Organic Chemistry Unit IX

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Organic ChemistryUnit IX
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I Introduction

• A. Definition
• study of carbon compounds
• forms thousands more compounds than inorganic
  elements do
• carbon has four bonding sites and can bond to
  itself in chains, rings or networks

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• B. Properties
• Insoluble in water
• Nonelectrolytes
• Low melting points
• Slow to react
• High activation energies

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• C. Bonding
• Carbon has 4 valence electrons
• Forms 4 covalent bonds
• Tetrahedral structure
• Bond angle 109.5
• 3 different ways to bond to itself
• Single bonded
• saturated
• Double bonded
• unsaturated
• Triple bonded
• unsaturated

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• D Representations
• Molecular Formula
• ex. C4H10
• Structural Formula
• H H H H
• H C C C C H
• H H H H
• Condensed Structural Formula
• CH3CH2CH2CH3

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II Hydrocarbons

• A hydrocarbon is a compound that contains carbon
  and hydrogen only
• A. Types of hydrocarbons
• Alkanes
• Single bonded carbons in compound
• CnH2n2
• Alkenes
• A double bonded carbon in compound
• CnH2n
• Alkynes
• A triple bonded carbon in compound
• CnH2n-2

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Classify the following

• CH3CH2CHCH2
• C 4
• H 8
• 8 is 2(4)
• Alkene
• CH3CCH
• C 3
• H 4
• 4 is 2(3)-2
• Alkyne
• CH3CH2CH2CH2CH2CH3
• C 6
• H 14
• 14 is 2(6)2
• Alkane

n4
n3
n6
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• B. Naming Hydrocarbons
• Count the longest string of carbons
• Use a prefix to indicate the number of carbons
  (Table P)
• Identify the type of hydrocarbon
• Use a suffix to indicate the type
• Alkane -ane
• Alkene -ene
• Aklyne -yne
• Indicate any addition to the carbon chain using a
  
• prefix indicates amount
• number to show location
• Use the lowest possible number

Example 2-butyne
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Name the hydrocarbon C5H10

• Whats the structure?
• Longest string of carbons
• 5
• Prefix from Table P
• pent-
• Type of hydrocarbon
• alkene
• Suffix for an alkene is -ene
• Indicate any addition to the carbon chain using a
  
• prefix for the amount
• one double bondno prefix
• a number to show location
• 4th carbon or 1st carbon
• 1st carbon is the lowest
• Use the lowest possible number
• 1-pentene
• which means 5 carbons double bond in the 1st
  position

CH3CH2CH2CHCH2
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• C. Writing Formulas for Hydrocarbons
• Write the number of carbons according to prefix
  used
• Place bonds according to suffix used
• Place bonds according to number used
• ex. 3-hexene
• 3-hexene
• 6 carbons
• 3-hexene
• double bond
• 3-hexene
• 3rd position
• CH3CH2CHCHCH2CH3

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ex. 1,3,5-cyclohexatriene 1,3,5-cyclohexatriene
6 carbons 1,3,5-cyclohexatriene Double
bond 1,3,5-cyclohexatriene Three double
bonds 1,3,5-cyclohexatriene In a
ring 1,3,5-cyclohexatriene Double bonds are
on the 1st, 3rd and 5th carbons
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D. Complications

• Occurs when another substance replaces hydrogen
• Can be halogens ( Group 17) or carbon groups
• -F
• fluoro
• -Cl
• chloro
• -Br
• bromo
• -I
• Iodo
• -CH3
• Methyl group
• -CH3CH2
• Ethyl group

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• Prefixes used to represent number of replacement
  elements
• Mono
• Di
• Tri
• Tetra
• When writing formulas or naming
• Build the hydrocarbon name or formula
• Determine the new pieces
• How many
• Where are they located

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Examples

• CH3CHClCH2CH2Cl
• CH3CH(CH3)CH2CH2CH3

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Examples

• 1,1,1-tribromo 3-hexene
• 2,2-dimethylpropane

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III Functional Groups

• Replace hydrogen
• Change the properties of the substance
• Groups found on Reference Table R
• Attach to end of chain (terminal)
• Connect two carbon chains (bridge)
• Join anywhere on the carbon chain (floater)

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A. Terminal Functional Groups

• Types
• Aldehydes
• CH3COH
• ethanal
• Organic Acids
• CH3CH2COOH
• propanoic acid

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B. Floaters

• Functional group can go anywhere on the carbon
  chain
• Types
• Halide
• CH3CHClCH3
• 2-chloropropane
• Alcohol
• CH3CH2CH2OH
• 1-propanol
• Amine
• CH3CHNH2CH2CH3
• 2-aminobutane

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C. Bridges

• Connects two carbon chains
• Types
• Ketone
• CH3CH2CH2COCH3
• 2-pentanone
• Ether
• CH3OCH2CH3
• Methyl ethyl ether
• Ester
• CH3CH2CH2COOCH2CH3
• Ethyl butanoate

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IV Isomers

• Isomers are compounds with the same molecular
  formula and different structure
• C4H8
• C2H6O

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V Reactions

• Substitution
• Alkane halogen
• CH3CH2CH3 Cl2 ? CH2ClCH2CH3 HCl
• Addition
• Alkene or alkyne halogen or hydrogen
• CH3CHCH2 Cl2 ? CH3CHClCH2Cl
• CH3CHCH2 H2 ? CH3CH2CH3

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• Esterification
• acid alcohol ? ester water
• CH3COOH CH3OH ? CH3COOCH3 H2O
• Saponification
• fat base ? soap glycerol
• Fermentation
• sugar ? alcohol CO2
• C6H12O6 ? 2 CH3CH2OH 2 CO2

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• Combustion
• hydrocarbon O2 ? CO2 H2 O
• C6H12 9 O2 ? 6 CO2 6 H2 O
• Polymerization
• monomers ? polymer
• n CH2 ? (-CH2-)n
• ex. 7 CH2 ? (-CH2-)7
• Condensation Polymerization
• -OH containing monomer produces polymer and water
• Addition Polymerization
• Unsaturated monomer makes a saturated polymer