(see also book pg 856)
Ester

50. Worksheet Review

51. Definition
Contains an amino group (-NH2) attached to hydrocarbon chain
General Formula
R-NH ◦ = R-NHR’ ◦ = R-NR’R”
Naming
(IUPAC)
-add suffix –amine to root name of hydrocarbon
Properties
-amino group is polar
-higher boiling points than HC but lower than alcohols
-weak bases
Structure
Examples
-amino groups found in DNA, vitamins, anesthetic drug
-basis of nicotine, cocaine, amphetamines
-unpleasant odors = cadaverine produced by bacteria on decaying organisms – can cause food poisoning
-found in suntan lotion
Amines

52. Amides Definition Amino group attached to carbon of carboxyl group
General Formula
R-CONH2
Naming
(IUPAC)
-add suffix –amide to root of hydrocarbon
Properties
Structure
Examples
Amides
nylon and urea, which exist in chains, and caffeine, which exists in a ring

53. Worksheet Review